Structure and Hirshfeld surface analysis of the salt N,N,N-trimethyl-1-(4-vinyl­phen­yl)methanaminium 4-vinyl­benzene­sulfonate

The mol­ecular and crystal structure of the salt N,N,N-trimethyl-1-(4-vinyl­phen­yl)methanaminium 4-vinyl­benzene­sulfonate is reported. A Hirshfeld surface analysis of the salt and its individual components is also presented.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.103
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0056 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15A     ..O1       .       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16B     ..O1       .       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H42B     ..O1       .       2.63 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         65 %

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          4 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          4 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        15% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         10 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         62 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b) and TITAN (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

N,N,N-Trimethyl-1-(4-vinylphenyl)methanaminium 4-vinylbenzenesulfonate

Crystal data

C12H18N^+·C8H7O3S^−	Dx = 1.280 Mg m^−3
Mr = 359.47	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 2591 reflections
a = 8.3344 (3) Å	θ = 4.2–72.3°
b = 10.5937 (4) Å	µ = 1.69 mm^−1
c = 21.1228 (8) Å	T = 100 K
V = 1864.98 (12) Å^3	Irregular block, colourless
Z = 4	0.20 × 0.18 × 0.08 mm
F(000) = 768

Data collection

Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas diffractometer	3103 independent reflections
Radiation source: micro-focus sealed X-ray tube	2784 reflections with I > 2σ(I)
Detector resolution: 5.1725 pixels mm^-1	Rint = 0.029
ω scans	θmax = 72.8°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	h = −6→10
Tmin = 0.911, Tmax = 1.000	k = −12→12
4767 measured reflections	l = −25→24

