Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053470/at2451sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053470/at2451Isup2.hkl |
CCDC reference: 672804
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.061
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTY03_ALERT_1_C The _exptl_absorpt_correction_type has been given as none. However values have been given for Tmin and Tmax. Remove these if an absorption correction has not been applied. From the CIF: _exptl_absorpt_correction_T_min 0.873 From the CIF: _exptl_absorpt_correction_T_max 0.950 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT350_ALERT_3_C Short C-H Bond (0.96A) C6 - H11 ... 0.84 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.36 From the CIF: _reflns_number_total 1956 Count of symmetry unique reflns 1169 Completeness (_total/calc) 167.32% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 787 Fraction of Friedel pairs measured 0.673 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
1-(2-Pyridinyl)piperazine (1 mmol) and trimethyltin chloride (1 mmol) were suspended in dry chloroform (150 ml) in a round bottom two necked flask. The mixture was stirred at room temperature. Colourless crystals of the title compound obtained accidently after recrystallization in acetone. (Yield 70%°; m.p. 393 K).
H atoms were included in difference map positions and refined freely, with C—H distances ranging from 0.84 (2) - 1.00 (2) Å and N—H distances of 0.91 (2) and 0.98 (2) Å.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C9H14ClN3 | F(000) = 424 |
Mr = 199.68 | Dx = 1.364 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2404 reflections |
a = 7.1757 (6) Å | θ = 3.0–26.3° |
b = 7.2196 (6) Å | µ = 0.35 mm−1 |
c = 18.7629 (16) Å | T = 100 K |
V = 972.02 (14) Å3 | Plate, colourless |
Z = 4 | 0.40 × 0.25 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 1781 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 26.4°, θmin = 2.2° |
ϕ and ω scans | h = −8→8 |
5613 measured reflections | k = −9→8 |
1956 independent reflections | l = −20→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | Only H-atom coordinates refined |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0272P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
1956 reflections | Δρmax = 0.22 e Å−3 |
160 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 787 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (7) |
C9H14ClN3 | V = 972.02 (14) Å3 |
Mr = 199.68 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.1757 (6) Å | µ = 0.35 mm−1 |
b = 7.2196 (6) Å | T = 100 K |
c = 18.7629 (16) Å | 0.40 × 0.25 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 1781 reflections with I > 2σ(I) |
5613 measured reflections | Rint = 0.044 |
1956 independent reflections |
R[F2 > 2σ(F2)] = 0.029 | Only H-atom coordinates refined |
wR(F2) = 0.061 | Δρmax = 0.22 e Å−3 |
S = 0.96 | Δρmin = −0.16 e Å−3 |
1956 reflections | Absolute structure: Flack (1983), 787 Freidel pairs |
160 parameters | Absolute structure parameter: 0.04 (7) |
0 restraints |
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.24771 (7) | 0.33171 (5) | 0.23724 (2) | 0.02020 (12) | |
N1 | 0.3814 (2) | 0.6758 (2) | 0.32203 (8) | 0.0201 (4) | |
N2 | 0.3397 (2) | 0.90492 (19) | 0.44477 (7) | 0.0157 (3) | |
