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In the crystal structure of the title compound, C
12H
14N
3+·C
7H
7O
3S
−, cations and anions are linked by intermolecular N—H
O and C—H
O hydrogen-bonding interactions, forming channels running along the
b axis.
Supporting information
CCDC reference: 640466
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.126
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.07 Ratio
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
2-Anilino-4,6-dimethylpyrimidinium
p-toluenesulfonate
top
Crystal data top
C12H14N3+·C7H7O3S− | F(000) = 784 |
Mr = 371.45 | Dx = 1.313 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1879 reflections |
a = 8.0092 (11) Å | θ = 2.4–22.3° |
b = 9.7882 (13) Å | µ = 0.20 mm−1 |
c = 24.937 (3) Å | T = 293 K |
β = 106.069 (4)° | Block, colourless |
V = 1878.6 (4) Å3 | 0.48 × 0.39 × 0.38 mm |
Z = 4 | |
Data collection top
Bruker APEX area-dectector diffractometer | 3303 independent reflections |
Radiation source: fine-focus sealed tube | 2683 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.912, Tmax = 0.929 | k = −11→11 |
10011 measured reflections | l = −21→29 |
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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.067P)2 + 0.4961P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3303 reflections | Δρmax = 0.24 e Å−3 |
255 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.044 (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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.78684 (7) | 0.77165 (6) | 0.88039 (2) | 0.0567 (2) | |
O1 | 0.9210 (2) | 0.8481 (2) | 0.86617 (8) | 0.0843 (6) | |
O2 | 0.7731 (2) | 0.63079 (16) | 0.86121 (7) | 0.0759 (5) | |
O3 | 0.7962 (2) | 0.77676 (16) | 0.93952 (6) | 0.0673 (5) | |
C13 | 0.1082 (4) | 1.0473 (4) | 0.76111 (14) | 0.1049 (11) | |
H13A | 0.0129 | 0.9852 | 0.7575 | 0.142 (15)* | |
H13B | 0.1114 | 1.0773 | 0.7248 | 0.126 (13)* | |
H13C | 0.0933 | 1.1248 | 0.7829 | 0.20 (2)* | |
C14 | 0.2769 (3) | 0.9763 (3) | 0.78937 (10) | 0.0732 (7) | |
C15 | 0.4267 (3) | 1.0035 (3) | 0.77414 (10) | 0.0729 (7) | |
H15 | 0.4225 | 1.0645 | 0.7452 | 0.074 (7)* | |
C16 | 0.5816 (3) | 0.9411 (2) | 0.80134 (9) | 0.0627 (6) | |
H16 | 0.6812 | 0.9594 | 0.7904 | 0.073 (7)* | |
C17 | 0.5895 (3) | 0.8517 (2) | 0.84458 (8) | 0.0525 (5) | |
C18 | 0.4414 (3) | 0.8249 (3) | 0.86023 (12) | 0.0719 (7) | |
H18 | 0.4455 | 0.7655 | 0.8897 | 0.083 (8)* | |
C19 | 0.2878 (4) | 0.8856 (3) | 0.83267 (12) | 0.0813 (8) | |
H19 | 0.1879 | 0.8653 | 0.8432 | 0.095 (9)* | |
N1 | 0.1984 (2) | 0.59024 (17) | 1.07156 (7) | 0.0528 (4) | |
H1 | 0.1969 | 0.5155 | 1.0896 | 0.063* | |
N2 | 0.2366 (2) | 0.69754 (17) | 0.99161 (7) | 0.0545 (4) | |
