1-Isobutyl-8,9-dimeth­oxy-3-phenyl-5,6-dihidro­imidazo[5,1-a]isoquinolin-2-ium chloride

The molecular salt, C₂₃H₂₆N₂O₂⁺·Cl⁻, was obtained from 1-isobutyl-8,9-dimeth­oxy-3-phenyl-5,6-di­hydro­imidazo[5,1-a]iso­quinoline, which was synthesized by cyclo­condensation of α-benzoyl­amino-γ-methyl-N-[2-(3,4-di­meth­oxy­phen­yl)eth­yl]valeramide in the presence of phosphoryl chloride. The tetra­hydro­pyridine ring adopts a twist–boat conformation. In the crystal structure, centrosymmetric dimers are formed by N—H...Cl and C—H...Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.050
• wR factor = 0.142
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS7 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

1-Isobutyl-8,9-dimethoxy-3-phenyl-5,6-dihydroimidazo[5,1-a]isoquinolin-2-ium chloride

Crystal data

C23H27N2O2^+·Cl^−	F(000) = 848
Mr = 398.92	Dx = 1.242 Mg m^−3
Monoclinic, P21/c	Melting point: 475(2) K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 13.595 (3) Å	Cell parameters from 2082 reflections
b = 14.337 (3) Å	θ = 4.5–75.8°
c = 10.958 (2) Å	µ = 1.74 mm^−1
β = 92.23 (3)°	T = 291 K
V = 2134.1 (7) Å^3	Prizmatic, colorless
Z = 4	0.60 × 0.53 × 0.48 mm

Data collection

Rigaku Xcalibur Ruby diffractometer	4347 independent reflections
Radiation source: fine-focus sealed tube	2990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 10.2576 pixels mm^-1	θmax = 76.0°, θmin = 4.5°
ω scans	h = −16→17
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −18→16
Tmin = 0.371, Tmax = 0.434	l = −9→13
9283 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0678P)^2 + 0.2438P] where P = (Fo^2 + 2Fc^2)/3
4347 reflections	(Δ/σ)max = 0.001
261 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 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 > 2sigma(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.

The H atoms bonded to C atoms were placed geometrically (with C—H distances of 0.98 Å for CH, 0.97 Å for CH₂, 0.96 Å for CH₃ and 0.93 Å for C_ar) and included in the refinement in a riding motion approximation, with U_iso(H) = 1.2U_eq(C) [U_iso(H) = 1.5U_eq(C) for methyl H atoms]. The H atom of N2 was located in a difference Fourier synthesis and refined with a N2—H1 distance = 0.79 (3) Å.

