The structure and Hirshfeld surface analysis of the salt 3-methacryl­amido-N,N,N-tri­methyl­propan-1-aminium 2-acryl­amido-2-methyl­propane-1-sulfonate

Wickramasinhage, R.N.; McAdam, C.J.; Hanton, L.R.; Moratti, S.C.; Simpson, J.

doi:10.1107/S2056989019012003

The structure and Hirshfeld surface analysis of the salt 3-methacrylamido-N,N,N-trimethylpropan-1-aminium 2-acrylamido-2-methylpropane-1-sulfonate

R. N. Wickramasinhage, C. J. McAdam, L. R. Hanton, S. C. Moratti and J. Simpson

The molecular and crystal structure of the salt 3-methacrylamido-N,N,N-trimethylpropan-1-aminium 2-acrylamido-2-methylpropane-1-sulfonate, that crystallizes with two unique pairs of cations and anions in the asymmetric unit, is reported. Hirshfeld surface analysis of the asymmetric unit and of the two individual salts is also carried out.

Keywords: crystal structure; 3-methacrylamido-N,N,N-trimethylpropan-1-aminium; 2-acrylamido-2-methylpropane-1-sulfonate; hydrogen bonding; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019012003/vm2221sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019012003/vm2221Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019012003/vm2221Isup3.cml Supplementary material

CCDC reference: 1950279

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.009 Å
R factor = 0.060
wR factor = 0.173
Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT915_ALERT_3_B No Flack x Check Done: Low Friedel Pair Coverage         46 %

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.470
           From the CIF: _refine_ls_abs_structure_Flack_su    0.040
PLAT213_ALERT_2_C Atom O23             has ADP max/min Ratio .....        3.1 prolat
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S2 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0088 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12A     ..O14      .       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13B     ..O12      .       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19A     ..O24      .       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B     ..O21      .       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H116     ..O11      .       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11N     ..N12      .       2.73 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23B     ..O22      .       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21F     ..O21      .       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H216     ..O21      .       2.69 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          5 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.10 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         31 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        120 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

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

Computing details top

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: SHELXL2018 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip 2010) and WinGX (Farrugia, 2012).

3-Methacrylamido-N,N,N-trimethylpropan-1-aminium 2-acrylamido-2-methylpropane-1-sulfonate top

Crystal data top

C₁₀H₂₁N₂O⁺·C₇H₁₂NO₄S⁻	D_x = 1.255 Mg m⁻³
M_r = 391.52	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pca2₁	Cell parameters from 4725 reflections
a = 17.5093 (7) Å	θ = 5.2–72.8°
b = 7.8052 (3) Å	µ = 1.65 mm⁻¹
c = 30.3155 (13) Å	T = 100 K
V = 4143.0 (3) Å³	Plate, colourless
Z = 8	0.46 × 0.27 × 0.11 mm
F(000) = 1696

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	5961 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	5040 reflections with I > 2σ(I)
Detector resolution: 5.1725 pixels mm^-1	R_int = 0.054
ω scans	θ_max = 72.8°, θ_min = 5.1°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	h = −21→15
T_min = 0.589, T_max = 1.000	k = −9→6
10436 measured reflections	l = −36→36

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.060	w = 1/[σ²(F_o²) + (0.1018P)² + 1.0621P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.173	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.64 e Å⁻³
5961 reflections	Δρ_min = −0.32 e Å⁻³
494 parameters	Absolute structure: Refined as an inversion twin.
31 restraints	Absolute structure parameter: 0.47 (4)

