The crystallographic analysis of the title compound, C
12H
28N
+·ClO
4−, (I), shows that intermolecular C—H
O interactions stabilize the crystal structure. The compound is isomorphous with tetra-
n-propylammonium iodide, whose structure has been described by Yoshida
et al. [
Acta Cryst. (1994). C
50, 1758–1760].
Supporting information
CCDC reference: 272122
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.108
- Data-to-parameter ratio = 22.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for Cl1
| Author Response: The oxygen atoms in perchlorate anion often
show higer U(eq) compared with the chloride atoms located in the center
of molecule. The alert is caused by large Ueq of oxygen atoms.
|
Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ?
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 27.90
From the CIF: _reflns_number_total 3723
Count of symmetry unique reflns 2130
Completeness (_total/calc) 174.79%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1593
Fraction of Friedel pairs measured 0.748
Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.
Crystal data top
C12H28N+·ClO4− | F(000) = 624 |
Mr = 285.80 | Dx = 1.218 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2126 reflections |
a = 13.3335 (9) Å | θ = 2.3–21.6° |
b = 12.1528 (8) Å | µ = 0.25 mm−1 |
c = 9.6210 (6) Å | T = 173 K |
V = 1558.98 (18) Å3 | Needle, colorless |
Z = 4 | 0.48 × 0.21 × 0.20 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3723 independent reflections |
Radiation source: fine-focus sealed tube | 2851 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.9°, θmin = 2.3° |
φ and ω scans | h = −17→14 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −15→15 |
Tmin = 0.889, Tmax = 0.951 | l = −12→12 |
11458 measured 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0417P)2] where P = (Fo2 + 2Fc2)/3 |
3723 reflections | (Δ/σ)max < 0.001 |
167 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.29 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 | |
O1 | 0.62769 (17) | 0.49229 (17) | 0.0345 (3) | 0.0729 (7) | |
O2 | 0.47890 (18) | 0.5683 (2) | 0.1123 (2) | 0.0751 (8) | |
O3 | 0.5084 (2) | 0.5547 (2) | −0.1192 (2) | 0.0893 (10) | |
O4 | 0.59767 (16) | 0.67824 (17) | 0.0110 (4) | 0.1045 (10) | |
Cl1 | 0.55488 (4) | 0.57450 (4) | 0.01051 (6) | 0.02855 (15) | |
C1 | 0.3800 (2) | 0.9238 (2) | −0.1155 (2) | 0.0335 (6) | |