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

	x	y	z	Uiso*/Ueq
O1	0.85755 (14)	0.77486 (11)	0.41517 (17)	0.0640 (5)
O2	0.89458 (14)	0.91068 (12)	0.56498 (16)	0.0623 (5)
N2	0.66229 (14)	1.27667 (13)	0.26859 (17)	0.0478 (4)
N4	0.63568 (14)	1.13705 (12)	0.20336 (17)	0.0452 (4)
C1	0.72530 (17)	1.21988 (15)	0.3370 (2)	0.0457 (5)
C3	0.60827 (16)	1.22675 (15)	0.1889 (2)	0.0459 (5)
C5	0.5983 (2)	1.05567 (16)	0.1344 (2)	0.0569 (6)
H5A	0.5742	1.0748	0.0537	0.068*
H5B	0.5443	1.0273	0.1763	0.068*
C6	0.6813 (2)	0.98620 (19)	0.1235 (3)	0.0692 (8)
H6A	0.6550	0.9283	0.0901	0.083*
H6B	0.7283	1.0103	0.0670	0.083*
C6A	0.7336 (2)	0.96661 (16)	0.2439 (2)	0.0545 (6)
C7	0.7699 (2)	0.87809 (16)	0.2724 (2)	0.0589 (6)
H7A	0.7587	0.8298	0.2169	0.071*
C8	0.82169 (18)	0.85996 (15)	0.3799 (2)	0.0503 (5)
C9	0.83978 (17)	0.93362 (15)	0.4627 (2)	0.0474 (5)
C10	0.80171 (17)	1.02087 (15)	0.4369 (2)	0.0467 (5)
H10A	0.8115	1.0688	0.4932	0.056*
C10A	0.74883 (17)	1.03854 (14)	0.3279 (2)	0.0451 (5)
C10B	0.70861 (17)	1.13078 (15)	0.29649 (19)	0.0443 (5)
C11	0.8322 (2)	0.69713 (18)	0.3379 (3)	0.0744 (8)
H11A	0.8595	0.6411	0.3732	0.112*
H11B	0.8584	0.7067	0.2588	0.112*
H11C	0.7619	0.6915	0.3301	0.112*
C12	0.9174 (2)	0.98354 (18)	0.6494 (2)	0.0648 (7)
H12A	0.9622	0.9607	0.7123	0.097*
H12B	0.8580	1.0047	0.6853	0.097*
H12C	0.9472	1.0344	0.6076	0.097*
C13	0.79478 (19)	1.26228 (17)	0.4306 (2)	0.0551 (6)
H13A	0.8276	1.2126	0.4764	0.066*
H13B	0.7571	1.2983	0.4874	0.066*
C14	0.8726 (2)	1.32535 (19)	0.3772 (3)	0.0671 (7)
H14A	0.8384	1.3731	0.3277	0.080*
C15	0.9379 (3)	1.2716 (3)	0.2951 (4)	0.1234 (15)
H15A	0.8984	1.2425	0.2313	0.185*
H15B	0.9728	1.2246	0.3417	0.185*
H15C	0.9841	1.3133	0.2598	0.185*
C16	0.9321 (3)	1.3745 (3)	0.4774 (4)	0.1160 (15)
H16A	0.9796	1.4147	0.4418	0.174*
H16B	0.9654	1.3291	0.5284	0.174*
H16C	0.8889	1.4110	0.5257	0.174*
C17	0.53556 (17)	1.26476 (16)	0.1005 (2)	0.0479 (5)
C18	0.44587 (19)	1.22054 (18)	0.0757 (2)	0.0583 (6)
H18A	0.4311	1.1652	0.1153	0.070*
C19	0.3789 (2)	1.2590 (2)	−0.0080 (3)	0.0668 (7)
H19A	0.3185	1.2299	−0.0232	0.080*
C20	0.4007 (2)	1.34047 (19)	−0.0695 (2)	0.0653 (7)
H20A	0.3561	1.3651	−0.1273	0.078*
C21	0.4889 (2)	1.38447 (18)	−0.0442 (2)	0.0648 (7)
H21A	0.5035	1.4395	−0.0847	0.078*
C22	0.5564 (2)	1.34783 (17)	0.0408 (2)	0.0558 (6)