Special details top

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. Refined as a 2-component inversion twin. Two reflections with Fo >>> Fc were omitted from the final refinement cycles.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C18	0.6830 (4)	0.9831 (8)	0.5183 (3)	0.0247 (16)
H18A	0.690198	0.878168	0.535604	0.037*
H18B	0.693085	1.083025	0.537028	0.037*
H18C	0.718325	0.983217	0.493281	0.037*
C19	0.5921 (5)	1.1545 (9)	0.4766 (3)	0.0349 (17)
H19A	0.595183	1.252064	0.496889	0.052*
H19B	0.541887	1.153142	0.462385	0.052*
H19C	0.631985	1.165139	0.454063	0.052*
C110	0.5495 (5)	0.9882 (10)	0.5403 (3)	0.037 (2)
H11A	0.560070	1.086234	0.559514	0.055*
H11B	0.556169	0.881640	0.556894	0.055*
H11C	0.496835	0.995378	0.529420	0.055*
N11	0.6035 (4)	0.9905 (6)	0.5019 (2)	0.0258 (14)
C11	0.5863 (4)	0.8365 (8)	0.4734 (2)	0.0247 (14)
H11D	0.530261	0.826601	0.470045	0.030*
H11E	0.604392	0.732378	0.488861	0.030*
C12	0.6220 (3)	0.8411 (7)	0.4280 (2)	0.0250 (12)
H12A	0.677882	0.857686	0.430586	0.030*
H12B	0.600668	0.937774	0.410867	0.030*
C13	0.6053 (3)	0.6730 (7)	0.4046 (2)	0.0249 (12)
H13A	0.637844	0.581781	0.417331	0.030*
H13B	0.551289	0.640957	0.409807	0.030*
N12	0.6191 (3)	0.6838 (6)	0.35712 (17)	0.0224 (10)
H12N	0.578 (4)	0.693 (9)	0.343 (3)	0.027*
C14	0.6881 (3)	0.6571 (7)	0.3401 (2)	0.0198 (11)
O11	0.7443 (2)	0.6223 (6)	0.36331 (15)	0.0272 (9)
C15	0.6946 (4)	0.6717 (8)	0.2908 (2)	0.0261 (13)
C16	0.7639 (4)	0.6354 (9)	0.2722 (2)	0.0358 (15)
H16A	0.770611	0.644668	0.241236	0.043*
H16B	0.805393	0.600812	0.290379	0.043*
C17	0.6299 (4)	0.7244 (13)	0.2650 (3)	0.047 (2)
H17A	0.644894	0.733716	0.233933	0.071*
H17B	0.611814	0.835987	0.275506	0.071*
H17C	0.588996	0.639623	0.267955	0.071*
O12	0.4219 (3)	0.8164 (6)	0.42637 (18)	0.0348 (11)
O13	0.4113 (5)	1.1199 (7)	0.4319 (2)	0.067 (2)
O14	0.3005 (3)	0.9400 (12)	0.4408 (2)	0.070 (2)
S1	0.37335 (9)	0.9620 (2)	0.41979 (5)	0.0265 (4)
C111	0.3578 (4)	0.9838 (7)	0.3621 (3)	0.0221 (15)
H11F	0.330598	1.093499	0.357282	0.026*
H11G	0.408354	0.994452	0.347790	0.026*
C112	0.3129 (3)	0.8423 (7)	0.33741 (19)	0.0195 (11)
C113	0.2292 (3)	0.8345 (8)	0.3513 (2)	0.0302 (14)
H11H	0.203429	0.742638	0.335013	0.045*
H11I	0.204478	0.944182	0.344692	0.045*
H11J	0.225960	0.811578	0.382995	0.045*
C114	0.3169 (4)	0.8832 (9)	0.2880 (2)	0.0285 (13)
H11K	0.370443	0.891877	0.278843	0.043*
H11L	0.290935	0.992159	0.282197	0.043*
H11M	0.291816	0.791602	0.271238	0.043*
N13	0.3453 (3)	0.6713 (6)	0.34566 (17)	0.0204 (10)
H13N	0.309 (4)	0.600 (9)	0.354 (2)	0.025*
C115	0.4176 (3)	0.6236 (7)	0.33943 (19)	0.0198 (11)
O15	0.4681 (2)	0.7184 (5)	0.32397 (14)	0.0233 (8)
C116	0.4340 (3)	0.4425 (8)	0.3526 (2)	0.0238 (12)
H116	0.396813	0.383181	0.369559	0.029*
C117	0.4965 (4)	0.3618 (8)	0.3420 (3)	0.0337 (15)
H11N	0.534618	0.418056	0.324986	0.040*
H11O	0.504003	0.246658	0.351177	0.040*
C28	0.4323 (4)	0.4759 (9)	0.4825 (3)	0.0251 (16)
H28A	0.438522	0.577869	0.464020	0.038*
H28B	0.440159	0.372881	0.464636	0.038*
H28C	0.469854	0.478512	0.506503	0.038*
