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The asymmetric unit of the title compound, C
7H
11N
2+·ClO
4−, contains a 4-(
N,
N-dimethylamino)pyridinium cation and a perchlorate anion linked
via an N—H
O hydrogen bond. Glide-related molecules are linked by C—H
O hydrogen bonds to form a chain along the
c axis. The chains are arranged to form a layered structure parallel to the
bc plane.
Supporting information
CCDC reference: 289699
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.174
- Data-to-parameter ratio = 22.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O4 .. 2.62 Ang.
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang.
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
4-(
N,
N-Dimethylamino)pyridinium perchlorate
top
Crystal data top
C7H11N2+·ClO4− | F(000) = 464 |
Mr = 222.63 | Dx = 1.504 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5229 reflections |
a = 8.1429 (1) Å | θ = 2.8–30.1° |
b = 14.8202 (2) Å | µ = 0.38 mm−1 |
c = 10.4493 (1) Å | T = 293 K |
β = 128.771 (1)° | Needle, colourless |
V = 983.16 (2) Å3 | 0.70 × 0.33 × 0.16 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX2 CCD area-detector diffractometer | 2881 independent reflections |
Radiation source: fine-focus sealed tube | 2368 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.1°, θmin = 2.8° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −20→20 |
Tmin = 0.747, Tmax = 0.942 | l = −14→14 |
15960 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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0974P)2 + 0.3658P] where P = (Fo2 + 2Fc2)/3 |
2881 reflections | (Δ/σ)max = 0.001 |
129 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.52 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 | 0.08098 (8) | 0.12272 (3) | 0.10812 (6) | 0.04409 (18) | |
O1 | 0.1986 (3) | 0.03870 (11) | 0.1923 (2) | 0.0604 (5) | |
O2 | 0.1379 (3) | 0.16163 (13) | 0.0158 (2) | 0.0621 (5) | |
O3 | 0.1013 (3) | 0.18496 (11) | 0.2232 (2) | 0.0577 (4) | |
O4 | −0.1536 (3) | 0.09625 (12) | −0.0111 (2) | 0.0541 (4) | |
N1 | 0.2271 (3) | 0.35911 (14) | 0.1973 (3) | 0.0567 (5) | |
H1 | 0.2075 | 0.3042 | 0.2116 | 0.068* | |
N2 | 0.3045 (3) | 0.62216 (12) | 0.1223 (3) | 0.0512 (5) | |
C1 | 0.2864 (3) | 0.53576 (13) | 0.1494 (2) | 0.0394 (4) | |
C2 | 0.2717 (3) | 0.46409 (15) | 0.0530 (3) | 0.0461 (4) | |
H2 | 0.2829 | 0.4760 | −0.0287 | 0.055* | |
C3 | 0.2413 (4) | 0.37831 (15) | 0.0791 (3) | 0.0523 (5) | |
H3 | 0.2302 | 0.3320 | 0.0139 | 0.063* | |
C4 | 0.2429 (4) | 0.42352 (18) | 0.2922 (3) | 0.0552 (6) | |
H4 | 0.2324 | 0.4084 | 0.3732 | 0.066* | |
C5 | 0.2741 (3) | 0.51116 (16) | 0.2741 (3) | 0.0475 (5) | |
H5 | 0.2873 | 0.5550 | 0.3437 | 0.057* | |
C6 | 0.3234 (5) | 0.6476 (2) | −0.0031 (4) | 0.0712 (8) | |
H6A | 0.2130 | 0.6193 | −0.1052 | 0.107* | |
H6B | 0.4576 | 0.6283 | 0.0302 | 0.107* | |
H6C | 0.3119 | 0.7120 | −0.0166 | 0.107* | |
C7 | 0.3211 (5) | 0.69396 (17) | 0.2259 (4) | 0.0691 (8) | |
H7A | 0.2058 | 0.6895 | 0.2287 | 0.104* | |
H7B | 0.3168 | 0.7516 | 0.1818 | 0.104* | |
H7C | 0.4517 | 0.6880 | 0.3351 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0566 (3) | 0.0360 (3) | 0.0477 (3) | −0.00284 (18) | 0.0365 (3) | −0.00399 (17) |
