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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018018224/mw2140sup1.cif
Contains datablocks I, II, III, IV, V, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140IVsup5.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018018224/mw2140Vsup6.hkl
Contains datablock V

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018018224/mw2140Isup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018018224/mw2140IIsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018018224/mw2140IIIsup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018018224/mw2140IVsup10.cml
Supplementary material

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

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • Mean [sigma](C-C) = 0.007 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.008 Å
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.038
  • wR factor = 0.089
  • Data-to-parameter ratio = 17.6

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+·C8H7O2F(000) = 372
Mr = 346.48Dx = 1.208 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
a = 10.1879 (5) ÅCell parameters from 5914 reflections
b = 11.6149 (5) Åθ = 2.2–28.1°
c = 8.7790 (4) ŵ = 0.18 mm1
β = 113.480 (6)°T = 173 K
V = 952.82 (9) Å3Plate, colourless
Z = 20.24 × 0.11 × 0.02 mm
Data collection top
Rigaku XtaLAB P200 HPC
diffractometer
4056 independent reflections
Radiation source: rotating anode, Rigaku FR-X3440 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromatorRint = 0.029
ω scansθmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku, 2017)
h = 1312
Tmin = 0.793, Tmax = 1.000k = 1515
12189 measured reflectionsl = 1111
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.0463P)2 + 0.0807P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.089(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.20 e Å3
4056 reflectionsΔρmin = 0.17 e Å3
230 parametersAbsolute structure: Flack x determined using 1371 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).
2 restraintsAbsolute 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
xyzUiso*/UeqOcc. (<1)
C10.3617 (3)0.6584 (2)0.8458 (3)0.0363 (6)
C20.2322 (3)0.6675 (3)0.8865 (4)0.0466 (7)
C3A0.1685 (10)0.7939 (8)0.8152 (12)0.058 (3)*0.398 (10)
H3A10.07400.80280.82100.069*0.398 (10)
H3A20.23290.85340.88780.069*0.398 (10)
C4A0.1525 (10)0.8143 (9)0.6457 (13)0.048 (2)*0.398 (10)
H4A10.10030.88740.60500.058*0.398 (10)
H4A20.09570.75120.57350.058*0.398 (10)
C3B0.1217 (6)0.7333 (5)0.7440 (7)0.0467 (18)*0.602 (10)
H3B10.04010.75350.77300.056*0.602 (10)
H3B20.08520.68360.64410.056*0.602 (10)
C4B0.1860 (7)0.8447 (6)0.7047 (9)0.0468 (15)*0.602 (10)
H4B10.10810.89070.62250.056*0.602 (10)
H4B20.22910.89110.80740.056*0.602 (10)
C50.3013 (3)0.8207 (2)0.6356 (4)0.0412 (7)
C60.3917 (3)0.7225 (2)0.7371 (3)0.0342 (6)
C70.5894 (3)0.6071 (2)0.8256 (3)0.0341 (6)
C80.1541 (6)0.5542 (4)0.8622 (7)0.111 (2)
H8A0.06730.56430.88330.167*
H8B0.21640.49710.93970.167*
H8C0.12800.52750.74800.167*
C90.2747 (4)0.7056 (4)1.0652 (5)0.0783 (12)
H9A0.18840.72261.08470.117*
H9B0.33420.77491.08620.117*
H9C0.32880.64401.14010.117*
C100.2527 (4)0.7945 (3)0.4504 (4)0.0648 (10)
H10A0.19050.85660.38530.097*
H10B0.20000.72160.42460.097*
H10C0.33660.78860.42270.097*
C110.3888 (4)0.9315 (3)0.6748 (5)0.0622 (9)
H11A0.42160.94870.79350.093*
H11B0.32930.99500.61000.093*
H11C0.47180.92200.64610.093*
N10.5199 (2)0.69242 (19)0.7257 (3)0.0352 (5)
H1N0.559 (3)0.719 (3)0.660 (4)0.042*
N20.7129 (3)0.5644 (2)0.8356 (3)0.0406 (6)
H2N0.738 (3)0.583 (3)0.759 (4)0.049*
H3N0.742 (3)0.502 (3)0.900 (4)0.049*
S10.49793 (8)0.55753 (6)0.94144 (8)0.04197 (19)
C120.7414 (3)0.7561 (2)0.3383 (3)0.0353 (6)
C130.8440 (3)0.6995 (3)0.2992 (3)0.0393 (6)
H130.89150.63390.36130.047*
C140.8774 (3)0.7387 (3)0.1694 (3)0.0428 (7)
H140.94700.69860.14320.051*
C150.8121 (3)0.8343 (3)0.0779 (4)0.0457 (7)
C160.7089 (4)0.8898 (3)0.1168 (4)0.0533 (8)
