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organic compounds
In the chiral title salt, C9H14N+·Cl−, cations and anions are held together by N—HCl hydrogen bonds, forming a one-dimensional network in the crystal structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003753/bv2046sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003753/bv2046Isup2.hkl |
CCDC reference: 636179
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.116
- Data-to-parameter ratio = 19.2
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 30.00 From the CIF: _reflns_number_total 2128 Count of symmetry unique reflns 1701 Completeness (_total/calc) 125.10% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 427 Fraction of Friedel pairs measured 0.251 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.
(S)-(-)-1-(4-Methylphenyl)ethylammonium chloride top
Crystal data top
C9H14N+·Cl− | F(000) = 368 |
Mr = 171.66 | Dx = 1.143 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 62 reflections |
a = 5.4849 (9) Å | θ = 4.8–12.6° |
b = 9.1520 (13) Å | µ = 0.33 mm−1 |
c = 19.867 (4) Å | T = 296 K |
V = 997.3 (3) Å3 | Prism, colourless |
Z = 4 | 0.60 × 0.40 × 0.22 mm |
Data collection top
Bruker P4 diffractometer | 1779 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube, FN4 | Rint = 0.039 |
Graphite monochromator | θmax = 30.0°, θmin = 2.1° |
2θ/ω scans | h = −7→1 |
Absorption correction: ψ scan (XSCANS; Siemens, 1996) | k = −12→1 |
Tmin = 0.767, Tmax = 0.929 | l = −1→27 |
2315 measured reflections | 3 standard reflections every 97 reflections |
2128 independent reflections | intensity decay: 5.3% |
Refinement top
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)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0642P)2 + 0.076P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2128 reflections | Δρmax = 0.30 e Å−3 |
111 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 431 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (9) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.94744 (10) | 0.56490 (5) | 0.45943 (2) | 0.05079 (16) | |
N1 | 0.4450 (4) | 0.5904 (2) | 0.53840 (9) | 0.0476 (4) | |
H1 | 0.442 (6) | 0.686 (4) | 0.5500 (13) | 0.071* | |
H2 | 0.339 (7) | 0.570 (3) | 0.5107 (15) | 0.071* | |
H3 | 0.585 (6) | 0.583 (3) | 0.5158 (15) | 0.071* | |
C1 | 0.4228 (4) | 0.4876 (2) | 0.59666 (10) | 0.0466 (4) | |
H1A | 0.2524 | 0.4878 | 0.6115 | 0.056* | |
C2 | 0.4835 (6) | 0.3347 (2) | 0.57123 (13) | 0.0677 (8) | |
H2A | 0.3813 | 0.3116 | 0.5335 | 0.102* | |
H2B | 0.4562 | 0.2650 | 0.6065 | 0.102* | |
H2C | 0.6514 | 0.3312 | 0.5576 | 0.102* | |
C3 | 0.5796 (4) | 0.5342 (2) | 0.65528 (10) | 0.0436 (4) | |
C4 | 0.7775 (5) | 0.6272 (3) | 0.64946 (11) | 0.0541 (5) | |
H4 | 0.8151 | 0.6676 | 0.6078 | 0.065* | |
C5 | 0.9206 (5) | 0.6611 (3) | 0.70503 (12) | 0.0642 (6) | |
H5 | 1.0525 | 0.7240 | 0.6999 | 0.077* | |
C6 | 0.8710 (5) | 0.6032 (3) | 0.76771 (11) | 0.0611 (7) | |
C7 | 0.6725 (6) | 0.5106 (3) | 0.77365 (11) | 0.0666 (7) | |
H7 | 0.6355 | 0.4704 | 0.8154 | 0.080* | |
C8 | 0.5276 (5) | 0.4764 (3) | 0.71841 (11) | 0.0589 (6) | |
H8 | 0.3948 | 0.4143 | 0.7237 | 0.071* | |
C9 | 1.0297 (6) | 0.6401 (5) | 0.82792 (14) | 0.0952 (12) | |