C29	0.3427 (5)	0.3137 (9)	0.5288 (3)	0.0353 (17)
H29A	0.381784	0.309600	0.551935	0.053*
H29B	0.347640	0.212808	0.509783	0.053*
H29C	0.291909	0.314495	0.542420	0.053*
C210	0.2971 (4)	0.4666 (10)	0.4641 (3)	0.0319 (16)
H21A	0.245390	0.450262	0.475731	0.048*
H21B	0.310127	0.370769	0.444590	0.048*
H21C	0.299313	0.574064	0.447434	0.048*
N21	0.3530 (3)	0.4736 (6)	0.5017 (2)	0.0192 (11)
C21	0.3369 (4)	0.6330 (8)	0.5277 (2)	0.0246 (14)
H21D	0.280949	0.644582	0.531300	0.030*
H21E	0.355032	0.733184	0.510638	0.030*
C22	0.3744 (3)	0.6368 (8)	0.5736 (2)	0.0264 (12)
H22A	0.353621	0.543142	0.592074	0.032*
H22B	0.430212	0.620149	0.570793	0.032*
C23	0.3579 (3)	0.8094 (8)	0.59519 (19)	0.0257 (13)
H23A	0.390392	0.898458	0.581496	0.031*
H23B	0.303840	0.840767	0.589997	0.031*
N22	0.3725 (3)	0.8040 (6)	0.64248 (17)	0.0223 (10)
H22N	0.332 (4)	0.785 (9)	0.662 (2)	0.027*
C24	0.4405 (3)	0.8420 (7)	0.6600 (2)	0.0214 (11)
O21	0.4954 (2)	0.8854 (5)	0.63690 (15)	0.0255 (9)
C25	0.4467 (3)	0.8314 (8)	0.7094 (2)	0.0242 (12)
C26	0.5143 (4)	0.8731 (9)	0.7281 (2)	0.0354 (15)
H26A	0.520137	0.868026	0.759239	0.042*
H26B	0.555964	0.907559	0.710104	0.042*
C27	0.3810 (4)	0.7778 (11)	0.7356 (2)	0.0415 (17)
H27A	0.395103	0.775397	0.766843	0.062*
H27B	0.364896	0.663109	0.726266	0.062*
H27C	0.338970	0.858807	0.731144	0.062*
O22	0.1734 (3)	0.6760 (6)	0.57622 (17)	0.0310 (10)
O23	0.1667 (4)	0.3726 (7)	0.5717 (2)	0.0591 (18)
O24	0.0536 (3)	0.5449 (11)	0.5619 (2)	0.0624 (19)
S2	0.12650 (9)	0.52727 (18)	0.58283 (5)	0.0240 (4)
C211	0.1106 (5)	0.5078 (7)	0.6408 (3)	0.0217 (15)
H21F	0.083063	0.398716	0.645875	0.026*
H21G	0.161104	0.496867	0.655210	0.026*
C212	0.0661 (3)	0.6508 (7)	0.6651 (2)	0.0215 (11)
C213	−0.0178 (3)	0.6588 (8)	0.6509 (2)	0.0304 (14)
H21H	−0.043509	0.751535	0.666856	0.046*
H21I	−0.042740	0.549617	0.657698	0.046*
H21J	−0.020728	0.680539	0.619112	0.046*
C214	0.0700 (4)	0.6112 (8)	0.7144 (2)	0.0274 (13)
H21K	0.123502	0.609082	0.723913	0.041*
H21L	0.046610	0.499244	0.720077	0.041*
H21M	0.042408	0.699737	0.730856	0.041*
N23	0.0982 (3)	0.8228 (6)	0.65627 (16)	0.0205 (10)
H23N	0.071 (4)	0.904 (10)	0.649 (2)	0.025*
C215	0.1711 (3)	0.8691 (8)	0.6618 (2)	0.0215 (12)
O25	0.2210 (2)	0.7750 (5)	0.67734 (14)	0.0240 (9)
C216	0.1867 (3)	1.0492 (8)	0.6480 (2)	0.0234 (12)
H216	0.148817	1.107951	0.631384	0.028*
C217	0.2507 (3)	1.1311 (8)	0.6577 (3)	0.0346 (16)
H21N	0.289415	1.075050	0.674228	0.041*
H21O	0.257890	1.245841	0.648134	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C18	0.025 (4)	0.027 (3)	0.022 (4)	−0.002 (2)	0.001 (3)	−0.002 (2)
C19	0.054 (5)	0.028 (3)	0.022 (4)	0.017 (3)	−0.003 (3)	0.001 (3)
C110	0.026 (4)	0.055 (5)	0.028 (4)	−0.002 (3)	0.013 (3)	−0.010 (3)
N11	0.031 (3)	0.027 (3)	0.019 (3)	0.003 (2)	0.004 (3)	−0.0038 (19)
C11	0.024 (3)	0.031 (3)	0.019 (3)	−0.008 (2)	0.003 (3)	−0.005 (2)
C12	0.023 (3)	0.030 (3)	0.022 (3)	−0.001 (2)	0.001 (2)	−0.005 (2)
C13	0.024 (3)	0.026 (3)	0.025 (3)	−0.002 (2)	−0.001 (2)	−0.004 (2)
N12	0.020 (2)	0.027 (2)	0.021 (2)	0.0001 (19)	−0.004 (2)	−0.0041 (19)