H22A	0.6155	1.3786	0.0580	0.067*
Cl1	0.65752 (5)	1.48541 (4)	0.30437 (6)	0.0602 (2)
H1	0.661 (2)	1.345 (2)	0.280 (3)	0.076 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0725 (11)	0.0376 (8)	0.0803 (12)	0.0105 (8)	−0.0194 (9)	−0.0055 (8)
O2	0.0825 (12)	0.0436 (9)	0.0588 (10)	0.0087 (8)	−0.0214 (9)	−0.0025 (8)
N2	0.0565 (11)	0.0344 (9)	0.0520 (11)	0.0013 (8)	−0.0040 (9)	−0.0001 (8)
N4	0.0521 (10)	0.0357 (9)	0.0472 (10)	−0.0002 (8)	−0.0038 (8)	0.0003 (8)
C1	0.0519 (12)	0.0374 (11)	0.0475 (12)	−0.0005 (9)	−0.0018 (10)	0.0013 (9)
C3	0.0508 (12)	0.0376 (11)	0.0492 (12)	0.0021 (9)	0.0012 (10)	0.0027 (9)
C5	0.0723 (16)	0.0405 (12)	0.0565 (14)	−0.0001 (11)	−0.0169 (12)	−0.0052 (11)
C6	0.095 (2)	0.0496 (14)	0.0608 (16)	0.0164 (14)	−0.0204 (15)	−0.0142 (12)
C6A	0.0677 (15)	0.0418 (12)	0.0532 (14)	0.0064 (11)	−0.0093 (12)	−0.0053 (10)
C7	0.0737 (16)	0.0394 (12)	0.0624 (15)	0.0062 (11)	−0.0145 (13)	−0.0113 (11)
C8	0.0542 (13)	0.0351 (11)	0.0612 (14)	0.0045 (9)	−0.0050 (11)	−0.0011 (10)
C9	0.0511 (12)	0.0400 (11)	0.0508 (12)	0.0007 (10)	−0.0030 (10)	0.0025 (10)
C10	0.0537 (12)	0.0376 (11)	0.0484 (12)	0.0001 (9)	−0.0040 (10)	−0.0032 (10)
C10A	0.0509 (12)	0.0360 (11)	0.0481 (12)	0.0006 (9)	−0.0017 (10)	−0.0006 (9)
C10B	0.0509 (12)	0.0389 (11)	0.0428 (11)	0.0002 (9)	−0.0018 (10)	−0.0008 (9)
C11	0.0809 (19)	0.0387 (13)	0.102 (2)	0.0087 (13)	−0.0182 (17)	−0.0127 (14)
C12	0.0815 (18)	0.0543 (14)	0.0567 (15)	0.0021 (13)	−0.0198 (13)	−0.0041 (12)
C13	0.0684 (15)	0.0421 (12)	0.0540 (13)	−0.0063 (11)	−0.0065 (11)	−0.0041 (11)
C14	0.0576 (15)	0.0552 (15)	0.087 (2)	−0.0029 (12)	−0.0157 (14)	0.0146 (14)
C15	0.092 (3)	0.142 (4)	0.139 (4)	−0.012 (3)	0.043 (3)	−0.017 (3)
C16	0.093 (3)	0.093 (3)	0.159 (4)	−0.036 (2)	−0.035 (3)	−0.009 (3)
C17	0.0572 (13)	0.0414 (12)	0.0449 (12)	0.0057 (10)	−0.0011 (10)	−0.0003 (9)
C18	0.0631 (15)	0.0484 (13)	0.0627 (15)	0.0028 (11)	−0.0067 (12)	0.0042 (11)
C19	0.0687 (16)	0.0615 (16)	0.0689 (17)	0.0069 (13)	−0.0158 (13)	−0.0083 (14)
C20	0.0848 (19)	0.0565 (15)	0.0534 (15)	0.0194 (14)	−0.0134 (14)	−0.0014 (12)
C21	0.097 (2)	0.0451 (13)	0.0514 (14)	0.0094 (14)	−0.0001 (14)	0.0068 (11)
C22	0.0710 (15)	0.0434 (12)	0.0531 (14)	0.0017 (11)	0.0012 (12)	0.0017 (11)
Cl1	0.0777 (4)	0.0391 (3)	0.0627 (4)	0.0086 (3)	−0.0097 (3)	−0.0026 (3)

