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The title compound, C24H31N2O2+·Cl, is a potential drug designed as a hybrid mol­ecule with antihypertensive, antioxidant and β-adrenolytic activity. It contains nearly planar benzo­furan and benzene ring systems, and a piperazine ring which adopts an almost perfect chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024894/nc6001sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024894/nc6001Isup2.hkl
Contains datablock I

CCDC reference: 255889

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.085
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H13B .. CL1 .. 2.86 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. CL1 .. 2.97 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. CL1 .. 2.96 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H21A .. CL1 .. 2.96 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B .. CL1 .. 2.87 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnet & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-[2-Ethoxy-2-(3-methyl-1-benzofuran-2-yl)ethyl]-4-(o-tolyl)piperazin-1-ium chloride top
Crystal data top
C24H31N2O2+·ClF(000) = 888
Mr = 414.96Dx = 1.234 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3591 reflections
a = 17.446 (2) Åθ = 2.7–28.1°
b = 10.4855 (9) ŵ = 0.19 mm1
c = 13.0224 (14) ÅT = 120 K
β = 110.304 (11)°Prism, white
V = 2234.2 (4) Å30.50 × 0.50 × 0.50 mm
Z = 4
Data collection top
Kuma KM-4 with CCD area-detector
diffractometer
3431 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Enhance (Oxford Diffraction) monochromatorθmax = 25.0°, θmin = 3.9°
Detector resolution: 16.3 pixels mm-1h = 2019
rotation method, ω scansk = 1210
8342 measured reflectionsl = 1215
3918 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.04P)2 + P]
where P = (Fo2 + 2Fc2)/3
3918 reflections(Δ/σ)max = 0.001
265 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

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
xyzUiso*/Ueq
Cl10.53271 (2)0.15071 (3)0.58331 (3)0.02297 (11)
O10.28919 (6)0.24045 (9)0.12885 (8)0.0203 (2)
O20.39860 (6)0.28999 (9)0.34075 (7)0.0173 (2)
N10.53947 (7)0.13213 (10)0.34790 (9)0.0152 (2)
H10.53340.10840.41340.018*
N20.71455 (7)0.16501 (11)0.40833 (10)0.0180 (3)
C10.30671 (8)0.14621 (13)0.20914 (11)0.0171 (3)
C20.24789 (8)0.05595 (14)0.18581 (12)0.0202 (3)
C30.18725 (8)0.09308 (14)0.08217 (12)0.0221 (3)
C40.11385 (9)0.04070 (16)0.01219 (13)0.0309 (4)
H40.09300.03640.03050.037*
C50.07251 (10)0.10401 (18)0.08417 (14)0.0366 (4)
H50.02300.06920.13310.044*
C60.10222 (10)0.21837 (18)0.11099 (14)0.0350 (4)
H60.07220.25990.17760.042*
C70.17436 (9)0.27268 (16)0.04293 (13)0.0287 (4)
H70.19450.35080.06050.034*
C80.21523 (8)0.20632 (14)0.05200 (12)0.0215 (3)
C90.38732 (8)0.16310 (13)0.30041 (11)0.0165 (3)
H90.38970.10380.36160.020*
C100.45669 (8)0.13114 (13)0.25922 (11)0.0171 (3)
H10A0.44680.04570.22480.020*
H10B0.45650.19360.20210.020*
C110.59332 (8)0.03609 (13)0.32058 (12)0.0194 (3)
H11A0.59550.05500.24720.023*
H11B0.56970.05020.31830.023*
C120.67863 (8)0.03807 (13)0.40368 (12)0.0199 (3)
H12A0.67700.01510.47660.024*
H12B0.71280.02560.38350.024*
C130.66605 (8)0.25694 (13)0.44408 (11)0.0188 (3)
H13A0.69120.34250.45040.023*
H13B0.66520.23220.51710.023*
