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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
CCDC reference: 255889
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (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
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+·Cl− | F(000) = 888 |
Mr = 414.96 | Dx = 1.234 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3591 reflections |
a = 17.446 (2) Å | θ = 2.7–28.1° |
b = 10.4855 (9) Å | µ = 0.19 mm−1 |
c = 13.0224 (14) Å | T = 120 K |
β = 110.304 (11)° | Prism, white |
V = 2234.2 (4) Å3 | 0.50 × 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 tube | Rint = 0.029 |
Enhance (Oxford Diffraction) monochromator | θmax = 25.0°, θmin = 3.9° |
Detector resolution: 16.3 pixels mm-1 | h = −20→19 |
rotation method, ω scans | k = −12→10 |
8342 measured reflections | l = −12→15 |
3918 independent 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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.53271 (2) | 0.15071 (3) | 0.58331 (3) | 0.02297 (11) | |
O1 | 0.28919 (6) | 0.24045 (9) | 0.12885 (8) | 0.0203 (2) | |
O2 | 0.39860 (6) | 0.28999 (9) | 0.34075 (7) | 0.0173 (2) | |
N1 | 0.53947 (7) | 0.13213 (10) | 0.34790 (9) | 0.0152 (2) | |
H1 | 0.5334 | 0.1084 | 0.4134 | 0.018* | |
N2 | 0.71455 (7) | 0.16501 (11) | 0.40833 (10) | 0.0180 (3) | |
C1 | 0.30671 (8) | 0.14621 (13) | 0.20914 (11) | 0.0171 (3) | |
C2 | 0.24789 (8) | 0.05595 (14) | 0.18581 (12) | 0.0202 (3) | |
C3 | 0.18725 (8) | 0.09308 (14) | 0.08217 (12) | 0.0221 (3) | |
C4 | 0.11385 (9) | 0.04070 (16) | 0.01219 (13) | 0.0309 (4) | |
H4 | 0.0930 | −0.0364 | 0.0305 | 0.037* | |
C5 | 0.07251 (10) | 0.10401 (18) | −0.08417 (14) | 0.0366 (4) | |
H5 | 0.0230 | 0.0692 | −0.1331 | 0.044* | |
C6 | 0.10222 (10) | 0.21837 (18) | −0.11099 (14) | 0.0350 (4) | |
H6 | 0.0722 | 0.2599 | −0.1776 | 0.042* | |
C7 | 0.17436 (9) | 0.27268 (16) | −0.04293 (13) | 0.0287 (4) | |
H7 | 0.1945 | 0.3508 | −0.0605 | 0.034* | |
C8 | 0.21523 (8) | 0.20632 (14) | 0.05200 (12) | 0.0215 (3) | |
C9 | 0.38732 (8) | 0.16310 (13) | 0.30041 (11) | 0.0165 (3) | |
H9 | 0.3897 | 0.1038 | 0.3616 | 0.020* | |
C10 | 0.45669 (8) | 0.13114 (13) | 0.25922 (11) | 0.0171 (3) | |
H10A | 0.4468 | 0.0457 | 0.2248 | 0.020* | |
H10B | 0.4565 | 0.1936 | 0.2021 | 0.020* | |