C14	0.017 (2)	0.015 (2)	0.027 (3)	−0.002 (2)	0.000 (2)	−0.004 (2)
O11	0.0191 (19)	0.035 (2)	0.028 (2)	0.0022 (16)	−0.0012 (17)	−0.0033 (19)
C15	0.031 (3)	0.023 (3)	0.024 (3)	−0.004 (2)	0.004 (2)	−0.001 (2)
C16	0.031 (3)	0.047 (4)	0.029 (3)	0.012 (3)	0.005 (3)	0.009 (3)
C17	0.023 (3)	0.087 (6)	0.032 (4)	0.009 (4)	0.003 (3)	0.018 (4)
O12	0.046 (2)	0.030 (2)	0.028 (3)	0.0111 (19)	−0.012 (2)	−0.002 (2)
O13	0.128 (6)	0.029 (3)	0.044 (4)	−0.008 (3)	−0.038 (4)	−0.004 (3)
O14	0.031 (3)	0.154 (6)	0.024 (3)	0.020 (4)	0.002 (2)	0.006 (4)
S1	0.0313 (9)	0.0304 (8)	0.0177 (8)	0.0080 (6)	−0.0038 (7)	−0.0061 (7)
C111	0.021 (3)	0.021 (3)	0.024 (5)	−0.002 (2)	−0.002 (3)	−0.002 (2)
C112	0.019 (3)	0.015 (2)	0.025 (3)	0.003 (2)	−0.002 (2)	−0.007 (2)
C113	0.020 (3)	0.028 (3)	0.042 (4)	0.005 (2)	0.005 (3)	−0.003 (3)
C114	0.031 (3)	0.032 (3)	0.022 (3)	0.009 (3)	−0.004 (3)	−0.004 (2)
N13	0.017 (2)	0.021 (2)	0.023 (2)	−0.0006 (18)	0.0009 (19)	−0.0006 (19)
C115	0.019 (3)	0.024 (3)	0.016 (3)	−0.003 (2)	0.000 (2)	−0.006 (2)
O15	0.0176 (18)	0.029 (2)	0.024 (2)	−0.0012 (16)	0.0026 (16)	−0.0008 (17)
C116	0.022 (3)	0.021 (3)	0.029 (3)	0.003 (2)	−0.002 (2)	0.001 (3)
C117	0.029 (3)	0.023 (3)	0.049 (4)	0.000 (2)	0.002 (3)	−0.012 (3)
C28	0.017 (3)	0.035 (3)	0.024 (4)	0.000 (2)	0.003 (3)	−0.005 (3)
C29	0.051 (5)	0.024 (3)	0.031 (4)	−0.009 (3)	0.006 (3)	0.002 (3)
C210	0.022 (4)	0.049 (4)	0.025 (4)	0.000 (3)	−0.002 (3)	−0.011 (3)
N21	0.013 (2)	0.025 (2)	0.020 (3)	−0.0014 (18)	0.000 (2)	−0.003 (2)
C21	0.023 (3)	0.029 (3)	0.022 (3)	0.002 (2)	−0.003 (3)	−0.007 (3)
C22	0.025 (3)	0.034 (3)	0.021 (3)	0.005 (2)	0.000 (2)	−0.004 (2)
C23	0.024 (3)	0.034 (3)	0.019 (3)	−0.001 (2)	−0.005 (2)	0.001 (2)
N22	0.016 (2)	0.031 (2)	0.020 (2)	−0.0014 (19)	0.0027 (19)	−0.002 (2)
C24	0.023 (3)	0.020 (3)	0.021 (3)	−0.003 (2)	0.000 (2)	−0.002 (2)
O21	0.0214 (19)	0.030 (2)	0.025 (2)	−0.0029 (17)	0.0025 (17)	−0.0014 (18)
C25	0.026 (3)	0.024 (3)	0.023 (3)	0.002 (2)	0.003 (2)	−0.002 (2)
C26	0.038 (3)	0.043 (4)	0.026 (3)	−0.012 (3)	−0.006 (3)	0.012 (3)
C27	0.028 (3)	0.072 (5)	0.024 (3)	−0.007 (3)	0.000 (3)	0.007 (3)
O22	0.038 (2)	0.031 (2)	0.024 (2)	−0.0106 (18)	0.0061 (19)	−0.0002 (19)
O23	0.116 (5)	0.030 (3)	0.032 (3)	0.013 (3)	0.034 (3)	−0.006 (2)
O24	0.034 (3)	0.130 (5)	0.023 (3)	−0.025 (3)	−0.003 (2)	0.006 (4)
S2	0.0250 (8)	0.0296 (8)	0.0173 (8)	−0.0039 (6)	0.0017 (6)	−0.0010 (7)
C211	0.034 (4)	0.017 (3)	0.014 (4)	0.005 (2)	0.000 (3)	−0.0022 (19)
C212	0.019 (2)	0.020 (3)	0.026 (3)	−0.004 (2)	0.003 (2)	−0.002 (2)
C213	0.026 (3)	0.032 (3)	0.033 (4)	0.000 (2)	−0.001 (3)	−0.002 (3)
C214	0.028 (3)	0.033 (3)	0.022 (3)	−0.004 (2)	0.005 (2)	−0.003 (3)
N23	0.022 (2)	0.019 (2)	0.021 (2)	0.0039 (18)	−0.0001 (19)	0.0009 (19)
C215	0.020 (3)	0.025 (3)	0.019 (3)	0.000 (2)	0.001 (2)	−0.007 (2)
O25	0.0188 (19)	0.029 (2)	0.024 (2)	0.0009 (16)	−0.0004 (16)	0.0006 (18)
C216	0.022 (3)	0.023 (3)	0.025 (3)	0.004 (2)	−0.003 (2)	−0.003 (3)
C217	0.025 (3)	0.025 (3)	0.053 (4)	−0.003 (2)	0.001 (3)	−0.004 (3)