Geometric parameters (Å, º)

O1—C8	1.364 (3)	C11—H11B	0.9600
O1—C11	1.433 (3)	C11—H11C	0.9600
O2—C9	1.362 (3)	C12—H12A	0.9600
O2—C12	1.421 (3)	C12—H12B	0.9600
N2—C3	1.328 (3)	C12—H12C	0.9600
N2—C1	1.381 (3)	C13—C14	1.526 (4)
N2—H1	0.98 (3)	C13—H13A	0.9700
N4—C3	1.346 (3)	C13—H13B	0.9700
N4—C10B	1.398 (3)	C14—C15	1.501 (5)
N4—C5	1.470 (3)	C14—C16	1.512 (4)
C1—C10B	1.368 (3)	C14—H14A	0.9800
C1—C13	1.497 (3)	C15—H15A	0.9600
C3—C17	1.462 (3)	C15—H15B	0.9600
C5—C6	1.513 (4)	C15—H15C	0.9600
C5—H5A	0.9700	C16—H16A	0.9600
C5—H5B	0.9700	C16—H16B	0.9600
C6—C6A	1.500 (3)	C16—H16C	0.9600
C6—H6A	0.9700	C17—C18	1.392 (3)
C6—H6B	0.9700	C17—C22	1.393 (3)
C6A—C10A	1.393 (3)	C18—C19	1.381 (3)
C6A—C7	1.393 (3)	C18—H18A	0.9300
C7—C8	1.374 (3)	C19—C20	1.387 (4)
C7—H7A	0.9300	C19—H19A	0.9300
C8—C9	1.408 (3)	C20—C21	1.373 (4)
C9—C10	1.379 (3)	C20—H20A	0.9300
C10—C10A	1.393 (3)	C21—C22	1.385 (4)
C10—H10A	0.9300	C21—H21A	0.9300
C10A—C10B	1.467 (3)	C22—H22A	0.9300
C11—H11A	0.9600	Cl1—Cl1	0.0000 (19)
C8—O1—C11	116.95 (19)	H11A—C11—H11C	109.5
C9—O2—C12	117.16 (18)	H11B—C11—H11C	109.5
C3—N2—C1	110.75 (18)	O2—C12—H12A	109.5
C3—N2—H1	127.1 (16)	O2—C12—H12B	109.5
C1—N2—H1	122.1 (16)	H12A—C12—H12B	109.5
C3—N4—C10B	109.42 (18)	O2—C12—H12C	109.5
C3—N4—C5	127.51 (19)	H12A—C12—H12C	109.5
C10B—N4—C5	123.07 (18)	H12B—C12—H12C	109.5
C10B—C1—N2	106.43 (19)	C1—C13—C14	114.0 (2)
C10B—C1—C13	133.9 (2)	C1—C13—H13A	108.8
N2—C1—C13	119.61 (19)	C14—C13—H13A	108.8
N2—C3—N4	107.08 (19)	C1—C13—H13B	108.8
N2—C3—C17	125.23 (19)	C14—C13—H13B	108.8
N4—C3—C17	127.7 (2)	H13A—C13—H13B	107.7
N4—C5—C6	108.6 (2)	C15—C14—C16	111.3 (3)
N4—C5—H5A	110.0	C15—C14—C13	111.1 (3)
C6—C5—H5A	110.0	C16—C14—C13	110.9 (3)
N4—C5—H5B	110.0	C15—C14—H14A	107.8
C6—C5—H5B	110.0	C16—C14—H14A	107.8
H5A—C5—H5B	108.4	C13—C14—H14A	107.8
C6A—C6—C5	112.5 (2)	C14—C15—H15A	109.5
C6A—C6—H6A	109.1	C14—C15—H15B	109.5
C5—C6—H6A	109.1	H15A—C15—H15B	109.5
C6A—C6—H6B	109.1	C14—C15—H15C	109.5
C5—C6—H6B	109.1	H15A—C15—H15C	109.5
H6A—C6—H6B	107.8	H15B—C15—H15C	109.5
C10A—C6A—C7	118.9 (2)	C14—C16—H16A	109.5
C10A—C6A—C6	119.7 (2)	C14—C16—H16B	109.5
C7—C6A—C6	121.3 (2)	H16A—C16—H16B	109.5
C8—C7—C6A	122.0 (2)	C14—C16—H16C	109.5
C8—C7—H7A	119.0	H16A—C16—H16C	109.5
C6A—C7—H7A	119.0	H16B—C16—H16C	109.5
O1—C8—C7	125.3 (2)	C18—C17—C22	119.3 (2)
O1—C8—C9	115.9 (2)	C18—C17—C3	121.6 (2)
C7—C8—C9	118.8 (2)	C22—C17—C3	119.0 (2)