C11 | 0.59332 (8) | 0.03609 (13) | 0.32058 (12) | 0.0194 (3) | |
H11A | 0.5955 | 0.0550 | 0.2472 | 0.023* | |
H11B | 0.5697 | −0.0502 | 0.3183 | 0.023* | |
C12 | 0.67863 (8) | 0.03807 (13) | 0.40368 (12) | 0.0199 (3) | |
H12A | 0.6770 | 0.0151 | 0.4766 | 0.024* | |
H12B | 0.7128 | −0.0256 | 0.3835 | 0.024* | |
C13 | 0.66605 (8) | 0.25694 (13) | 0.44408 (11) | 0.0188 (3) | |
H13A | 0.6912 | 0.3425 | 0.4504 | 0.023* | |
H13B | 0.6652 | 0.2322 | 0.5171 | 0.023* | |
C14 | 0.57951 (8) | 0.26148 (13) | 0.36289 (11) | 0.0178 (3) | |
H14A | 0.5470 | 0.3224 | 0.3891 | 0.021* | |
H14B | 0.5803 | 0.2925 | 0.2915 | 0.021* | |
C15 | 0.80096 (9) | 0.16997 (13) | 0.46306 (12) | 0.0203 (3) | |
C16 | 0.83580 (9) | 0.22824 (15) | 0.56474 (13) | 0.0268 (3) | |
H16 | 0.8014 | 0.2628 | 0.6004 | 0.032* | |
C17 | 0.92014 (10) | 0.23672 (16) | 0.61494 (15) | 0.0353 (4) | |
H17 | 0.9428 | 0.2762 | 0.6846 | 0.042* | |
C18 | 0.97094 (10) | 0.18782 (17) | 0.56362 (16) | 0.0382 (4) | |
H18 | 1.0286 | 0.1934 | 0.5975 | 0.046* | |
C19 | 0.93662 (10) | 0.13057 (16) | 0.46204 (15) | 0.0335 (4) | |
H19 | 0.9717 | 0.0978 | 0.4266 | 0.040* | |
C20 | 0.85238 (9) | 0.11935 (14) | 0.41005 (13) | 0.0254 (3) | |
C21 | 0.24394 (10) | −0.05943 (15) | 0.25125 (13) | 0.0291 (4) | |
H21A | 0.2954 | −0.0682 | 0.3130 | 0.044* | |
H21B | 0.2352 | −0.1354 | 0.2047 | 0.044* | |
H21C | 0.1986 | −0.0503 | 0.2789 | 0.044* | |
C22 | 0.35052 (9) | 0.31598 (15) | 0.40799 (12) | 0.0228 (3) | |
H22A | 0.3582 | 0.2474 | 0.4630 | 0.027* | |
H22B | 0.2919 | 0.3196 | 0.3623 | 0.027* | |
C23 | 0.37730 (11) | 0.44138 (15) | 0.46427 (13) | 0.0302 (4) | |
H23A | 0.4356 | 0.4374 | 0.5084 | 0.045* | |
H23B | 0.3457 | 0.4598 | 0.5118 | 0.045* | |
H23C | 0.3681 | 0.5090 | 0.4093 | 0.045* | |
C24 | 0.81853 (10) | 0.05823 (17) | 0.29900 (14) | 0.0333 (4) | |
H24A | 0.8589 | 0.0638 | 0.2624 | 0.050* | |
H24B | 0.7685 | 0.1026 | 0.2550 | 0.050* | |
H24C | 0.8061 | −0.0315 | 0.3071 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0309 (2) | 0.0248 (2) | 0.01455 (17) | 0.00180 (14) | 0.00961 (14) | 0.00010 (14) |
O1 | 0.0196 (5) | 0.0198 (5) | 0.0181 (5) | −0.0015 (4) | 0.0021 (4) | 0.0028 (4) |
O2 | 0.0211 (5) | 0.0168 (5) | 0.0158 (5) | −0.0008 (4) | 0.0085 (4) | −0.0026 (4) |