H160.66180.95560.05470.064*
C170.6734 (3)0.8509 (3)0.2443 (4)0.0474 (8)
H170.60150.88980.26780.057*
C180.7053 (3)0.7165 (2)0.4803 (3)0.0382 (6)
C190.8510 (4)0.8777 (4)0.0609 (4)0.0688 (10)
H19A0.82630.95950.08060.103*
H19B0.79810.83390.16240.103*
H19C0.95410.86800.02980.103*
O10.6233 (2)0.77900 (19)0.5192 (3)0.0518 (5)
O20.7604 (2)0.62322 (16)0.5523 (2)0.0428 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0372 (15)0.0423 (14)0.0285 (13)0.0010 (12)0.0124 (11)0.0022 (11)
C20.0447 (17)0.0600 (18)0.0416 (16)0.0010 (14)0.0240 (14)0.0026 (13)
C50.0452 (17)0.0385 (14)0.0416 (15)0.0057 (13)0.0193 (13)0.0040 (12)
C60.0349 (14)0.0371 (14)0.0302 (13)0.0036 (11)0.0125 (11)0.0062 (11)
C70.0367 (15)0.0371 (14)0.0297 (12)0.0024 (12)0.0145 (11)0.0032 (11)
C80.093 (3)0.120 (4)0.166 (5)0.062 (3)0.099 (4)0.071 (4)
C90.071 (3)0.121 (3)0.061 (2)0.016 (2)0.046 (2)0.024 (2)
C100.067 (2)0.070 (2)0.0382 (17)0.0162 (19)0.0001 (16)0.0003 (15)
C110.078 (3)0.0420 (18)0.060 (2)0.0011 (17)0.0206 (19)0.0045 (16)
N10.0393 (13)0.0379 (12)0.0330 (11)0.0016 (10)0.0193 (10)0.0002 (9)
N20.0422 (15)0.0462 (14)0.0355 (13)0.0056 (12)0.0176 (11)0.0022 (11)
S10.0427 (4)0.0504 (4)0.0366 (3)0.0040 (4)0.0197 (3)0.0082 (3)
C120.0346 (14)0.0440 (15)0.0286 (12)0.0072 (12)0.0138 (11)0.0075 (11)
C130.0291 (14)0.0486 (16)0.0385 (15)0.0007 (12)0.0116 (12)0.0027 (12)
C140.0293 (15)0.0632 (19)0.0391 (15)0.0007 (14)0.0171 (13)0.0070 (14)
C150.0437 (17)0.0619 (19)0.0347 (14)0.0018 (15)0.0190 (13)0.0020 (14)
C160.065 (2)0.0589 (19)0.0413 (17)0.0144 (17)0.0273 (16)0.0111 (14)
C170.0539 (19)0.0529 (18)0.0432 (17)0.0113 (15)0.0276 (15)0.0007 (14)
C180.0381 (15)0.0422 (15)0.0364 (14)0.0066 (13)0.0173 (12)0.0057 (12)
C190.075 (2)0.095 (3)0.0514 (19)0.017 (2)0.0410 (18)0.0169 (18)
O10.0653 (14)0.0525 (12)0.0554 (13)0.0081 (10)0.0429 (11)0.0050 (10)
O20.0452 (11)0.0479 (11)0.0386 (10)0.0012 (9)0.0203 (9)0.0012 (9)
Geometric parameters (Å, º) top
C1—C61.338 (4)C9—H9A0.9800
C1—C21.502 (4)C9—H9B0.9800
C1—S11.753 (3)C9—H9C0.9800
C2—C81.509 (5)C10—H10A0.9800
C2—C3B1.514 (6)C10—H10B0.9800
C2—C91.518 (5)C10—H10C0.9800
C2—C3A1.626 (9)C11—H11A0.9800
C3A—C4A1.451 (14)C11—H11B0.9800
C3A—H3A10.9900C11—H11C0.9800
C3A—H3A20.9900N1—H1N0.88 (3)
C4A—C51.555 (9)N2—H2N0.83 (3)
C4A—H4A10.9900N2—H3N0.89 (3)
C4A—H4A20.9900C12—C171.385 (4)
C3B—C4B1.551 (9)C12—C131.389 (4)
C3B—H3B10.9900C12—C181.506 (4)
C3B—H3B20.9900C13—C141.389 (4)
C4B—C51.547 (6)C13—H130.9500
C4B—H4B10.9900C14—C151.377 (4)
C4B—H4B20.9900C14—H140.9500
C5—C61.514 (4)C15—C161.386 (4)
C5—C111.524 (4)C15—C191.510 (4)
C5—C101.529 (4)C16—C171.383 (4)
C6—N11.394 (4)C16—H160.9500
C7—N21.322 (4)C17—H170.9500
C7—N11.325 (3)C18—O11.252 (3)
C7—S11.729 (3)C18—O21.267 (3)
C8—H8A0.9800C19—H19A0.9800
C8—H8B0.9800C19—H19B0.9800
C8—H8C0.9800C19—H19C0.9800
C6—C1—C2127.0 (3)H8A—C8—H8C109.5
C6—C1—S1110.6 (2)H8B—C8—H8C109.5
C2—C1—S1122.4 (2)C2—C9—H9A109.5
C1—C2—C8111.6 (3)C2—C9—H9B109.5
C1—C2—C3B105.9 (3)H9A—C9—H9B109.5
C8—C2—C3B98.4 (4)C2—C9—H9C109.5
C1—C2—C9110.6 (3)H9A—C9—H9C109.5
C8—C2—C9108.5 (3)H9B—C9—H9C109.5
C3B—C2—C9121.2 (4)C5—C10—H10A109.5
C1—C2—C3A103.1 (4)C5—C10—H10B109.5
C8—C2—C3A128.8 (5)H10A—C10—H10B109.5
C9—C2—C3A92.3 (4)C5—C10—H10C109.5
C4A—C3A—C2114.0 (8)H10A—C10—H10C109.5
C4A—C3A—H3A1108.8H10B—C10—H10C109.5
C2—C3A—H3A1108.8C5—C11—H11A109.5
C4A—C3A—H3A2108.8C5—C11—H11B109.5
C2—C3A—H3A2108.8H11A—C11—H11B109.5
H3A1—C3A—H3A2107.7C5—C11—H11C109.5
C3A—C4A—C5110.6 (8)H11A—C11—H11C109.5
C3A—C4A—H4A1109.5H11B—C11—H11C109.5
C5—C4A—H4A1109.5C7—N1—C6114.1 (2)
C3A—C4A—H4A2109.5C7—N1—H1N116 (2)
C5—C4A—H4A2109.5C6—N1—H1N130.1 (19)
H4A1—C4A—H4A2108.1C7—N2—H2N116 (2)
C2—C3B—C4B111.3 (5)C7—N2—H3N115 (2)
C2—C3B—H3B1109.4H2N—N2—H3N126 (3)
C4B—C3B—H3B1109.4C7—S1—C190.27 (13)
C2—C3B—H3B2109.4C17—C12—C13118.4 (3)
C4B—C3B—H3B2109.4C17—C12—C18120.5 (3)
H3B1—C3B—H3B2108.0C13—C12—C18121.1 (3)
C5—C4B—C3B113.0 (5)C14—C13—C12120.2 (3)
C5—C4B—H4B1109.0C14—C13—H13119.9