C140.57951 (8)0.26148 (13)0.36289 (11)0.0178 (3)
H14A0.54700.32240.38910.021*
H14B0.58030.29250.29150.021*
C150.80096 (9)0.16997 (13)0.46306 (12)0.0203 (3)
C160.83580 (9)0.22824 (15)0.56474 (13)0.0268 (3)
H160.80140.26280.60040.032*
C170.92014 (10)0.23672 (16)0.61494 (15)0.0353 (4)
H170.94280.27620.68460.042*
C180.97094 (10)0.18782 (17)0.56362 (16)0.0382 (4)
H181.02860.19340.59750.046*
C190.93662 (10)0.13057 (16)0.46204 (15)0.0335 (4)
H190.97170.09780.42660.040*
C200.85238 (9)0.11935 (14)0.41005 (13)0.0254 (3)
C210.24394 (10)0.05943 (15)0.25125 (13)0.0291 (4)
H21A0.29540.06820.31300.044*
H21B0.23520.13540.20470.044*
H21C0.19860.05030.27890.044*
C220.35052 (9)0.31598 (15)0.40799 (12)0.0228 (3)
H22A0.35820.24740.46300.027*
H22B0.29190.31960.36230.027*
C230.37730 (11)0.44138 (15)0.46427 (13)0.0302 (4)
H23A0.43560.43740.50840.045*
H23B0.34570.45980.51180.045*
H23C0.36810.50900.40930.045*
C240.81853 (10)0.05823 (17)0.29900 (14)0.0333 (4)
H24A0.85890.06380.26240.050*
H24B0.76850.10260.25500.050*
H24C0.80610.03150.30710.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0309 (2)0.0248 (2)0.01455 (17)0.00180 (14)0.00961 (14)0.00010 (14)
O10.0196 (5)0.0198 (5)0.0181 (5)0.0015 (4)0.0021 (4)0.0028 (4)
O20.0211 (5)0.0168 (5)0.0158 (5)0.0008 (4)0.0085 (4)0.0026 (4)
N10.0190 (6)0.0160 (6)0.0117 (5)0.0003 (5)0.0067 (5)0.0002 (5)
N20.0191 (6)0.0149 (6)0.0205 (6)0.0007 (5)0.0074 (5)0.0007 (5)
C10.0212 (7)0.0163 (7)0.0152 (7)0.0018 (5)0.0079 (6)0.0012 (6)
C20.0216 (7)0.0209 (7)0.0204 (7)0.0020 (6)0.0100 (6)0.0034 (6)
C30.0202 (7)0.0250 (8)0.0227 (7)0.0009 (6)0.0093 (6)0.0054 (6)
C40.0245 (8)0.0361 (9)0.0323 (9)0.0079 (7)0.0101 (7)0.0096 (7)
C50.0191 (8)0.0527 (11)0.0316 (9)0.0044 (7)0.0008 (7)0.0115 (8)
C60.0248 (8)0.0493 (11)0.0245 (8)0.0067 (7)0.0002 (7)0.0000 (8)
C70.0263 (8)0.0315 (9)0.0246 (8)0.0033 (7)0.0042 (7)0.0022 (7)
C80.0176 (7)0.0248 (8)0.0205 (7)0.0012 (6)0.0046 (6)0.0037 (6)
C90.0199 (7)0.0153 (7)0.0144 (7)0.0001 (5)0.0060 (5)0.0005 (5)
C100.0196 (7)0.0183 (7)0.0122 (6)0.0003 (5)0.0041 (5)0.0012 (5)
C110.0216 (7)0.0162 (7)0.0219 (7)0.0004 (5)0.0097 (6)0.0040 (6)
C120.0212 (7)0.0159 (7)0.0234 (7)0.0013 (5)0.0087 (6)0.0006 (6)
C130.0211 (7)0.0161 (7)0.0190 (7)0.0001 (5)0.0067 (6)0.0028 (6)
C140.0222 (7)0.0135 (7)0.0181 (7)0.0009 (5)0.0074 (6)0.0004 (6)
C150.0202 (7)0.0164 (7)0.0236 (7)0.0010 (5)0.0066 (6)0.0051 (6)
C160.0255 (8)0.0260 (8)0.0268 (8)0.0013 (6)0.0063 (6)0.0005 (7)
C170.0279 (8)0.0319 (9)0.0362 (9)0.0001 (7)0.0013 (7)0.0025 (8)
C180.0197 (8)0.0356 (10)0.0519 (11)0.0022 (7)0.0030 (7)0.0043 (8)
C190.0247 (8)0.0311 (9)0.0472 (10)0.0068 (7)0.0157 (8)0.0070 (8)
C200.0259 (8)0.0209 (8)0.0318 (8)0.0028 (6)0.0131 (7)0.0066 (7)
C210.0346 (9)0.0260 (8)0.0278 (8)0.0089 (7)0.0121 (7)0.0014 (7)
C220.0241 (7)0.0267 (8)0.0217 (7)0.0022 (6)0.0133 (6)0.0018 (6)
C230.0488 (10)0.0237 (8)0.0250 (8)0.0024 (7)0.0214 (7)0.0019 (7)
C240.0340 (9)0.0391 (10)0.0336 (9)0.0044 (7)0.0202 (7)0.0020 (8)
Geometric parameters (Å, º) top
O1—C81.3777 (17)C11—H11B0.9900
O1—C11.3934 (16)C12—H12A0.9900
O2—C91.4189 (16)C12—H12B0.9900
O2—C221.4333 (16)C13—C141.5139 (19)
N1—C111.5017 (17)C13—H13A0.9900
N1—C101.5039 (17)C13—H13B0.9900
N1—C141.5070 (17)C14—H14A0.9900
N1—H10.9300C14—H14B0.9900