N1 | 0.0190 (6) | 0.0160 (6) | 0.0117 (5) | 0.0003 (5) | 0.0067 (5) | −0.0002 (5) |
N2 | 0.0191 (6) | 0.0149 (6) | 0.0205 (6) | 0.0007 (5) | 0.0074 (5) | −0.0007 (5) |
C1 | 0.0212 (7) | 0.0163 (7) | 0.0152 (7) | 0.0018 (5) | 0.0079 (6) | 0.0012 (6) |
C2 | 0.0216 (7) | 0.0209 (7) | 0.0204 (7) | −0.0020 (6) | 0.0100 (6) | −0.0034 (6) |
C3 | 0.0202 (7) | 0.0250 (8) | 0.0227 (7) | −0.0009 (6) | 0.0093 (6) | −0.0054 (6) |
C4 | 0.0245 (8) | 0.0361 (9) | 0.0323 (9) | −0.0079 (7) | 0.0101 (7) | −0.0096 (7) |
C5 | 0.0191 (8) | 0.0527 (11) | 0.0316 (9) | −0.0044 (7) | 0.0008 (7) | −0.0115 (8) |
C6 | 0.0248 (8) | 0.0493 (11) | 0.0245 (8) | 0.0067 (7) | 0.0002 (7) | 0.0000 (8) |
C7 | 0.0263 (8) | 0.0315 (9) | 0.0246 (8) | 0.0033 (7) | 0.0042 (7) | 0.0022 (7) |
C8 | 0.0176 (7) | 0.0248 (8) | 0.0205 (7) | 0.0012 (6) | 0.0046 (6) | −0.0037 (6) |
C9 | 0.0199 (7) | 0.0153 (7) | 0.0144 (7) | −0.0001 (5) | 0.0060 (5) | 0.0005 (5) |
C10 | 0.0196 (7) | 0.0183 (7) | 0.0122 (6) | −0.0003 (5) | 0.0041 (5) | −0.0012 (5) |
C11 | 0.0216 (7) | 0.0162 (7) | 0.0219 (7) | 0.0004 (5) | 0.0097 (6) | −0.0040 (6) |
C12 | 0.0212 (7) | 0.0159 (7) | 0.0234 (7) | 0.0013 (5) | 0.0087 (6) | 0.0006 (6) |
C13 | 0.0211 (7) | 0.0161 (7) | 0.0190 (7) | −0.0001 (5) | 0.0067 (6) | −0.0028 (6) |
C14 | 0.0222 (7) | 0.0135 (7) | 0.0181 (7) | 0.0009 (5) | 0.0074 (6) | −0.0004 (6) |
C15 | 0.0202 (7) | 0.0164 (7) | 0.0236 (7) | 0.0010 (5) | 0.0066 (6) | 0.0051 (6) |
C16 | 0.0255 (8) | 0.0260 (8) | 0.0268 (8) | 0.0013 (6) | 0.0063 (6) | 0.0005 (7) |
C17 | 0.0279 (8) | 0.0319 (9) | 0.0362 (9) | −0.0001 (7) | −0.0013 (7) | −0.0025 (8) |
C18 | 0.0197 (8) | 0.0356 (10) | 0.0519 (11) | 0.0022 (7) | 0.0030 (7) | 0.0043 (8) |
C19 | 0.0247 (8) | 0.0311 (9) | 0.0472 (10) | 0.0068 (7) | 0.0157 (8) | 0.0070 (8) |
C20 | 0.0259 (8) | 0.0209 (8) | 0.0318 (8) | 0.0028 (6) | 0.0131 (7) | 0.0066 (7) |
C21 | 0.0346 (9) | 0.0260 (8) | 0.0278 (8) | −0.0089 (7) | 0.0121 (7) | 0.0014 (7) |
C22 | 0.0241 (7) | 0.0267 (8) | 0.0217 (7) | 0.0022 (6) | 0.0133 (6) | −0.0018 (6) |
C23 | 0.0488 (10) | 0.0237 (8) | 0.0250 (8) | 0.0024 (7) | 0.0214 (7) | −0.0019 (7) |
C24 | 0.0340 (9) | 0.0391 (10) | 0.0336 (9) | 0.0044 (7) | 0.0202 (7) | −0.0020 (8) |
Geometric parameters (Å, º) top
O1—C8 | 1.3777 (17) | C11—H11B | 0.9900 |
O1—C1 | 1.3934 (16) | C12—H12A | 0.9900 |