Geometric parameters (Å, º) top

C18—N11	1.479 (10)	C28—N21	1.504 (9)
C18—H18A	0.9800	C28—H28A	0.9800
C18—H18B	0.9800	C28—H28B	0.9800
C18—H18C	0.9800	C28—H28C	0.9800
C19—N11	1.506 (9)	C29—N21	1.506 (9)
C19—H19A	0.9800	C29—H29A	0.9800
C19—H19B	0.9800	C29—H29B	0.9800
C19—H19C	0.9800	C29—H29C	0.9800
C110—N11	1.498 (11)	C210—N21	1.504 (10)
C110—H11A	0.9800	C210—H21A	0.9800
C110—H11B	0.9800	C210—H21B	0.9800
C110—H11C	0.9800	C210—H21C	0.9800
N11—C11	1.511 (8)	N21—C21	1.500 (8)
C11—C12	1.511 (9)	C21—C22	1.539 (9)
C11—H11D	0.9900	C21—H21D	0.9900
C11—H11E	0.9900	C21—H21E	0.9900
C12—C13	1.520 (8)	C22—C23	1.525 (8)
C12—H12A	0.9900	C22—H22A	0.9900
C12—H12B	0.9900	C22—H22B	0.9900
C13—N12	1.463 (7)	C23—N22	1.457 (7)
C13—H13A	0.9900	C23—H23A	0.9900
C13—H13B	0.9900	C23—H23B	0.9900
N12—C14	1.330 (7)	N22—C24	1.338 (7)
N12—H12N	0.84 (7)	N22—H22N	0.93 (7)
C14—O11	1.239 (7)	C24—O21	1.236 (7)
C14—C15	1.505 (8)	C24—C25	1.505 (8)
C15—C16	1.367 (9)	C25—C26	1.352 (9)
C15—C17	1.436 (9)	C25—C27	1.457 (9)
C16—H16A	0.9500	C26—H26A	0.9500
C16—H16B	0.9500	C26—H26B	0.9500
C17—H17A	0.9800	C27—H27A	0.9800
C17—H17B	0.9800	C27—H27B	0.9800
C17—H17C	0.9800	C27—H27C	0.9800
O12—S1	1.434 (5)	O22—S2	1.436 (4)
O13—S1	1.447 (6)	O23—S2	1.437 (6)
O14—S1	1.436 (7)	O24—S2	1.432 (7)
S1—C111	1.778 (8)	S2—C211	1.786 (8)
C111—C112	1.548 (8)	C211—C212	1.547 (8)
C111—H11F	0.9900	C211—H21F	0.9900
C111—H11G	0.9900	C211—H21G	0.9900
C112—N13	1.472 (7)	C212—N23	1.479 (7)
C112—C113	1.526 (7)	C212—C214	1.529 (8)
C112—C114	1.534 (8)	C212—C213	1.532 (8)
C113—H11H	0.9800	C213—H21H	0.9800
C113—H11I	0.9800	C213—H21I	0.9800
C113—H11J	0.9800	C213—H21J	0.9800
C114—H11K	0.9800	C214—H21K	0.9800
C114—H11L	0.9800	C214—H21L	0.9800
C114—H11M	0.9800	C214—H21M	0.9800
N13—C115	1.333 (7)	N23—C215	1.338 (7)
N13—H13N	0.88 (7)	N23—H23N	0.82 (7)
C115—O15	1.245 (7)	C215—O25	1.235 (7)
C115—C116	1.496 (8)	C215—C216	1.492 (9)
C116—C117	1.304 (9)	C216—C217	1.323 (9)
C116—H116	0.9500	C216—H216	0.9500
C117—H11N	0.9500	C217—H21N	0.9500
C117—H11O	0.9500	C217—H21O	0.9500

