Hydrogen-bonded mol­ecular salts of reduced benzo­thia­zole derivatives with carboxyl­ates: a robust R_{2}^{2}(8) supra­molecular motif (even when disordered)

Shaibah, M.A.E.; Sagar, B.K.; Yathirajan, H.S.; Cordes, D.B.; Slawin, A.M.Z.; Harrison, W.T.A.

doi:10.1107/S2056989018018224

Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust $R_{2}^{2}$ (8) supramolecular motif (even when disordered)

M. A. E. Shaibah, B. K. Sagar, H. S. Yathirajan, D. B. Cordes, A. M. Z. Slawin and W. T. A. Harrison

The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C₁₁H₁₉N₂S⁺) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported·In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH⁺=C—NH₂ fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N⁺H₂ resonance form to the structure.

Keywords: benzothiazole; hydrogen bond; molecular salt; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018018224/mw2140sup1.cif Contains datablocks I, II, III, IV, V, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140IVsup5.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140Vsup6.hkl Contains datablock V
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018018224/mw2140Isup7.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018018224/mw2140IIsup8.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018018224/mw2140IIIsup9.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018018224/mw2140IVsup10.cml Supplementary material

CCDC references: 1886885; 1886884; 1886883; 1886882; 1886881

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.038
wR factor = 0.089
Data-to-parameter ratio = 17.6

Structure: II

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.007 Å
R factor = 0.032
wR factor = 0.083
Data-to-parameter ratio = 17.4

Structure: III

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.042
wR factor = 0.116
Data-to-parameter ratio = 17.1

Structure: IV

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.062
wR factor = 0.128
Data-to-parameter ratio = 18.4

Structure: V

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.039
wR factor = 0.094
Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          2 Report

Author Response: these atoms are positionally disorderd over adjacent sites (see refinement section)


Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.3 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00467 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H9B      ..H3A2     .       1.87 Ang.
                                                      x,y,z  =      1_555 Check
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         72 %

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C19 H26 N2 O2 S1
            Atom count from _chemical_formula_moiety:C27 H26 N2 O2 S1
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        14% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          8 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        299 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

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

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




Datablock: II


Alert level B
PLAT241_ALERT_2_B High   'MainMol' Ueq as Compared to Neighbors of         C3 Check

Author Response: this may be indiciative of disorder of the C3 and C4 methylene groups over two sets of sites but attempts to model it were not convincing.


Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.3 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3       --C4       .        5.6 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C5 Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00706 Ang.
PLAT352_ALERT_3_C Short  N-H (X0.87,N1.01A)  N2       - H2N      .       0.72 Ang.
PLAT353_ALERT_3_C Long   N-H (N0.87,N1.01A)  N1       - H1N      .       1.02 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C3       - C4       .       1.41 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         70 %

Alert level G
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        346 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
  10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 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
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: III



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          2 Report
PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H8C      ..H3B1     .       1.73 Ang.
                                                      x,y,z  =      1_555 Check
PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H11C     ..H4B2     .       1.74 Ang.
                                                      x,y,z  =      1_555 Check

Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00785 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C11 H19 N2 S
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.059 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         77 %

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
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        644 Note
PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ           2 Units
PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ           2 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: IV


Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          2 Report

Author Response: these atoms are positionally disorderd over adjacent sites (see refinement section)

PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H8C      ..H3B1     .       1.73 Ang.
                                                      x,y,z  =      1_555 Check

Author Response: we believe that this short contact is genuine.

PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H11C     ..H4B2     .       1.74 Ang.
                                                      x,y,z  =      1_555 Check

Author Response: we believe that this short contact is genuine.


Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.460
           From the CIF: _refine_ls_abs_structure_Flack_su    0.070
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00785 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C11 H19 N2 S
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.059 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         77 %

Alert level G
PLAT033_ALERT_4_G Flack x Value Deviates > 3.0 * sigma from Zero .      0.460 Note
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        14% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          8 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C11 H19 N2 S
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        525 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
   3 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: V


Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          2 Report

Author Response: these atoms are positionally disorderd over adjacent sites (see refinement section)


Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.6 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00445 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H8C      ..H3B1     .       1.86 Ang.
                                                      x,y,z  =      1_555 Check
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H11C     ..H4B1     .       1.84 Ang.
                                                      x,y,z  =      1_555 Check
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C11 H19 N2 S
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         17 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         74 %

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        14% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  2         32.50 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  3         12.50 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          8 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C11 H18.50 N2 S
PLAT850_ALERT_4_G Check Flack Parameter Exact Value 0.00 and s.u.        0.03 Check
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        558 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   7 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
   5 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

For all structures, data collection: CrystalClear-SM (Rigaku, 2017); cell refinement: CrysAlis PRO (Rigaku, 2017); data reduction: CrysAlis PRO (Rigaku, 2017); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium 4-methylbenzoate (I) top

Crystal data top

C₁₁H₁₉N₂S⁺·C₈H₇O₂⁻	F(000) = 372
M_r = 346.48	D_x = 1.208 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 10.1879 (5) Å	Cell parameters from 5914 reflections
b = 11.6149 (5) Å	θ = 2.2–28.1°
c = 8.7790 (4) Å	µ = 0.18 mm⁻¹
β = 113.480 (6)°	T = 173 K
V = 952.82 (9) Å³	Plate, colourless
Z = 2	0.24 × 0.11 × 0.02 mm

Data collection top

Rigaku XtaLAB P200 HPC diffractometer	4056 independent reflections
Radiation source: rotating anode, Rigaku FR-X	3440 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromator	R_int = 0.029
ω scans	θ_max = 29.0°, θ_min = 1.8°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)	h = −13→12
T_min = 0.793, T_max = 1.000	k = −15→15
12189 measured reflections	l = −11→11

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)] = 0.038	w = 1/[σ²(F_o²) + (0.0463P)² + 0.0807P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.089	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.20 e Å⁻³
4056 reflections	Δρ_min = −0.17 e Å⁻³
230 parameters	Absolute structure: Flack x determined using 1371 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013).
2 restraints	Absolute structure parameter: 0.03 (3)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.3617 (3)	0.6584 (2)	0.8458 (3)	0.0363 (6)
C2	0.2322 (3)	0.6675 (3)	0.8865 (4)	0.0466 (7)
C3A	0.1685 (10)	0.7939 (8)	0.8152 (12)	0.058 (3)*	0.398 (10)
H3A1	0.0740	0.8028	0.8210	0.069*	0.398 (10)
H3A2	0.2329	0.8534	0.8878	0.069*	0.398 (10)
C4A	0.1525 (10)	0.8143 (9)	0.6457 (13)	0.048 (2)*	0.398 (10)
H4A1	0.1003	0.8874	0.6050	0.058*	0.398 (10)
H4A2	0.0957	0.7512	0.5735	0.058*	0.398 (10)
C3B	0.1217 (6)	0.7333 (5)	0.7440 (7)	0.0467 (18)*	0.602 (10)
H3B1	0.0401	0.7535	0.7730	0.056*	0.602 (10)
H3B2	0.0852	0.6836	0.6441	0.056*	0.602 (10)
C4B	0.1860 (7)	0.8447 (6)	0.7047 (9)	0.0468 (15)*	0.602 (10)
H4B1	0.1081	0.8907	0.6225	0.056*	0.602 (10)
H4B2	0.2291	0.8911	0.8074	0.056*	0.602 (10)
C5	0.3013 (3)	0.8207 (2)	0.6356 (4)	0.0412 (7)
C6	0.3917 (3)	0.7225 (2)	0.7371 (3)	0.0342 (6)
C7	0.5894 (3)	0.6071 (2)	0.8256 (3)	0.0341 (6)
C8	0.1541 (6)	0.5542 (4)	0.8622 (7)	0.111 (2)
H8A	0.0673	0.5643	0.8833	0.167*
H8B	0.2164	0.4971	0.9397	0.167*
H8C	0.1280	0.5275	0.7480	0.167*
C9	0.2747 (4)	0.7056 (4)	1.0652 (5)	0.0783 (12)
H9A	0.1884	0.7226	1.0847	0.117*
H9B	0.3342	0.7749	1.0862	0.117*
H9C	0.3288	0.6440	1.1401	0.117*
C10	0.2527 (4)	0.7945 (3)	0.4504 (4)	0.0648 (10)
H10A	0.1905	0.8566	0.3853	0.097*
H10B	0.2000	0.7216	0.4246	0.097*
H10C	0.3366	0.7886	0.4227	0.097*
C11	0.3888 (4)	0.9315 (3)	0.6748 (5)	0.0622 (9)
H11A	0.4216	0.9487	0.7935	0.093*
H11B	0.3293	0.9950	0.6100	0.093*
H11C	0.4718	0.9220	0.6461	0.093*
N1	0.5199 (2)	0.69242 (19)	0.7257 (3)	0.0352 (5)
H1N	0.559 (3)	0.719 (3)	0.660 (4)	0.042*
N2	0.7129 (3)	0.5644 (2)	0.8356 (3)	0.0406 (6)
H2N	0.738 (3)	0.583 (3)	0.759 (4)	0.049*
H3N	0.742 (3)	0.502 (3)	0.900 (4)	0.049*
S1	0.49793 (8)	0.55753 (6)	0.94144 (8)	0.04197 (19)
C12	0.7414 (3)	0.7561 (2)	0.3383 (3)	0.0353 (6)
C13	0.8440 (3)	0.6995 (3)	0.2992 (3)	0.0393 (6)
H13	0.8915	0.6339	0.3613	0.047*
C14	0.8774 (3)	0.7387 (3)	0.1694 (3)	0.0428 (7)
H14	0.9470	0.6986	0.1432	0.051*
C15	0.8121 (3)	0.8343 (3)	0.0779 (4)	0.0457 (7)
C16	0.7089 (4)	0.8898 (3)	0.1168 (4)	0.0533 (8)
H16	0.6618	0.9556	0.0547	0.064*
C17	0.6734 (3)	0.8509 (3)	0.2443 (4)	0.0474 (8)
H17	0.6015	0.8898	0.2678	0.057*
C18	0.7053 (3)	0.7165 (2)	0.4803 (3)	0.0382 (6)
C19	0.8510 (4)	0.8777 (4)	−0.0609 (4)	0.0688 (10)
H19A	0.8263	0.9595	−0.0806	0.103*
H19B	0.7981	0.8339	−0.1624	0.103*
H19C	0.9541	0.8680	−0.0298	0.103*
O1	0.6233 (2)	0.77900 (19)	0.5192 (3)	0.0518 (5)
O2	0.7604 (2)	0.62322 (16)	0.5523 (2)	0.0428 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0372 (15)	0.0423 (14)	0.0285 (13)	−0.0010 (12)	0.0124 (11)	−0.0022 (11)
C2	0.0447 (17)	0.0600 (18)	0.0416 (16)	0.0010 (14)	0.0240 (14)	0.0026 (13)
C5	0.0452 (17)	0.0385 (14)	0.0416 (15)	0.0057 (13)	0.0193 (13)	0.0040 (12)
C6	0.0349 (14)	0.0371 (14)	0.0302 (13)	−0.0036 (11)	0.0125 (11)	−0.0062 (11)
C7	0.0367 (15)	0.0371 (14)	0.0297 (12)	−0.0024 (12)	0.0145 (11)	−0.0032 (11)
C8	0.093 (3)	0.120 (4)	0.166 (5)	−0.062 (3)	0.099 (4)	−0.071 (4)
C9	0.071 (3)	0.121 (3)	0.061 (2)	−0.016 (2)	0.046 (2)	−0.024 (2)
C10	0.067 (2)	0.070 (2)	0.0382 (17)	0.0162 (19)	−0.0001 (16)	0.0003 (15)
C11	0.078 (3)	0.0420 (18)	0.060 (2)	−0.0011 (17)	0.0206 (19)	0.0045 (16)
N1	0.0393 (13)	0.0379 (12)	0.0330 (11)	−0.0016 (10)	0.0193 (10)	0.0002 (9)
N2	0.0422 (15)	0.0462 (14)	0.0355 (13)	0.0056 (12)	0.0176 (11)	0.0022 (11)
S1	0.0427 (4)	0.0504 (4)	0.0366 (3)	0.0040 (4)	0.0197 (3)	0.0082 (3)
C12	0.0346 (14)	0.0440 (15)	0.0286 (12)	−0.0072 (12)	0.0138 (11)	−0.0075 (11)
C13	0.0291 (14)	0.0486 (16)	0.0385 (15)	−0.0007 (12)	0.0116 (12)	−0.0027 (12)
C14	0.0293 (15)	0.0632 (19)	0.0391 (15)	−0.0007 (14)	0.0171 (13)	−0.0070 (14)
C15	0.0437 (17)	0.0619 (19)	0.0347 (14)	−0.0018 (15)	0.0190 (13)	−0.0020 (14)
C16	0.065 (2)	0.0589 (19)	0.0413 (17)	0.0144 (17)	0.0273 (16)	0.0111 (14)
C17	0.0539 (19)	0.0529 (18)	0.0432 (17)	0.0113 (15)	0.0276 (15)	0.0007 (14)
C18	0.0381 (15)	0.0422 (15)	0.0364 (14)	−0.0066 (13)	0.0173 (12)	−0.0057 (12)
C19	0.075 (2)	0.095 (3)	0.0514 (19)	0.017 (2)	0.0410 (18)	0.0169 (18)
O1	0.0653 (14)	0.0525 (12)	0.0554 (13)	0.0081 (10)	0.0429 (11)	0.0050 (10)
O2	0.0452 (11)	0.0479 (11)	0.0386 (10)	−0.0012 (9)	0.0203 (9)	0.0012 (9)