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0465P)^2 + 0.5842P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.103	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.37 e Å^−3
3103 reflections	Δρmin = −0.29 e Å^−3
248 parameters	Absolute structure: Flack x determined using 870 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
10 restraints	Absolute structure parameter: −0.040 (19)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The vinyl substituent on the benzene ring of the cation is disordered over two sites with a refined occupancy ratio of 0.542 (11):0.458 (11).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.7129 (3)	0.3773 (2)	0.23060 (11)	0.0340 (6)
O2	0.9047 (3)	0.2234 (2)	0.19192 (11)	0.0324 (6)
O3	0.6241 (3)	0.1666 (2)	0.20070 (11)	0.0316 (6)
S1	0.73918 (10)	0.26835 (7)	0.19052 (3)	0.0240 (2)
C1	0.7098 (4)	0.3210 (3)	0.11156 (14)	0.0213 (7)
C2	0.8167 (4)	0.4059 (3)	0.08477 (16)	0.0254 (7)
H2	0.901987	0.439140	0.109530	0.030*
C3	0.8000 (4)	0.4426 (3)	0.02186 (16)	0.0267 (8)
H3	0.873464	0.501524	0.004257	0.032*
C4	0.6771 (4)	0.3943 (3)	−0.01563 (16)	0.0259 (7)
C41	0.6602 (5)	0.4228 (3)	−0.08413 (17)	0.0304 (8)
H41	0.567919	0.390300	−0.104880	0.036*
C42	0.7607 (5)	0.4885 (3)	−0.11868 (16)	0.0351 (8)
H42A	0.854786	0.522910	−0.100025	0.042*
H42B	0.739494	0.501740	−0.162365	0.042*
C5	0.5676 (4)	0.3129 (3)	0.01217 (17)	0.0302 (8)
H5	0.480488	0.281673	−0.012223	0.036*
C6	0.5829 (4)	0.2760 (3)	0.07539 (16)	0.0283 (8)
H6	0.506511	0.220260	0.093620	0.034*
C7	0.3486 (4)	0.3494 (4)	0.39999 (17)	0.0282 (8)
C8	0.2924 (5)	0.4592 (4)	0.4279 (2)	0.0391 (10)
H8	0.270082	0.530860	0.402275	0.047*
C9	0.2687 (6)	0.4656 (5)	0.4924 (2)	0.0577 (14)
H9	0.228496	0.541594	0.510296	0.069*
C10	0.3017 (5)	0.3649 (6)	0.5319 (2)	0.0600 (15)
C101	0.2819 (10)	0.3361 (8)	0.6023 (3)	0.038 (2)	0.542 (11)
H101	0.324589	0.260969	0.620146	0.046*	0.542 (11)
C102	0.2045 (14)	0.4175 (8)	0.6374 (4)	0.066 (4)	0.542 (11)
H10A	0.162395	0.492277	0.618983	0.080*	0.542 (11)
H10B	0.190496	0.401869	0.681348	0.080*	0.542 (11)
C103	0.2724 (12)	0.4160 (9)	0.5973 (3)	0.033 (2)	0.458 (11)
H103	0.251488	0.503001	0.604321	0.040*	0.458 (11)
C104	0.2771 (11)	0.3345 (9)	0.6444 (4)	0.038 (3)	0.458 (11)
H10C	0.298320	0.247947	0.636175	0.045*	0.458 (11)
H10D	0.259356	0.362379	0.686556	0.045*	0.458 (11)
C11	0.3597 (5)	0.2564 (6)	0.5043 (2)	0.0538 (13)
H11	0.384283	0.185948	0.530359	0.065*
C12	0.3830 (5)	0.2473 (4)	0.43947 (19)	0.0385 (9)
H12	0.422829	0.171040	0.421795	0.046*
C13	0.3803 (4)	0.3451 (4)	0.32982 (17)	0.0329 (8)
H13A	0.468168	0.284452	0.321549	0.039*