N11—C18—H18A	109.5	N21—C28—H28A	109.5
N11—C18—H18B	109.5	N21—C28—H28B	109.5
H18A—C18—H18B	109.5	H28A—C28—H28B	109.5
N11—C18—H18C	109.5	N21—C28—H28C	109.5
H18A—C18—H18C	109.5	H28A—C28—H28C	109.5
H18B—C18—H18C	109.5	H28B—C28—H28C	109.5
N11—C19—H19A	109.5	N21—C29—H29A	109.5
N11—C19—H19B	109.5	N21—C29—H29B	109.5
H19A—C19—H19B	109.5	H29A—C29—H29B	109.5
N11—C19—H19C	109.5	N21—C29—H29C	109.5
H19A—C19—H19C	109.5	H29A—C29—H29C	109.5
H19B—C19—H19C	109.5	H29B—C29—H29C	109.5
N11—C110—H11A	109.5	N21—C210—H21A	109.5
N11—C110—H11B	109.5	N21—C210—H21B	109.5
H11A—C110—H11B	109.5	H21A—C210—H21B	109.5
N11—C110—H11C	109.5	N21—C210—H21C	109.5
H11A—C110—H11C	109.5	H21A—C210—H21C	109.5
H11B—C110—H11C	109.5	H21B—C210—H21C	109.5
C18—N11—C110	109.4 (7)	C21—N21—C210	107.8 (5)
C18—N11—C19	109.2 (6)	C21—N21—C28	111.5 (5)
C110—N11—C19	108.8 (6)	C210—N21—C28	108.0 (6)
C18—N11—C11	110.4 (5)	C21—N21—C29	112.2 (6)
C110—N11—C11	108.0 (6)	C210—N21—C29	107.8 (6)
C19—N11—C11	111.0 (6)	C28—N21—C29	109.4 (6)
N11—C11—C12	114.8 (5)	N21—C21—C22	114.3 (5)
N11—C11—H11D	108.6	N21—C21—H21D	108.7
C12—C11—H11D	108.6	C22—C21—H21D	108.7
N11—C11—H11E	108.6	N21—C21—H21E	108.7
C12—C11—H11E	108.6	C22—C21—H21E	108.7
H11D—C11—H11E	107.5	H21D—C21—H21E	107.6
C11—C12—C13	108.9 (5)	C23—C22—C21	108.9 (5)
C11—C12—H12A	109.9	C23—C22—H22A	109.9
C13—C12—H12A	109.9	C21—C22—H22A	109.9
C11—C12—H12B	109.9	C23—C22—H22B	109.9
C13—C12—H12B	109.9	C21—C22—H22B	109.9
H12A—C12—H12B	108.3	H22A—C22—H22B	108.3
N12—C13—C12	112.2 (5)	N22—C23—C22	111.3 (5)
N12—C13—H13A	109.2	N22—C23—H23A	109.4
C12—C13—H13A	109.2	C22—C23—H23A	109.4
N12—C13—H13B	109.2	N22—C23—H23B	109.4
C12—C13—H13B	109.2	C22—C23—H23B	109.4
H13A—C13—H13B	107.9	H23A—C23—H23B	108.0
C14—N12—C13	121.5 (5)	C24—N22—C23	122.7 (5)
C14—N12—H12N	127 (5)	C24—N22—H22N	118 (4)
C13—N12—H12N	111 (5)	C23—N22—H22N	119 (4)
O11—C14—N12	122.4 (6)	O21—C24—N22	121.9 (5)
O11—C14—C15	121.4 (5)	O21—C24—C25	121.6 (5)
N12—C14—C15	116.2 (5)	N22—C24—C25	116.5 (5)
C16—C15—C17	122.4 (6)	C26—C25—C27	122.2 (6)
C16—C15—C14	117.4 (6)	C26—C25—C24	117.8 (5)
C17—C15—C14	120.2 (5)	C27—C25—C24	120.1 (5)
C15—C16—H16A	120.0	C25—C26—H26A	120.0
C15—C16—H16B	120.0	C25—C26—H26B	120.0
H16A—C16—H16B	120.0	H26A—C26—H26B	120.0
C15—C17—H17A	109.5	C25—C27—H27A	109.5
C15—C17—H17B	109.5	C25—C27—H27B	109.5
H17A—C17—H17B	109.5	H27A—C27—H27B	109.5
C15—C17—H17C	109.5	C25—C27—H27C	109.5
H17A—C17—H17C	109.5	H27A—C27—H27C	109.5
H17B—C17—H17C	109.5	H27B—C27—H27C	109.5
O12—S1—O14	111.7 (4)	O24—S2—O22	111.7 (4)
O12—S1—O13	111.6 (4)	O24—S2—O23	114.4 (5)
O14—S1—O13	113.4 (5)	O22—S2—O23	111.5 (4)
O12—S1—C111	107.7 (3)	O24—S2—C211	107.8 (4)
O14—S1—C111	108.1 (4)	O22—S2—C211	107.2 (3)
O13—S1—C111	103.8 (3)	O23—S2—C211	103.6 (3)
C112—C111—S1	119.0 (5)	C212—C211—S2	119.0 (5)
C112—C111—H11F	107.6	C212—C211—H21F	107.6
S1—C111—H11F	107.6	S2—C211—H21F	107.6
C112—C111—H11G	107.6	C212—C211—H21G	107.6
S1—C111—H11G	107.6	S2—C211—H21G	107.6
H11F—C111—H11G	107.0	H21F—C211—H21G	107.0
N13—C112—C113	106.7 (5)	N23—C212—C214	110.1 (5)
N13—C112—C114	109.7 (4)	N23—C212—C213	106.0 (5)
C113—C112—C114	108.7 (5)	C214—C212—C213	109.0 (5)
N13—C112—C111	111.7 (5)	N23—C212—C211	112.3 (5)
C113—C112—C111	112.5 (5)	C214—C212—C211	107.3 (5)
C114—C112—C111	107.5 (5)	C213—C212—C211	112.3 (5)
C112—C113—H11H	109.5	C212—C213—H21H	109.5
C112—C113—H11I	109.5	C212—C213—H21I	109.5
H11H—C113—H11I	109.5	H21H—C213—H21I	109.5
C112—C113—H11J	109.5	C212—C213—H21J	109.5
H11H—C113—H11J	109.5	H21H—C213—H21J	109.5
H11I—C113—H11J	109.5	H21I—C213—H21J	109.5
C112—C114—H11K	109.5	C212—C214—H21K	109.5
C112—C114—H11L	109.5	C212—C214—H21L	109.5
H11K—C114—H11L	109.5	H21K—C214—H21L	109.5
C112—C114—H11M	109.5	C212—C214—H21M	109.5
H11K—C114—H11M	109.5	H21K—C214—H21M	109.5
H11L—C114—H11M	109.5	H21L—C214—H21M	109.5
C115—N13—C112	126.5 (5)	C215—N23—C212	125.8 (5)
C115—N13—H13N	123 (4)	C215—N23—H23N	112 (5)
C112—N13—H13N	110 (4)	C212—N23—H23N	122 (5)
O15—C115—N13	124.2 (6)	O25—C215—N23	124.2 (6)
O15—C115—C116	121.7 (5)	O25—C215—C216	122.6 (5)
N13—C115—C116	114.1 (5)	N23—C215—C216	113.2 (5)
C117—C116—C115	123.5 (6)	C217—C216—C215	123.2 (6)
C117—C116—H116	118.3	C217—C216—H216	118.4
C115—C116—H116	118.3	C215—C216—H216	118.4
C116—C117—H11N	120.0	C216—C217—H21N	120.0
C116—C117—H11O	120.0	C216—C217—H21O	120.0
H11N—C117—H11O	120.0	H21N—C217—H21O	120.0

