The title compound, C
17H
19Cl
2N
2OS
+·Cl
−, was synthesized from 2-acetothiophene, 1-(2,3-dichlorophenyl)piperazine and paraformaldehyde. In the cation, the thienyl ring is coplanar with the oxopropyl group. The protonated piperazine ring exhibits a chair conformation. In the crystal packing the cations are connected by C—H
O and C—H
Cl hydrogen bonds.
Supporting information
CCDC reference: 293975
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.058
- wR factor = 0.139
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C11 .. 3.00 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
3-(4-(2,3-dichlorophenyl)piperazin-1-yl)-1-(thiophen-2-yl)propan-1-one
hydrochloride
top
Crystal data top
C17H19Cl2N2OS+·Cl− | F(000) = 1680 |
Mr = 405.75 | Dx = 1.401 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6615 reflections |
a = 15.400 (2) Å | θ = 2.4–26.4° |
b = 7.4361 (11) Å | µ = 0.59 mm−1 |
c = 33.601 (5) Å | T = 294 K |
V = 3847.9 (9) Å3 | Block, colourless |
Z = 8 | 0.22 × 0.18 × 0.16 mm |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 3934 independent reflections |
Radiation source: fine-focus sealed tube | 2963 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 26.4°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −11→19 |
Tmin = 0.850, Tmax = 0.910 | k = −9→8 |
20192 measured reflections | l = −42→33 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.044P)2 + 4.8252P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.139 | (Δ/σ)max = 0.001 |
S = 1.12 | Δρmax = 0.35 e Å−3 |
3934 reflections | Δρmin = −0.31 e Å−3 |
221 parameters | |
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 | 0.67928 (6) | 0.67971 (16) | 0.32502 (3) | 0.0716 (3) | |
Cl2 | 0.75875 (8) | 0.68792 (17) | 0.23973 (4) | 0.0931 (4) | |
S1 | 0.22525 (7) | 0.56383 (17) | 0.57614 (3) | 0.0691 (3) | |
O1 | 0.37928 (17) | 0.5437 (6) | 0.52508 (8) | 0.1014 (13) | |
N1 | 0.42628 (15) | 0.4417 (4) | 0.40583 (7) | 0.0357 (5) | |
H1A | 0.401 (2) | 0.325 (5) | 0.4025 (10) | 0.048 (9)* | |
N2 | 0.50252 (15) | 0.5250 (4) | 0.33007 (7) | 0.0389 (6) | |
C1 | 0.1160 (3) | 0.5563 (6) | 0.57623 (12) | 0.0741 (12) | |
H1 | 0.0825 | 0.5678 | 0.5991 | 0.089* | |
C2 | 0.0821 (3) | 0.5320 (7) | 0.53965 (13) | 0.0798 (13) | |
H2 | 0.0228 | 0.5264 | 0.5345 | 0.096* | |
C3 | 0.1478 (2) | 0.5157 (6) | 0.50969 (11) | 0.0595 (10) | |
H3 | 0.1364 | 0.4975 | 0.4828 | 0.071* | |
C4 | 0.2292 (2) | 0.5302 (5) | 0.52540 (9) | 0.0440 (8) | |
C5 | 0.3140 (2) | 0.5220 (5) | 0.50606 (9) | 0.0477 (8) | |
C6 | 0.3190 (2) | 0.4855 (5) | 0.46179 (9) | 0.0428 (7) | |