Geometric parameters (Å, º) top

C1—C6	1.338 (4)	C9—H9A	0.9800
C1—C2	1.502 (4)	C9—H9B	0.9800
C1—S1	1.753 (3)	C9—H9C	0.9800
C2—C8	1.509 (5)	C10—H10A	0.9800
C2—C3B	1.514 (6)	C10—H10B	0.9800
C2—C9	1.518 (5)	C10—H10C	0.9800
C2—C3A	1.626 (9)	C11—H11A	0.9800
C3A—C4A	1.451 (14)	C11—H11B	0.9800
C3A—H3A1	0.9900	C11—H11C	0.9800
C3A—H3A2	0.9900	N1—H1N	0.88 (3)
C4A—C5	1.555 (9)	N2—H2N	0.83 (3)
C4A—H4A1	0.9900	N2—H3N	0.89 (3)
C4A—H4A2	0.9900	C12—C17	1.385 (4)
C3B—C4B	1.551 (9)	C12—C13	1.389 (4)
C3B—H3B1	0.9900	C12—C18	1.506 (4)
C3B—H3B2	0.9900	C13—C14	1.389 (4)
C4B—C5	1.547 (6)	C13—H13	0.9500
C4B—H4B1	0.9900	C14—C15	1.377 (4)
C4B—H4B2	0.9900	C14—H14	0.9500
C5—C6	1.514 (4)	C15—C16	1.386 (4)
C5—C11	1.524 (4)	C15—C19	1.510 (4)
C5—C10	1.529 (4)	C16—C17	1.383 (4)
C6—N1	1.394 (4)	C16—H16	0.9500
C7—N2	1.322 (4)	C17—H17	0.9500
C7—N1	1.325 (3)	C18—O1	1.252 (3)
C7—S1	1.729 (3)	C18—O2	1.267 (3)
C8—H8A	0.9800	C19—H19A	0.9800
C8—H8B	0.9800	C19—H19B	0.9800
C8—H8C	0.9800	C19—H19C	0.9800

C6—C1—C2	127.0 (3)	H8A—C8—H8C	109.5
C6—C1—S1	110.6 (2)	H8B—C8—H8C	109.5
C2—C1—S1	122.4 (2)	C2—C9—H9A	109.5
C1—C2—C8	111.6 (3)	C2—C9—H9B	109.5
C1—C2—C3B	105.9 (3)	H9A—C9—H9B	109.5
C8—C2—C3B	98.4 (4)	C2—C9—H9C	109.5
C1—C2—C9	110.6 (3)	H9A—C9—H9C	109.5
C8—C2—C9	108.5 (3)	H9B—C9—H9C	109.5
C3B—C2—C9	121.2 (4)	C5—C10—H10A	109.5
C1—C2—C3A	103.1 (4)	C5—C10—H10B	109.5
C8—C2—C3A	128.8 (5)	H10A—C10—H10B	109.5
C9—C2—C3A	92.3 (4)	C5—C10—H10C	109.5
C4A—C3A—C2	114.0 (8)	H10A—C10—H10C	109.5
C4A—C3A—H3A1	108.8	H10B—C10—H10C	109.5
C2—C3A—H3A1	108.8	C5—C11—H11A	109.5
C4A—C3A—H3A2	108.8	C5—C11—H11B	109.5
C2—C3A—H3A2	108.8	H11A—C11—H11B	109.5
H3A1—C3A—H3A2	107.7	C5—C11—H11C	109.5
C3A—C4A—C5	110.6 (8)	H11A—C11—H11C	109.5
C3A—C4A—H4A1	109.5	H11B—C11—H11C	109.5
C5—C4A—H4A1	109.5	C7—N1—C6	114.1 (2)
C3A—C4A—H4A2	109.5	C7—N1—H1N	116 (2)
C5—C4A—H4A2	109.5	C6—N1—H1N	130.1 (19)
H4A1—C4A—H4A2	108.1	C7—N2—H2N	116 (2)
C2—C3B—C4B	111.3 (5)	C7—N2—H3N	115 (2)
C2—C3B—H3B1	109.4	H2N—N2—H3N	126 (3)
C4B—C3B—H3B1	109.4	C7—S1—C1	90.27 (13)
C2—C3B—H3B2	109.4	C17—C12—C13	118.4 (3)
C4B—C3B—H3B2	109.4	C17—C12—C18	120.5 (3)
H3B1—C3B—H3B2	108.0	C13—C12—C18	121.1 (3)
C5—C4B—C3B	113.0 (5)	C14—C13—C12	120.2 (3)
C5—C4B—H4B1	109.0	C14—C13—H13	119.9
C3B—C4B—H4B1	109.0	C12—C13—H13	119.9
C5—C4B—H4B2	109.0	C15—C14—C13	121.6 (3)
C3B—C4B—H4B2	109.0	C15—C14—H14	119.2
H4B1—C4B—H4B2	107.8	C13—C14—H14	119.2
C6—C5—C11	109.8 (2)	C14—C15—C16	117.9 (3)
C6—C5—C10	109.8 (2)	C14—C15—C19	121.2 (3)
C11—C5—C10	108.7 (3)	C16—C15—C19	120.8 (3)
C6—C5—C4B	106.5 (3)	C17—C16—C15	121.1 (3)
C11—C5—C4B	103.1 (4)	C17—C16—H16	119.4
C10—C5—C4B	118.6 (4)	C15—C16—H16	119.4
C6—C5—C4A	107.9 (4)	C16—C17—C12	120.8 (3)
C11—C5—C4A	121.6 (5)	C16—C17—H17	119.6
C10—C5—C4A	98.1 (5)	C12—C17—H17	119.6
C1—C6—N1	113.5 (2)	O1—C18—O2	124.9 (2)
C1—C6—C5	125.6 (3)	O1—C18—C12	117.2 (3)
N1—C6—C5	121.0 (2)	O2—C18—C12	117.9 (2)
N2—C7—N1	124.6 (2)	C15—C19—H19A	109.5
N2—C7—S1	123.9 (2)	C15—C19—H19B	109.5
N1—C7—S1	111.6 (2)	H19A—C19—H19B	109.5
C2—C8—H8A	109.5	C15—C19—H19C	109.5
C2—C8—H8B	109.5	H19A—C19—H19C	109.5
H8A—C8—H8B	109.5	H19B—C19—H19C	109.5
C2—C8—H8C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.88 (3)	1.76 (3)	2.632 (3)	175 (3)
N2—H2N···O2	0.83 (3)	1.98 (4)	2.801 (3)	170 (3)
N2—H3N···O2ⁱ	0.89 (3)	1.93 (3)	2.805 (3)	164 (3)

Symmetry code: (i) x, −y+1, z+1/2.

2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 4-bromobenzoate (II) top

Crystal data top

C₁₁H₁₉N₂S⁺·C₇H₄BrO₂⁻	F(000) = 424
M_r = 411.35	D_x = 1.424 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 10.2506 (5) Å	Cell parameters from 6835 reflections
b = 11.5855 (4) Å	θ = 2.2–28.2°
c = 8.8269 (4) Å	µ = 2.26 mm⁻¹
β = 113.807 (6)°	T = 173 K
V = 959.07 (8) Å³	Plate, colourless
Z = 2	0.12 × 0.08 × 0.02 mm

Data collection top

Rigaku XtaLAB P200 HPC diffractometer	3993 independent reflections
Radiation source: rotating anode, Rigaku FR-X	3311 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromator	R_int = 0.026
ω scans	θ_max = 29.1°, θ_min = 2.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)	h = −13→13
T_min = 0.761, T_max = 1.000	k = −15→15
12220 measured reflections	l = −10→11

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)] = 0.032	w = 1/[σ²(F_o²) + (0.0407P)² + 0.0111P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.083	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.62 e Å⁻³
3993 reflections	Δρ_min = −0.38 e Å⁻³
230 parameters	Absolute structure: Flack x determined using 1344 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013).
2 restraints	Absolute structure parameter: 0.005 (4)
Primary atom site location: structure-invariant direct methods

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.6357 (4)	0.6587 (3)	0.1418 (5)	0.0359 (8)
C2	0.7655 (5)	0.6679 (4)	0.1027 (5)	0.0446 (9)
C3	0.8711 (8)	0.7399 (8)	0.2385 (10)	0.113 (3)
H3A	0.9213	0.6883	0.3338	0.136*
H3B	0.9431	0.7681	0.1991	0.136*
C4	0.8218 (6)	0.8359 (5)	0.2982 (9)	0.0780 (17)
H4A	0.7931	0.8956	0.2105	0.094*
H4B	0.9040	0.8673	0.3937	0.094*
C5	0.6976 (4)	0.8213 (3)	0.3532 (5)	0.0403 (9)
C6	0.6067 (4)	0.7238 (3)	0.2502 (5)	0.0339 (8)
C7	0.4084 (4)	0.6086 (3)	0.1598 (5)	0.0345 (8)
C8	0.8389 (8)	0.5492 (7)	0.1190 (12)	0.110 (3)
H8A	0.9299	0.5590	0.1087	0.164*
H8B	0.7771	0.4976	0.0314	0.164*
H8C	0.8561	0.5156	0.2274	0.164*
C9	0.7278 (7)	0.7092 (6)	−0.0719 (7)	0.0772 (17)
H9A	0.8147	0.7152	−0.0923	0.116*
H9B	0.6820	0.7850	−0.0868	0.116*
H9C	0.6622	0.6541	−0.1501	0.116*
C10	0.7484 (6)	0.7930 (5)	0.5371 (6)	0.0664 (14)
H10A	0.8122	0.8542	0.6028	0.100*
H10B	0.7995	0.7193	0.5604	0.100*
H10C	0.6659	0.7875	0.5663	0.100*
C11	0.6095 (6)	0.9320 (4)	0.3150 (6)	0.0578 (12)
H11A	0.5714	0.9473	0.1957	0.087*
H11B	0.6699	0.9966	0.3751	0.087*
H11C	0.5304	0.9231	0.3496	0.087*
N1	0.4781 (3)	0.6939 (3)	0.2604 (4)	0.0348 (7)
H1N	0.441 (5)	0.732 (4)	0.339 (5)	0.042*
N2	0.2855 (4)	0.5667 (3)	0.1482 (5)	0.0408 (8)
H2N	0.257 (6)	0.582 (4)	0.208 (6)	0.049*
H3N	0.264 (5)	0.505 (4)	0.086 (6)	0.049*
S1	0.49893 (11)	0.55873 (9)	0.04481 (11)	0.0398 (2)
C12	0.2601 (4)	0.7536 (3)	0.6483 (4)	0.0352 (8)
C13	0.1566 (4)	0.6980 (3)	0.6846 (5)	0.0369 (8)
H13	0.1094	0.6326	0.6213	0.044*
C14	0.1208 (4)	0.7360 (4)	0.8116 (5)	0.0422 (9)
H14	0.0501	0.6970	0.8361	0.051*
C15	0.1893 (4)	0.8310 (4)	0.9017 (5)	0.0402 (9)
C16	0.2946 (5)	0.8860 (3)	0.8709 (6)	0.0490 (11)
H16	0.3434	0.9499	0.9369	0.059*
C17	0.3291 (5)	0.8481 (4)	0.7443 (5)	0.0466 (10)
H17	0.4009	0.8871	0.7220	0.056*
C18	0.2979 (4)	0.7141 (3)	0.5095 (5)	0.0370 (8)
O1	0.3836 (4)	0.7755 (3)	0.4748 (4)	0.0505 (7)
O2	0.2410 (3)	0.6225 (2)	0.4343 (4)	0.0419 (6)
Br1	0.13945 (5)	0.88476 (4)	1.07398 (5)	0.0676 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.037 (2)	0.0392 (18)	0.0320 (18)	0.0012 (17)	0.0138 (17)	0.0030 (16)
C2	0.043 (2)	0.057 (2)	0.040 (2)	−0.004 (2)	0.0238 (19)	−0.0023 (19)
C3	0.087 (5)	0.160 (7)	0.120 (6)	−0.057 (5)	0.071 (5)	−0.073 (6)
C4	0.061 (3)	0.080 (3)	0.109 (5)	−0.032 (3)	0.050 (3)	−0.039 (3)
C5	0.037 (2)	0.0370 (19)	0.043 (2)	−0.0060 (17)	0.0129 (17)	−0.0009 (17)
C6	0.036 (2)	0.0329 (18)	0.0323 (18)	0.0019 (16)	0.0131 (16)	0.0038 (15)
C7	0.037 (2)	0.0365 (19)	0.0293 (18)	0.0022 (17)	0.0123 (16)	0.0043 (16)
C8	0.091 (5)	0.109 (5)	0.167 (8)	0.055 (5)	0.092 (6)	0.064 (5)
C9	0.074 (4)	0.113 (4)	0.058 (3)	0.020 (3)	0.040 (3)	0.028 (3)
C10	0.071 (3)	0.066 (3)	0.039 (2)	−0.016 (3)	−0.002 (2)	−0.001 (2)
C11	0.072 (3)	0.037 (2)	0.059 (3)	0.003 (2)	0.022 (3)	−0.001 (2)
N1	0.0359 (18)	0.0375 (16)	0.0333 (17)	0.0013 (14)	0.0163 (14)	−0.0001 (14)
N2	0.042 (2)	0.0461 (19)	0.037 (2)	−0.0047 (17)	0.0190 (16)	−0.0057 (16)
S1	0.0407 (5)	0.0451 (5)	0.0352 (5)	−0.0029 (5)	0.0168 (4)	−0.0061 (4)
C12	0.034 (2)	0.0390 (19)	0.0305 (19)	0.0064 (16)	0.0109 (16)	0.0081 (16)
C13	0.030 (2)	0.0416 (19)	0.036 (2)	−0.0015 (16)	0.0102 (16)	−0.0011 (16)
C14	0.030 (2)	0.056 (2)	0.041 (2)	0.0004 (19)	0.0153 (18)	0.0030 (19)
C15	0.042 (2)	0.050 (2)	0.0308 (19)	0.0041 (19)	0.0170 (18)	0.0051 (18)
C16	0.060 (3)	0.050 (2)	0.039 (2)	−0.012 (2)	0.023 (2)	−0.0053 (19)
C17	0.055 (3)	0.049 (2)	0.042 (2)	−0.010 (2)	0.026 (2)	0.0014 (19)
C18	0.036 (2)	0.040 (2)	0.035 (2)	0.0061 (18)	0.0153 (17)	0.0025 (18)
O1	0.060 (2)	0.0519 (16)	0.0526 (18)	−0.0091 (15)	0.0365 (16)	−0.0072 (14)
O2	0.0422 (16)	0.0477 (16)	0.0367 (15)	0.0025 (13)	0.0168 (12)	−0.0012 (12)
Br1	0.0863 (4)	0.0796 (3)	0.0542 (3)	−0.0123 (3)	0.0462 (3)	−0.0134 (3)