H13B	0.417035	0.429445	0.315753	0.039*
C14	0.2826 (5)	0.3111 (5)	0.22225 (17)	0.0528 (13)
H14A	0.190237	0.290203	0.195519	0.079*
H14B	0.368715	0.249929	0.214829	0.079*
H14C	0.320828	0.396094	0.211787	0.079*
C15	0.0986 (4)	0.3955 (3)	0.30061 (19)	0.0330 (8)
H15A	0.010714	0.374402	0.271685	0.050*
H15B	0.134872	0.481981	0.292401	0.050*
H15C	0.061038	0.388818	0.344442	0.050*
N1	0.2336 (4)	0.3069 (3)	0.29050 (13)	0.0289 (7)
C16	0.1808 (5)	0.1749 (3)	0.3060 (2)	0.0444 (10)
H16A	0.148219	0.170607	0.350491	0.067*
H16B	0.269731	0.116280	0.298539	0.067*
H16C	0.089814	0.151749	0.278940	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0421 (16)	0.0313 (13)	0.0287 (12)	0.0004 (12)	0.0005 (11)	−0.0081 (10)
O2	0.0250 (12)	0.0454 (14)	0.0269 (12)	0.0102 (11)	−0.0034 (10)	−0.0010 (13)
O3	0.0370 (14)	0.0303 (13)	0.0275 (13)	−0.0076 (12)	−0.0008 (11)	0.0046 (11)
S1	0.0258 (4)	0.0259 (4)	0.0203 (3)	0.0004 (4)	−0.0009 (3)	−0.0022 (3)
C1	0.0243 (17)	0.0198 (14)	0.0198 (14)	0.0036 (14)	−0.0016 (13)	−0.0010 (12)
C2	0.0218 (16)	0.0237 (16)	0.0307 (17)	−0.0006 (15)	−0.0001 (14)	−0.0042 (14)
C3	0.0259 (18)	0.0232 (16)	0.0311 (17)	−0.0003 (15)	0.0064 (15)	0.0011 (14)
C4	0.0283 (18)	0.0244 (16)	0.0249 (17)	0.0043 (15)	−0.0011 (14)	−0.0019 (14)
C41	0.035 (2)	0.0286 (18)	0.0280 (18)	0.0035 (17)	−0.0043 (16)	0.0003 (15)
C42	0.035 (2)	0.0423 (19)	0.0275 (17)	0.005 (2)	0.0014 (18)	0.0049 (15)
C5	0.0280 (18)	0.0302 (18)	0.0324 (19)	−0.0023 (16)	−0.0100 (15)	0.0016 (15)
C6	0.0283 (18)	0.0257 (17)	0.0308 (18)	−0.0034 (16)	−0.0057 (14)	0.0030 (16)
C7	0.0211 (17)	0.0344 (19)	0.0292 (18)	−0.0060 (16)	−0.0032 (14)	−0.0010 (16)
C8	0.034 (2)	0.038 (2)	0.046 (2)	0.0006 (18)	−0.0138 (18)	−0.0090 (18)
C9	0.034 (2)	0.088 (4)	0.051 (3)	0.008 (3)	−0.013 (2)	−0.036 (3)
C10	0.031 (2)	0.116 (5)	0.034 (2)	−0.018 (3)	−0.0053 (18)	−0.012 (3)
C101	0.045 (5)	0.032 (5)	0.038 (5)	−0.016 (4)	−0.016 (4)	0.009 (4)
C102	0.126 (11)	0.043 (5)	0.030 (5)	−0.009 (6)	−0.009 (6)	0.005 (4)
C103	0.040 (5)	0.031 (5)	0.028 (5)	−0.003 (5)	−0.002 (4)	−0.001 (4)
C104	0.044 (6)	0.045 (6)	0.023 (5)	−0.010 (5)	0.002 (4)	0.002 (4)
C11	0.048 (3)	0.073 (3)	0.040 (2)	−0.026 (3)	−0.0168 (19)	0.025 (2)
C12	0.036 (2)	0.033 (2)	0.046 (2)	−0.007 (2)	−0.0098 (17)	0.0038 (18)
C13	0.0223 (17)	0.042 (2)	0.0347 (19)	−0.0019 (17)	−0.0027 (15)	0.0019 (17)
C14	0.039 (2)	0.094 (4)	0.0250 (19)	0.000 (3)	0.0010 (17)	−0.007 (2)
C15	0.0293 (18)	0.0291 (18)	0.041 (2)	0.0064 (16)	−0.0063 (17)	−0.0055 (17)
N1	0.0267 (15)	0.0331 (15)	0.0271 (14)	0.0018 (14)	−0.0027 (13)	−0.0027 (11)
C16	0.056 (2)	0.0216 (17)	0.055 (3)	−0.0022 (18)	−0.019 (2)	−0.0020 (19)