H1A | 0.3974 | 0.9736 | −0.1932 | 0.040* | |
H1B | 0.3093 | 0.9384 | −0.0902 | 0.040* | |
C2 | 0.3879 (2) | 0.8059 (2) | −0.1668 (3) | 0.0420 (7) | |
H2A | 0.4551 | 0.7932 | −0.2075 | 0.050* | |
H2B | 0.3791 | 0.7545 | −0.0879 | 0.050* | |
C3 | 0.3083 (2) | 0.7848 (3) | −0.2749 (3) | 0.0487 (8) | |
H3A | 0.2419 | 0.7969 | −0.2340 | 0.073* | |
H3B | 0.3133 | 0.7086 | −0.3075 | 0.073* | |
H3C | 0.3179 | 0.8350 | −0.3534 | 0.073* | |
C4 | 0.4261 (2) | 0.8749 (2) | 0.1297 (2) | 0.0353 (7) | |
H4A | 0.4548 | 0.8021 | 0.1068 | 0.042* | |
H4B | 0.4624 | 0.9033 | 0.2121 | 0.042* | |
C5 | 0.3166 (2) | 0.8594 (3) | 0.1686 (3) | 0.0451 (7) | |
H5A | 0.2886 | 0.9294 | 0.2042 | 0.054* | |
H5B | 0.2775 | 0.8372 | 0.0857 | 0.054* | |
C6 | 0.3096 (3) | 0.7715 (2) | 0.2791 (3) | 0.0511 (9) | |
H6A | 0.3434 | 0.7046 | 0.2466 | 0.077* | |
H6B | 0.2389 | 0.7551 | 0.2980 | 0.077* | |
H6C | 0.3419 | 0.7976 | 0.3644 | 0.077* | |
C7 | 0.42077 (19) | 1.07017 (19) | 0.0541 (2) | 0.0354 (6) | |
H7A | 0.3473 | 1.0759 | 0.0670 | 0.043* | |
H7B | 0.4525 | 1.0831 | 0.1457 | 0.043* | |
C8 | 0.4538 (2) | 1.1608 (2) | −0.0440 (3) | 0.0476 (7) | |
H8A | 0.4221 | 1.1503 | −0.1361 | 0.057* | |
H8B | 0.5275 | 1.1582 | −0.0562 | 0.057* | |
C9 | 0.4230 (2) | 1.27240 (19) | 0.0164 (3) | 0.0489 (7) | |
H9A | 0.3498 | 1.2754 | 0.0253 | 0.073* | |
H9B | 0.4457 | 1.3313 | −0.0456 | 0.073* | |
H9C | 0.4537 | 1.2819 | 0.1082 | 0.073* | |
C10 | 0.55467 (18) | 0.94209 (19) | −0.0352 (2) | 0.0343 (6) | |
H10A | 0.5668 | 0.8650 | −0.0640 | 0.041* | |
H10B | 0.5658 | 0.9892 | −0.1177 | 0.041* | |
C11 | 0.6316 (2) | 0.9723 (3) | 0.0733 (3) | 0.0511 (8) | |
H11A | 0.6249 | 0.9225 | 0.1542 | 0.061* | |
H11B | 0.6195 | 1.0485 | 0.1056 | 0.061* | |
C12 | 0.73682 (19) | 0.9633 (3) | 0.0139 (4) | 0.0615 (9) | |
H12A | 0.7483 | 0.8881 | −0.0192 | 0.092* | |
H12B | 0.7859 | 0.9812 | 0.0862 | 0.092* | |
H12C | 0.7441 | 1.0148 | −0.0638 | 0.092* | |
N1 | 0.44549 (15) | 0.95270 (14) | 0.0078 (2) | 0.0306 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0588 (14) | 0.0543 (12) | 0.106 (2) | 0.0098 (12) | −0.0019 (15) | 0.0155 (14) |
O2 | 0.0608 (15) | 0.116 (2) | 0.0490 (11) | 0.0003 (17) | 0.0062 (11) | 0.0012 (15) |
O3 | 0.114 (2) | 0.107 (2) | 0.0469 (12) | 0.0387 (19) | 0.0068 (14) | −0.0079 (14) |
O4 | 0.0567 (15) | 0.0458 (12) | 0.211 (3) | −0.0001 (11) | 0.011 (2) | 0.002 (2) |