C3B—C4B—H4B1109.0C12—C13—H13119.9
C5—C4B—H4B2109.0C15—C14—C13121.6 (3)
C3B—C4B—H4B2109.0C15—C14—H14119.2
H4B1—C4B—H4B2107.8C13—C14—H14119.2
C6—C5—C11109.8 (2)C14—C15—C16117.9 (3)
C6—C5—C10109.8 (2)C14—C15—C19121.2 (3)
C11—C5—C10108.7 (3)C16—C15—C19120.8 (3)
C6—C5—C4B106.5 (3)C17—C16—C15121.1 (3)
C11—C5—C4B103.1 (4)C17—C16—H16119.4
C10—C5—C4B118.6 (4)C15—C16—H16119.4
C6—C5—C4A107.9 (4)C16—C17—C12120.8 (3)
C11—C5—C4A121.6 (5)C16—C17—H17119.6
C10—C5—C4A98.1 (5)C12—C17—H17119.6
C1—C6—N1113.5 (2)O1—C18—O2124.9 (2)
C1—C6—C5125.6 (3)O1—C18—C12117.2 (3)
N1—C6—C5121.0 (2)O2—C18—C12117.9 (2)
N2—C7—N1124.6 (2)C15—C19—H19A109.5
N2—C7—S1123.9 (2)C15—C19—H19B109.5
N1—C7—S1111.6 (2)H19A—C19—H19B109.5
C2—C8—H8A109.5C15—C19—H19C109.5
C2—C8—H8B109.5H19A—C19—H19C109.5
H8A—C8—H8B109.5H19B—C19—H19C109.5
C2—C8—H8C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.88 (3)1.76 (3)2.632 (3)175 (3)
N2—H2N···O20.83 (3)1.98 (4)2.801 (3)170 (3)
N2—H3N···O2i0.89 (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+·C7H4BrO2F(000) = 424
Mr = 411.35Dx = 1.424 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
a = 10.2506 (5) ÅCell parameters from 6835 reflections
b = 11.5855 (4) Åθ = 2.2–28.2°
c = 8.8269 (4) ŵ = 2.26 mm1
β = 113.807 (6)°T = 173 K
V = 959.07 (8) Å3Plate, colourless
Z = 20.12 × 0.08 × 0.02 mm
Data collection top
Rigaku XtaLAB P200 HPC
diffractometer
3993 independent reflections
Radiation source: rotating anode, Rigaku FR-X3311 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromatorRint = 0.026
ω scansθmax = 29.1°, θmin = 2.2°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku, 2017)
h = 1313
Tmin = 0.761, Tmax = 1.000k = 1515
12220 measured reflectionsl = 1011
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0407P)2 + 0.0111P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.083(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.62 e Å3
3993 reflectionsΔρmin = 0.38 e Å3
230 parametersAbsolute structure: Flack x determined using 1344 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).
2 restraintsAbsolute structure parameter: 0.005 (4)
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
xyzUiso*/Ueq
C10.6357 (4)0.6587 (3)0.1418 (5)0.0359 (8)
C20.7655 (5)0.6679 (4)0.1027 (5)0.0446 (9)
C30.8711 (8)0.7399 (8)0.2385 (10)0.113 (3)
H3A0.92130.68830.33380.136*
H3B0.94310.76810.19910.136*
C40.8218 (6)0.8359 (5)0.2982 (9)0.0780 (17)
H4A0.79310.89560.21050.094*
H4B0.90400.86730.39370.094*
C50.6976 (4)0.8213 (3)0.3532 (5)0.0403 (9)
C60.6067 (4)0.7238 (3)0.2502 (5)0.0339 (8)
C70.4084 (4)0.6086 (3)0.1598 (5)0.0345 (8)
C80.8389 (8)0.5492 (7)0.1190 (12)0.110 (3)
H8A0.92990.55900.10870.164*
H8B0.77710.49760.03140.164*
H8C0.85610.51560.22740.164*
C90.7278 (7)0.7092 (6)0.0719 (7)0.0772 (17)
H9A0.81470.71520.09230.116*
H9B0.68200.78500.08680.116*
H9C0.66220.65410.15010.116*
C100.7484 (6)0.7930 (5)0.5371 (6)0.0664 (14)
H10A0.81220.85420.60280.100*
H10B0.79950.71930.56040.100*
H10C0.66590.78750.56630.100*
C110.6095 (6)0.9320 (4)0.3150 (6)0.0578 (12)
H11A0.57140.94730.19570.087*
H11B0.66990.99660.37510.087*
H11C0.53040.92310.34960.087*
N10.4781 (3)0.6939 (3)0.2604 (4)0.0348 (7)
H1N0.441 (5)0.732 (4)0.339 (5)0.042*
N20.2855 (4)0.5667 (3)0.1482 (5)0.0408 (8)
H2N0.257 (6)0.582 (4)0.208 (6)0.049*
H3N0.264 (5)0.505 (4)0.086 (6)0.049*
S10.49893 (11)0.55873 (9)0.04481 (11)0.0398 (2)
C120.2601 (4)0.7536 (3)0.6483 (4)0.0352 (8)
C130.1566 (4)0.6980 (3)0.6846 (5)0.0369 (8)
H130.10940.63260.62130.044*
C140.1208 (4)0.7360 (4)0.8116 (5)0.0422 (9)
H140.05010.69700.83610.051*
C150.1893 (4)0.8310 (4)0.9017 (5)0.0402 (9)
C160.2946 (5)0.8860 (3)0.8709 (6)0.0490 (11)
H160.34340.94990.93690.059*
C170.3291 (5)0.8481 (4)0.7443 (5)0.0466 (10)
H170.40090.88710.72200.056*
C180.2979 (4)0.7141 (3)0.5095 (5)0.0370 (8)
O10.3836 (4)0.7755 (3)0.4748 (4)0.0505 (7)
O20.2410 (3)0.6225 (2)0.4343 (4)0.0419 (6)
Br10.13945 (5)0.88476 (4)1.07398 (5)0.0676 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.037 (2)0.0392 (18)0.0320 (18)0.0012 (17)0.0138 (17)0.0030 (16)