H6A | 0.2946 | 0.3681 | 0.4560 | 0.051* | |
H6B | 0.2856 | 0.5751 | 0.4475 | 0.051* | |
C7 | 0.4126 (2) | 0.4919 (5) | 0.44846 (9) | 0.0481 (8) | |
H7A | 0.4347 | 0.6126 | 0.4527 | 0.058* | |
H7B | 0.4463 | 0.4110 | 0.4650 | 0.058* | |
C8 | 0.38451 (19) | 0.5699 (4) | 0.37738 (9) | 0.0417 (7) | |
H8A | 0.4032 | 0.6915 | 0.3835 | 0.050* | |
H8B | 0.3220 | 0.5647 | 0.3805 | 0.050* | |
C9 | 0.40802 (19) | 0.5255 (5) | 0.33472 (9) | 0.0427 (7) | |
H9A | 0.3849 | 0.4084 | 0.3277 | 0.051* | |
H9B | 0.3826 | 0.6140 | 0.3170 | 0.051* | |
C10 | 0.5395 (2) | 0.3833 (4) | 0.35523 (9) | 0.0416 (7) | |
H10A | 0.6016 | 0.3751 | 0.3507 | 0.050* | |
H10B | 0.5136 | 0.2684 | 0.3485 | 0.050* | |
C11 | 0.52203 (18) | 0.4261 (5) | 0.39815 (9) | 0.0414 (7) | |
H11A | 0.5503 | 0.5383 | 0.4051 | 0.050* | |
H11B | 0.5462 | 0.3320 | 0.4148 | 0.050* | |
C12 | 0.5359 (2) | 0.5314 (4) | 0.29065 (9) | 0.0385 (7) | |
C13 | 0.4887 (2) | 0.4802 (4) | 0.25763 (9) | 0.0488 (8) | |
H13 | 0.4319 | 0.4401 | 0.2608 | 0.059* | |
C14 | 0.5245 (3) | 0.4877 (5) | 0.21985 (10) | 0.0599 (10) | |
H14 | 0.4913 | 0.4531 | 0.1980 | 0.072* | |
C15 | 0.6083 (3) | 0.5455 (5) | 0.21427 (11) | 0.0612 (11) | |
H15 | 0.6329 | 0.5462 | 0.1890 | 0.073* | |
C16 | 0.6555 (2) | 0.6025 (4) | 0.24681 (12) | 0.0537 (9) | |
C17 | 0.6203 (2) | 0.5969 (4) | 0.28484 (10) | 0.0444 (8) | |
Cl3 | 0.37094 (6) | 0.05225 (11) | 0.39880 (3) | 0.0521 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0486 (5) | 0.0887 (8) | 0.0776 (7) | −0.0209 (5) | 0.0046 (5) | −0.0190 (6) |
Cl2 | 0.0791 (7) | 0.0756 (7) | 0.1244 (10) | −0.0130 (6) | 0.0628 (7) | −0.0052 (7) |
S1 | 0.0823 (8) | 0.0867 (8) | 0.0384 (5) | 0.0070 (6) | 0.0051 (4) | −0.0061 (5) |
O1 | 0.0483 (16) | 0.211 (4) | 0.0454 (15) | 0.005 (2) | −0.0103 (13) | −0.039 (2) |
N1 | 0.0313 (12) | 0.0421 (14) | 0.0336 (13) | −0.0018 (11) | −0.0016 (10) | −0.0024 (11) |
N2 | 0.0321 (13) | 0.0476 (15) | 0.0369 (13) | 0.0009 (11) | 0.0018 (10) | 0.0071 (11) |
C1 | 0.081 (3) | 0.085 (3) | 0.057 (2) | 0.003 (2) | 0.030 (2) | 0.001 (2) |
C2 | 0.056 (2) | 0.118 (4) | 0.065 (3) | −0.005 (3) | 0.018 (2) | −0.008 (3) |
C3 | 0.048 (2) | 0.086 (3) | 0.0438 (19) | −0.0041 (19) | 0.0032 (16) | −0.0024 (19) |
C4 | 0.0483 (19) | 0.049 (2) | 0.0343 (15) | 0.0027 (15) | 0.0017 (13) | −0.0011 (14) |
C5 | 0.0427 (18) | 0.061 (2) | 0.0398 (17) | 0.0028 (16) | −0.0063 (14) | −0.0080 (15) |
C6 | 0.0393 (16) | 0.0543 (19) | 0.0348 (15) | 0.0020 (15) | −0.0031 (13) | −0.0057 (14) |
C7 | 0.0414 (17) | 0.066 (2) | 0.0375 (16) | −0.0039 (16) | −0.0009 (14) | −0.0136 (16) |