N2—C151.4274 (18)C15—C161.392 (2)
N2—C131.4613 (17)C15—C201.412 (2)
N2—C121.4635 (18)C16—C171.390 (2)
C1—C21.351 (2)C16—H160.9500
C1—C91.5039 (19)C17—C181.381 (3)
C2—C31.450 (2)C17—H170.9500
C2—C211.495 (2)C18—C191.385 (3)
C3—C81.391 (2)C18—H180.9500
C3—C41.401 (2)C19—C201.393 (2)
C4—C51.381 (2)C19—H190.9500
C4—H40.9500C20—C241.503 (2)
C5—C61.398 (3)C21—H21A0.9800
C5—H50.9500C21—H21B0.9800
C6—C71.385 (2)C21—H21C0.9800
C6—H60.9500C22—C231.499 (2)
C7—C81.382 (2)C22—H22A0.9900
C7—H70.9500C22—H22B0.9900
C9—C101.5216 (18)C23—H23A0.9800
C9—H91.0000C23—H23B0.9800
C10—H10A0.9900C23—H23C0.9800
C10—H10B0.9900C24—H24A0.9800
C11—C121.5063 (19)C24—H24B0.9800
C11—H11A0.9900C24—H24C0.9800
C8—O1—C1105.50 (11)C11—C12—H12B109.6
C9—O2—C22111.65 (10)H12A—C12—H12B108.1
C11—N1—C10109.05 (10)N2—C13—C14110.22 (11)
C11—N1—C14109.53 (10)N2—C13—H13A109.6
C10—N1—C14112.59 (10)C14—C13—H13A109.6
C11—N1—H1108.5N2—C13—H13B109.6
C10—N1—H1108.5C14—C13—H13B109.6
C14—N1—H1108.5H13A—C13—H13B108.1
C15—N2—C13116.41 (11)N1—C14—C13111.55 (11)
C15—N2—C12114.62 (11)N1—C14—H14A109.3
C13—N2—C12109.03 (11)C13—C14—H14A109.3
C2—C1—O1112.11 (12)N1—C14—H14B109.3
C2—C1—C9133.58 (13)C13—C14—H14B109.3
O1—C1—C9114.27 (11)H14A—C14—H14B108.0
C1—C2—C3105.86 (13)C16—C15—C20119.24 (14)
C1—C2—C21128.35 (13)C16—C15—N2121.86 (13)
C3—C2—C21125.80 (13)C20—C15—N2118.83 (13)
C8—C3—C4118.81 (14)C17—C16—C15121.12 (15)
C8—C3—C2106.14 (12)C17—C16—H16119.4
C4—C3—C2135.03 (15)C15—C16—H16119.4
C5—C4—C3118.30 (15)C18—C17—C16120.07 (16)
C5—C4—H4120.9C18—C17—H17120.0
C3—C4—H4120.9C16—C17—H17120.0
C4—C5—C6121.15 (15)C17—C18—C19119.06 (15)
C4—C5—H5119.4C17—C18—H18120.5
C6—C5—H5119.4C19—C18—H18120.5
C7—C6—C5121.73 (15)C18—C19—C20122.29 (16)
C7—C6—H6119.1C18—C19—H19118.9
C5—C6—H6119.1C20—C19—H19118.9
C8—C7—C6115.95 (15)C19—C20—C15118.21 (15)
C8—C7—H7122.0C19—C20—C24119.99 (14)
C6—C7—H7122.0C15—C20—C24121.78 (14)
O1—C8—C7125.56 (14)C2—C21—H21A109.5
O1—C8—C3110.39 (12)C2—C21—H21B109.5
C7—C8—C3124.04 (14)H21A—C21—H21B109.5
O2—C9—C1112.00 (11)C2—C21—H21C109.5
O2—C9—C10108.18 (11)H21A—C21—H21C109.5
C1—C9—C10109.60 (11)H21B—C21—H21C109.5
O2—C9—H9109.0O2—C22—C23108.43 (12)
C1—C9—H9109.0O2—C22—H22A110.0
C10—C9—H9109.0C23—C22—H22A110.0
N1—C10—C9113.40 (11)O2—C22—H22B110.0
N1—C10—H10A108.9C23—C22—H22B110.0
C9—C10—H10A108.9H22A—C22—H22B108.4
N1—C10—H10B108.9C22—C23—H23A109.5
C9—C10—H10B108.9C22—C23—H23B109.5
H10A—C10—H10B107.7H23A—C23—H23B109.5
N1—C11—C12111.34 (11)C22—C23—H23C109.5
N1—C11—H11A109.4H23A—C23—H23C109.5
C12—C11—H11A109.4H23B—C23—H23C109.5
N1—C11—H11B109.4C20—C24—H24A109.5
C12—C11—H11B109.4C20—C24—H24B109.5
H11A—C11—H11B108.0H24A—C24—H24B109.5
N2—C12—C11110.15 (11)C20—C24—H24C109.5
N2—C12—H12A109.6H24A—C24—H24C109.5
C11—C12—H12A109.6H24B—C24—H24C109.5
N2—C12—H12B109.6
O1—C1—C9—C1072.94 (14)C9—C10—N1—C11148.68 (11)
C1—C9—C10—N1174.01 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.932.263.1145 (12)152
C13—H13B···Cl10.992.863.5870 (15)131
C9—H9···Cl1i1.002.973.6879 (14)130
N1—H1···Cl1i0.932.963.4592 (12)115
C21—H21A···Cl1i0.982.963.8621 (18)154
C11—H11B···Cl1i0.992.743.4852 (15)132
C10—H10B···Cl1ii0.992.873.7878 (14)154
C14—H14B···Cl1ii0.992.613.5647 (15)161
Symmetry codes: (i) x+1, y, z+1; (ii) x, y+1/2, z1/2.
 

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