C20.043 (2)0.057 (2)0.040 (2)0.004 (2)0.0238 (19)0.0023 (19)
C30.087 (5)0.160 (7)0.120 (6)0.057 (5)0.071 (5)0.073 (6)
C40.061 (3)0.080 (3)0.109 (5)0.032 (3)0.050 (3)0.039 (3)
C50.037 (2)0.0370 (19)0.043 (2)0.0060 (17)0.0129 (17)0.0009 (17)
C60.036 (2)0.0329 (18)0.0323 (18)0.0019 (16)0.0131 (16)0.0038 (15)
C70.037 (2)0.0365 (19)0.0293 (18)0.0022 (17)0.0123 (16)0.0043 (16)
C80.091 (5)0.109 (5)0.167 (8)0.055 (5)0.092 (6)0.064 (5)
C90.074 (4)0.113 (4)0.058 (3)0.020 (3)0.040 (3)0.028 (3)
C100.071 (3)0.066 (3)0.039 (2)0.016 (3)0.002 (2)0.001 (2)
C110.072 (3)0.037 (2)0.059 (3)0.003 (2)0.022 (3)0.001 (2)
N10.0359 (18)0.0375 (16)0.0333 (17)0.0013 (14)0.0163 (14)0.0001 (14)
N20.042 (2)0.0461 (19)0.037 (2)0.0047 (17)0.0190 (16)0.0057 (16)
S10.0407 (5)0.0451 (5)0.0352 (5)0.0029 (5)0.0168 (4)0.0061 (4)
C120.034 (2)0.0390 (19)0.0305 (19)0.0064 (16)0.0109 (16)0.0081 (16)
C130.030 (2)0.0416 (19)0.036 (2)0.0015 (16)0.0102 (16)0.0011 (16)
C140.030 (2)0.056 (2)0.041 (2)0.0004 (19)0.0153 (18)0.0030 (19)
C150.042 (2)0.050 (2)0.0308 (19)0.0041 (19)0.0170 (18)0.0051 (18)
C160.060 (3)0.050 (2)0.039 (2)0.012 (2)0.023 (2)0.0053 (19)
C170.055 (3)0.049 (2)0.042 (2)0.010 (2)0.026 (2)0.0014 (19)
C180.036 (2)0.040 (2)0.035 (2)0.0061 (18)0.0153 (17)0.0025 (18)
O10.060 (2)0.0519 (16)0.0526 (18)0.0091 (15)0.0365 (16)0.0072 (14)
O20.0422 (16)0.0477 (16)0.0367 (15)0.0025 (13)0.0168 (12)0.0012 (12)
Br10.0863 (4)0.0796 (3)0.0542 (3)0.0123 (3)0.0462 (3)0.0134 (3)
Geometric parameters (Å, º) top
C1—C61.342 (5)C9—H9C0.9800
C1—C21.508 (6)C10—H10A0.9800
C1—S11.752 (4)C10—H10B0.9800
C2—C31.503 (8)C10—H10C0.9800
C2—C91.507 (7)C11—H11A0.9800
C2—C81.546 (8)C11—H11B0.9800
C3—C41.408 (10)C11—H11C0.9800
C3—H3A0.9900N1—H1N1.01 (5)
C3—H3B0.9900N2—H2N0.72 (5)
C4—C51.544 (7)N2—H3N0.88 (5)
C4—H4A0.9900C12—C131.385 (5)
C4—H4B0.9900C12—C171.391 (6)
C5—C61.513 (6)C12—C181.498 (5)
C5—C111.526 (6)C13—C141.385 (5)
C5—C101.528 (6)C13—H130.9500
C6—N11.400 (5)C14—C151.374 (6)
C7—N21.316 (5)C14—H140.9500
C7—N11.327 (5)C15—C161.371 (6)
C7—S11.728 (4)C15—Br11.895 (4)
C8—H8A0.9800C16—C171.373 (7)
C8—H8B0.9800C16—H160.9500
C8—H8C0.9800C17—H170.9500
C9—H9A0.9800C18—O11.260 (5)
C9—H9B0.9800C18—O21.263 (5)
C6—C1—C2126.4 (4)H9A—C9—H9C109.5
C6—C1—S1110.8 (3)H9B—C9—H9C109.5
C2—C1—S1122.7 (3)C5—C10—H10A109.5
C3—C2—C9116.4 (5)C5—C10—H10B109.5
C3—C2—C1105.9 (4)H10A—C10—H10B109.5
C9—C2—C1111.8 (4)C5—C10—H10C109.5
C3—C2—C8104.7 (6)H10A—C10—H10C109.5
C9—C2—C8107.0 (5)H10B—C10—H10C109.5
C1—C2—C8110.9 (4)C5—C11—H11A109.5
C4—C3—C2119.0 (6)C5—C11—H11B109.5
C4—C3—H3A107.6H11A—C11—H11B109.5
C2—C3—H3A107.6C5—C11—H11C109.5
C4—C3—H3B107.6H11A—C11—H11C109.5
C2—C3—H3B107.6H11B—C11—H11C109.5
H3A—C3—H3B107.0C7—N1—C6114.0 (3)
C3—C4—C5119.8 (5)C7—N1—H1N122 (2)
C3—C4—H4A107.4C6—N1—H1N124 (2)
C5—C4—H4A107.4C7—N2—H2N121 (4)
C3—C4—H4B107.4C7—N2—H3N110 (3)
C5—C4—H4B107.4H2N—N2—H3N126 (5)
H4A—C4—H4B106.9C7—S1—C190.29 (18)
C6—C5—C11109.2 (3)C13—C12—C17118.3 (4)
C6—C5—C10110.0 (3)C13—C12—C18121.5 (3)
C11—C5—C10109.4 (4)C17—C12—C18120.2 (4)
C6—C5—C4106.2 (4)C14—C13—C12121.2 (4)
C11—C5—C4109.2 (4)C14—C13—H13119.4
C10—C5—C4112.8 (5)C12—C13—H13119.4
C1—C6—N1113.1 (3)C15—C14—C13118.9 (4)
C1—C6—C5126.0 (3)C15—C14—H14120.6
N1—C6—C5120.9 (3)C13—C14—H14120.6
N2—C7—N1124.5 (4)C16—C15—C14121.2 (4)
N2—C7—S1123.7 (3)C16—C15—Br1119.7 (3)
N1—C7—S1111.7 (3)C14—C15—Br1119.2 (3)
C2—C8—H8A109.5C15—C16—C17119.6 (4)
C2—C8—H8B109.5C15—C16—H16120.2
H8A—C8—H8B109.5C17—C16—H16120.2
C2—C8—H8C109.5C16—C17—C12120.9 (4)
H8A—C8—H8C109.5C16—C17—H17119.5
H8B—C8—H8C109.5C12—C17—H17119.5
C2—C9—H9A109.5O1—C18—O2124.5 (4)
C2—C9—H9B109.5O1—C18—C12117.5 (4)
H9A—C9—H9B109.5O2—C18—C12118.0 (3)
C2—C9—H9C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O11.01 (5)1.62 (5)2.626 (4)172 (4)
N2—H2N···O20.72 (5)2.12 (5)2.816 (5)162 (6)
N2—H3N···O2i0.88 (5)1.94 (5)2.808 (5)170 (4)
Symmetry code: (i) x, y+1, z1/2.