Geometric parameters (Å, º)

O1—S1	1.448 (2)	C10—C101	1.527 (7)
O2—S1	1.460 (2)	C101—C102	1.307 (9)
O3—S1	1.459 (2)	C101—H101	0.9500
S1—C1	1.776 (3)	C102—H10A	0.9500
C1—C2	1.387 (4)	C102—H10B	0.9500
C1—C6	1.389 (5)	C103—C104	1.317 (9)
C2—C3	1.392 (5)	C103—H103	0.9500
C2—H2	0.9500	C104—H10C	0.9500
C3—C4	1.392 (5)	C104—H10D	0.9500
C3—H3	0.9500	C11—C12	1.387 (6)
C4—C5	1.386 (5)	C11—H11	0.9500
C4—C41	1.485 (5)	C12—H12	0.9500
C41—C42	1.311 (5)	C13—N1	1.533 (5)
C41—H41	0.9500	C13—H13A	0.9900
C42—H42A	0.9500	C13—H13B	0.9900
C42—H42B	0.9500	C14—N1	1.499 (4)
C5—C6	1.397 (4)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C6—H6	0.9500	C14—H14C	0.9800
C7—C8	1.386 (5)	C15—N1	1.481 (4)
C7—C12	1.395 (5)	C15—H15A	0.9800
C7—C13	1.506 (5)	C15—H15B	0.9800
C8—C9	1.380 (6)	C15—H15C	0.9800
C8—H8	0.9500	N1—C16	1.501 (4)
C9—C10	1.382 (8)	C16—H16A	0.9800
C9—H9	0.9500	C16—H16B	0.9800
C10—C11	1.376 (8)	C16—H16C	0.9800
C10—C103	1.504 (7)
O1—S1—O3	113.77 (15)	C10—C101—H101	120.8
O1—S1—O2	113.04 (15)	C101—C102—H10A	120.0
O3—S1—O2	112.16 (16)	C101—C102—H10B	120.0
O1—S1—C1	106.15 (14)	H10A—C102—H10B	120.0
O3—S1—C1	106.25 (15)	C104—C103—C10	116.9 (8)
O2—S1—C1	104.59 (15)	C104—C103—H103	121.5
C2—C1—C6	119.2 (3)	C10—C103—H103	121.5
C2—C1—S1	119.9 (2)	C103—C104—H10C	120.0
C6—C1—S1	120.9 (3)	C103—C104—H10D	120.0
C1—C2—C3	120.4 (3)	H10C—C104—H10D	120.0
C1—C2—H2	119.8	C10—C11—C12	121.7 (5)
C3—C2—H2	119.8	C10—C11—H11	119.1
C2—C3—C4	120.9 (3)	C12—C11—H11	119.1
C2—C3—H3	119.5	C11—C12—C7	120.5 (4)
C4—C3—H3	119.5	C11—C12—H12	119.8
C5—C4—C3	118.2 (3)	C7—C12—H12	119.8
C5—C4—C41	118.5 (3)	C7—C13—N1	113.7 (3)
C3—C4—C41	123.3 (3)	C7—C13—H13A	108.8
C42—C41—C4	126.1 (4)	N1—C13—H13A	108.8
C42—C41—H41	116.9	C7—C13—H13B	108.8
C4—C41—H41	116.9	N1—C13—H13B	108.8
C41—C42—H42A	120.0	H13A—C13—H13B	107.7
C41—C42—H42B	120.0	N1—C14—H14A	109.5
H42A—C42—H42B	120.0	N1—C14—H14B	109.5
C4—C5—C6	121.3 (3)	H14A—C14—H14B	109.5
C4—C5—H5	119.4	N1—C14—H14C	109.5
C6—C5—H5	119.4	H14A—C14—H14C	109.5
C1—C6—C5	119.9 (3)	H14B—C14—H14C	109.5
C1—C6—H6	120.0	N1—C15—H15A	109.5
C5—C6—H6	120.0	N1—C15—H15B	109.5
C8—C7—C12	117.8 (4)	H15A—C15—H15B	109.5
C8—C7—C13	120.1 (4)	N1—C15—H15C	109.5
C12—C7—C13	121.9 (4)	H15A—C15—H15C	109.5
C9—C8—C7	120.6 (4)	H15B—C15—H15C	109.5
C9—C8—H8	119.7	C15—N1—C16	109.7 (3)
C7—C8—H8	119.7	C15—N1—C14	109.1 (3)
C8—C9—C10	122.0 (5)	C16—N1—C14	108.5 (3)
C8—C9—H9	119.0	C15—N1—C13	111.1 (3)
C10—C9—H9	119.0	C16—N1—C13	111.2 (3)
C11—C10—C9	117.4 (4)	C14—N1—C13	107.2 (3)
C11—C10—C103	138.3 (6)	N1—C16—H16A	109.5
C9—C10—C103	104.1 (6)	N1—C16—H16B	109.5
C11—C10—C101	106.5 (6)	H16A—C16—H16B	109.5
C9—C10—C101	136.0 (6)	N1—C16—H16C	109.5
C102—C101—C10	118.3 (8)	H16A—C16—H16C	109.5
C102—C101—H101	120.8	H16B—C16—H16C	109.5
O1—S1—C1—C2	67.5 (3)	C7—C8—C9—C10	1.0 (7)
O3—S1—C1—C2	−171.1 (2)	C8—C9—C10—C11	−0.1 (7)
O2—S1—C1—C2	−52.3 (3)	C8—C9—C10—C103	175.4 (6)
O1—S1—C1—C6	−114.1 (3)	C8—C9—C10—C101	−175.7 (6)
O3—S1—C1—C6	7.3 (3)	C11—C10—C101—C102	−169.3 (7)
O2—S1—C1—C6	126.1 (3)	C9—C10—C101—C102	6.6 (12)
C6—C1—C2—C3	−1.9 (5)	C11—C10—C103—C104	−13.7 (13)
S1—C1—C2—C3	176.5 (3)	C9—C10—C103—C104	172.3 (8)
C1—C2—C3—C4	−0.7 (5)	C9—C10—C11—C12	−0.6 (7)
C2—C3—C4—C5	2.9 (5)	C103—C10—C11—C12	−174.0 (7)
C2—C3—C4—C41	−175.4 (3)	C101—C10—C11—C12	176.3 (5)
C5—C4—C41—C42	−173.8 (4)	C10—C11—C12—C7	0.2 (6)
C3—C4—C41—C42	4.5 (6)	C8—C7—C12—C11	0.7 (5)
C3—C4—C5—C6	−2.5 (5)	C13—C7—C12—C11	176.9 (4)
C41—C4—C5—C6	175.9 (3)	C8—C7—C13—N1	−88.7 (4)
C2—C1—C6—C5	2.3 (5)	C12—C7—C13—N1	95.2 (4)
S1—C1—C6—C5	−176.2 (3)	C7—C13—N1—C15	59.1 (4)
C4—C5—C6—C1	−0.1 (6)	C7—C13—N1—C16	−63.3 (4)
C12—C7—C8—C9	−1.3 (6)	C7—C13—N1—C14	178.2 (3)
C13—C7—C8—C9	−177.6 (4)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O3	0.98	2.32	3.264 (5)	161
C14—H14A···O2^i	0.98	2.48	3.346 (5)	147
C15—H15A···O1^i	0.98	2.63	3.544 (4)	155
C15—H15A···O2^i	0.98	2.49	3.348 (4)	147
C13—H13B···O3^ii	0.99	2.56	3.466 (5)	152
C15—H15B···O2^ii	0.98	2.60	3.477 (4)	149
C16—H16B···O1^iii	0.98	2.61	3.365 (4)	134
C16—H16C···O2^i	0.98	2.52	3.370 (5)	146
C41—H41···O2^iv	0.95	2.58	3.481 (4)	157
C42—H42B···O1^v	0.95	2.63	3.494 (4)	151
C5—H5···Cg1^iv	0.95	2.93	3.837 (4)	161

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1/2, −y+1/2, −z; (v) −x+3/2, −y+1, z−1/2.