O2—C9—C10	125.2 (2)	C19—C18—C17	119.9 (2)
O2—C9—C8	115.19 (19)	C19—C18—H18A	120.1
C10—C9—C8	119.6 (2)	C17—C18—H18A	120.1
C9—C10—C10A	121.2 (2)	C18—C19—C20	120.7 (3)
C9—C10—H10A	119.4	C18—C19—H19A	119.7
C10A—C10—H10A	119.4	C20—C19—H19A	119.7
C10—C10A—C6A	119.4 (2)	C21—C20—C19	119.4 (2)
C10—C10A—C10B	122.7 (2)	C21—C20—H20A	120.3
C6A—C10A—C10B	117.9 (2)	C19—C20—H20A	120.3
C1—C10B—N4	106.30 (18)	C20—C21—C22	120.7 (3)
C1—C10B—C10A	135.2 (2)	C20—C21—H21A	119.6
N4—C10B—C10A	118.47 (19)	C22—C21—H21A	119.6
O1—C11—H11A	109.5	C21—C22—C17	119.9 (3)
O1—C11—H11B	109.5	C21—C22—H22A	120.0
H11A—C11—H11B	109.5	C17—C22—H22A	120.0
O1—C11—H11C	109.5
C3—N2—C1—C10B	0.0 (3)	C7—C6A—C10A—C10B	−179.1 (2)
C3—N2—C1—C13	178.6 (2)	C6—C6A—C10A—C10B	2.7 (4)
C1—N2—C3—N4	−0.5 (3)	N2—C1—C10B—N4	0.4 (3)
C1—N2—C3—C17	−178.7 (2)	C13—C1—C10B—N4	−177.8 (3)
C10B—N4—C3—N2	0.7 (3)	N2—C1—C10B—C10A	179.9 (3)
C5—N4—C3—N2	−178.7 (2)	C13—C1—C10B—C10A	1.7 (5)
C10B—N4—C3—C17	178.9 (2)	C3—N4—C10B—C1	−0.7 (3)
C5—N4—C3—C17	−0.6 (4)	C5—N4—C10B—C1	178.8 (2)
C3—N4—C5—C6	146.8 (2)	C3—N4—C10B—C10A	179.7 (2)
C10B—N4—C5—C6	−32.6 (3)	C5—N4—C10B—C10A	−0.8 (3)
N4—C5—C6—C6A	49.5 (3)	C10—C10A—C10B—C1	17.4 (4)
C5—C6—C6A—C10A	−37.4 (4)	C6A—C10A—C10B—C1	−162.0 (3)
C5—C6—C6A—C7	144.4 (3)	C10—C10A—C10B—N4	−163.1 (2)
C10A—C6A—C7—C8	−1.1 (4)	C6A—C10A—C10B—N4	17.4 (3)
C6—C6A—C7—C8	177.1 (3)	C10B—C1—C13—C14	112.9 (3)
C11—O1—C8—C7	−5.2 (4)	N2—C1—C13—C14	−65.2 (3)
C11—O1—C8—C9	174.3 (2)	C1—C13—C14—C15	−62.4 (3)
C6A—C7—C8—O1	178.5 (3)	C1—C13—C14—C16	173.2 (3)
C6A—C7—C8—C9	−1.0 (4)	N2—C3—C17—C18	−139.6 (3)
C12—O2—C9—C10	−2.6 (4)	N4—C3—C17—C18	42.6 (4)
C12—O2—C9—C8	178.1 (2)	N2—C3—C17—C22	39.8 (3)
O1—C8—C9—O2	2.7 (3)	N4—C3—C17—C22	−138.0 (3)
C7—C8—C9—O2	−177.7 (2)	C22—C17—C18—C19	0.3 (4)
O1—C8—C9—C10	−176.7 (2)	C3—C17—C18—C19	179.7 (2)
C7—C8—C9—C10	2.8 (4)	C17—C18—C19—C20	1.2 (4)
O2—C9—C10—C10A	178.1 (2)	C18—C19—C20—C21	−1.7 (4)
C8—C9—C10—C10A	−2.6 (4)	C19—C20—C21—C22	0.7 (4)
C9—C10—C10A—C6A	0.4 (4)	C20—C21—C22—C17	0.9 (4)
C9—C10—C10A—C10B	−179.0 (2)	C18—C17—C22—C21	−1.4 (4)
C7—C6A—C10A—C10	1.4 (4)	C3—C17—C22—C21	179.3 (2)
C6—C6A—C10A—C10	−176.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···Cl1	0.98 (3)	2.04 (3)	3.019 (2)	179
C20—H20A···Cl1^i	0.93	2.89	3.650 (3)	140
C5—H5B···Cl1^ii	0.97	2.83	3.707 (3)	152

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