C18—N11—C11—C12	−74.4 (7)	C210—N21—C21—C22	164.9 (6)
C110—N11—C11—C12	165.9 (6)	C28—N21—C21—C22	−76.7 (7)
C19—N11—C11—C12	46.8 (9)	C29—N21—C21—C22	46.4 (8)
N11—C11—C12—C13	175.5 (5)	N21—C21—C22—C23	176.3 (5)
C11—C12—C13—N12	164.4 (5)	C21—C22—C23—N22	163.8 (5)
C12—C13—N12—C14	85.9 (6)	C22—C23—N22—C24	90.1 (7)
C13—N12—C14—O11	−0.2 (8)	C23—N22—C24—O21	0.5 (9)
C13—N12—C14—C15	179.8 (5)	C23—N22—C24—C25	179.7 (5)
O11—C14—C15—C16	3.7 (9)	O21—C24—C25—C26	0.8 (9)
N12—C14—C15—C16	−176.4 (6)	N22—C24—C25—C26	−178.5 (6)
O11—C14—C15—C17	−175.4 (7)	O21—C24—C25—C27	−179.3 (6)
N12—C14—C15—C17	4.5 (9)	N22—C24—C25—C27	1.4 (9)
O12—S1—C111—C112	65.6 (6)	O24—S2—C211—C212	−56.9 (7)
O14—S1—C111—C112	−55.3 (7)	O22—S2—C211—C212	63.5 (6)
O13—S1—C111—C112	−176.0 (6)	O23—S2—C211—C212	−178.5 (6)
S1—C111—C112—N13	−52.7 (7)	S2—C211—C212—N23	−52.1 (7)
S1—C111—C112—C113	67.2 (7)	S2—C211—C212—C214	−173.1 (5)
S1—C111—C112—C114	−173.1 (5)	S2—C211—C212—C213	67.2 (7)
C113—C112—N13—C115	−177.8 (5)	C214—C212—N23—C215	66.0 (7)
C114—C112—N13—C115	64.6 (7)	C213—C212—N23—C215	−176.3 (5)
C111—C112—N13—C115	−54.5 (7)	C211—C212—N23—C215	−53.4 (8)
C112—N13—C115—O15	−2.6 (9)	C212—N23—C215—O25	−4.1 (9)
C112—N13—C115—C116	177.6 (5)	C212—N23—C215—C216	177.1 (5)
O15—C115—C116—C117	−12.6 (10)	O25—C215—C216—C217	−11.3 (10)
N13—C115—C116—C117	167.2 (6)	N23—C215—C216—C217	167.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12N···O15	0.84 (7)	2.02 (7)	2.841 (6)	167 (7)
N13—H13N···O11ⁱ	0.88 (7)	2.10 (7)	2.943 (6)	162 (6)
N22—H22N···O25	0.93 (7)	2.00 (7)	2.865 (6)	154 (6)
N23—H23N···O21ⁱⁱ	0.82 (7)	2.15 (7)	2.961 (6)	174 (7)
C11—H11D···O12	0.99	2.31	3.216 (8)	151
C12—H12A···O14ⁱⁱⁱ	0.99	2.68	3.583 (8)	151
C13—H13B···O12	0.99	2.69	3.463 (8)	135
C18—H18C···O14ⁱⁱⁱ	0.98	2.23	3.182 (10)	164
C18—H18B···O22ⁱⁱⁱ	0.98	2.25	3.192 (8)	160
C18—H18A···O23^iv	0.98	2.28	3.226 (9)	162
C19—H19A···O24ⁱⁱⁱ	0.98	2.63	3.555 (10)	157
C110—H11B···O21	0.98	2.65	3.182 (11)	114
C116—H116···O11ⁱ	0.95	2.68	3.375 (7)	131
C117—H11N···N12	0.95	2.73	3.338 (8)	123
C21—H21D···O22	0.99	2.34	3.236 (8)	151
C22—H22B···O24^iv	0.99	2.53	3.463 (8)	157
C23—H23B···O22	0.99	2.65	3.442 (7)	137
C28—H28A···O12	0.98	2.20	3.162 (9)	166
C28—H28B···O13^v	0.98	2.27	3.195 (9)	158
C29—H29C···O23	0.98	2.41	3.377 (10)	169
C211—H21F···O21ⁱ	0.99	2.71	3.674 (8)	164
C216—H216···O21ⁱⁱ	0.95	2.69	3.405 (7)	132

