2-Anilino-4,6-dimethyl­pyrimidinium p-toluene­sulfonate

Li, J.-C.; Feng, Y.-H.; Lin, Q.; Zhang, D.-L.

doi:10.1107/S1600536807004722

2-Anilino-4,6-dimethylpyrimidinium p-toluenesulfonate

J.-C. Li, Y.-H. Feng, Q. Lin and D.-L. Zhang

In the crystal structure of the title compound, C₁₂H₁₄N₃⁺·C₇H₇O₃S⁻, cations and anions are linked by intermolecular N—H

O and C—H

O hydrogen-bonding interactions, forming channels running along the b axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004722/rz2098sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004722/rz2098Isup2.hkl Contains datablock I

CCDC reference: 640466

checkCIF report

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

Computing details top

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
M_r = 371.45	D_x = 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	R_int = 0.025
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.912, T_max = 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(F_o²) + (0.067P)² + 0.4961P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3303 reflections	Δρ_max = 0.24 e Å⁻³
255 parameters	Δρ_min = −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	U_iso*/U_eq
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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2-Anilino-4,6-dimethyl­pyrimidinium p-toluene­sulfonate

Supporting information

Key indicators

checkCIF/PLATON results

2-Anilino-4,6-dimethylpyrimidinium p-toluenesulfonate