Geometric parameters (Å, º) top

C1—C6	1.342 (5)	C9—H9C	0.9800
C1—C2	1.508 (6)	C10—H10A	0.9800
C1—S1	1.752 (4)	C10—H10B	0.9800
C2—C3	1.503 (8)	C10—H10C	0.9800
C2—C9	1.507 (7)	C11—H11A	0.9800
C2—C8	1.546 (8)	C11—H11B	0.9800
C3—C4	1.408 (10)	C11—H11C	0.9800
C3—H3A	0.9900	N1—H1N	1.01 (5)
C3—H3B	0.9900	N2—H2N	0.72 (5)
C4—C5	1.544 (7)	N2—H3N	0.88 (5)
C4—H4A	0.9900	C12—C13	1.385 (5)
C4—H4B	0.9900	C12—C17	1.391 (6)
C5—C6	1.513 (6)	C12—C18	1.498 (5)
C5—C11	1.526 (6)	C13—C14	1.385 (5)
C5—C10	1.528 (6)	C13—H13	0.9500
C6—N1	1.400 (5)	C14—C15	1.374 (6)
C7—N2	1.316 (5)	C14—H14	0.9500
C7—N1	1.327 (5)	C15—C16	1.371 (6)
C7—S1	1.728 (4)	C15—Br1	1.895 (4)
C8—H8A	0.9800	C16—C17	1.373 (7)
C8—H8B	0.9800	C16—H16	0.9500
C8—H8C	0.9800	C17—H17	0.9500
C9—H9A	0.9800	C18—O1	1.260 (5)
C9—H9B	0.9800	C18—O2	1.263 (5)

C6—C1—C2	126.4 (4)	H9A—C9—H9C	109.5
C6—C1—S1	110.8 (3)	H9B—C9—H9C	109.5
C2—C1—S1	122.7 (3)	C5—C10—H10A	109.5
C3—C2—C9	116.4 (5)	C5—C10—H10B	109.5
C3—C2—C1	105.9 (4)	H10A—C10—H10B	109.5
C9—C2—C1	111.8 (4)	C5—C10—H10C	109.5
C3—C2—C8	104.7 (6)	H10A—C10—H10C	109.5
C9—C2—C8	107.0 (5)	H10B—C10—H10C	109.5
C1—C2—C8	110.9 (4)	C5—C11—H11A	109.5
C4—C3—C2	119.0 (6)	C5—C11—H11B	109.5
C4—C3—H3A	107.6	H11A—C11—H11B	109.5
C2—C3—H3A	107.6	C5—C11—H11C	109.5
C4—C3—H3B	107.6	H11A—C11—H11C	109.5
C2—C3—H3B	107.6	H11B—C11—H11C	109.5
H3A—C3—H3B	107.0	C7—N1—C6	114.0 (3)
C3—C4—C5	119.8 (5)	C7—N1—H1N	122 (2)
C3—C4—H4A	107.4	C6—N1—H1N	124 (2)
C5—C4—H4A	107.4	C7—N2—H2N	121 (4)
C3—C4—H4B	107.4	C7—N2—H3N	110 (3)
C5—C4—H4B	107.4	H2N—N2—H3N	126 (5)
H4A—C4—H4B	106.9	C7—S1—C1	90.29 (18)
C6—C5—C11	109.2 (3)	C13—C12—C17	118.3 (4)
C6—C5—C10	110.0 (3)	C13—C12—C18	121.5 (3)
C11—C5—C10	109.4 (4)	C17—C12—C18	120.2 (4)
C6—C5—C4	106.2 (4)	C14—C13—C12	121.2 (4)
C11—C5—C4	109.2 (4)	C14—C13—H13	119.4
C10—C5—C4	112.8 (5)	C12—C13—H13	119.4
C1—C6—N1	113.1 (3)	C15—C14—C13	118.9 (4)
C1—C6—C5	126.0 (3)	C15—C14—H14	120.6
N1—C6—C5	120.9 (3)	C13—C14—H14	120.6
N2—C7—N1	124.5 (4)	C16—C15—C14	121.2 (4)
N2—C7—S1	123.7 (3)	C16—C15—Br1	119.7 (3)
N1—C7—S1	111.7 (3)	C14—C15—Br1	119.2 (3)
C2—C8—H8A	109.5	C15—C16—C17	119.6 (4)
C2—C8—H8B	109.5	C15—C16—H16	120.2
H8A—C8—H8B	109.5	C17—C16—H16	120.2
C2—C8—H8C	109.5	C16—C17—C12	120.9 (4)
H8A—C8—H8C	109.5	C16—C17—H17	119.5
H8B—C8—H8C	109.5	C12—C17—H17	119.5
C2—C9—H9A	109.5	O1—C18—O2	124.5 (4)
C2—C9—H9B	109.5	O1—C18—C12	117.5 (4)
H9A—C9—H9B	109.5	O2—C18—C12	118.0 (3)
C2—C9—H9C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	1.01 (5)	1.62 (5)	2.626 (4)	172 (4)
N2—H2N···O2	0.72 (5)	2.12 (5)	2.816 (5)	162 (6)
N2—H3N···O2ⁱ	0.88 (5)	1.94 (5)	2.808 (5)	170 (4)

Symmetry code: (i) x, −y+1, z−1/2.

2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 3,5-dinitrobenzoate (III) top

Crystal data top

C₁₁H₁₉N₂S⁺·C₇H₃N₂O₆⁻	F(000) = 888
M_r = 422.45	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.3232 (6) Å	Cell parameters from 10667 reflections
b = 5.84087 (17) Å	θ = 2.0–27.8°
c = 21.0876 (8) Å	µ = 0.21 mm⁻¹
β = 109.875 (4)°	T = 173 K
V = 2006.60 (12) Å³	Plate, colourless
Z = 4	0.27 × 0.10 × 0.03 mm

Data collection top

Rigaku XtaLAB P200 HPC diffractometer	4698 independent reflections
Radiation source: rotating anode, Rigaku FR-X	3712 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromator	R_int = 0.056
ω scans	θ_max = 29.2°, θ_min = 1.9°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)	h = −21→23
T_min = 0.566, T_max = 1.000	k = −7→7
25034 measured reflections	l = −26→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0567P)² + 0.5151P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4698 reflections	Δρ_max = 0.49 e Å⁻³
275 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.26545 (9)	0.4584 (3)	0.49126 (7)	0.0264 (3)
C2	0.19150 (9)	0.3629 (3)	0.50428 (8)	0.0298 (3)
C3	0.13800 (10)	0.2456 (3)	0.43879 (9)	0.0419 (4)
H3A	0.0996	0.1392	0.4494	0.050*
H3B	0.1048	0.3636	0.4077	0.050*
C4	0.18675 (11)	0.1131 (3)	0.40303 (9)	0.0397 (4)
H4A	0.1479	0.0344	0.3634	0.048*
H4B	0.2196	−0.0059	0.4340	0.048*
C5	0.24503 (10)	0.2636 (3)	0.37920 (8)	0.0319 (4)
C6	0.28907 (9)	0.4173 (3)	0.43809 (7)	0.0260 (3)
C7	0.39559 (9)	0.6469 (3)	0.49858 (7)	0.0266 (3)
C8	0.21999 (11)	0.1932 (3)	0.56307 (9)	0.0388 (4)
H8A	0.1720	0.1286	0.5713	0.058*
H8B	0.2547	0.2727	0.6037	0.058*
H8C	0.2514	0.0697	0.5518	0.058*
C9	0.14165 (11)	0.5539 (3)	0.52232 (10)	0.0427 (4)
H9A	0.0925	0.4881	0.5283	0.064*
H9B	0.1253	0.6672	0.4859	0.064*
H9C	0.1753	0.6282	0.5643	0.064*
C10	0.30657 (12)	0.1076 (3)	0.36271 (10)	0.0442 (4)
H10A	0.2769	−0.0070	0.3294	0.066*
H10B	0.3410	0.0304	0.4039	0.066*
H10C	0.3413	0.1996	0.3443	0.066*
C11	0.19849 (13)	0.4072 (4)	0.31745 (9)	0.0516 (5)
H11A	0.1707	0.3058	0.2795	0.077*
H11B	0.2372	0.5057	0.3054	0.077*
H11C	0.1577	0.5024	0.3278	0.077*
N1	0.36224 (8)	0.5279 (2)	0.44229 (6)	0.0271 (3)
H1N	0.3856 (11)	0.524 (3)	0.4110 (9)	0.033*
N2	0.46553 (9)	0.7605 (3)	0.51363 (7)	0.0337 (3)
H2N	0.4887 (12)	0.780 (3)	0.4812 (10)	0.040*
H3N	0.4791 (12)	0.857 (3)	0.5486 (10)	0.040*
S1	0.33701 (2)	0.63371 (7)	0.55004 (2)	0.02882 (12)
C12	0.53091 (9)	0.7205 (3)	0.30278 (7)	0.0283 (3)
C13	0.58549 (9)	0.8968 (3)	0.30559 (8)	0.0304 (3)
H13	0.5992	1.0042	0.3416	0.037*
C14	0.61975 (9)	0.9144 (3)	0.25552 (8)	0.0313 (4)
C15	0.60233 (9)	0.7633 (3)	0.20218 (8)	0.0327 (4)
H15	0.6256	0.7796	0.1676	0.039*
C16	0.54918 (9)	0.5872 (3)	0.20198 (8)	0.0306 (3)
C17	0.51322 (9)	0.5616 (3)	0.25084 (7)	0.0294 (3)
H17	0.4770	0.4375	0.2489	0.035*
C18	0.49110 (10)	0.7013 (3)	0.35667 (8)	0.0312 (3)
N3	0.67709 (8)	1.1050 (3)	0.25924 (7)	0.0380 (3)
N4	0.52907 (8)	0.4200 (3)	0.14618 (7)	0.0386 (4)
O1	0.43858 (8)	0.5479 (2)	0.34910 (6)	0.0427 (3)
O2	0.51480 (8)	0.8407 (2)	0.40440 (6)	0.0410 (3)
O3	0.69300 (8)	1.1515 (2)	0.20855 (7)	0.0500 (4)
O4	0.70535 (9)	1.2066 (3)	0.31259 (7)	0.0596 (4)
O5	0.49224 (9)	0.2464 (3)	0.15173 (7)	0.0508 (3)
O6	0.54967 (8)	0.4645 (3)	0.09754 (6)	0.0522 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0251 (7)	0.0287 (8)	0.0255 (8)	−0.0025 (6)	0.0086 (6)	−0.0005 (6)
C2	0.0252 (8)	0.0364 (8)	0.0307 (8)	−0.0032 (6)	0.0130 (6)	0.0006 (7)
C3	0.0301 (9)	0.0543 (11)	0.0417 (10)	−0.0134 (8)	0.0129 (7)	−0.0047 (9)
C4	0.0385 (10)	0.0457 (10)	0.0350 (9)	−0.0158 (8)	0.0126 (7)	−0.0077 (8)
C5	0.0335 (8)	0.0374 (9)	0.0250 (8)	−0.0096 (7)	0.0103 (6)	−0.0039 (7)
C6	0.0252 (7)	0.0286 (8)	0.0248 (7)	−0.0034 (6)	0.0094 (6)	0.0005 (6)
C7	0.0290 (8)	0.0282 (8)	0.0250 (8)	−0.0031 (6)	0.0123 (6)	−0.0006 (6)
C8	0.0378 (9)	0.0441 (10)	0.0412 (10)	−0.0014 (8)	0.0222 (8)	0.0061 (8)
C9	0.0329 (9)	0.0470 (10)	0.0535 (11)	0.0034 (8)	0.0215 (8)	0.0005 (9)
C10	0.0509 (11)	0.0441 (10)	0.0437 (10)	−0.0122 (8)	0.0239 (9)	−0.0160 (8)
C11	0.0576 (12)	0.0607 (13)	0.0276 (9)	−0.0091 (10)	0.0029 (8)	0.0015 (9)
N1	0.0296 (7)	0.0320 (7)	0.0236 (6)	−0.0064 (5)	0.0140 (5)	−0.0029 (5)
N2	0.0352 (8)	0.0398 (8)	0.0304 (7)	−0.0140 (6)	0.0168 (6)	−0.0085 (6)
S1	0.0292 (2)	0.0350 (2)	0.0259 (2)	−0.00573 (16)	0.01407 (16)	−0.00554 (15)
C12	0.0239 (7)	0.0392 (9)	0.0224 (7)	0.0017 (6)	0.0088 (6)	0.0036 (6)
C13	0.0273 (8)	0.0396 (9)	0.0254 (8)	−0.0003 (7)	0.0103 (6)	0.0020 (7)
C14	0.0230 (8)	0.0425 (9)	0.0291 (8)	0.0021 (7)	0.0099 (6)	0.0083 (7)
C15	0.0236 (8)	0.0520 (10)	0.0243 (8)	0.0090 (7)	0.0106 (6)	0.0086 (7)
C16	0.0230 (7)	0.0451 (9)	0.0220 (7)	0.0085 (7)	0.0056 (6)	0.0002 (7)
C17	0.0221 (7)	0.0390 (8)	0.0257 (8)	0.0006 (6)	0.0063 (6)	0.0015 (7)
C18	0.0300 (8)	0.0392 (9)	0.0271 (8)	−0.0042 (7)	0.0133 (6)	−0.0005 (7)
N3	0.0305 (7)	0.0491 (9)	0.0396 (8)	−0.0014 (6)	0.0184 (6)	0.0090 (7)
N4	0.0273 (7)	0.0557 (10)	0.0313 (8)	0.0099 (7)	0.0081 (6)	−0.0056 (7)
O1	0.0462 (7)	0.0556 (8)	0.0347 (7)	−0.0218 (6)	0.0244 (6)	−0.0106 (6)
O2	0.0512 (8)	0.0453 (7)	0.0363 (7)	−0.0158 (6)	0.0275 (6)	−0.0114 (5)
O3	0.0466 (8)	0.0666 (9)	0.0461 (8)	−0.0058 (6)	0.0280 (6)	0.0147 (6)
O4	0.0662 (10)	0.0704 (10)	0.0507 (9)	−0.0328 (8)	0.0311 (7)	−0.0119 (7)
O5	0.0504 (8)	0.0563 (9)	0.0448 (8)	−0.0036 (7)	0.0149 (6)	−0.0156 (6)
O6	0.0452 (8)	0.0852 (10)	0.0316 (7)	0.0108 (7)	0.0199 (6)	−0.0082 (7)