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

Selected bond lengths (Å) for salts 1 and 2 top

Salt 1		Salt 2
C18—N11	1.479 (10)	C28—N21	1.504 (9)
C19—N11	1.506 (9)	C29—N21	1.506 (9)
C110—N11	1.498 (11)	C210—N21	1.504 (10)
N11—C11	1.511 (8)	N21—C21	1.500 (8)
C13—N12	1.463 (7)	C23—N22	1.457 (7)
N12—C14	1.330 (7)	N22—C24	1.338 (7)
C14—O11	1.239 (7)	C24—O21	1.236 (7)
C15—C16	1.367 (9)	C25—C26	1.352 (9)
O12—S1	1.434 (5)	O22—S2	1.436 (4)
O13—S1	1.447 (6)	O23—S2	1.437 (6)
O14—S1	1.436 (7)	O24—S2	1.432 (7)
S1—C111	1.778 (8)	S2—C211	1.786 (8)
N13—C115	1.333 (7)	N23—C215	1.338 (7)
C115—O15	1.245 (7)	C215—O25	1.235 (7)
C116—C117	1.304 (9)	C216—C217	1.323 (9)

Percentage contributions of the interatomic contacts to the Hirshfeld surface of the asymmetric unit of (1) top

Contacts	Included surface area (%)
H···H	68.9
H···O/O···H	22.6
H···C/C···H	8.0
H···N/N···H	0.5

Percentage contributions of the interatomic contacts to the Hirshfeld surface of the individual salts of (1) top

Contact	Salt 1	Cation	Anion	Salt 2	Cation	Anion
H···H	68.9	67.3	54.9	68.9	67.2	54.5
H···O/O···H	23.5	24.9	35.4	23.6	25.1	35.7
H···C/C···H	7.2	7.0	8.8	7.0	6.7	8.7
H···N/N···H	0.4	0.8	0.8	0.5	0.9	1.0

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The structure and Hirshfeld surface analysis of the salt 3-methacryl­amido-N,N,N-tri­methyl­propan-1-aminium 2-acryl­amido-2-methyl­propane-1-sulfonate

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The structure and Hirshfeld surface analysis of the salt 3-methacrylamido-N,N,N-trimethylpropan-1-aminium 2-acrylamido-2-methylpropane-1-sulfonate