N3 | 0.2403 (2) | 0.46065 (17) | 0.99940 (7) | 0.0541 (5) | |
H3A | 0.2253 | 0.3932 | 1.0197 | 0.065* | |
C1 | 0.1472 (4) | 0.7047 (3) | 1.15184 (11) | 0.0765 (7) | |
H1A | 0.2438 | 0.6590 | 1.1769 | 0.126 (12)* | |
H1B | 0.1388 | 0.7961 | 1.1649 | 0.116 (11)* | |
H1C | 0.0421 | 0.6559 | 1.1504 | 0.169 (17)* | |
C2 | 0.1741 (3) | 0.7100 (2) | 1.09487 (9) | 0.0561 (5) | |
C3 | 0.1784 (3) | 0.8263 (2) | 1.06563 (10) | 0.0618 (6) | |
H3 | 0.1576 | 0.9106 | 1.0798 | 0.068 (7)* | |
C4 | 0.2140 (3) | 0.8175 (2) | 1.01417 (9) | 0.0573 (5) | |
C5 | 0.2327 (4) | 0.9412 (2) | 0.98187 (11) | 0.0772 (7) | |
H5A | 0.1565 | 0.9338 | 0.9447 | 0.135 (13)* | |
H5B | 0.2023 | 1.0207 | 0.9997 | 0.103 (9)* | |
H5C | 0.3505 | 0.9491 | 0.9802 | 0.124 (13)* | |
C6 | 0.2253 (3) | 0.5853 (2) | 1.01991 (8) | 0.0486 (5) | |
C7 | 0.2775 (3) | 0.4250 (2) | 0.94878 (8) | 0.0501 (5) | |
C8 | 0.2616 (3) | 0.5123 (2) | 0.90382 (9) | 0.0655 (6) | |
H8 | 0.2232 | 0.6015 | 0.9053 | 0.074 (7)* | |
C9 | 0.3033 (4) | 0.4653 (3) | 0.85691 (11) | 0.0739 (7) | |
H9 | 0.2971 | 0.5247 | 0.8273 | 0.091 (9)* | |
C10 | 0.3542 (3) | 0.3328 (3) | 0.85300 (11) | 0.0711 (7) | |
H10 | 0.3803 | 0.3020 | 0.8210 | 0.079 (8)* | |
C11 | 0.3654 (3) | 0.2462 (3) | 0.89669 (11) | 0.0710 (7) | |
H11 | 0.3990 | 0.1561 | 0.8941 | 0.086 (8)* | |
C12 | 0.3279 (3) | 0.2909 (2) | 0.94461 (10) | 0.0608 (6) | |
H12 | 0.3364 | 0.2307 | 0.9741 | 0.055 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0670 (4) | 0.0518 (3) | 0.0573 (4) | −0.0058 (2) | 0.0275 (3) | 0.0003 (2) |
O1 | 0.0629 (10) | 0.0979 (14) | 0.0974 (13) | −0.0080 (9) | 0.0315 (9) | 0.0280 (10) |
O2 | 0.1141 (14) | 0.0564 (10) | 0.0629 (10) | 0.0098 (9) | 0.0341 (9) | −0.0035 (7) |
O3 | 0.0910 (12) | 0.0576 (10) | 0.0551 (9) | −0.0086 (8) | 0.0232 (8) | −0.0045 (7) |
C13 | 0.075 (2) | 0.157 (3) | 0.079 (2) | 0.026 (2) | 0.0170 (15) | −0.020 (2) |
C14 | 0.0665 (15) | 0.0955 (19) | 0.0595 (14) | 0.0034 (13) | 0.0207 (12) | −0.0227 (13) |
C15 | 0.0763 (17) | 0.0885 (18) | 0.0560 (14) | 0.0051 (14) | 0.0215 (12) | 0.0041 (13) |
C16 | 0.0625 (14) | 0.0771 (16) | 0.0560 (13) | −0.0073 (11) | 0.0289 (11) | 0.0017 (11) |
C17 | 0.0623 (13) | 0.0503 (11) | 0.0521 (12) | −0.0123 (10) | 0.0278 (10) | −0.0090 (9) |
C18 | 0.0709 (16) | 0.0750 (16) | 0.0806 (17) | −0.0127 (13) | 0.0390 (13) | 0.0034 (13) |
C19 | 0.0656 (16) | 0.104 (2) | 0.0871 (19) | −0.0128 (15) | 0.0416 (15) | −0.0135 (16) |
N1 | 0.0591 (11) | 0.0466 (10) | 0.0545 (10) | −0.0021 (8) | 0.0185 (8) | −0.0026 (8) |
N2 | 0.0622 (11) | 0.0427 (9) | 0.0571 (10) | 0.0020 (8) | 0.0142 (8) | −0.0001 (8) |
N3 | 0.0730 (12) | 0.0392 (9) | 0.0536 (10) | −0.0012 (8) | 0.0235 (9) | −0.0009 (7) |