Geometric parameters (Å, º) top

C1—C6	1.340 (2)	C10—H10B	0.9800
C1—C2	1.506 (2)	C10—H10C	0.9800
C1—S1	1.7540 (15)	C11—H11A	0.9800
C2—C8	1.532 (2)	C11—H11B	0.9800
C2—C9	1.535 (2)	C11—H11C	0.9800
C2—C3	1.538 (2)	N1—H1N	0.885 (19)
C3—C4	1.521 (3)	N2—H2N	0.91 (2)
C3—H3A	0.9900	N2—H3N	0.90 (2)
C3—H3B	0.9900	C12—C13	1.385 (2)
C4—C5	1.546 (2)	C12—C17	1.388 (2)
C4—H4A	0.9900	C12—C18	1.521 (2)
C4—H4B	0.9900	C13—C14	1.380 (2)
C5—C6	1.512 (2)	C13—H13	0.9500
C5—C11	1.528 (2)	C14—C15	1.380 (2)
C5—C10	1.529 (2)	C14—N3	1.476 (2)
C6—N1	1.3981 (19)	C15—C16	1.380 (2)
C7—N2	1.322 (2)	C15—H15	0.9500
C7—N1	1.3267 (19)	C16—C17	1.381 (2)
C7—S1	1.7211 (15)	C16—N4	1.477 (2)
C8—H8A	0.9800	C17—H17	0.9500
C8—H8B	0.9800	C18—O1	1.2475 (19)
C8—H8C	0.9800	C18—O2	1.2506 (19)
C9—H9A	0.9800	N3—O4	1.2178 (19)
C9—H9B	0.9800	N3—O3	1.2218 (18)
C9—H9C	0.9800	N4—O6	1.2231 (19)
C10—H10A	0.9800	N4—O5	1.224 (2)

C6—C1—C2	127.39 (14)	C5—C10—H10B	109.5
C6—C1—S1	110.64 (11)	H10A—C10—H10B	109.5
C2—C1—S1	121.88 (11)	C5—C10—H10C	109.5
C1—C2—C8	109.11 (13)	H10A—C10—H10C	109.5
C1—C2—C9	111.17 (13)	H10B—C10—H10C	109.5
C8—C2—C9	108.85 (13)	C5—C11—H11A	109.5
C1—C2—C3	106.95 (12)	C5—C11—H11B	109.5
C8—C2—C3	111.61 (14)	H11A—C11—H11B	109.5
C9—C2—C3	109.15 (14)	C5—C11—H11C	109.5
C4—C3—C2	113.90 (14)	H11A—C11—H11C	109.5
C4—C3—H3A	108.8	H11B—C11—H11C	109.5
C2—C3—H3A	108.8	C7—N1—C6	114.09 (12)
C4—C3—H3B	108.8	C7—N1—H1N	120.8 (12)
C2—C3—H3B	108.8	C6—N1—H1N	125.1 (12)
H3A—C3—H3B	107.7	C7—N2—H2N	119.0 (12)
C3—C4—C5	113.96 (15)	C7—N2—H3N	118.5 (12)
C3—C4—H4A	108.8	H2N—N2—H3N	118.8 (17)
C5—C4—H4A	108.8	C7—S1—C1	90.40 (7)
C3—C4—H4B	108.8	C13—C12—C17	119.67 (14)
C5—C4—H4B	108.8	C13—C12—C18	119.95 (14)
H4A—C4—H4B	107.7	C17—C12—C18	120.38 (14)
C6—C5—C11	110.26 (14)	C14—C13—C12	119.18 (15)
C6—C5—C10	110.14 (13)	C14—C13—H13	120.4
C11—C5—C10	109.86 (15)	C12—C13—H13	120.4
C6—C5—C4	105.88 (12)	C13—C14—C15	122.97 (15)
C11—C5—C4	112.06 (15)	C13—C14—N3	118.18 (15)
C10—C5—C4	108.56 (14)	C15—C14—N3	118.85 (14)
C1—C6—N1	113.12 (13)	C16—C15—C14	116.12 (14)
C1—C6—C5	125.55 (13)	C16—C15—H15	121.9
N1—C6—C5	121.31 (12)	C14—C15—H15	121.9
N2—C7—N1	124.23 (14)	C15—C16—C17	123.23 (15)
N2—C7—S1	124.04 (12)	C15—C16—N4	118.16 (14)
N1—C7—S1	111.72 (11)	C17—C16—N4	118.60 (15)
C2—C8—H8A	109.5	C16—C17—C12	118.79 (15)
C2—C8—H8B	109.5	C16—C17—H17	120.6
H8A—C8—H8B	109.5	C12—C17—H17	120.6
C2—C8—H8C	109.5	O1—C18—O2	126.60 (14)
H8A—C8—H8C	109.5	O1—C18—C12	116.98 (14)
H8B—C8—H8C	109.5	O2—C18—C12	116.42 (13)
C2—C9—H9A	109.5	O4—N3—O3	124.09 (15)
C2—C9—H9B	109.5	O4—N3—C14	117.95 (13)
H9A—C9—H9B	109.5	O3—N3—C14	117.96 (15)
C2—C9—H9C	109.5	O6—N4—O5	124.50 (15)
H9A—C9—H9C	109.5	O6—N4—C16	118.07 (16)
H9B—C9—H9C	109.5	O5—N4—C16	117.43 (14)
C5—C10—H10A	109.5

C6—C1—C2—C8	109.98 (18)	N1—C7—S1—C1	0.11 (12)
S1—C1—C2—C8	−66.27 (17)	C6—C1—S1—C7	0.86 (12)
C6—C1—C2—C9	−129.96 (17)	C2—C1—S1—C7	177.68 (13)
S1—C1—C2—C9	53.79 (18)	C17—C12—C13—C14	1.7 (2)
C6—C1—C2—C3	−10.9 (2)	C18—C12—C13—C14	−178.67 (14)
S1—C1—C2—C3	172.86 (12)	C12—C13—C14—C15	−0.1 (2)
C1—C2—C3—C4	40.0 (2)	C12—C13—C14—N3	179.39 (13)
C8—C2—C3—C4	−79.31 (18)	C13—C14—C15—C16	−1.3 (2)
C9—C2—C3—C4	160.33 (15)	N3—C14—C15—C16	179.18 (13)
C2—C3—C4—C5	−62.4 (2)	C14—C15—C16—C17	1.3 (2)
C3—C4—C5—C6	46.04 (19)	C14—C15—C16—N4	−179.58 (13)
C3—C4—C5—C11	−74.21 (19)	C15—C16—C17—C12	0.2 (2)
C3—C4—C5—C10	164.27 (15)	N4—C16—C17—C12	−178.97 (14)
C2—C1—C6—N1	−178.20 (14)	C13—C12—C17—C16	−1.7 (2)
S1—C1—C6—N1	−1.60 (17)	C18—C12—C17—C16	178.65 (14)
C2—C1—C6—C5	0.1 (3)	C13—C12—C18—O1	175.54 (15)
S1—C1—C6—C5	176.71 (13)	C17—C12—C18—O1	−4.8 (2)
C11—C5—C6—C1	104.46 (19)	C13—C12—C18—O2	−4.8 (2)
C10—C5—C6—C1	−134.13 (17)	C17—C12—C18—O2	174.86 (15)
C4—C5—C6—C1	−16.9 (2)	C13—C14—N3—O4	15.8 (2)
C11—C5—C6—N1	−77.36 (19)	C15—C14—N3—O4	−164.70 (16)
C10—C5—C6—N1	44.0 (2)	C13—C14—N3—O3	−164.01 (15)
C4—C5—C6—N1	161.23 (14)	C15—C14—N3—O3	15.5 (2)
N2—C7—N1—C6	178.54 (15)	C15—C16—N4—O6	−11.4 (2)
S1—C7—N1—C6	−1.05 (17)	C17—C16—N4—O6	167.84 (14)
C1—C6—N1—C7	1.76 (19)	C15—C16—N4—O5	169.17 (14)
C5—C6—N1—C7	−176.63 (14)	C17—C16—N4—O5	−11.6 (2)
N2—C7—S1—C1	−179.48 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.885 (19)	1.838 (19)	2.7187 (17)	173.4 (17)
N2—H3N···O2ⁱ	0.90 (2)	2.01 (2)	2.8509 (19)	156.3 (17)
N2—H2N···O2	0.91 (2)	1.86 (2)	2.7551 (18)	168.3 (18)
C8—H8A···O6ⁱⁱ	0.98	2.43	3.397 (2)	170

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

Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) fumarate (IV) top

Crystal data top

2C₁₁H₁₉N₂S⁺·C₄H₂O₄²⁻	F(000) = 576
M_r = 536.74	D_x = 1.224 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.0259 (6) Å	Cell parameters from 4569 reflections
b = 14.7314 (11) Å	θ = 2.3–23.7°
c = 11.1993 (8) Å	µ = 0.22 mm⁻¹
β = 101.943 (6)°	T = 173 K
V = 1456.87 (18) Å³	Prism, orange
Z = 2	0.15 × 0.08 × 0.02 mm

Data collection top

Rigaku XtaLAB P200 HPC diffractometer	6424 independent reflections
Radiation source: rotating anode, Rigaku FR-X	3792 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromator	R_int = 0.080
ω scans	θ_max = 29.1°, θ_min = 1.9°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)	h = −12→11
T_min = 0.333, T_max = 1.000	k = −18→20
19263 measured reflections	l = −14→12

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)] = 0.062	w = 1/[σ²(F_o²) + (0.0488P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.128	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.27 e Å⁻³
6424 reflections	Δρ_min = −0.26 e Å⁻³
350 parameters	Absolute structure: Flack x determined using 1279 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013).
1 restraint	Absolute structure parameter: 0.46 (7)
Primary atom site location: structure-invariant direct methods