Cl1 | 0.0288 (3) | 0.0269 (2) | 0.0299 (3) | 0.0043 (3) | 0.0051 (3) | 0.0032 (3) |
C1 | 0.0361 (14) | 0.0353 (13) | 0.0291 (12) | 0.0024 (14) | −0.0017 (11) | −0.0003 (12) |
C2 | 0.0416 (17) | 0.0383 (15) | 0.0461 (16) | 0.0003 (15) | −0.0046 (14) | −0.0057 (13) |
C3 | 0.046 (2) | 0.0534 (19) | 0.0467 (18) | −0.0044 (18) | −0.0051 (16) | −0.0110 (16) |
C4 | 0.0414 (18) | 0.0340 (13) | 0.0305 (13) | 0.0029 (14) | −0.0010 (12) | 0.0048 (11) |
C5 | 0.0365 (17) | 0.0512 (18) | 0.0476 (16) | 0.0016 (15) | 0.0067 (15) | 0.0097 (15) |
C6 | 0.055 (2) | 0.0492 (19) | 0.0491 (19) | −0.0030 (19) | 0.0101 (17) | 0.0103 (16) |
C7 | 0.0333 (14) | 0.0336 (13) | 0.0394 (13) | 0.0040 (13) | 0.0019 (11) | −0.0038 (12) |
C8 | 0.0531 (19) | 0.0341 (14) | 0.0555 (17) | 0.0011 (14) | 0.0124 (16) | −0.0011 (13) |
C9 | 0.0537 (18) | 0.0316 (13) | 0.0615 (19) | −0.0017 (12) | −0.0063 (19) | −0.0026 (15) |
C10 | 0.0276 (12) | 0.0324 (13) | 0.0429 (14) | 0.0000 (12) | 0.0045 (12) | −0.0013 (11) |
C11 | 0.0340 (16) | 0.0541 (18) | 0.065 (2) | 0.0021 (16) | −0.0053 (15) | −0.0111 (16) |
C12 | 0.0311 (15) | 0.067 (2) | 0.087 (2) | −0.0011 (14) | 0.002 (2) | 0.004 (2) |
N1 | 0.0297 (10) | 0.0291 (9) | 0.0330 (10) | 0.0033 (9) | 0.0034 (12) | 0.0003 (10) |
Geometric parameters (Å, º) top
C1—N1 | 1.515 (3) | C7—H7A | 0.9900 |
C1—C2 | 1.519 (4) | C7—H7B | 0.9900 |
C1—H1A | 0.9900 | C8—C9 | 1.531 (3) |
C1—H1B | 0.9900 | C8—H8A | 0.9900 |
C2—C3 | 1.508 (4) | C8—H8B | 0.9900 |
C2—H2A | 0.9900 | C9—H9A | 0.9800 |
C2—H2B | 0.9900 | C9—H9B | 0.9800 |
C3—H3A | 0.9800 | C9—H9C | 0.9800 |
C3—H3B | 0.9800 | C10—C11 | 1.508 (3) |
C3—H3C | 0.9800 | C10—N1 | 1.519 (3) |
C4—C5 | 1.519 (4) | C10—H10A | 0.9900 |
C4—N1 | 1.528 (3) | C10—H10B | 0.9900 |
C4—H4A | 0.9900 | C11—C12 | 1.520 (4) |
C4—H4B | 0.9900 | C11—H11A | 0.9900 |
C5—C6 | 1.511 (4) | C11—H11B | 0.9900 |
C5—H5A | 0.9900 | C12—H12A | 0.9800 |
C5—H5B | 0.9900 | C12—H12B | 0.9800 |
C6—H6A | 0.9800 | C12—H12C | 0.9800 |
C6—H6B | 0.9800 | O1—Cl1 | 1.412 (2) |
C6—H6C | 0.9800 | O2—Cl1 | 1.411 (2) |
C7—C8 | 1.516 (4) | O3—Cl1 | 1.414 (2) |
C7—N1 | 1.531 (3) | O4—Cl1 | 1.384 (2) |
| | | |
N1—C1—C2 | 115.7 (2) | C7—C8—C9 | 109.2 (2) |
N1—C1—H1A | 108.4 | C7—C8—H8A | 109.8 |
C2—C1—H1A | 108.4 | C9—C8—H8A | 109.8 |
N1—C1—H1B | 108.4 | C7—C8—H8B | 109.8 |
C2—C1—H1B | 108.4 | C9—C8—H8B | 109.8 |
H1A—C1—H1B | 107.4 | H8A—C8—H8B | 108.3 |
C3—C2—C1 | 109.6 (2) | C8—C9—H9A | 109.5 |