C8 | 0.0362 (16) | 0.0416 (18) | 0.0472 (18) | 0.0039 (14) | 0.0010 (13) | 0.0040 (14) |
C9 | 0.0343 (16) | 0.0509 (19) | 0.0428 (17) | 0.0017 (14) | −0.0029 (13) | 0.0109 (15) |
C10 | 0.0385 (16) | 0.0492 (18) | 0.0371 (15) | 0.0056 (14) | 0.0001 (13) | 0.0030 (14) |
C11 | 0.0320 (15) | 0.0520 (19) | 0.0402 (16) | 0.0021 (14) | −0.0037 (13) | −0.0006 (15) |
C12 | 0.0437 (17) | 0.0314 (15) | 0.0404 (16) | 0.0007 (13) | 0.0055 (13) | 0.0052 (13) |
C13 | 0.061 (2) | 0.0405 (18) | 0.0448 (18) | −0.0064 (16) | −0.0012 (16) | 0.0079 (14) |
C14 | 0.099 (3) | 0.042 (2) | 0.0387 (18) | −0.001 (2) | −0.0018 (19) | 0.0044 (15) |
C15 | 0.098 (3) | 0.0388 (19) | 0.047 (2) | 0.013 (2) | 0.028 (2) | 0.0071 (16) |
C16 | 0.063 (2) | 0.0308 (16) | 0.067 (2) | 0.0020 (16) | 0.0296 (19) | 0.0045 (16) |
C17 | 0.0473 (18) | 0.0336 (16) | 0.0523 (19) | 0.0004 (14) | 0.0073 (15) | −0.0012 (14) |
Cl3 | 0.0614 (5) | 0.0432 (4) | 0.0519 (5) | −0.0070 (4) | 0.0100 (4) | −0.0042 (4) |
Geometric parameters (Å, º) top
Cl1—C17 | 1.740 (3) | C6—H6B | 0.9700 |
Cl2—C16 | 1.729 (4) | C7—H7A | 0.9700 |
S1—C1 | 1.683 (5) | C7—H7B | 0.9700 |
S1—C4 | 1.724 (3) | C8—C9 | 1.515 (4) |
O1—C5 | 1.203 (4) | C8—H8A | 0.9700 |
N1—C7 | 1.495 (4) | C8—H8B | 0.9700 |
N1—C8 | 1.496 (4) | C9—H9A | 0.9700 |
N1—C11 | 1.502 (4) | C9—H9B | 0.9700 |
N1—H1A | 0.95 (4) | C10—C11 | 1.501 (4) |
N2—C12 | 1.422 (4) | C10—H10A | 0.9700 |
N2—C9 | 1.464 (4) | C10—H10B | 0.9700 |
N2—C10 | 1.465 (4) | C11—H11A | 0.9700 |
C1—C2 | 1.348 (6) | C11—H11B | 0.9700 |
C1—H1 | 0.9300 | C12—C13 | 1.380 (4) |
C2—C3 | 1.433 (5) | C12—C17 | 1.401 (4) |
C2—H2 | 0.9300 | C13—C14 | 1.385 (5) |
C3—C4 | 1.364 (5) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.374 (6) |
C4—C5 | 1.460 (5) | C14—H14 | 0.9300 |
C5—C6 | 1.514 (4) | C15—C16 | 1.380 (6) |
C6—C7 | 1.510 (4) | C15—H15 | 0.9300 |
C6—H6A | 0.9700 | C16—C17 | 1.389 (5) |
| | | |
C1—S1—C4 | 91.83 (19) | N1—C8—H8B | 109.4 |
C7—N1—C8 | 113.1 (2) | C9—C8—H8B | 109.4 |
C7—N1—C11 | 108.8 (2) | H8A—C8—H8B | 108.0 |
C8—N1—C11 | 111.2 (2) | N2—C9—C8 | 109.8 (2) |
C7—N1—H1A | 106 (2) | N2—C9—H9A | 109.7 |
C8—N1—H1A | 109 (2) | C8—C9—H9A | 109.7 |
C11—N1—H1A | 108 (2) | N2—C9—H9B | 109.7 |
C12—N2—C9 | 117.3 (2) | C8—C9—H9B | 109.7 |
C12—N2—C10 | 114.9 (2) | H9A—C9—H9B | 108.2 |
C9—N2—C10 | 109.0 (2) | N2—C10—C11 | 109.4 (3) |
C2—C1—S1 | 113.0 (3) | N2—C10—H10A | 109.8 |
C2—C1—H1 | 123.5 | C11—C10—H10A | 109.8 |
S1—C1—H1 | 123.5 | N2—C10—H10B | 109.8 |
C1—C2—C3 | 112.2 (4) | C11—C10—H10B | 109.8 |