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	1.2869 (6)	0.3952 (4)	0.6937 (4)	0.0339 (13)
C2	1.3939 (6)	0.4406 (4)	0.7989 (5)	0.0467 (15)
C3A	1.2984 (8)	0.5068 (7)	0.8546 (8)	0.052 (3)*	0.78 (2)
H3A1	1.2720	0.5596	0.7996	0.062*	0.78 (2)
H3A2	1.3578	0.5293	0.9334	0.062*	0.78 (2)
C4A	1.1520 (10)	0.4615 (8)	0.8755 (8)	0.047 (2)*	0.78 (2)
H4A1	1.1017	0.5022	0.9252	0.056*	0.78 (2)
H4A2	1.1780	0.4044	0.9216	0.056*	0.78 (2)
C3B	1.284 (3)	0.456 (3)	0.899 (3)	0.063 (12)*	0.22 (2)
H3B1	1.2677	0.3968	0.9362	0.075*	0.22 (2)
H3B2	1.3377	0.4959	0.9657	0.075*	0.22 (2)
C4B	1.130 (3)	0.498 (2)	0.846 (3)	0.033 (8)*	0.22 (2)
H4B1	1.0735	0.5078	0.9121	0.039*	0.22 (2)
H4B2	1.1445	0.5582	0.8102	0.039*	0.22 (2)
C5	1.0394 (6)	0.4401 (4)	0.7513 (4)	0.0372 (13)
C6	1.1349 (6)	0.3955 (3)	0.6728 (4)	0.0312 (13)
C7	1.1687 (6)	0.3114 (3)	0.5087 (4)	0.0320 (13)
C8	1.4824 (7)	0.3683 (4)	0.8815 (6)	0.067 (2)
H8A	1.5474	0.3975	0.9519	0.101*
H8B	1.5451	0.3337	0.8359	0.101*
H8C	1.4115	0.3272	0.9098	0.101*
C9	1.5096 (8)	0.4998 (5)	0.7490 (6)	0.076 (2)
H9A	1.5751	0.5316	0.8168	0.114*
H9B	1.4553	0.5443	0.6909	0.114*
H9C	1.5715	0.4610	0.7077	0.114*
C10	0.9232 (6)	0.3732 (4)	0.7813 (5)	0.0506 (16)
H10A	0.8700	0.4009	0.8400	0.076*
H10B	0.9750	0.3180	0.8167	0.076*
H10C	0.8501	0.3578	0.7065	0.076*
C11	0.9553 (8)	0.5223 (5)	0.6843 (6)	0.070 (2)
H11A	0.8941	0.5512	0.7364	0.105*
H11B	0.8892	0.5020	0.6083	0.105*
H11C	1.0291	0.5661	0.6656	0.105*
N1	1.0694 (5)	0.3476 (3)	0.5669 (4)	0.0298 (11)
H1N	0.976 (6)	0.334 (4)	0.544 (4)	0.036*
N2	1.1307 (6)	0.2614 (4)	0.4096 (4)	0.0452 (13)
H2N	1.029 (7)	0.263 (4)	0.369 (5)	0.054*
H3N	1.202 (6)	0.248 (4)	0.365 (5)	0.054*
S1	1.35226 (14)	0.33370 (9)	0.58194 (12)	0.0396 (4)
C12	−0.1633 (6)	0.1107 (4)	−0.1894 (4)	0.0340 (13)
C13	−0.2578 (6)	0.0698 (4)	−0.3022 (5)	0.0408 (14)
C14	−0.1503 (6)	0.0460 (4)	−0.3869 (5)	0.0501 (16)
H14A	−0.2031	0.0048	−0.4519	0.060*
H14B	−0.1244	0.1022	−0.4265	0.060*
C15	−0.0046 (6)	0.0005 (4)	−0.3204 (5)	0.0493 (15)
H15A	0.0557	−0.0170	−0.3813	0.059*
H15B	−0.0312	−0.0558	−0.2816	0.059*
C16	0.0948 (6)	0.0599 (4)	−0.2219 (4)	0.0353 (13)
C17	−0.0114 (5)	0.1088 (3)	−0.1552 (4)	0.0286 (12)
C18	−0.0619 (6)	0.1945 (4)	0.0014 (5)	0.0338 (13)
C19	−0.3410 (7)	−0.0144 (4)	−0.2709 (6)	0.0662 (19)
H19A	−0.4097	−0.0366	−0.3446	0.099*
H19B	−0.3995	0.0012	−0.2092	0.099*
H19C	−0.2672	−0.0618	−0.2389	0.099*
C20	−0.3760 (6)	0.1378 (4)	−0.3673 (6)	0.0556 (17)
H20A	−0.4356	0.1098	−0.4412	0.083*
H20B	−0.3246	0.1919	−0.3896	0.083*
H20C	−0.4432	0.1552	−0.3127	0.083*
C21	0.2029 (6)	−0.0017 (4)	−0.1334 (5)	0.0498 (15)
H21A	0.2615	−0.0391	−0.1793	0.075*
H21B	0.1441	−0.0412	−0.0901	0.075*
H21C	0.2720	0.0357	−0.0743	0.075*
C22	0.1855 (7)	0.1290 (4)	−0.2784 (5)	0.0520 (17)
H22A	0.2544	0.0971	−0.3212	0.078*
H22B	0.2443	0.1671	−0.2140	0.078*
H22C	0.1162	0.1671	−0.3364	0.078*
N3	0.0446 (5)	0.1575 (3)	−0.0477 (4)	0.0329 (11)
H4N	0.151 (6)	0.163 (4)	−0.013 (4)	0.040*
N4	−0.0317 (6)	0.2444 (4)	0.1013 (4)	0.0457 (13)
H5N	0.078 (7)	0.242 (4)	0.141 (5)	0.055*
H6N	−0.104 (7)	0.256 (4)	0.130 (5)	0.055*
S2	−0.24072 (14)	0.17401 (9)	−0.08375 (12)	0.0386 (4)
C23	0.7409 (6)	0.2901 (4)	0.3641 (5)	0.0358 (13)
C24	0.5781 (6)	0.2738 (4)	0.3122 (5)	0.0392 (14)
H24	0.5076	0.2871	0.3621	0.047*
C25	0.5242 (6)	0.2420 (4)	0.2013 (5)	0.0380 (13)
H25	0.5942	0.2310	0.1502	0.046*
C26	0.3622 (6)	0.2223 (4)	0.1512 (5)	0.0371 (14)
O1	0.7763 (4)	0.3234 (3)	0.4689 (3)	0.0469 (10)
O2	0.8346 (4)	0.2695 (3)	0.2995 (3)	0.0591 (12)
O3	0.3301 (4)	0.1922 (3)	0.0429 (3)	0.0473 (11)
O4	0.2689 (4)	0.2349 (4)	0.2157 (3)	0.0642 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.035 (3)	0.035 (3)	0.031 (3)	0.003 (2)	0.003 (2)	−0.002 (2)
C2	0.040 (3)	0.053 (4)	0.042 (3)	0.004 (3)	−0.001 (3)	−0.011 (3)
C5	0.039 (3)	0.040 (3)	0.033 (3)	0.001 (3)	0.008 (3)	−0.007 (3)
C6	0.041 (3)	0.026 (3)	0.025 (3)	−0.002 (3)	0.003 (2)	−0.003 (2)
C7	0.039 (3)	0.035 (3)	0.022 (3)	−0.004 (2)	0.007 (2)	0.000 (2)
C8	0.064 (4)	0.073 (5)	0.048 (4)	−0.007 (3)	−0.028 (3)	0.007 (3)
C9	0.070 (5)	0.058 (5)	0.090 (5)	−0.021 (4)	−0.006 (4)	−0.004 (4)
C10	0.047 (4)	0.064 (4)	0.047 (4)	−0.003 (3)	0.022 (3)	0.002 (3)
C11	0.085 (5)	0.060 (5)	0.077 (5)	0.025 (4)	0.044 (4)	0.015 (4)
N1	0.030 (2)	0.035 (3)	0.024 (2)	−0.001 (2)	0.006 (2)	0.000 (2)
N2	0.035 (3)	0.064 (4)	0.037 (3)	0.003 (3)	0.007 (2)	−0.013 (3)
S1	0.0327 (7)	0.0473 (9)	0.0377 (8)	0.0049 (7)	0.0045 (6)	−0.0037 (7)
C12	0.039 (3)	0.033 (3)	0.029 (3)	0.001 (3)	0.005 (2)	0.002 (2)
C13	0.038 (3)	0.043 (4)	0.039 (3)	−0.005 (3)	0.001 (3)	0.002 (3)
C14	0.046 (3)	0.066 (4)	0.035 (3)	0.003 (3)	0.000 (3)	−0.018 (3)
C15	0.049 (4)	0.053 (4)	0.043 (3)	−0.002 (3)	0.004 (3)	−0.017 (3)
C16	0.035 (3)	0.041 (3)	0.031 (3)	0.002 (3)	0.007 (2)	−0.005 (3)
C17	0.031 (3)	0.029 (3)	0.024 (3)	0.000 (2)	0.000 (2)	0.003 (2)
C18	0.036 (3)	0.035 (4)	0.030 (3)	0.005 (2)	0.008 (3)	−0.001 (2)
C19	0.068 (4)	0.055 (4)	0.070 (4)	−0.023 (4)	0.001 (4)	−0.004 (3)
C20	0.047 (4)	0.068 (5)	0.048 (4)	0.000 (3)	0.000 (3)	−0.003 (3)
C21	0.054 (4)	0.044 (4)	0.046 (3)	0.016 (3)	0.000 (3)	−0.007 (3)
C22	0.053 (4)	0.064 (5)	0.044 (4)	−0.002 (3)	0.021 (3)	−0.006 (3)
N3	0.027 (2)	0.043 (3)	0.028 (2)	0.000 (2)	0.0033 (19)	−0.003 (2)
N4	0.035 (3)	0.071 (4)	0.033 (3)	0.009 (3)	0.011 (2)	−0.012 (3)
S2	0.0323 (7)	0.0488 (10)	0.0352 (8)	0.0019 (7)	0.0081 (6)	0.0029 (7)
C23	0.033 (3)	0.040 (4)	0.035 (3)	−0.002 (3)	0.008 (3)	0.000 (3)
C24	0.032 (3)	0.047 (4)	0.040 (4)	−0.004 (3)	0.011 (3)	−0.008 (3)
C25	0.035 (3)	0.050 (4)	0.031 (3)	−0.002 (3)	0.011 (3)	−0.003 (3)
C26	0.036 (3)	0.042 (4)	0.032 (3)	0.000 (3)	0.004 (3)	−0.002 (3)
O1	0.036 (2)	0.072 (3)	0.031 (2)	−0.010 (2)	0.0048 (17)	−0.019 (2)
O2	0.037 (2)	0.108 (4)	0.033 (2)	−0.007 (2)	0.0091 (19)	−0.020 (2)
O3	0.037 (2)	0.071 (3)	0.033 (2)	−0.0045 (19)	0.0055 (17)	−0.017 (2)
O4	0.035 (2)	0.121 (4)	0.039 (2)	−0.010 (2)	0.013 (2)	−0.028 (2)

Geometric parameters (Å, º) top

C1—C6	1.344 (7)	C12—C13	1.496 (7)
C1—C2	1.514 (7)	C12—S2	1.761 (5)
C1—S1	1.744 (5)	C13—C19	1.527 (8)
C2—C3A	1.520 (9)	C13—C14	1.532 (7)
C2—C8	1.524 (8)	C13—C20	1.533 (8)
C2—C9	1.551 (9)	C14—C15	1.526 (8)
C2—C3B	1.66 (3)	C14—H14A	0.9900
C3A—C4A	1.541 (14)	C14—H14B	0.9900
C3A—H3A1	0.9900	C15—C16	1.542 (7)
C3A—H3A2	0.9900	C15—H15A	0.9900
C4A—C5	1.575 (10)	C15—H15B	0.9900
C4A—H4A1	0.9900	C16—C17	1.513 (7)
C4A—H4A2	0.9900	C16—C22	1.523 (7)
C3B—C4B	1.53 (5)	C16—C21	1.536 (7)
C3B—H3B1	0.9900	C17—N3	1.404 (6)
C3B—H3B2	0.9900	C18—N4	1.319 (7)
C4B—C5	1.47 (2)	C18—N3	1.320 (6)
C4B—H4B1	0.9900	C18—S2	1.723 (5)
C4B—H4B2	0.9900	C19—H19A	0.9800
C5—C6	1.504 (7)	C19—H19B	0.9800
C5—C10	1.526 (8)	C19—H19C	0.9800
C5—C11	1.540 (8)	C20—H20A	0.9800
C6—N1	1.401 (6)	C20—H20B	0.9800
C7—N2	1.318 (6)	C20—H20C	0.9800
C7—N1	1.325 (6)	C21—H21A	0.9800
C7—S1	1.721 (5)	C21—H21B	0.9800
C8—H8A	0.9800	C21—H21C	0.9800
C8—H8B	0.9800	C22—H22A	0.9800
C8—H8C	0.9800	C22—H22B	0.9800
C9—H9A	0.9800	C22—H22C	0.9800
C9—H9B	0.9800	N3—H4N	0.96 (5)
C9—H9C	0.9800	N4—H5N	1.00 (6)
C10—H10A	0.9800	N4—H6N	0.81 (6)
C10—H10B	0.9800	C23—O1	1.251 (6)
C10—H10C	0.9800	C23—O2	1.258 (6)
C11—H11A	0.9800	C23—C24	1.484 (7)
C11—H11B	0.9800	C24—C25	1.321 (6)
C11—H11C	0.9800	C24—H24	0.9500
N1—H1N	0.85 (5)	C25—C26	1.483 (7)
N2—H2N	0.94 (6)	C25—H25	0.9500
N2—H3N	0.91 (6)	C26—O4	1.232 (6)
C12—C17	1.345 (7)	C26—O3	1.267 (6)