N3 | 0.4096 (2) | 0.9562 (2) | 0.56481 (8) | 0.0194 (3) | |
C1 | 0.4004 (3) | 0.5979 (3) | 0.39523 (10) | 0.0195 (4) | |
C2 | 0.4664 (3) | 0.7455 (3) | 0.44616 (10) | 0.0178 (4) | |
C3 | 0.3159 (3) | 0.9827 (3) | 0.37348 (9) | 0.0186 (4) | |
C4 | 0.2510 (3) | 0.8355 (3) | 0.32164 (9) | 0.0221 (4) | |
C5 | 0.3404 (3) | 1.0234 (2) | 0.50341 (9) | 0.0150 (4) | |
C6 | 0.2672 (3) | 1.2021 (2) | 0.49926 (9) | 0.0174 (4) | |
C7 | 0.2704 (3) | 1.3113 (2) | 0.55864 (9) | 0.0218 (4) | |
C8 | 0.3435 (3) | 1.2463 (3) | 0.62216 (10) | 0.0201 (4) | |
C9 | 0.4074 (3) | 1.0673 (3) | 0.62279 (9) | 0.0202 (4) | |
H1 | 0.494 (3) | 0.714 (3) | 0.3056 (9) | 0.024* | |
H2 | 0.336 (3) | 0.584 (3) | 0.2878 (9) | 0.024* | |
H3 | 0.485 (3) | 0.500 (3) | 0.3933 (9) | 0.024* | |
H4 | 0.274 (3) | 0.553 (2) | 0.4082 (8) | 0.024* | |
H5 | 0.595 (3) | 0.784 (2) | 0.4338 (9) | 0.024* | |
H6 | 0.474 (3) | 0.697 (2) | 0.4932 (10) | 0.024* | |
H7 | 0.219 (3) | 1.082 (3) | 0.3732 (9) | 0.024* | |
H8 | 0.431 (3) | 1.036 (3) | 0.3556 (9) | 0.024* | |
H9 | 0.244 (3) | 0.885 (2) | 0.2767 (9) | 0.024* | |
H10 | 0.129 (3) | 0.795 (3) | 0.3334 (9) | 0.024* | |
H11 | 0.217 (3) | 1.237 (3) | 0.4612 (9) | 0.024* | |
H12 | 0.223 (3) | 1.440 (2) | 0.5546 (9) | 0.024* | |
H13 | 0.350 (3) | 1.317 (3) | 0.6642 (9) | 0.024* | |
H14 | 0.453 (3) | 1.016 (3) | 0.6682 (9) | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0216 (2) | 0.0179 (2) | 0.0211 (2) | −0.0011 (2) | 0.0015 (2) | −0.00328 (17) |
N1 | 0.0234 (9) | 0.0198 (8) | 0.0171 (8) | −0.0057 (8) | 0.0008 (7) | −0.0045 (7) |
N2 | 0.0198 (8) | 0.0144 (7) | 0.0129 (7) | 0.0023 (7) | −0.0015 (6) | 0.0020 (6) |
N3 | 0.0203 (8) | 0.0213 (8) | 0.0167 (8) | −0.0004 (7) | −0.0005 (6) | −0.0002 (7) |
C1 | 0.0193 (10) | 0.0171 (10) | 0.0222 (10) | −0.0004 (8) | 0.0002 (9) | −0.0002 (8) |
C2 | 0.0198 (11) | 0.0171 (9) | 0.0165 (9) | 0.0031 (8) | −0.0025 (8) | 0.0015 (8) |
C3 | 0.0229 (10) | 0.0181 (9) | 0.0149 (9) | 0.0010 (8) | −0.0030 (8) | 0.0015 (8) |
C4 | 0.0253 (10) | 0.0245 (9) | 0.0164 (8) | −0.0004 (13) | −0.0044 (10) | 0.0020 (8) |
C5 | 0.0125 (9) | 0.0167 (9) | 0.0158 (9) | −0.0015 (8) | 0.0024 (7) | 0.0025 (8) |
C6 | 0.0179 (10) | 0.0170 (9) | 0.0172 (8) | 0.0007 (9) | −0.0012 (9) | 0.0042 (7) |
C7 | 0.0198 (11) | 0.0159 (9) | 0.0297 (10) | 0.0004 (9) | 0.0028 (9) | 0.0016 (8) |
C8 | 0.0189 (10) | 0.0222 (10) | 0.0191 (10) | −0.0035 (9) | 0.0039 (8) | −0.0062 (8) |
C9 | 0.0185 (10) | 0.0277 (11) | 0.0143 (9) | −0.0012 (8) | −0.0003 (8) | 0.0027 (8) |
N1—C4 | 1.485 (3) | C3—C4 | 1.514 (2) |
N1—C1 | 1.490 (2) | C3—H7 | 0.998 (19) |
N1—H1 | 0.91 (2) | C3—H8 | 0.97 (2) |
N1—H2 | 0.979 (19) | C4—H9 | 0.918 (17) |
N2—C5 | 1.394 (2) | C4—H10 | 0.95 (2) |
N2—C3 | 1.461 (2) | C5—C6 | 1.395 (2) |
N2—C2 | 1.467 (2) | C6—C7 | 1.365 (2) |
N3—C5 | 1.345 (2) | C6—H11 | 0.840 (19) |
N3—C9 | 1.352 (2) | C7—C8 | 1.384 (3) |
C1—C2 | 1.508 (3) | C7—H12 | 0.991 (19) |
C1—H3 | 0.93 (2) | C8—C9 | 1.371 (3) |
C1—H4 | 1.00 (2) | C8—H13 | 0.939 (18) |
C2—H5 | 0.99 (2) | C9—H14 | 0.985 (17) |
C2—H6 | 0.951 (18) | ||
C4—N1—C1 | 110.81 (14) | N2—C3—H8 | 111.7 (11) |
C4—N1—H1 | 108.9 (12) | C4—C3—H8 | 108.5 (11) |
C1—N1—H1 | 110.2 (11) | H7—C3—H8 | 107.6 (15) |
C4—N1—H2 | 108.4 (11) | N1—C4—C3 | 110.37 (16) |