O2—C9 | 1.4189 (16) | C12—H12B | 0.9900 |
O2—C22 | 1.4333 (16) | C13—C14 | 1.5139 (19) |
N1—C11 | 1.5017 (17) | C13—H13A | 0.9900 |
N1—C10 | 1.5039 (17) | C13—H13B | 0.9900 |
N1—C14 | 1.5070 (17) | C14—H14A | 0.9900 |
N1—H1 | 0.9300 | C14—H14B | 0.9900 |
N2—C15 | 1.4274 (18) | C15—C16 | 1.392 (2) |
N2—C13 | 1.4613 (17) | C15—C20 | 1.412 (2) |
N2—C12 | 1.4635 (18) | C16—C17 | 1.390 (2) |
C1—C2 | 1.351 (2) | C16—H16 | 0.9500 |
C1—C9 | 1.5039 (19) | C17—C18 | 1.381 (3) |
C2—C3 | 1.450 (2) | C17—H17 | 0.9500 |
C2—C21 | 1.495 (2) | C18—C19 | 1.385 (3) |
C3—C8 | 1.391 (2) | C18—H18 | 0.9500 |
C3—C4 | 1.401 (2) | C19—C20 | 1.393 (2) |
C4—C5 | 1.381 (2) | C19—H19 | 0.9500 |
C4—H4 | 0.9500 | C20—C24 | 1.503 (2) |
C5—C6 | 1.398 (3) | C21—H21A | 0.9800 |
C5—H5 | 0.9500 | C21—H21B | 0.9800 |
C6—C7 | 1.385 (2) | C21—H21C | 0.9800 |
C6—H6 | 0.9500 | C22—C23 | 1.499 (2) |
C7—C8 | 1.382 (2) | C22—H22A | 0.9900 |
C7—H7 | 0.9500 | C22—H22B | 0.9900 |
C9—C10 | 1.5216 (18) | C23—H23A | 0.9800 |
C9—H9 | 1.0000 | C23—H23B | 0.9800 |
C10—H10A | 0.9900 | C23—H23C | 0.9800 |
C10—H10B | 0.9900 | C24—H24A | 0.9800 |
C11—C12 | 1.5063 (19) | C24—H24B | 0.9800 |
C11—H11A | 0.9900 | C24—H24C | 0.9800 |
| | | |
C8—O1—C1 | 105.50 (11) | C11—C12—H12B | 109.6 |
C9—O2—C22 | 111.65 (10) | H12A—C12—H12B | 108.1 |
C11—N1—C10 | 109.05 (10) | N2—C13—C14 | 110.22 (11) |
C11—N1—C14 | 109.53 (10) | N2—C13—H13A | 109.6 |
C10—N1—C14 | 112.59 (10) | C14—C13—H13A | 109.6 |
C11—N1—H1 | 108.5 | N2—C13—H13B | 109.6 |
C10—N1—H1 | 108.5 | C14—C13—H13B | 109.6 |
C14—N1—H1 | 108.5 | H13A—C13—H13B | 108.1 |
C15—N2—C13 | 116.41 (11) | N1—C14—C13 | 111.55 (11) |
C15—N2—C12 | 114.62 (11) | N1—C14—H14A | 109.3 |
C13—N2—C12 | 109.03 (11) | C13—C14—H14A | 109.3 |
C2—C1—O1 | 112.11 (12) | N1—C14—H14B | 109.3 |
C2—C1—C9 | 133.58 (13) | C13—C14—H14B | 109.3 |
O1—C1—C9 | 114.27 (11) | H14A—C14—H14B | 108.0 |
C1—C2—C3 | 105.86 (13) | C16—C15—C20 | 119.24 (14) |
C1—C2—C21 | 128.35 (13) | C16—C15—N2 | 121.86 (13) |
C3—C2—C21 | 125.80 (13) | C20—C15—N2 | 118.83 (13) |
C8—C3—C4 | 118.81 (14) | C17—C16—C15 | 121.12 (15) |
C8—C3—C2 | 106.14 (12) | C17—C16—H16 | 119.4 |
C4—C3—C2 | 135.03 (15) | C15—C16—H16 | 119.4 |
C5—C4—C3 | 118.30 (15) | C18—C17—C16 | 120.07 (16) |
C5—C4—H4 | 120.9 | C18—C17—H17 | 120.0 |