C6—C1—C2	126.7 (5)	C7—N2—H3N	119 (4)
C6—C1—S1	111.2 (4)	H2N—N2—H3N	118 (5)
C2—C1—S1	122.1 (4)	C7—S1—C1	90.3 (2)
C1—C2—C3A	106.1 (5)	C17—C12—C13	127.0 (5)
C1—C2—C8	109.5 (5)	C17—C12—S2	110.0 (4)
C3A—C2—C8	118.0 (6)	C13—C12—S2	122.9 (4)
C1—C2—C9	109.7 (5)	C12—C13—C19	110.8 (5)
C3A—C2—C9	105.5 (6)	C12—C13—C14	106.9 (4)
C8—C2—C9	107.7 (5)	C19—C13—C14	111.1 (5)
C1—C2—C3B	102.3 (11)	C12—C13—C20	110.9 (5)
C8—C2—C3B	89.8 (15)	C19—C13—C20	108.2 (5)
C9—C2—C3B	134.9 (15)	C14—C13—C20	108.8 (5)
C2—C3A—C4A	111.1 (9)	C15—C14—C13	113.0 (5)
C2—C3A—H3A1	109.4	C15—C14—H14A	109.0
C4A—C3A—H3A1	109.4	C13—C14—H14A	109.0
C2—C3A—H3A2	109.4	C15—C14—H14B	109.0
C4A—C3A—H3A2	109.4	C13—C14—H14B	109.0
H3A1—C3A—H3A2	108.0	H14A—C14—H14B	107.8
C3A—C4A—C5	111.7 (8)	C14—C15—C16	114.5 (5)
C3A—C4A—H4A1	109.3	C14—C15—H15A	108.6
C5—C4A—H4A1	109.3	C16—C15—H15A	108.6
C3A—C4A—H4A2	109.3	C14—C15—H15B	108.6
C5—C4A—H4A2	109.3	C16—C15—H15B	108.6
H4A1—C4A—H4A2	107.9	H15A—C15—H15B	107.6
C4B—C3B—C2	114 (3)	C17—C16—C22	109.7 (4)
C4B—C3B—H3B1	108.7	C17—C16—C21	110.2 (4)
C2—C3B—H3B1	108.7	C22—C16—C21	109.8 (5)
C4B—C3B—H3B2	108.7	C17—C16—C15	106.8 (4)
C2—C3B—H3B2	108.7	C22—C16—C15	111.4 (4)
H3B1—C3B—H3B2	107.6	C21—C16—C15	108.9 (5)
C5—C4B—C3B	112 (3)	C12—C17—N3	113.5 (4)
C5—C4B—H4B1	109.3	C12—C17—C16	125.6 (4)
C3B—C4B—H4B1	109.3	N3—C17—C16	120.9 (4)
C5—C4B—H4B2	109.3	N4—C18—N3	122.9 (5)
C3B—C4B—H4B2	109.3	N4—C18—S2	124.9 (4)
H4B1—C4B—H4B2	107.9	N3—C18—S2	112.1 (4)
C4B—C5—C6	112.1 (10)	C13—C19—H19A	109.5
C4B—C5—C10	121.4 (12)	C13—C19—H19B	109.5
C6—C5—C10	110.5 (5)	H19A—C19—H19B	109.5
C4B—C5—C11	92.1 (15)	C13—C19—H19C	109.5
C6—C5—C11	110.1 (4)	H19A—C19—H19C	109.5
C10—C5—C11	108.9 (5)	H19B—C19—H19C	109.5
C6—C5—C4A	105.1 (5)	C13—C20—H20A	109.5
C10—C5—C4A	106.4 (5)	C13—C20—H20B	109.5
C11—C5—C4A	115.8 (6)	H20A—C20—H20B	109.5
C1—C6—N1	112.5 (4)	C13—C20—H20C	109.5
C1—C6—C5	126.0 (4)	H20A—C20—H20C	109.5
N1—C6—C5	121.5 (4)	H20B—C20—H20C	109.5
N2—C7—N1	123.7 (5)	C16—C21—H21A	109.5
N2—C7—S1	124.4 (4)	C16—C21—H21B	109.5
N1—C7—S1	111.8 (4)	H21A—C21—H21B	109.5
C2—C8—H8A	109.5	C16—C21—H21C	109.5
C2—C8—H8B	109.5	H21A—C21—H21C	109.5
H8A—C8—H8B	109.5	H21B—C21—H21C	109.5
C2—C8—H8C	109.5	C16—C22—H22A	109.5
H8A—C8—H8C	109.5	C16—C22—H22B	109.5
H8B—C8—H8C	109.5	H22A—C22—H22B	109.5
C2—C9—H9A	109.5	C16—C22—H22C	109.5
C2—C9—H9B	109.5	H22A—C22—H22C	109.5
H9A—C9—H9B	109.5	H22B—C22—H22C	109.5
C2—C9—H9C	109.5	C18—N3—C17	113.9 (4)
H9A—C9—H9C	109.5	C18—N3—H4N	123 (3)
H9B—C9—H9C	109.5	C17—N3—H4N	123 (3)
C5—C10—H10A	109.5	C18—N4—H5N	112 (3)
C5—C10—H10B	109.5	C18—N4—H6N	115 (4)
H10A—C10—H10B	109.5	H5N—N4—H6N	130 (5)
C5—C10—H10C	109.5	C18—S2—C12	90.5 (2)
H10A—C10—H10C	109.5	O1—C23—O2	124.2 (5)
H10B—C10—H10C	109.5	O1—C23—C24	118.1 (5)
C5—C11—H11A	109.5	O2—C23—C24	117.7 (5)
C5—C11—H11B	109.5	C25—C24—C23	124.6 (5)
H11A—C11—H11B	109.5	C25—C24—H24	117.7
C5—C11—H11C	109.5	C23—C24—H24	117.7
H11A—C11—H11C	109.5	C24—C25—C26	124.6 (5)
H11B—C11—H11C	109.5	C24—C25—H25	117.7
C7—N1—C6	114.1 (4)	C26—C25—H25	117.7
C7—N1—H1N	119 (3)	O4—C26—O3	124.4 (5)
C6—N1—H1N	126 (3)	O4—C26—C25	119.2 (5)
C7—N2—H2N	117 (4)	O3—C26—C25	116.3 (5)

C6—C1—C2—C3A	−15.4 (9)	N1—C7—S1—C1	−0.6 (4)
S1—C1—C2—C3A	165.0 (6)	C6—C1—S1—C7	0.8 (4)
C6—C1—C2—C8	113.1 (6)	C2—C1—S1—C7	−179.5 (5)
S1—C1—C2—C8	−66.6 (6)	C17—C12—C13—C19	107.5 (6)
C6—C1—C2—C9	−128.9 (6)	S2—C12—C13—C19	−75.3 (6)
S1—C1—C2—C9	51.4 (6)	C17—C12—C13—C14	−13.7 (7)
C6—C1—C2—C3B	18.8 (17)	S2—C12—C13—C14	163.5 (4)
S1—C1—C2—C3B	−160.8 (16)	C17—C12—C13—C20	−132.2 (6)
C1—C2—C3A—C4A	47.8 (10)	S2—C12—C13—C20	45.0 (6)
C8—C2—C3A—C4A	−75.5 (9)	C12—C13—C14—C15	44.1 (6)
C9—C2—C3A—C4A	164.1 (8)	C19—C13—C14—C15	−77.0 (6)
C2—C3A—C4A—C5	−69.2 (12)	C20—C13—C14—C15	163.9 (5)
C1—C2—C3B—C4B	−48 (3)	C13—C14—C15—C16	−62.5 (7)
C8—C2—C3B—C4B	−158 (3)	C14—C15—C16—C17	40.9 (6)
C9—C2—C3B—C4B	87 (3)	C14—C15—C16—C22	−78.9 (6)
C2—C3B—C4B—C5	62 (4)	C14—C15—C16—C21	159.9 (5)
C3B—C4B—C5—C6	−38 (3)	C13—C12—C17—N3	176.7 (5)
C3B—C4B—C5—C10	95 (3)	S2—C12—C17—N3	−0.8 (6)
C3B—C4B—C5—C11	−151 (3)	C13—C12—C17—C16	−3.4 (8)
C3A—C4A—C5—C6	47.3 (10)	S2—C12—C17—C16	179.1 (4)
C3A—C4A—C5—C10	164.5 (8)	C22—C16—C17—C12	111.1 (6)
C3A—C4A—C5—C11	−74.4 (10)	C21—C16—C17—C12	−127.9 (5)
C2—C1—C6—N1	179.6 (5)	C15—C16—C17—C12	−9.8 (7)
S1—C1—C6—N1	−0.7 (5)	C22—C16—C17—N3	−69.1 (6)
C2—C1—C6—C5	−0.9 (9)	C21—C16—C17—N3	51.9 (6)
S1—C1—C6—C5	178.8 (4)	C15—C16—C17—N3	170.1 (5)
C4B—C5—C6—C1	9.7 (17)	N4—C18—N3—C17	−178.6 (5)
C10—C5—C6—C1	−129.1 (5)	S2—C18—N3—C17	−1.4 (6)
C11—C5—C6—C1	110.6 (6)	C12—C17—N3—C18	1.5 (6)
C4A—C5—C6—C1	−14.7 (8)	C16—C17—N3—C18	−178.4 (4)
C4B—C5—C6—N1	−170.9 (16)	N4—C18—S2—C12	177.9 (5)
C10—C5—C6—N1	50.4 (6)	N3—C18—S2—C12	0.8 (4)
C11—C5—C6—N1	−69.9 (6)	C17—C12—S2—C18	0.0 (4)
C4A—C5—C6—N1	164.7 (6)	C13—C12—S2—C18	−177.6 (4)
N2—C7—N1—C6	177.7 (5)	O1—C23—C24—C25	177.5 (5)
S1—C7—N1—C6	0.3 (6)	O2—C23—C24—C25	−2.4 (8)
C1—C6—N1—C7	0.3 (6)	C23—C24—C25—C26	177.5 (5)
C5—C6—N1—C7	−179.2 (5)	C24—C25—C26—O4	−0.8 (8)
N2—C7—S1—C1	−177.9 (5)	C24—C25—C26—O3	179.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.85 (5)	1.84 (5)	2.670 (5)	167 (5)
N2—H2N···O2	0.94 (6)	1.77 (6)	2.704 (6)	177 (5)
N2—H3N···O4ⁱ	0.91 (6)	1.90 (6)	2.746 (6)	153 (5)
N3—H4N···O3	0.96 (5)	1.67 (5)	2.617 (5)	169 (5)
N4—H5N···O4	1.00 (6)	1.75 (6)	2.754 (7)	178 (5)
N4—H6N···O2ⁱⁱ	0.81 (6)	2.09 (6)	2.763 (6)	141 (6)

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) succinate–2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1) (V) top

Crystal data top

1.5C₁₁H₁₉N₂S⁺·0.5C₄H₄O₄²⁻·0.5C₄H₅O₄⁻·0.5C₁₁H₁₈N₂S	F(000) = 580
M_r = 538.75	D_x = 1.226 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.9437 (3) Å	Cell parameters from 9613 reflections
b = 14.7253 (4) Å	θ = 2.3–28.0°
c = 11.2676 (4) Å	µ = 0.22 mm⁻¹
β = 100.493 (3)°	T = 173 K
V = 1459.11 (8) Å³	Plate, colourless
Z = 2	0.32 × 0.15 × 0.02 mm

Data collection top

Rigaku XtaLAB P200 HPC diffractometer	6272 independent reflections
Radiation source: rotating anode, Rigaku FR-X	5511 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromator	R_int = 0.034
ω scans	θ_max = 29.1°, θ_min = 2.3°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)	h = −10→12
T_min = 0.779, T_max = 1.000	k = −19→19
19079 measured reflections	l = −14→14

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)] = 0.039	w = 1/[σ²(F_o²) + (0.0529P)² + 0.1056P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.094	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.26 e Å⁻³
6272 reflections	Δρ_min = −0.25 e Å⁻³
354 parameters	Absolute structure: Flack x determined using 2211 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.00 (3)
Primary atom site location: structure-invariant direct methods