C1 | 0.091 (2) | 0.0779 (18) | 0.0699 (16) | −0.0033 (15) | 0.0369 (15) | −0.0162 (13) |
C2 | 0.0528 (12) | 0.0559 (13) | 0.0597 (13) | −0.0007 (9) | 0.0160 (10) | −0.0110 (10) |
C3 | 0.0658 (14) | 0.0491 (13) | 0.0698 (15) | 0.0047 (10) | 0.0180 (11) | −0.0121 (11) |
C4 | 0.0597 (13) | 0.0451 (11) | 0.0633 (13) | 0.0024 (9) | 0.0110 (10) | −0.0045 (10) |
C5 | 0.106 (2) | 0.0454 (13) | 0.0806 (19) | 0.0031 (13) | 0.0263 (16) | 0.0030 (11) |
C6 | 0.0482 (11) | 0.0443 (11) | 0.0526 (11) | −0.0005 (8) | 0.0127 (9) | −0.0020 (9) |
C7 | 0.0513 (11) | 0.0455 (11) | 0.0544 (12) | −0.0044 (9) | 0.0163 (9) | −0.0056 (9) |
C8 | 0.0882 (17) | 0.0500 (13) | 0.0631 (14) | −0.0016 (12) | 0.0290 (12) | −0.0009 (10) |
C9 | 0.0946 (18) | 0.0700 (16) | 0.0650 (15) | −0.0063 (14) | 0.0352 (13) | −0.0008 (13) |
C10 | 0.0733 (16) | 0.0803 (17) | 0.0667 (16) | −0.0049 (13) | 0.0310 (12) | −0.0171 (13) |
C11 | 0.0779 (16) | 0.0610 (15) | 0.0755 (17) | 0.0113 (12) | 0.0234 (13) | −0.0125 (12) |
C12 | 0.0718 (15) | 0.0491 (13) | 0.0618 (14) | 0.0050 (10) | 0.0192 (11) | −0.0003 (10) |
Geometric parameters (Å, º) top
S1—O1 | 1.4318 (17) | N3—C7 | 1.419 (3) |
S1—O2 | 1.4535 (17) | N3—H3A | 0.8600 |
S1—O3 | 1.4565 (16) | C1—C2 | 1.496 (3) |
S1—C17 | 1.768 (2) | C1—H1A | 0.9600 |
C13—C14 | 1.510 (4) | C1—H1B | 0.9600 |
C13—H13A | 0.9601 | C1—H1C | 0.9600 |
C13—H13B | 0.9600 | C2—C3 | 1.358 (3) |
C13—H13C | 0.9600 | C3—C4 | 1.392 (3) |
C14—C15 | 1.381 (4) | C3—H3 | 0.9299 |
C14—C19 | 1.381 (4) | C4—C5 | 1.485 (3) |
C15—C16 | 1.381 (3) | C5—H5A | 0.9601 |
C15—H15 | 0.9299 | C5—H5B | 0.9600 |
C16—C17 | 1.376 (3) | C5—H5C | 0.9600 |
C16—H16 | 0.9300 | C7—C12 | 1.385 (3) |
C17—C18 | 1.373 (3) | C7—C8 | 1.387 (3) |
C18—C19 | 1.368 (4) | C8—C9 | 1.381 (3) |
C18—H18 | 0.9299 | C8—H8 | 0.9299 |
C19—H19 | 0.9300 | C9—C10 | 1.371 (4) |
N1—C2 | 1.346 (3) | C9—H9 | 0.9299 |
N1—C6 | 1.365 (2) | C10—C11 | 1.363 (4) |
N1—H1 | 0.8600 | C10—H10 | 0.9300 |
N2—C6 | 1.323 (3) | C11—C12 | 1.381 (3) |
N2—C4 | 1.335 (3) | C11—H11 | 0.9300 |
N3—C6 | 1.341 (2) | C12—H12 | 0.9300 |
| | | |
O1—S1—O2 | 114.07 (12) | C2—C1—H1C | 109.7 |
O1—S1—O3 | 113.65 (11) | H1A—C1—H1C | 109.5 |
O2—S1—O3 | 110.10 (9) | H1B—C1—H1C | 109.5 |
O1—S1—C17 | 105.68 (10) | N1—C2—C3 | 118.1 (2) |
O2—S1—C17 | 106.16 (10) | N1—C2—C1 | 117.1 (2) |
O3—S1—C17 | 106.51 (10) | C3—C2—C1 | 124.8 (2) |
C14—C13—H13A | 109.7 | C2—C3—C4 | 119.0 (2) |
C14—C13—H13B | 109.1 | C2—C3—H3 | 120.4 |
H13A—C13—H13B | 109.5 | C4—C3—H3 | 120.6 |
C14—C13—H13C | 109.6 | N2—C4—C3 | 122.0 (2) |
H13A—C13—H13C | 109.5 | N2—C4—C5 | 116.3 (2) |
H13B—C13—H13C | 109.5 | C3—C4—C5 | 121.7 (2) |
C15—C14—C19 | 117.9 (2) | C4—C5—H5A | 109.2 |
C15—C14—C13 | 121.1 (3) | C4—C5—H5B | 109.5 |