C1—N1—H2 | 112.2 (11) | N1—C4—H9 | 110.1 (12) |
H1—N1—H2 | 106.2 (15) | C3—C4—H9 | 109.3 (11) |
C5—N2—C3 | 119.17 (14) | N1—C4—H10 | 109.8 (12) |
C5—N2—C2 | 117.74 (14) | C3—C4—H10 | 110.6 (11) |
C3—N2—C2 | 112.98 (14) | H9—C4—H10 | 106.5 (17) |
C5—N3—C9 | 118.09 (15) | N3—C5—N2 | 117.13 (15) |
N1—C1—C2 | 110.24 (15) | N3—C5—C6 | 121.36 (15) |
N1—C1—H3 | 108.1 (11) | N2—C5—C6 | 121.48 (15) |
C2—C1—H3 | 110.9 (12) | C7—C6—C5 | 118.83 (16) |
N1—C1—H4 | 105.4 (10) | C7—C6—H11 | 121.8 (13) |
C2—C1—H4 | 111.3 (9) | C5—C6—H11 | 119.2 (13) |
H3—C1—H4 | 110.7 (16) | C6—C7—C8 | 120.90 (17) |
N2—C2—C1 | 110.42 (15) | C6—C7—H12 | 118.2 (10) |
N2—C2—H5 | 110.6 (11) | C8—C7—H12 | 120.9 (10) |
C1—C2—H5 | 110.0 (11) | C9—C8—C7 | 116.97 (17) |
N2—C2—H6 | 110.0 (11) | C9—C8—H13 | 119.1 (12) |
C1—C2—H6 | 110.3 (10) | C7—C8—H13 | 123.9 (12) |
H5—C2—H6 | 105.4 (16) | N3—C9—C8 | 123.80 (17) |
N2—C3—C4 | 110.76 (15) | N3—C9—H14 | 118.1 (11) |
N2—C3—H7 | 111.3 (10) | C8—C9—H14 | 118.1 (11) |
C4—C3—H7 | 106.7 (10) | ||
C4—N1—C1—C2 | −57.5 (2) | C3—N2—C5—N3 | −163.18 (16) |
C5—N2—C2—C1 | 158.72 (16) | C2—N2—C5—N3 | −20.2 (2) |
C3—N2—C2—C1 | −56.1 (2) | C3—N2—C5—C6 | 18.7 (3) |
N1—C1—C2—N2 | 56.1 (2) | C2—N2—C5—C6 | 161.74 (17) |
C5—N2—C3—C4 | −159.81 (17) | N3—C5—C6—C7 | 1.5 (3) |
C2—N2—C3—C4 | 55.5 (2) | N2—C5—C6—C7 | 179.50 (18) |
C1—N1—C4—C3 | 56.9 (2) | C5—C6—C7—C8 | −0.5 (3) |
N2—C3—C4—N1 | −55.2 (2) | C6—C7—C8—C9 | −1.5 (3) |
C9—N3—C5—N2 | −178.43 (16) | C5—N3—C9—C8 | −1.9 (3) |
C9—N3—C5—C6 | −0.3 (3) | C7—C8—C9—N3 | 2.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H2···Cl1 | 0.979 (19) | 2.15 (2) | 3.1020 (17) | 164.3 (15) |
N1—H1···Cl1i | 0.91 (2) | 2.19 (2) | 3.0961 (17) | 174.3 (17) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C9H14ClN3 |
Mr | 199.68 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 100 |
a, b, c (Å) | 7.1757 (6), 7.2196 (6), 18.7629 (16) |
V (Å3) | 972.02 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.40 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5613, 1956, 1781 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.061, 0.96 |
No. of reflections | 1956 |
No. of parameters | 160 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 0.22, −0.16 |
Absolute structure | Flack (1983), 787 Freidel pairs |
Absolute structure parameter | 0.04 (7) |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H2···Cl1 | 0.979 (19) | 2.15 (2) | 3.1020 (17) | 164.3 (15) |
N1—H1···Cl1i | 0.91 (2) | 2.19 (2) | 3.0961 (17) | 174.3 (17) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
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Piperazine is freely soluble in water and ethylene glycol, but insoluble in diethyl ether. It is a weak base with a pKb of 4.19; the pH of a 10% aqueous solution is 10.8–11.8. A large number of piperazine compounds have anthelmintic action. Piperazines are also used in the manufacture of plastics, resins, pesticides, brake fluid and other industrial materials (The Merck Index, 1989). The structure of (I) is shown in Fig. 1.
The N—C distances in piperazin-4-ium ring are 1.485 (3) and 1.490 (2) Å, while in the pyridine ring the N—C distance are 1.345 (2) Å. Hydrogen bonds of the type N—H···Cl link the molecules into chains, with N···Cl separation of 3.0961 (17) and 3.1020 (17) Å (Fig. 2).