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	1.2888 (3)	0.39542 (19)	0.6860 (2)	0.0263 (6)
C2	1.3946 (3)	0.4407 (2)	0.7881 (3)	0.0357 (7)
C3A	1.2962 (6)	0.5069 (4)	0.8461 (5)	0.0365 (17)*	0.593 (11)
H3A1	1.2689	0.5598	0.7923	0.044*	0.593 (11)
H3A2	1.3548	0.5293	0.9237	0.044*	0.593 (11)
C4A	1.1500 (6)	0.4594 (5)	0.8685 (6)	0.0366 (16)*	0.593 (11)
H4A1	1.0979	0.4985	0.9198	0.044*	0.593 (11)
H4A2	1.1768	0.4015	0.9118	0.044*	0.593 (11)
C3B	1.2917 (10)	0.4598 (8)	0.8865 (9)	0.049 (3)*	0.407 (11)
H3B1	1.2754	0.4020	0.9271	0.059*	0.407 (11)
H3B2	1.3468	0.5015	0.9483	0.059*	0.407 (11)
C4B	1.1399 (9)	0.5005 (7)	0.8353 (8)	0.038 (2)*	0.407 (11)
H4B1	1.1564	0.5586	0.7954	0.046*	0.407 (11)
H4B2	1.0860	0.5143	0.9025	0.046*	0.407 (11)
C5	1.0393 (3)	0.4400 (2)	0.7449 (3)	0.0308 (6)
C6	1.1354 (3)	0.39467 (18)	0.6659 (2)	0.0236 (6)
C7	1.1723 (3)	0.30960 (19)	0.5050 (2)	0.0265 (6)
C8	1.4933 (5)	0.3708 (3)	0.8639 (4)	0.0612 (11)
H8A	1.5574	0.4010	0.9324	0.092*
H8B	1.5579	0.3404	0.8146	0.092*
H8C	1.4285	0.3258	0.8939	0.092*
C9	1.5000 (5)	0.5061 (3)	0.7370 (4)	0.0690 (12)
H9A	1.5592	0.5414	0.8030	0.103*
H9B	1.4390	0.5474	0.6793	0.103*
H9C	1.5691	0.4714	0.6961	0.103*
C10	0.9296 (4)	0.3719 (2)	0.7834 (3)	0.0480 (9)
H10A	0.8715	0.4014	0.8385	0.072*
H10B	0.9869	0.3207	0.8245	0.072*
H10C	0.8596	0.3499	0.7121	0.072*
C11	0.9468 (5)	0.5170 (3)	0.6769 (4)	0.0669 (13)
H11A	0.8820	0.5444	0.7285	0.100*
H11B	0.8830	0.4928	0.6036	0.100*
H11C	1.0158	0.5631	0.6547	0.100*
N1	1.0710 (3)	0.34631 (16)	0.5629 (2)	0.0246 (5)
H1N	0.968 (4)	0.335 (2)	0.534 (3)	0.030*
N2	1.1368 (3)	0.2592 (2)	0.4072 (2)	0.0397 (7)
H2N	1.209 (4)	0.241 (3)	0.369 (3)	0.048*
H3N	1.047 (4)	0.257 (3)	0.374 (3)	0.048*
S1	1.35670 (7)	0.33342 (5)	0.57387 (6)	0.03090 (18)
C12	−0.1518 (3)	0.11232 (19)	−0.1824 (3)	0.0261 (6)
C13	−0.2459 (4)	0.0700 (2)	−0.2927 (3)	0.0345 (7)
C14	−0.1355 (4)	0.0472 (2)	−0.3784 (3)	0.0405 (8)
H14A	−0.1871	0.0066	−0.4431	0.049*
H14B	−0.1081	0.1038	−0.4167	0.049*
C15	0.0097 (4)	0.0011 (2)	−0.3133 (3)	0.0426 (8)
H15A	0.0715	−0.0172	−0.3738	0.051*
H15B	−0.0183	−0.0547	−0.2736	0.051*
C16	0.1071 (3)	0.06150 (19)	−0.2180 (3)	0.0295 (6)
C17	0.0007 (3)	0.11035 (18)	−0.1495 (2)	0.0245 (6)
C18	−0.0513 (3)	0.19535 (18)	0.0048 (2)	0.0263 (6)
C19	−0.3270 (5)	−0.0149 (3)	−0.2585 (4)	0.0581 (10)
H19A	−0.3866	−0.0421	−0.3315	0.087*
H19B	−0.3950	0.0018	−0.2030	0.087*
H19C	−0.2516	−0.0588	−0.2193	0.087*
C20	−0.3652 (4)	0.1381 (2)	−0.3552 (3)	0.0459 (8)
H20A	−0.4216	0.1112	−0.4295	0.069*
H20B	−0.3141	0.1936	−0.3748	0.069*
H20C	−0.4358	0.1530	−0.3010	0.069*
C21	0.2173 (4)	0.0007 (2)	−0.1322 (3)	0.0446 (8)
H21A	0.2785	−0.0351	−0.1789	0.067*
H21B	0.1593	−0.0401	−0.0890	0.067*
H21C	0.2844	0.0388	−0.0739	0.067*
C22	0.1982 (4)	0.1307 (2)	−0.2773 (3)	0.0426 (8)
H22A	0.2681	0.0986	−0.3203	0.064*
H22B	0.2564	0.1697	−0.2150	0.064*
H22C	0.1283	0.1680	−0.3344	0.064*
N3	0.0575 (3)	0.15834 (16)	−0.0442 (2)	0.0248 (5)
H4N	0.153 (9)	0.165 (5)	−0.011 (6)	0.030*	0.50 (5)
N4	−0.0255 (3)	0.2469 (2)	0.1041 (2)	0.0387 (7)
H5N	−0.096 (4)	0.249 (3)	0.142 (3)	0.046*
H6N	0.073 (4)	0.245 (2)	0.147 (3)	0.046*
S2	−0.23122 (8)	0.17442 (5)	−0.07649 (6)	0.02918 (18)
C26	0.3743 (3)	0.22426 (19)	0.1462 (3)	0.0271 (6)
C25	0.5352 (3)	0.2536 (2)	0.1889 (3)	0.0298 (6)
H25A	0.5538	0.3096	0.1451	0.036*
H25B	0.6039	0.2060	0.1676	0.036*
C24	0.5760 (3)	0.2717 (2)	0.3238 (3)	0.0300 (7)
H24A	0.5202	0.3264	0.3427	0.036*
H24B	0.5406	0.2199	0.3672	0.036*
C23	0.7441 (3)	0.2859 (2)	0.3709 (3)	0.0284 (6)
O1	0.7810 (2)	0.32184 (16)	0.47272 (18)	0.0379 (5)
O2	0.8363 (2)	0.2585 (2)	0.3079 (2)	0.0575 (7)
O3	0.3395 (3)	0.20074 (16)	0.03486 (19)	0.0388 (6)
H1O	0.249 (11)	0.191 (5)	0.008 (7)	0.047*	0.50 (5)
O4	0.2832 (2)	0.2213 (2)	0.21545 (19)	0.0500 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0280 (14)	0.0258 (13)	0.0253 (14)	0.0017 (11)	0.0051 (11)	−0.0003 (12)
C2	0.0308 (15)	0.0380 (16)	0.0364 (17)	0.0002 (13)	0.0009 (13)	−0.0095 (15)
C5	0.0322 (15)	0.0316 (15)	0.0295 (15)	−0.0011 (13)	0.0082 (13)	−0.0073 (13)
C6	0.0287 (14)	0.0218 (12)	0.0207 (13)	−0.0020 (11)	0.0050 (11)	0.0005 (11)
C7	0.0236 (14)	0.0331 (15)	0.0223 (14)	0.0018 (11)	0.0032 (11)	0.0001 (12)
C8	0.063 (2)	0.059 (2)	0.048 (2)	−0.019 (2)	−0.0263 (19)	0.0101 (19)
C9	0.069 (3)	0.047 (2)	0.079 (3)	−0.026 (2)	−0.018 (2)	0.003 (2)
C10	0.054 (2)	0.0462 (19)	0.053 (2)	0.0011 (17)	0.0319 (18)	0.0051 (17)
C11	0.079 (3)	0.048 (2)	0.088 (3)	0.031 (2)	0.052 (3)	0.023 (2)
N1	0.0226 (12)	0.0286 (12)	0.0226 (12)	−0.0009 (10)	0.0037 (9)	−0.0015 (10)
N2	0.0287 (14)	0.0613 (19)	0.0288 (15)	0.0056 (13)	0.0044 (12)	−0.0156 (14)
S1	0.0231 (3)	0.0400 (4)	0.0290 (4)	0.0043 (3)	0.0032 (3)	−0.0045 (3)
C12	0.0266 (14)	0.0253 (13)	0.0267 (14)	−0.0014 (11)	0.0058 (12)	0.0007 (12)
C13	0.0337 (16)	0.0343 (15)	0.0331 (16)	−0.0093 (13)	−0.0005 (13)	−0.0047 (14)
C14	0.0425 (18)	0.0461 (18)	0.0305 (16)	−0.0013 (14)	0.0000 (14)	−0.0137 (15)
C15	0.0437 (18)	0.0420 (17)	0.0408 (18)	0.0018 (15)	0.0044 (15)	−0.0170 (15)
C16	0.0303 (14)	0.0295 (14)	0.0287 (15)	0.0027 (12)	0.0052 (12)	−0.0028 (13)
C17	0.0276 (14)	0.0231 (12)	0.0225 (14)	−0.0007 (11)	0.0038 (11)	0.0016 (11)
C18	0.0262 (14)	0.0297 (15)	0.0225 (14)	0.0023 (11)	0.0032 (12)	0.0017 (11)
C19	0.062 (2)	0.048 (2)	0.061 (2)	−0.0282 (18)	0.004 (2)	−0.0068 (19)
C20	0.0333 (17)	0.060 (2)	0.0387 (19)	0.0004 (16)	−0.0078 (14)	−0.0049 (17)
C21	0.0418 (18)	0.0429 (18)	0.0472 (19)	0.0173 (15)	0.0028 (16)	−0.0068 (16)
C22	0.0396 (18)	0.0499 (19)	0.0433 (19)	−0.0023 (15)	0.0206 (16)	−0.0042 (16)
N3	0.0218 (11)	0.0306 (13)	0.0210 (12)	0.0003 (10)	0.0015 (9)	−0.0004 (10)
N4	0.0286 (14)	0.0594 (17)	0.0277 (15)	0.0047 (13)	0.0038 (12)	−0.0121 (13)
S2	0.0230 (3)	0.0361 (4)	0.0287 (4)	0.0008 (3)	0.0053 (3)	0.0016 (3)
C26	0.0268 (14)	0.0289 (14)	0.0248 (14)	0.0020 (12)	0.0021 (12)	−0.0022 (12)
C25	0.0281 (15)	0.0363 (15)	0.0243 (15)	−0.0015 (12)	0.0031 (12)	−0.0019 (13)
C24	0.0250 (14)	0.0386 (16)	0.0256 (15)	0.0016 (12)	0.0025 (12)	−0.0064 (13)
C23	0.0279 (15)	0.0321 (14)	0.0251 (15)	−0.0012 (12)	0.0045 (12)	−0.0019 (13)
O1	0.0275 (10)	0.0581 (14)	0.0274 (11)	−0.0050 (10)	0.0029 (8)	−0.0178 (11)
O2	0.0259 (12)	0.109 (2)	0.0368 (13)	−0.0003 (13)	0.0035 (10)	−0.0313 (14)
O3	0.0263 (11)	0.0618 (16)	0.0273 (12)	−0.0077 (10)	0.0022 (9)	−0.0105 (10)
O4	0.0280 (11)	0.0919 (19)	0.0312 (12)	−0.0076 (12)	0.0084 (10)	−0.0186 (13)

Geometric parameters (Å, º) top

C1—C6	1.349 (4)	C13—C19	1.530 (4)
C1—C2	1.506 (4)	C13—C20	1.538 (5)
C1—S1	1.754 (3)	C13—C14	1.538 (4)
C2—C8	1.515 (5)	C14—C15	1.528 (5)
C2—C9	1.531 (5)	C14—H14A	0.9900
C2—C3A	1.537 (6)	C14—H14B	0.9900
C2—C3B	1.589 (10)	C15—C16	1.536 (4)
C3A—C4A	1.544 (9)	C15—H15A	0.9900
C3A—H3A1	0.9900	C15—H15B	0.9900
C3A—H3A2	0.9900	C16—C17	1.512 (4)
C4A—C5	1.581 (6)	C16—C22	1.532 (4)
C4A—H4A1	0.9900	C16—C21	1.536 (4)
C4A—H4A2	0.9900	C17—N3	1.395 (4)
C3B—C4B	1.499 (14)	C18—N3	1.321 (3)
C3B—H3B1	0.9900	C18—N4	1.337 (4)
C3B—H3B2	0.9900	C18—S2	1.728 (3)
C4B—C5	1.519 (8)	C19—H19A	0.9800
C4B—H4B1	0.9900	C19—H19B	0.9800
C4B—H4B2	0.9900	C19—H19C	0.9800
C5—C6	1.502 (4)	C20—H20A	0.9800
C5—C10	1.520 (4)	C20—H20B	0.9800
C5—C11	1.525 (5)	C20—H20C	0.9800
C6—N1	1.394 (3)	C21—H21A	0.9800
C7—N2	1.319 (4)	C21—H21B	0.9800
C7—N1	1.325 (3)	C21—H21C	0.9800
C7—S1	1.726 (3)	C22—H22A	0.9800
C8—H8A	0.9800	C22—H22B	0.9800
C8—H8B	0.9800	C22—H22C	0.9800
C8—H8C	0.9800	N3—H4N	0.87 (8)
C9—H9A	0.9800	N4—H5N	0.82 (4)
C9—H9B	0.9800	N4—H6N	0.92 (4)
C9—H9C	0.9800	C26—O4	1.228 (3)
C10—H10A	0.9800	C26—O3	1.283 (4)
C10—H10B	0.9800	C26—C25	1.496 (4)
C10—H10C	0.9800	C25—C24	1.521 (4)
C11—H11A	0.9800	C25—H25A	0.9900
C11—H11B	0.9800	C25—H25B	0.9900
C11—H11C	0.9800	C24—C23	1.515 (4)
N1—H1N	0.93 (3)	C24—H24A	0.9900
N2—H2N	0.89 (4)	C24—H24B	0.9900
N2—H3N	0.82 (4)	C23—O2	1.249 (4)
C12—C17	1.348 (4)	C23—O1	1.252 (3)
C12—C13	1.503 (4)	O3—H1O	0.82 (10)
C12—S2	1.753 (3)