H9A | 1.0439 | 0.7443 | 0.8320 | 0.143* | |
H9B | 1.1887 | 0.5983 | 0.8219 | 0.143* | |
H9C | 0.9570 | 0.6011 | 0.8680 | 0.143* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0496 (3) | 0.0522 (3) | 0.0505 (2) | −0.0034 (3) | −0.0031 (3) | −0.0048 (2) |
N1 | 0.0459 (9) | 0.0481 (8) | 0.0489 (8) | 0.0004 (9) | −0.0121 (11) | 0.0029 (7) |
C1 | 0.0423 (10) | 0.0492 (9) | 0.0483 (10) | −0.0037 (10) | −0.0023 (10) | 0.0024 (8) |
C2 | 0.091 (2) | 0.0449 (9) | 0.0678 (13) | −0.0048 (14) | −0.0217 (15) | −0.0033 (10) |
C3 | 0.0418 (10) | 0.0456 (9) | 0.0434 (8) | 0.0040 (10) | 0.0001 (9) | −0.0043 (7) |
C4 | 0.0502 (12) | 0.0641 (13) | 0.0480 (10) | −0.0059 (12) | −0.0017 (10) | 0.0001 (10) |
C5 | 0.0528 (14) | 0.0775 (14) | 0.0624 (13) | −0.0065 (15) | −0.0074 (12) | −0.0125 (12) |
C6 | 0.0500 (12) | 0.0857 (17) | 0.0477 (11) | 0.0174 (13) | −0.0053 (10) | −0.0173 (11) |
C7 | 0.0648 (14) | 0.0931 (18) | 0.0417 (10) | 0.0102 (17) | 0.0019 (11) | 0.0003 (12) |
C8 | 0.0583 (13) | 0.0695 (13) | 0.0490 (10) | −0.0053 (13) | 0.0059 (11) | 0.0051 (10) |
C9 | 0.0723 (18) | 0.155 (3) | 0.0584 (14) | 0.013 (3) | −0.0184 (15) | −0.0314 (18) |
Geometric parameters (Å, º) top
N1—C1 | 1.497 (3) | C4—C5 | 1.390 (3) |
N1—H1 | 0.90 (3) | C4—H4 | 0.9300 |
N1—H2 | 0.82 (4) | C5—C6 | 1.380 (4) |
N1—H3 | 0.89 (4) | C5—H5 | 0.9300 |
C1—C3 | 1.509 (3) | C6—C7 | 1.385 (4) |
C1—C2 | 1.525 (3) | C6—C9 | 1.518 (4) |
C1—H1A | 0.9800 | C7—C8 | 1.391 (4) |
C2—H2A | 0.9600 | C7—H7 | 0.9300 |
C2—H2B | 0.9600 | C8—H8 | 0.9300 |
C2—H2C | 0.9600 | C9—H9A | 0.9600 |
C3—C4 | 1.384 (3) | C9—H9B | 0.9600 |
C3—C8 | 1.391 (3) | C9—H9C | 0.9600 |
C1—N1—H1 | 114.0 (17) | C3—C4—C5 | 120.9 (2) |
C1—N1—H2 | 109 (2) | C3—C4—H4 | 119.5 |
H1—N1—H2 | 112 (3) | C5—C4—H4 | 119.5 |
C1—N1—H3 | 114 (2) | C6—C5—C4 | 121.3 (3) |
H1—N1—H3 | 103 (3) | C6—C5—H5 | 119.3 |
H2—N1—H3 | 105 (3) | C4—C5—H5 | 119.3 |
N1—C1—C3 | 111.87 (17) | C5—C6—C7 | 117.8 (2) |
N1—C1—C2 | 107.62 (18) | C5—C6—C9 | 120.8 (3) |
C3—C1—C2 | 113.00 (19) | C7—C6—C9 | 121.3 (3) |
N1—C1—H1A | 108.1 | C6—C7—C8 | 121.3 (2) |
C3—C1—H1A | 108.1 | C6—C7—H7 | 119.3 |
C2—C1—H1A | 108.1 | C8—C7—H7 | 119.3 |
C1—C2—H2A | 109.5 | C7—C8—C3 | 120.6 (2) |
C1—C2—H2B | 109.5 | C7—C8—H8 | 119.7 |
H2A—C2—H2B | 109.5 | C3—C8—H8 | 119.7 |
C1—C2—H2C | 109.5 | C6—C9—H9A | 109.5 |
H2A—C2—H2C | 109.5 | C6—C9—H9B | 109.5 |
H2B—C2—H2C | 109.5 | H9A—C9—H9B | 109.5 |
C4—C3—C8 | 118.0 (2) | C6—C9—H9C | 109.5 |
C4—C3—C1 | 123.80 (19) | H9A—C9—H9C | 109.5 |
C8—C3—C1 | 118.1 (2) | H9B—C9—H9C | 109.5 |
N1—C1—C3—C4 | −20.5 (3) | C4—C5—C6—C7 | −0.3 (4) |
C2—C1—C3—C4 | 101.1 (3) | C4—C5—C6—C9 | 179.6 (3) |
N1—C1—C3—C8 | 161.9 (2) | C5—C6—C7—C8 | 0.1 (4) |
C2—C1—C3—C8 | −76.5 (3) | C9—C6—C7—C8 | −179.8 (3) |
C8—C3—C4—C5 | 0.3 (4) | C6—C7—C8—C3 | 0.3 (4) |
C1—C3—C4—C5 | −177.3 (2) | C4—C3—C8—C7 | −0.6 (4) |
C3—C4—C5—C6 | 0.1 (4) | C1—C3—C8—C7 | 177.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1i | 0.90 (3) | 2.29 (3) | 3.1552 (19) | 160 (2) |
N1—H2···Cl1ii | 0.82 (4) | 2.38 (4) | 3.157 (2) | 159 (3) |
N1—H3···Cl1 | 0.89 (4) | 2.29 (4) | 3.180 (2) | 179 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x−1, y, z. |
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