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+·C7H3N2O6F(000) = 888
Mr = 422.45Dx = 1.398 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 17.3232 (6) ÅCell parameters from 10667 reflections
b = 5.84087 (17) Åθ = 2.0–27.8°
c = 21.0876 (8) ŵ = 0.21 mm1
β = 109.875 (4)°T = 173 K
V = 2006.60 (12) Å3Plate, colourless
Z = 40.27 × 0.10 × 0.03 mm
Data collection top
Rigaku XtaLAB P200 HPC
diffractometer
4698 independent reflections
Radiation source: rotating anode, Rigaku FR-X3712 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromatorRint = 0.056
ω scansθmax = 29.2°, θmin = 1.9°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku, 2017)
h = 2123
Tmin = 0.566, Tmax = 1.000k = 77
25034 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0567P)2 + 0.5151P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4698 reflectionsΔρmax = 0.49 e Å3
275 parametersΔρmin = 0.25 e Å3
0 restraints
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
xyzUiso*/Ueq
C10.26545 (9)0.4584 (3)0.49126 (7)0.0264 (3)
C20.19150 (9)0.3629 (3)0.50428 (8)0.0298 (3)
C30.13800 (10)0.2456 (3)0.43879 (9)0.0419 (4)
H3A0.09960.13920.44940.050*
H3B0.10480.36360.40770.050*
C40.18675 (11)0.1131 (3)0.40303 (9)0.0397 (4)
H4A0.14790.03440.36340.048*
H4B0.21960.00590.43400.048*
C50.24503 (10)0.2636 (3)0.37920 (8)0.0319 (4)
C60.28907 (9)0.4173 (3)0.43809 (7)0.0260 (3)
C70.39559 (9)0.6469 (3)0.49858 (7)0.0266 (3)
C80.21999 (11)0.1932 (3)0.56307 (9)0.0388 (4)
H8A0.17200.12860.57130.058*
H8B0.25470.27270.60370.058*
H8C0.25140.06970.55180.058*
C90.14165 (11)0.5539 (3)0.52232 (10)0.0427 (4)
H9A0.09250.48810.52830.064*
H9B0.12530.66720.48590.064*
H9C0.17530.62820.56430.064*
C100.30657 (12)0.1076 (3)0.36271 (10)0.0442 (4)
H10A0.27690.00700.32940.066*
H10B0.34100.03040.40390.066*
H10C0.34130.19960.34430.066*
C110.19849 (13)0.4072 (4)0.31745 (9)0.0516 (5)
H11A0.17070.30580.27950.077*
H11B0.23720.50570.30540.077*
H11C0.15770.50240.32780.077*
N10.36224 (8)0.5279 (2)0.44229 (6)0.0271 (3)
H1N0.3856 (11)0.524 (3)0.4110 (9)0.033*
N20.46553 (9)0.7605 (3)0.51363 (7)0.0337 (3)
H2N0.4887 (12)0.780 (3)0.4812 (10)0.040*
H3N0.4791 (12)0.857 (3)0.5486 (10)0.040*
S10.33701 (2)0.63371 (7)0.55004 (2)0.02882 (12)
C120.53091 (9)0.7205 (3)0.30278 (7)0.0283 (3)
C130.58549 (9)0.8968 (3)0.30559 (8)0.0304 (3)
H130.59921.00420.34160.037*
C140.61975 (9)0.9144 (3)0.25552 (8)0.0313 (4)
C150.60233 (9)0.7633 (3)0.20218 (8)0.0327 (4)
H150.62560.77960.16760.039*
C160.54918 (9)0.5872 (3)0.20198 (8)0.0306 (3)
C170.51322 (9)0.5616 (3)0.25084 (7)0.0294 (3)
H170.47700.43750.24890.035*
C180.49110 (10)0.7013 (3)0.35667 (8)0.0312 (3)
N30.67709 (8)1.1050 (3)0.25924 (7)0.0380 (3)
N40.52907 (8)0.4200 (3)0.14618 (7)0.0386 (4)
O10.43858 (8)0.5479 (2)0.34910 (6)0.0427 (3)
O20.51480 (8)0.8407 (2)0.40440 (6)0.0410 (3)
O30.69300 (8)1.1515 (2)0.20855 (7)0.0500 (4)
O40.70535 (9)1.2066 (3)0.31259 (7)0.0596 (4)
O50.49224 (9)0.2464 (3)0.15173 (7)0.0508 (3)
O60.54967 (8)0.4645 (3)0.09754 (6)0.0522 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0251 (7)0.0287 (8)0.0255 (8)0.0025 (6)0.0086 (6)0.0005 (6)
C20.0252 (8)0.0364 (8)0.0307 (8)0.0032 (6)0.0130 (6)0.0006 (7)
C30.0301 (9)0.0543 (11)0.0417 (10)0.0134 (8)0.0129 (7)0.0047 (9)
C40.0385 (10)0.0457 (10)0.0350 (9)0.0158 (8)0.0126 (7)0.0077 (8)
C50.0335 (8)0.0374 (9)0.0250 (8)0.0096 (7)0.0103 (6)0.0039 (7)