C6—C1—C2	127.6 (3)	C17—C12—S2	109.8 (2)
C6—C1—S1	110.5 (2)	C13—C12—S2	123.0 (2)
C2—C1—S1	122.0 (2)	C12—C13—C19	110.5 (3)
C1—C2—C8	110.5 (3)	C12—C13—C20	110.2 (3)
C1—C2—C9	109.6 (3)	C19—C13—C20	109.1 (3)
C8—C2—C9	107.7 (3)	C12—C13—C14	106.4 (2)
C1—C2—C3A	106.1 (3)	C19—C13—C14	111.6 (3)
C8—C2—C3A	120.8 (4)	C20—C13—C14	109.1 (3)
C9—C2—C3A	101.6 (4)	C15—C14—C13	112.5 (3)
C1—C2—C3B	104.4 (4)	C15—C14—H14A	109.1
C8—C2—C3B	94.5 (5)	C13—C14—H14A	109.1
C9—C2—C3B	128.7 (5)	C15—C14—H14B	109.1
C2—C3A—C4A	110.5 (5)	C13—C14—H14B	109.1
C2—C3A—H3A1	109.6	H14A—C14—H14B	107.8
C4A—C3A—H3A1	109.6	C14—C15—C16	113.7 (3)
C2—C3A—H3A2	109.6	C14—C15—H15A	108.8
C4A—C3A—H3A2	109.6	C16—C15—H15A	108.8
H3A1—C3A—H3A2	108.1	C14—C15—H15B	108.8
C3A—C4A—C5	110.5 (5)	C16—C15—H15B	108.8
C3A—C4A—H4A1	109.5	H15A—C15—H15B	107.7
C5—C4A—H4A1	109.5	C17—C16—C22	109.9 (2)
C3A—C4A—H4A2	109.5	C17—C16—C21	110.3 (2)
C5—C4A—H4A2	109.5	C22—C16—C21	109.3 (3)
H4A1—C4A—H4A2	108.1	C17—C16—C15	107.6 (2)
C4B—C3B—C2	113.6 (8)	C22—C16—C15	111.0 (3)
C4B—C3B—H3B1	108.8	C21—C16—C15	108.7 (3)
C2—C3B—H3B1	108.8	C12—C17—N3	114.6 (2)
C4B—C3B—H3B2	108.8	C12—C17—C16	124.7 (2)
C2—C3B—H3B2	108.8	N3—C17—C16	120.7 (2)
H3B1—C3B—H3B2	107.7	N3—C18—N4	123.8 (3)
C3B—C4B—C5	114.1 (8)	N3—C18—S2	113.0 (2)
C3B—C4B—H4B1	108.7	N4—C18—S2	123.2 (2)
C5—C4B—H4B1	108.7	C13—C19—H19A	109.5
C3B—C4B—H4B2	108.7	C13—C19—H19B	109.5
C5—C4B—H4B2	108.7	H19A—C19—H19B	109.5
H4B1—C4B—H4B2	107.6	C13—C19—H19C	109.5
C6—C5—C4B	109.0 (4)	H19A—C19—H19C	109.5
C6—C5—C10	110.2 (2)	H19B—C19—H19C	109.5
C4B—C5—C10	122.0 (4)	C13—C20—H20A	109.5
C6—C5—C11	110.4 (3)	C13—C20—H20B	109.5
C4B—C5—C11	95.9 (5)	H20A—C20—H20B	109.5
C10—C5—C11	108.3 (3)	C13—C20—H20C	109.5
C6—C5—C4A	105.6 (3)	H20A—C20—H20C	109.5
C10—C5—C4A	101.6 (3)	H20B—C20—H20C	109.5
C11—C5—C4A	120.2 (4)	C16—C21—H21A	109.5
C1—C6—N1	113.4 (2)	C16—C21—H21B	109.5
C1—C6—C5	124.8 (3)	H21A—C21—H21B	109.5
N1—C6—C5	121.7 (2)	C16—C21—H21C	109.5
N2—C7—N1	124.0 (3)	H21A—C21—H21C	109.5
N2—C7—S1	123.7 (2)	H21B—C21—H21C	109.5
N1—C7—S1	112.3 (2)	C16—C22—H22A	109.5
C2—C8—H8A	109.5	C16—C22—H22B	109.5
C2—C8—H8B	109.5	H22A—C22—H22B	109.5
H8A—C8—H8B	109.5	C16—C22—H22C	109.5
C2—C8—H8C	109.5	H22A—C22—H22C	109.5
H8A—C8—H8C	109.5	H22B—C22—H22C	109.5
H8B—C8—H8C	109.5	C18—N3—C17	112.5 (2)
C2—C9—H9A	109.5	C18—N3—H4N	121 (4)
C2—C9—H9B	109.5	C17—N3—H4N	127 (4)
H9A—C9—H9B	109.5	C18—N4—H5N	115 (3)
C2—C9—H9C	109.5	C18—N4—H6N	115 (2)
H9A—C9—H9C	109.5	H5N—N4—H6N	118 (3)
H9B—C9—H9C	109.5	C18—S2—C12	90.03 (13)
C5—C10—H10A	109.5	O4—C26—O3	122.7 (3)
C5—C10—H10B	109.5	O4—C26—C25	121.1 (3)
H10A—C10—H10B	109.5	O3—C26—C25	116.1 (2)
C5—C10—H10C	109.5	C26—C25—C24	114.4 (2)
H10A—C10—H10C	109.5	C26—C25—H25A	108.7
H10B—C10—H10C	109.5	C24—C25—H25A	108.7
C5—C11—H11A	109.5	C26—C25—H25B	108.7
C5—C11—H11B	109.5	C24—C25—H25B	108.7
H11A—C11—H11B	109.5	H25A—C25—H25B	107.6
C5—C11—H11C	109.5	C23—C24—C25	114.6 (2)
H11A—C11—H11C	109.5	C23—C24—H24A	108.6
H11B—C11—H11C	109.5	C25—C24—H24A	108.6
C7—N1—C6	113.7 (2)	C23—C24—H24B	108.6
C7—N1—H1N	118.6 (18)	C25—C24—H24B	108.6
C6—N1—H1N	127.6 (18)	H24A—C24—H24B	107.6
C7—N2—H2N	120 (2)	O2—C23—O1	124.5 (3)
C7—N2—H3N	117 (3)	O2—C23—C24	118.2 (2)
H2N—N2—H3N	121 (4)	O1—C23—C24	117.3 (2)
C7—S1—C1	90.11 (13)	C26—O3—H1O	117 (5)
C17—C12—C13	127.2 (3)

C6—C1—C2—C8	117.8 (4)	N1—C7—S1—C1	0.3 (2)
S1—C1—C2—C8	−61.8 (3)	C6—C1—S1—C7	0.1 (2)
C6—C1—C2—C9	−123.7 (3)	C2—C1—S1—C7	179.7 (2)
S1—C1—C2—C9	56.7 (3)	C17—C12—C13—C19	105.9 (4)
C6—C1—C2—C3A	−14.8 (5)	S2—C12—C13—C19	−74.9 (3)
S1—C1—C2—C3A	165.7 (3)	C17—C12—C13—C20	−133.5 (3)
C6—C1—C2—C3B	17.2 (6)	S2—C12—C13—C20	45.7 (3)
S1—C1—C2—C3B	−162.3 (5)	C17—C12—C13—C14	−15.3 (4)
C1—C2—C3A—C4A	47.7 (6)	S2—C12—C13—C14	163.9 (2)
C8—C2—C3A—C4A	−78.9 (5)	C12—C13—C14—C15	45.6 (3)
C9—C2—C3A—C4A	162.2 (5)	C19—C13—C14—C15	−74.9 (3)
C2—C3A—C4A—C5	−70.2 (6)	C20—C13—C14—C15	164.5 (3)
C1—C2—C3B—C4B	−46.1 (9)	C13—C14—C15—C16	−63.9 (4)
C8—C2—C3B—C4B	−158.7 (8)	C14—C15—C16—C17	42.2 (3)
C9—C2—C3B—C4B	84.4 (9)	C14—C15—C16—C22	−78.1 (3)
C2—C3B—C4B—C5	62.4 (12)	C14—C15—C16—C21	161.6 (3)
C3B—C4B—C5—C6	−40.4 (10)	C13—C12—C17—N3	177.9 (3)
C3B—C4B—C5—C10	89.8 (8)	S2—C12—C17—N3	−1.4 (3)
C3B—C4B—C5—C11	−154.4 (8)	C13—C12—C17—C16	−1.9 (4)
C3A—C4A—C5—C6	49.7 (6)	S2—C12—C17—C16	178.8 (2)
C3A—C4A—C5—C10	164.7 (5)	C22—C16—C17—C12	110.0 (3)
C3A—C4A—C5—C11	−75.9 (5)	C21—C16—C17—C12	−129.4 (3)
C2—C1—C6—N1	−179.9 (3)	C15—C16—C17—C12	−11.0 (4)
S1—C1—C6—N1	−0.4 (3)	C22—C16—C17—N3	−69.8 (3)
C2—C1—C6—C5	−0.4 (5)	C21—C16—C17—N3	50.8 (3)
S1—C1—C6—C5	179.2 (2)	C15—C16—C17—N3	169.2 (3)
C4B—C5—C6—C1	10.6 (6)	N4—C18—N3—C17	−177.9 (3)
C10—C5—C6—C1	−125.7 (3)	S2—C18—N3—C17	−0.6 (3)
C11—C5—C6—C1	114.7 (3)	C12—C17—N3—C18	1.3 (3)
C4A—C5—C6—C1	−16.8 (4)	C16—C17—N3—C18	−178.9 (2)
C4B—C5—C6—N1	−169.9 (5)	N3—C18—S2—C12	−0.2 (2)
C10—C5—C6—N1	53.8 (4)	N4—C18—S2—C12	177.2 (3)
C11—C5—C6—N1	−65.8 (4)	C17—C12—S2—C18	0.9 (2)
C4A—C5—C6—N1	162.8 (4)	C13—C12—S2—C18	−178.4 (2)
N2—C7—N1—C6	178.3 (3)	O4—C26—C25—C24	4.3 (4)
S1—C7—N1—C6	−0.5 (3)	O3—C26—C25—C24	−174.1 (3)
C1—C6—N1—C7	0.6 (3)	C26—C25—C24—C23	170.2 (3)
C5—C6—N1—C7	−179.0 (2)	C25—C24—C23—O2	−18.9 (4)
N2—C7—S1—C1	−178.5 (3)	C25—C24—C23—O1	163.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.93 (3)	1.70 (3)	2.632 (3)	175 (3)
N2—H2N···O4ⁱ	0.89 (4)	1.98 (4)	2.779 (3)	149 (3)
N2—H3N···O2	0.82 (4)	1.89 (4)	2.716 (4)	176 (4)
N3—H4N···O3	0.87 (8)	1.73 (8)	2.594 (3)	166 (6)
N4—H5N···O2ⁱⁱ	0.82 (4)	2.07 (4)	2.804 (4)	148 (4)
N4—H6N···O4	0.92 (4)	1.93 (4)	2.842 (4)	169 (3)
O3—H1O···N3	0.82 (10)	1.78 (10)	2.594 (3)	174 (8)

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Hirshfeld contact interactions arising from the C₁₁H₁₉N₂S⁺ cation (%) in (I)–(V) top

Contact type	(I)	(II)	(III)	(IV)a	(IV)b	(V)a	(V)b
H···H	68.7	60.9	47.6	62.2	63.3	65.2	65.4
H···Br	–	6.2	–	–	–	–	–
H···O	10.9	12.0	29.1	13.5	13.0	13.4	12.0
H···C	5.9	6.7	6.6	6.0	5.5	3.7	4.2
H···S	2.1	1.8	1.6	3.5	3.0	3.3	2.6
C···all	2.8	2.9	2.9	3.1	3.1	3.1	3.0
N···all	2.7	2.7	2.7	3.0	2.9	2.8	3.2
S···all	6.5	6.3	6.4	6.2	6.4	6.2	6.5

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Hydrogen-bonded mol­ecular salts of reduced benzo­thia­zole derivatives with carboxyl­ates: a robust (8) supra­molecular motif (even when disordered)

Supporting information

Key indicators

checkCIF/PLATON results

Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust $R_{2}^{2}$ (8) supramolecular motif (even when disordered)