C3—C4—H4 | 120.9 | C16—C17—H17 | 120.0 |
C4—C5—C6 | 121.15 (15) | C17—C18—C19 | 119.06 (15) |
C4—C5—H5 | 119.4 | C17—C18—H18 | 120.5 |
C6—C5—H5 | 119.4 | C19—C18—H18 | 120.5 |
C7—C6—C5 | 121.73 (15) | C18—C19—C20 | 122.29 (16) |
C7—C6—H6 | 119.1 | C18—C19—H19 | 118.9 |
C5—C6—H6 | 119.1 | C20—C19—H19 | 118.9 |
C8—C7—C6 | 115.95 (15) | C19—C20—C15 | 118.21 (15) |
C8—C7—H7 | 122.0 | C19—C20—C24 | 119.99 (14) |
C6—C7—H7 | 122.0 | C15—C20—C24 | 121.78 (14) |
O1—C8—C7 | 125.56 (14) | C2—C21—H21A | 109.5 |
O1—C8—C3 | 110.39 (12) | C2—C21—H21B | 109.5 |
C7—C8—C3 | 124.04 (14) | H21A—C21—H21B | 109.5 |
O2—C9—C1 | 112.00 (11) | C2—C21—H21C | 109.5 |
O2—C9—C10 | 108.18 (11) | H21A—C21—H21C | 109.5 |
C1—C9—C10 | 109.60 (11) | H21B—C21—H21C | 109.5 |
O2—C9—H9 | 109.0 | O2—C22—C23 | 108.43 (12) |
C1—C9—H9 | 109.0 | O2—C22—H22A | 110.0 |
C10—C9—H9 | 109.0 | C23—C22—H22A | 110.0 |
N1—C10—C9 | 113.40 (11) | O2—C22—H22B | 110.0 |
N1—C10—H10A | 108.9 | C23—C22—H22B | 110.0 |
C9—C10—H10A | 108.9 | H22A—C22—H22B | 108.4 |
N1—C10—H10B | 108.9 | C22—C23—H23A | 109.5 |
C9—C10—H10B | 108.9 | C22—C23—H23B | 109.5 |
H10A—C10—H10B | 107.7 | H23A—C23—H23B | 109.5 |
N1—C11—C12 | 111.34 (11) | C22—C23—H23C | 109.5 |
N1—C11—H11A | 109.4 | H23A—C23—H23C | 109.5 |
C12—C11—H11A | 109.4 | H23B—C23—H23C | 109.5 |
N1—C11—H11B | 109.4 | C20—C24—H24A | 109.5 |
C12—C11—H11B | 109.4 | C20—C24—H24B | 109.5 |
H11A—C11—H11B | 108.0 | H24A—C24—H24B | 109.5 |
N2—C12—C11 | 110.15 (11) | C20—C24—H24C | 109.5 |
N2—C12—H12A | 109.6 | H24A—C24—H24C | 109.5 |
C11—C12—H12A | 109.6 | H24B—C24—H24C | 109.5 |
N2—C12—H12B | 109.6 | | |
| | | |
O1—C1—C9—C10 | −72.94 (14) | C9—C10—N1—C11 | 148.68 (11) |
C1—C9—C10—N1 | −174.01 (11) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1 | 0.93 | 2.26 | 3.1145 (12) | 152 |
C13—H13B···Cl1 | 0.99 | 2.86 | 3.5870 (15) | 131 |
C9—H9···Cl1i | 1.00 | 2.97 | 3.6879 (14) | 130 |
N1—H1···Cl1i | 0.93 | 2.96 | 3.4592 (12) | 115 |
C21—H21A···Cl1i | 0.98 | 2.96 | 3.8621 (18) | 154 |
C11—H11B···Cl1i | 0.99 | 2.74 | 3.4852 (15) | 132 |
C10—H10B···Cl1ii | 0.99 | 2.87 | 3.7878 (14) | 154 |
C14—H14B···Cl1ii | 0.99 | 2.61 | 3.5647 (15) | 161 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z−1/2. |
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