C60.0252 (7)0.0286 (8)0.0248 (7)0.0034 (6)0.0094 (6)0.0005 (6)
C70.0290 (8)0.0282 (8)0.0250 (8)0.0031 (6)0.0123 (6)0.0006 (6)
C80.0378 (9)0.0441 (10)0.0412 (10)0.0014 (8)0.0222 (8)0.0061 (8)
C90.0329 (9)0.0470 (10)0.0535 (11)0.0034 (8)0.0215 (8)0.0005 (9)
C100.0509 (11)0.0441 (10)0.0437 (10)0.0122 (8)0.0239 (9)0.0160 (8)
C110.0576 (12)0.0607 (13)0.0276 (9)0.0091 (10)0.0029 (8)0.0015 (9)
N10.0296 (7)0.0320 (7)0.0236 (6)0.0064 (5)0.0140 (5)0.0029 (5)
N20.0352 (8)0.0398 (8)0.0304 (7)0.0140 (6)0.0168 (6)0.0085 (6)
S10.0292 (2)0.0350 (2)0.0259 (2)0.00573 (16)0.01407 (16)0.00554 (15)
C120.0239 (7)0.0392 (9)0.0224 (7)0.0017 (6)0.0088 (6)0.0036 (6)
C130.0273 (8)0.0396 (9)0.0254 (8)0.0003 (7)0.0103 (6)0.0020 (7)
C140.0230 (8)0.0425 (9)0.0291 (8)0.0021 (7)0.0099 (6)0.0083 (7)
C150.0236 (8)0.0520 (10)0.0243 (8)0.0090 (7)0.0106 (6)0.0086 (7)
C160.0230 (7)0.0451 (9)0.0220 (7)0.0085 (7)0.0056 (6)0.0002 (7)
C170.0221 (7)0.0390 (8)0.0257 (8)0.0006 (6)0.0063 (6)0.0015 (7)
C180.0300 (8)0.0392 (9)0.0271 (8)0.0042 (7)0.0133 (6)0.0005 (7)
N30.0305 (7)0.0491 (9)0.0396 (8)0.0014 (6)0.0184 (6)0.0090 (7)
N40.0273 (7)0.0557 (10)0.0313 (8)0.0099 (7)0.0081 (6)0.0056 (7)
O10.0462 (7)0.0556 (8)0.0347 (7)0.0218 (6)0.0244 (6)0.0106 (6)
O20.0512 (8)0.0453 (7)0.0363 (7)0.0158 (6)0.0275 (6)0.0114 (5)
O30.0466 (8)0.0666 (9)0.0461 (8)0.0058 (6)0.0280 (6)0.0147 (6)
O40.0662 (10)0.0704 (10)0.0507 (9)0.0328 (8)0.0311 (7)0.0119 (7)
O50.0504 (8)0.0563 (9)0.0448 (8)0.0036 (7)0.0149 (6)0.0156 (6)
O60.0452 (8)0.0852 (10)0.0316 (7)0.0108 (7)0.0199 (6)0.0082 (7)
Geometric parameters (Å, º) top
C1—C61.340 (2)C10—H10B0.9800
C1—C21.506 (2)C10—H10C0.9800
C1—S11.7540 (15)C11—H11A0.9800
C2—C81.532 (2)C11—H11B0.9800
C2—C91.535 (2)C11—H11C0.9800
C2—C31.538 (2)N1—H1N0.885 (19)
C3—C41.521 (3)N2—H2N0.91 (2)
C3—H3A0.9900N2—H3N0.90 (2)
C3—H3B0.9900C12—C131.385 (2)
C4—C51.546 (2)C12—C171.388 (2)
C4—H4A0.9900C12—C181.521 (2)
C4—H4B0.9900C13—C141.380 (2)
C5—C61.512 (2)C13—H130.9500
C5—C111.528 (2)C14—C151.380 (2)
C5—C101.529 (2)C14—N31.476 (2)
C6—N11.3981 (19)C15—C161.380 (2)
C7—N21.322 (2)C15—H150.9500
C7—N11.3267 (19)C16—C171.381 (2)
C7—S11.7211 (15)C16—N41.477 (2)
C8—H8A0.9800C17—H170.9500
C8—H8B0.9800C18—O11.2475 (19)
C8—H8C0.9800C18—O21.2506 (19)
C9—H9A0.9800N3—O41.2178 (19)
C9—H9B0.9800N3—O31.2218 (18)
C9—H9C0.9800N4—O61.2231 (19)
C10—H10A0.9800N4—O51.224 (2)
C6—C1—C2127.39 (14)C5—C10—H10B109.5
C6—C1—S1110.64 (11)H10A—C10—H10B109.5
C2—C1—S1121.88 (11)C5—C10—H10C109.5
C1—C2—C8109.11 (13)H10A—C10—H10C109.5
C1—C2—C9111.17 (13)H10B—C10—H10C109.5
C8—C2—C9108.85 (13)C5—C11—H11A109.5
C1—C2—C3106.95 (12)C5—C11—H11B109.5
C8—C2—C3111.61 (14)H11A—C11—H11B109.5
C9—C2—C3109.15 (14)C5—C11—H11C109.5
C4—C3—C2113.90 (14)H11A—C11—H11C109.5
C4—C3—H3A108.8H11B—C11—H11C109.5
C2—C3—H3A108.8C7—N1—C6114.09 (12)
C4—C3—H3B108.8C7—N1—H1N120.8 (12)
C2—C3—H3B108.8C6—N1—H1N125.1 (12)
H3A—C3—H3B107.7C7—N2—H2N119.0 (12)
C3—C4—C5113.96 (15)C7—N2—H3N118.5 (12)
C3—C4—H4A108.8H2N—N2—H3N118.8 (17)
C5—C4—H4A108.8C7—S1—C190.40 (7)
C3—C4—H4B108.8C13—C12—C17119.67 (14)
C5—C4—H4B108.8C13—C12—C18119.95 (14)
H4A—C4—H4B107.7C17—C12—C18120.38 (14)
C6—C5—C11110.26 (14)C14—C13—C12119.18 (15)
C6—C5—C10110.14 (13)C14—C13—H13120.4
C11—C5—C10109.86 (15)C12—C13—H13120.4
C6—C5—C4105.88 (12)C13—C14—C15122.97 (15)