O1 | 0.0690 (11) | 0.0441 (8) | 0.0499 (9) | 0.0092 (7) | 0.0284 (8) | −0.0006 (7) |
O2 | 0.0878 (12) | 0.0551 (9) | 0.0778 (11) | −0.0139 (9) | 0.0686 (11) | −0.0078 (8) |
O3 | 0.0880 (12) | 0.0427 (8) | 0.0595 (9) | −0.0067 (8) | 0.0544 (10) | −0.0113 (7) |
O4 | 0.0516 (9) | 0.0497 (8) | 0.0639 (10) | −0.0035 (7) | 0.0376 (8) | −0.0060 (7) |
N1 | 0.0523 (10) | 0.0428 (9) | 0.0635 (12) | −0.0050 (8) | 0.0307 (10) | 0.0068 (8) |
N2 | 0.0505 (10) | 0.0402 (9) | 0.0662 (12) | 0.0041 (7) | 0.0381 (10) | 0.0095 (8) |
C1 | 0.0360 (8) | 0.0403 (9) | 0.0431 (9) | 0.0036 (7) | 0.0254 (8) | 0.0036 (7) |
C2 | 0.0499 (11) | 0.0508 (11) | 0.0438 (10) | 0.0039 (9) | 0.0325 (9) | −0.0001 (8) |
C3 | 0.0508 (12) | 0.0460 (11) | 0.0529 (12) | 0.0000 (9) | 0.0290 (10) | −0.0073 (9) |
C4 | 0.0528 (12) | 0.0673 (15) | 0.0491 (12) | −0.0005 (10) | 0.0337 (10) | 0.0127 (10) |
C5 | 0.0511 (11) | 0.0544 (12) | 0.0426 (10) | 0.0002 (9) | 0.0320 (9) | −0.0022 (8) |
C6 | 0.0727 (17) | 0.0659 (16) | 0.090 (2) | 0.0084 (13) | 0.0585 (16) | 0.0311 (15) |
C7 | 0.0653 (15) | 0.0391 (11) | 0.091 (2) | 0.0024 (10) | 0.0435 (15) | −0.0060 (12) |
Geometric parameters (Å, º) top
Cl1—O2 | 1.4277 (16) | C2—C3 | 1.355 (3) |
Cl1—O3 | 1.4405 (16) | C2—H2 | 0.93 |
Cl1—O1 | 1.4786 (17) | C3—H3 | 0.93 |
Cl1—O4 | 1.5412 (17) | C4—C5 | 1.359 (3) |
N1—C4 | 1.324 (3) | C4—H4 | 0.93 |
N1—C3 | 1.341 (3) | C5—H5 | 0.93 |
N1—H1 | 0.86 | C6—H6A | 0.96 |
N2—C1 | 1.339 (3) | C6—H6B | 0.96 |
N2—C6 | 1.461 (3) | C6—H6C | 0.96 |
N2—C7 | 1.462 (3) | C7—H7A | 0.96 |
C1—C5 | 1.416 (3) | C7—H7B | 0.96 |
C1—C2 | 1.416 (3) | C7—H7C | 0.96 |
| | | |
O2—Cl1—O3 | 112.92 (10) | C2—C3—H3 | 119.5 |
O2—Cl1—O1 | 112.25 (12) | N1—C4—C5 | 121.6 (2) |
O3—Cl1—O1 | 110.47 (10) | N1—C4—H4 | 119.2 |
O2—Cl1—O4 | 108.63 (11) | C5—C4—H4 | 119.2 |
O3—Cl1—O4 | 105.90 (10) | C4—C5—C1 | 120.1 (2) |
O1—Cl1—O4 | 106.24 (10) | C4—C5—H5 | 120.0 |
C4—N1—C3 | 120.9 (2) | C1—C5—H5 | 120.0 |
C4—N1—H1 | 119.6 | N2—C6—H6A | 109.5 |
C3—N1—H1 | 119.6 | N2—C6—H6B | 109.5 |
C1—N2—C6 | 121.6 (2) | H6A—C6—H6B | 109.5 |
C1—N2—C7 | 120.8 (2) | N2—C6—H6C | 109.5 |
C6—N2—C7 | 117.6 (2) | H6A—C6—H6C | 109.5 |
N2—C1—C5 | 121.4 (2) | H6B—C6—H6C | 109.5 |
N2—C1—C2 | 122.60 (19) | N2—C7—H7A | 109.5 |
C5—C1—C2 | 115.98 (18) | N2—C7—H7B | 109.5 |
C3—C2—C1 | 120.4 (2) | H7A—C7—H7B | 109.5 |
C3—C2—H2 | 119.8 | N2—C7—H7C | 109.5 |
C1—C2—H2 | 119.8 | H7A—C7—H7C | 109.5 |
N1—C3—C2 | 121.1 (2) | H7B—C7—H7C | 109.5 |
N1—C3—H3 | 119.5 | | |
| | | |
C6—N2—C1—C5 | 178.2 (2) | C4—N1—C3—C2 | −0.2 (4) |
C7—N2—C1—C5 | 2.6 (3) | C1—C2—C3—N1 | −0.8 (4) |
C6—N2—C1—C2 | −3.9 (3) | C3—N1—C4—C5 | −0.1 (4) |
C7—N2—C1—C2 | −179.5 (2) | N1—C4—C5—C1 | 1.2 (3) |
N2—C1—C2—C3 | −176.1 (2) | N2—C1—C5—C4 | 176.0 (2) |
C5—C1—C2—C3 | 1.9 (3) | C2—C1—C5—C4 | −2.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 2.00 | 2.851 (3) | 168 |
C2—H2···O1i | 0.93 | 2.55 | 3.428 (3) | 157 |
C3—H3···O3i | 0.93 | 2.53 | 3.271 (3) | 137 |
C4—H4···O2ii | 0.93 | 2.31 | 3.207 (4) | 163 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
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