C1—C2—H2 | 123.9 | H10A—C10—H10B | 108.2 |
C3—C2—H2 | 123.9 | C10—C11—N1 | 110.9 (2) |
C4—C3—C2 | 111.7 (3) | C10—C11—H11A | 109.5 |
C4—C3—H3 | 124.1 | N1—C11—H11A | 109.5 |
C2—C3—H3 | 124.1 | C10—C11—H11B | 109.5 |
C3—C4—C5 | 130.2 (3) | N1—C11—H11B | 109.5 |
C3—C4—S1 | 111.2 (2) | H11A—C11—H11B | 108.0 |
C5—C4—S1 | 118.5 (2) | C13—C12—C17 | 118.2 (3) |
O1—C5—C4 | 120.4 (3) | C13—C12—N2 | 123.3 (3) |
O1—C5—C6 | 120.2 (3) | C17—C12—N2 | 118.5 (3) |
C4—C5—C6 | 119.4 (3) | C12—C13—C14 | 121.1 (3) |
C7—C6—C5 | 109.6 (3) | C12—C13—H13 | 119.5 |
C7—C6—H6A | 109.8 | C14—C13—H13 | 119.5 |
C5—C6—H6A | 109.8 | C15—C14—C13 | 120.8 (4) |
C7—C6—H6B | 109.8 | C15—C14—H14 | 119.6 |
C5—C6—H6B | 109.8 | C13—C14—H14 | 119.6 |
H6A—C6—H6B | 108.2 | C14—C15—C16 | 118.9 (3) |
N1—C7—C6 | 114.3 (2) | C14—C15—H15 | 120.6 |
N1—C7—H7A | 108.7 | C16—C15—H15 | 120.6 |
C6—C7—H7A | 108.7 | C15—C16—C17 | 121.0 (3) |
N1—C7—H7B | 108.7 | C15—C16—Cl2 | 119.2 (3) |
C6—C7—H7B | 108.7 | C17—C16—Cl2 | 119.8 (3) |
H7A—C7—H7B | 107.6 | C16—C17—C12 | 120.0 (3) |
N1—C8—C9 | 111.3 (2) | C16—C17—Cl1 | 120.0 (3) |
N1—C8—H8A | 109.4 | C12—C17—Cl1 | 119.9 (2) |
C9—C8—H8A | 109.4 | | |
| | | |
C4—S1—C1—C2 | −0.8 (4) | C9—N2—C10—C11 | −64.1 (3) |
S1—C1—C2—C3 | 0.9 (6) | N2—C10—C11—N1 | 58.8 (3) |
C1—C2—C3—C4 | −0.5 (6) | C7—N1—C11—C10 | −177.6 (3) |
C2—C3—C4—C5 | −180.0 (4) | C8—N1—C11—C10 | −52.4 (3) |
C2—C3—C4—S1 | −0.1 (5) | C9—N2—C12—C13 | −21.8 (4) |
C1—S1—C4—C3 | 0.5 (3) | C10—N2—C12—C13 | 108.4 (3) |
C1—S1—C4—C5 | −179.6 (3) | C9—N2—C12—C17 | 156.7 (3) |
C3—C4—C5—O1 | 177.6 (5) | C10—N2—C12—C17 | −73.2 (4) |
S1—C4—C5—O1 | −2.2 (5) | C17—C12—C13—C14 | 2.1 (5) |
C3—C4—C5—C6 | −2.5 (6) | N2—C12—C13—C14 | −179.5 (3) |
S1—C4—C5—C6 | 177.7 (3) | C12—C13—C14—C15 | 0.3 (5) |
O1—C5—C6—C7 | −2.7 (5) | C13—C14—C15—C16 | −2.4 (5) |
C4—C5—C6—C7 | 177.4 (3) | C14—C15—C16—C17 | 2.0 (5) |
C8—N1—C7—C6 | 64.4 (4) | C14—C15—C16—Cl2 | −176.2 (3) |
C11—N1—C7—C6 | −171.5 (3) | C15—C16—C17—C12 | 0.5 (5) |
C5—C6—C7—N1 | 174.9 (3) | Cl2—C16—C17—C12 | 178.6 (2) |
C7—N1—C8—C9 | 173.9 (3) | C15—C16—C17—Cl1 | −176.9 (3) |
C11—N1—C8—C9 | 51.1 (3) | Cl2—C16—C17—Cl1 | 1.2 (4) |
C12—N2—C9—C8 | −164.4 (3) | C13—C12—C17—C16 | −2.5 (5) |
C10—N2—C9—C8 | 62.8 (3) | N2—C12—C17—C16 | 179.0 (3) |
N1—C8—C9—N2 | −56.5 (3) | C13—C12—C17—Cl1 | 174.9 (2) |
C12—N2—C10—C11 | 161.8 (3) | N2—C12—C17—Cl1 | −3.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···O1i | 0.97 | 2.50 | 3.002 (4) | 112 |
C9—H9B···Cl2ii | 0.97 | 2.75 | 3.606 (3) | 147 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, y, −z+1/2. |