C11—C5—C4112.06 (15)C13—C14—N3118.18 (15)
C10—C5—C4108.56 (14)C15—C14—N3118.85 (14)
C1—C6—N1113.12 (13)C16—C15—C14116.12 (14)
C1—C6—C5125.55 (13)C16—C15—H15121.9
N1—C6—C5121.31 (12)C14—C15—H15121.9
N2—C7—N1124.23 (14)C15—C16—C17123.23 (15)
N2—C7—S1124.04 (12)C15—C16—N4118.16 (14)
N1—C7—S1111.72 (11)C17—C16—N4118.60 (15)
C2—C8—H8A109.5C16—C17—C12118.79 (15)
C2—C8—H8B109.5C16—C17—H17120.6
H8A—C8—H8B109.5C12—C17—H17120.6
C2—C8—H8C109.5O1—C18—O2126.60 (14)
H8A—C8—H8C109.5O1—C18—C12116.98 (14)
H8B—C8—H8C109.5O2—C18—C12116.42 (13)
C2—C9—H9A109.5O4—N3—O3124.09 (15)
C2—C9—H9B109.5O4—N3—C14117.95 (13)
H9A—C9—H9B109.5O3—N3—C14117.96 (15)
C2—C9—H9C109.5O6—N4—O5124.50 (15)
H9A—C9—H9C109.5O6—N4—C16118.07 (16)
H9B—C9—H9C109.5O5—N4—C16117.43 (14)
C5—C10—H10A109.5
C6—C1—C2—C8109.98 (18)N1—C7—S1—C10.11 (12)
S1—C1—C2—C866.27 (17)C6—C1—S1—C70.86 (12)
C6—C1—C2—C9129.96 (17)C2—C1—S1—C7177.68 (13)
S1—C1—C2—C953.79 (18)C17—C12—C13—C141.7 (2)
C6—C1—C2—C310.9 (2)C18—C12—C13—C14178.67 (14)
S1—C1—C2—C3172.86 (12)C12—C13—C14—C150.1 (2)
C1—C2—C3—C440.0 (2)C12—C13—C14—N3179.39 (13)
C8—C2—C3—C479.31 (18)C13—C14—C15—C161.3 (2)
C9—C2—C3—C4160.33 (15)N3—C14—C15—C16179.18 (13)
C2—C3—C4—C562.4 (2)C14—C15—C16—C171.3 (2)
C3—C4—C5—C646.04 (19)C14—C15—C16—N4179.58 (13)
C3—C4—C5—C1174.21 (19)C15—C16—C17—C120.2 (2)
C3—C4—C5—C10164.27 (15)N4—C16—C17—C12178.97 (14)
C2—C1—C6—N1178.20 (14)C13—C12—C17—C161.7 (2)
S1—C1—C6—N11.60 (17)C18—C12—C17—C16178.65 (14)
C2—C1—C6—C50.1 (3)C13—C12—C18—O1175.54 (15)
S1—C1—C6—C5176.71 (13)C17—C12—C18—O14.8 (2)
C11—C5—C6—C1104.46 (19)C13—C12—C18—O24.8 (2)
C10—C5—C6—C1134.13 (17)C17—C12—C18—O2174.86 (15)
C4—C5—C6—C116.9 (2)C13—C14—N3—O415.8 (2)
C11—C5—C6—N177.36 (19)C15—C14—N3—O4164.70 (16)
C10—C5—C6—N144.0 (2)C13—C14—N3—O3164.01 (15)
C4—C5—C6—N1161.23 (14)C15—C14—N3—O315.5 (2)
N2—C7—N1—C6178.54 (15)C15—C16—N4—O611.4 (2)
S1—C7—N1—C61.05 (17)C17—C16—N4—O6167.84 (14)
C1—C6—N1—C71.76 (19)C15—C16—N4—O5169.17 (14)
C5—C6—N1—C7176.63 (14)C17—C16—N4—O511.6 (2)
N2—C7—S1—C1179.48 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.885 (19)1.838 (19)2.7187 (17)173.4 (17)
N2—H3N···O2i0.90 (2)2.01 (2)2.8509 (19)156.3 (17)
N2—H2N···O20.91 (2)1.86 (2)2.7551 (18)168.3 (18)
C8—H8A···O6ii0.982.433.397 (2)170
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1/2, 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+·C4H2O42F(000) = 576
Mr = 536.74Dx = 1.224 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.0259 (6) ÅCell parameters from 4569 reflections
b = 14.7314 (11) Åθ = 2.3–23.7°
c = 11.1993 (8) ŵ = 0.22 mm1
β = 101.943 (6)°T = 173 K
V = 1456.87 (18) Å3Prism, orange
Z = 20.15 × 0.08 × 0.02 mm
Data collection top
Rigaku XtaLAB P200 HPC
diffractometer
6424 independent reflections
Radiation source: rotating anode, Rigaku FR-X3792 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromatorRint = 0.080
ω scansθmax = 29.1°, θmin = 1.9°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku, 2017)
h = 1211
Tmin = 0.333, Tmax = 1.000k = 1820
19263 measured reflectionsl = 1412
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(Fo2) + (0.0488P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.128(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.27 e Å3
6424 reflectionsΔρmin = 0.26 e Å3
350 parametersAbsolute structure: Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).