C3—C2—H2A | 109.7 | C8—C9—H9B | 109.5 |
C1—C2—H2A | 109.7 | H9A—C9—H9B | 109.5 |
C3—C2—H2B | 109.7 | C8—C9—H9C | 109.5 |
C1—C2—H2B | 109.7 | H9A—C9—H9C | 109.5 |
H2A—C2—H2B | 108.2 | H9B—C9—H9C | 109.5 |
C2—C3—H3A | 109.5 | C11—C10—N1 | 116.2 (2) |
C2—C3—H3B | 109.5 | C11—C10—H10A | 108.2 |
H3A—C3—H3B | 109.5 | N1—C10—H10A | 108.2 |
C2—C3—H3C | 109.5 | C11—C10—H10B | 108.2 |
H3A—C3—H3C | 109.5 | N1—C10—H10B | 108.2 |
H3B—C3—H3C | 109.5 | H10A—C10—H10B | 107.4 |
C5—C4—N1 | 115.4 (2) | C10—C11—C12 | 110.5 (2) |
C5—C4—H4A | 108.4 | C10—C11—H11A | 109.6 |
N1—C4—H4A | 108.4 | C12—C11—H11A | 109.6 |
C5—C4—H4B | 108.4 | C10—C11—H11B | 109.6 |
N1—C4—H4B | 108.4 | C12—C11—H11B | 109.6 |
H4A—C4—H4B | 107.5 | H11A—C11—H11B | 108.1 |
C6—C5—C4 | 108.7 (3) | C11—C12—H12A | 109.5 |
C6—C5—H5A | 110.0 | C11—C12—H12B | 109.5 |
C4—C5—H5A | 110.0 | H12A—C12—H12B | 109.5 |
C6—C5—H5B | 110.0 | C11—C12—H12C | 109.5 |
C4—C5—H5B | 110.0 | H12A—C12—H12C | 109.5 |
H5A—C5—H5B | 108.3 | H12B—C12—H12C | 109.5 |
C5—C6—H6A | 109.5 | C1—N1—C10 | 108.64 (18) |
C5—C6—H6B | 109.5 | C1—N1—C4 | 111.11 (18) |
H6A—C6—H6B | 109.5 | C10—N1—C4 | 108.60 (18) |
C5—C6—H6C | 109.5 | C1—N1—C7 | 108.65 (18) |
H6A—C6—H6C | 109.5 | C10—N1—C7 | 111.38 (17) |
H6B—C6—H6C | 109.5 | C4—N1—C7 | 108.48 (17) |
C8—C7—N1 | 115.7 (2) | O4—Cl1—O2 | 110.03 (17) |
C8—C7—H7A | 108.4 | O4—Cl1—O1 | 111.13 (14) |
N1—C7—H7A | 108.4 | O2—Cl1—O1 | 110.01 (14) |
C8—C7—H7B | 108.4 | O4—Cl1—O3 | 109.81 (18) |
N1—C7—H7B | 108.4 | O2—Cl1—O3 | 106.78 (14) |
H7A—C7—H7B | 107.4 | O1—Cl1—O3 | 108.97 (15) |
| | | |
N1—C1—C2—C3 | 171.7 (2) | C11—C10—N1—C4 | −61.4 (3) |
N1—C4—C5—C6 | 173.8 (2) | C11—C10—N1—C7 | 58.0 (3) |
N1—C7—C8—C9 | 179.6 (2) | C5—C4—N1—C1 | −49.7 (3) |
N1—C10—C11—C12 | −177.2 (2) | C5—C4—N1—C10 | −169.2 (2) |
C2—C1—N1—C10 | 64.1 (3) | C5—C4—N1—C7 | 69.6 (3) |
C2—C1—N1—C4 | −55.3 (3) | C8—C7—N1—C1 | −70.1 (3) |
C2—C1—N1—C7 | −174.6 (2) | C8—C7—N1—C10 | 49.5 (3) |
C11—C10—N1—C1 | 177.6 (2) | C8—C7—N1—C4 | 169.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O4 | 0.99 | 2.42 | 3.288 (3) | 146 |
C7—H7B···O2i | 0.99 | 2.51 | 3.478 (3) | 166 |
C6—H6C···O1i | 0.98 | 2.59 | 3.334 (4) | 133 |
C5—H5B···O4ii | 0.99 | 2.58 | 3.423 (4) | 143 |
C4—H4A···O4 | 0.99 | 2.60 | 3.500 (3) | 152 |
C1—H1A···O3iii | 0.99 | 2.41 | 3.356 (4) | 160 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z; (iii) −x+1, y+1/2, −z−1/2. |