C19—C14—C13 | 121.0 (3) | H5A—C5—H5B | 109.5 |
C14—C15—C16 | 120.7 (2) | C4—C5—H5C | 109.7 |
C14—C15—H15 | 119.4 | H5A—C5—H5C | 109.5 |
C16—C15—H15 | 120.0 | H5B—C5—H5C | 109.5 |
C17—C16—C15 | 120.4 (2) | N2—C6—N3 | 121.72 (18) |
C17—C16—H16 | 119.7 | N2—C6—N1 | 121.74 (17) |
C15—C16—H16 | 119.9 | N3—C6—N1 | 116.54 (17) |
C18—C17—C16 | 119.2 (2) | C12—C7—C8 | 119.1 (2) |
C18—C17—S1 | 119.58 (18) | C12—C7—N3 | 115.94 (19) |
C16—C17—S1 | 121.23 (16) | C8—C7—N3 | 124.94 (19) |
C19—C18—C17 | 120.1 (2) | C9—C8—C7 | 119.3 (2) |
C19—C18—H18 | 119.9 | C9—C8—H8 | 120.4 |
C17—C18—H18 | 119.9 | C7—C8—H8 | 120.2 |
C18—C19—C14 | 121.7 (2) | C10—C9—C8 | 121.4 (2) |
C18—C19—H19 | 119.3 | C10—C9—H9 | 119.1 |
C14—C19—H19 | 119.0 | C8—C9—H9 | 119.5 |
C2—N1—C6 | 121.20 (18) | C11—C10—C9 | 119.1 (2) |
C2—N1—H1 | 119.4 | C11—C10—H10 | 120.2 |
C6—N1—H1 | 119.4 | C9—C10—H10 | 120.7 |
C6—N2—C4 | 117.92 (19) | C10—C11—C12 | 120.8 (2) |
C6—N3—C7 | 128.78 (17) | C10—C11—H11 | 119.4 |
C6—N3—H3A | 115.6 | C12—C11—H11 | 119.7 |
C7—N3—H3A | 115.6 | C11—C12—C7 | 120.2 (2) |
C2—C1—H1A | 109.4 | C11—C12—H12 | 119.9 |
C2—C1—H1B | 109.4 | C7—C12—H12 | 120.0 |
H1A—C1—H1B | 109.5 | | |
| | | |
C19—C14—C15—C16 | 0.4 (4) | C6—N2—C4—C3 | −0.4 (3) |
C13—C14—C15—C16 | 178.1 (3) | C6—N2—C4—C5 | 178.3 (2) |
C14—C15—C16—C17 | −0.7 (4) | C2—C3—C4—N2 | 3.0 (3) |
C15—C16—C17—C18 | 0.2 (3) | C2—C3—C4—C5 | −175.7 (2) |
C15—C16—C17—S1 | −179.47 (18) | C4—N2—C6—N3 | 177.64 (19) |
O1—S1—C17—C18 | −163.62 (19) | C4—N2—C6—N1 | −2.6 (3) |
O2—S1—C17—C18 | 74.9 (2) | C7—N3—C6—N2 | 3.5 (3) |
O3—S1—C17—C18 | −42.4 (2) | C7—N3—C6—N1 | −176.31 (18) |
O1—S1—C17—C16 | 16.1 (2) | C2—N1—C6—N2 | 3.1 (3) |
O2—S1—C17—C16 | −105.39 (19) | C2—N1—C6—N3 | −177.10 (18) |
O3—S1—C17—C16 | 137.28 (18) | C6—N3—C7—C12 | 164.4 (2) |
C16—C17—C18—C19 | 0.6 (4) | C6—N3—C7—C8 | −17.7 (3) |
S1—C17—C18—C19 | −179.6 (2) | C12—C7—C8—C9 | −2.7 (3) |
C17—C18—C19—C14 | −1.0 (4) | N3—C7—C8—C9 | 179.5 (2) |
C15—C14—C19—C18 | 0.5 (4) | C7—C8—C9—C10 | 2.3 (4) |
C13—C14—C19—C18 | −177.2 (3) | C8—C9—C10—C11 | −0.7 (4) |
C6—N1—C2—C3 | −0.5 (3) | C9—C10—C11—C12 | −0.6 (4) |
C6—N1—C2—C1 | −179.5 (2) | C10—C11—C12—C7 | 0.2 (4) |
N1—C2—C3—C4 | −2.4 (3) | C8—C7—C12—C11 | 1.4 (3) |
C1—C2—C3—C4 | 176.5 (2) | N3—C7—C12—C11 | 179.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3i | 0.86 | 1.98 | 2.837 (2) | 173 |
N1—H1···O2i | 0.86 | 1.86 | 2.708 (2) | 169 |
C5—H5A···O1ii | 0.96 | 2.46 | 3.376 (3) | 159 |
C5—H5B···O3iii | 0.96 | 2.49 | 3.430 (2) | 165 |
C19—H19···O1ii | 0.93 | 2.37 | 3.289 (4) | 171 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x−1, y, z; (iii) −x+1, −y+2, −z+2. |
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