1 restraintAbsolute structure parameter: 0.46 (7)
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
xyzUiso*/UeqOcc. (<1)
C11.2869 (6)0.3952 (4)0.6937 (4)0.0339 (13)
C21.3939 (6)0.4406 (4)0.7989 (5)0.0467 (15)
C3A1.2984 (8)0.5068 (7)0.8546 (8)0.052 (3)*0.78 (2)
H3A11.27200.55960.79960.062*0.78 (2)
H3A21.35780.52930.93340.062*0.78 (2)
C4A1.1520 (10)0.4615 (8)0.8755 (8)0.047 (2)*0.78 (2)
H4A11.10170.50220.92520.056*0.78 (2)
H4A21.17800.40440.92160.056*0.78 (2)
C3B1.284 (3)0.456 (3)0.899 (3)0.063 (12)*0.22 (2)
H3B11.26770.39680.93620.075*0.22 (2)
H3B21.33770.49590.96570.075*0.22 (2)
C4B1.130 (3)0.498 (2)0.846 (3)0.033 (8)*0.22 (2)
H4B11.07350.50780.91210.039*0.22 (2)
H4B21.14450.55820.81020.039*0.22 (2)
C51.0394 (6)0.4401 (4)0.7513 (4)0.0372 (13)
C61.1349 (6)0.3955 (3)0.6728 (4)0.0312 (13)
C71.1687 (6)0.3114 (3)0.5087 (4)0.0320 (13)
C81.4824 (7)0.3683 (4)0.8815 (6)0.067 (2)
H8A1.54740.39750.95190.101*
H8B1.54510.33370.83590.101*
H8C1.41150.32720.90980.101*
C91.5096 (8)0.4998 (5)0.7490 (6)0.076 (2)
H9A1.57510.53160.81680.114*
H9B1.45530.54430.69090.114*
H9C1.57150.46100.70770.114*
C100.9232 (6)0.3732 (4)0.7813 (5)0.0506 (16)
H10A0.87000.40090.84000.076*
H10B0.97500.31800.81670.076*
H10C0.85010.35780.70650.076*
C110.9553 (8)0.5223 (5)0.6843 (6)0.070 (2)
H11A0.89410.55120.73640.105*
H11B0.88920.50200.60830.105*
H11C1.02910.56610.66560.105*
N11.0694 (5)0.3476 (3)0.5669 (4)0.0298 (11)
H1N0.976 (6)0.334 (4)0.544 (4)0.036*
N21.1307 (6)0.2614 (4)0.4096 (4)0.0452 (13)
H2N1.029 (7)0.263 (4)0.369 (5)0.054*
H3N1.202 (6)0.248 (4)0.365 (5)0.054*
S11.35226 (14)0.33370 (9)0.58194 (12)0.0396 (4)
C120.1633 (6)0.1107 (4)0.1894 (4)0.0340 (13)
C130.2578 (6)0.0698 (4)0.3022 (5)0.0408 (14)
C140.1503 (6)0.0460 (4)0.3869 (5)0.0501 (16)
H14A0.20310.00480.45190.060*
H14B0.12440.10220.42650.060*
C150.0046 (6)0.0005 (4)0.3204 (5)0.0493 (15)
H15A0.05570.01700.38130.059*
H15B0.03120.05580.28160.059*
C160.0948 (6)0.0599 (4)0.2219 (4)0.0353 (13)
C170.0114 (5)0.1088 (3)0.1552 (4)0.0286 (12)
C180.0619 (6)0.1945 (4)0.0014 (5)0.0338 (13)
C190.3410 (7)0.0144 (4)0.2709 (6)0.0662 (19)
H19A0.40970.03660.34460.099*
H19B0.39950.00120.20920.099*
H19C0.26720.06180.23890.099*
C200.3760 (6)0.1378 (4)0.3673 (6)0.0556 (17)
H20A0.43560.10980.44120.083*
H20B0.32460.19190.38960.083*
H20C0.44320.15520.31270.083*
C210.2029 (6)0.0017 (4)0.1334 (5)0.0498 (15)
H21A0.26150.03910.17930.075*
H21B0.14410.04120.09010.075*
H21C0.27200.03570.07430.075*
C220.1855 (7)0.1290 (4)0.2784 (5)0.0520 (17)
H22A0.25440.09710.32120.078*
H22B0.24430.16710.21400.078*
H22C0.11620.16710.33640.078*
N30.0446 (5)0.1575 (3)0.0477 (4)0.0329 (11)
H4N0.151 (6)0.163 (4)0.013 (4)0.040*
N40.0317 (6)0.2444 (4)0.1013 (4)0.0457 (13)
H5N0.078 (7)0.242 (4)0.141 (5)0.055*
H6N0.104 (7)0.256 (4)0.130 (5)0.055*
S20.24072 (14)0.17401 (9)0.08375 (12)0.0386 (4)
C230.7409 (6)0.2901 (4)0.3641 (5)0.0358 (13)
C240.5781 (6)0.2738 (4)0.3122 (5)0.0392 (14)
H240.50760.28710.36210.047*
C250.5242 (6)0.2420 (4)0.2013 (5)0.0380 (13)
H250.59420.23100.15020.046*
C260.3622 (6)0.2223 (4)0.1512 (5)0.0371 (14)
O10.7763 (4)0.3234 (3)0.4689 (3)0.0469 (10)
O20.8346 (4)0.2695 (3)0.2995 (3)0.0591 (12)
O30.3301 (4)0.1922 (3)0.0429 (3)0.0473 (11)
O40.2689 (4)0.2349 (4)0.2157 (3)0.0642 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.035 (3)0.035 (3)0.031 (3)0.003 (2)0.003 (2)0.002 (2)
C20.040 (3)0.053 (4)0.042 (3)0.004 (3)0.001 (3)0.011 (3)
C50.039 (3)0.040 (3)0.033 (3)0.001 (3)0.008 (3)0.007 (3)
C60.041 (3)0.026 (3)0.025 (3)0.002 (3)0.003 (2)0.003 (2)
C70.039 (3)0.035 (3)0.022 (3)0.004 (2)0.007 (2)0.000 (2)
C80.064 (4)0.073 (5)0.048 (4)0.007 (3)0.028 (3)0.007 (3)
C90.070 (5)0.058 (5)0.090 (5)0.021 (4)0.006 (4)0.004 (4)
C100.047 (4)0.064 (4)0.047 (4)0.003 (3)0.022 (3)0.002 (3)
C110.085 (5)0.060 (5)0.077 (5)0.025 (4)0.044 (4)0.015 (4)
N10.030 (2)0.035 (3)0.024 (2)0.001 (2)0.006 (2)0.000 (2)
N20.035 (3)0.064 (4)0.037 (3)0.003 (3)0.007 (2)0.013 (3)
S10.0327 (7)0.0473 (9)0.0377 (8)0.0049 (7)0.0045 (6)0.0037 (7)
C120.039 (3)0.033 (3)0.029 (3)0.001 (3)0.005 (2)0.002 (2)
C130.038 (3)0.043 (4)0.039 (3)0.005 (3)0.001 (3)0.002 (3)
C140.046 (3)0.066 (4)0.035 (3)0.003 (3)0.000 (3)0.018 (3)
C150.049 (4)0.053 (4)0.043 (3)0.002 (3)0.004 (3)0.017 (3)
C160.035 (3)0.041 (3)0.031 (3)0.002 (3)0.007 (2)0.005 (3)
C170.031 (3)0.029 (3)0.024 (3)0.000 (2)0.000 (2)0.003 (2)
C180.036 (3)0.035 (4)0.030 (3)0.005 (2)0.008 (3)0.001 (2)
C190.068 (4)0.055 (4)0.070 (4)0.023 (4)0.001 (4)0.004 (3)
C200.047 (4)0.068 (5)0.048 (4)0.000 (3)0.000 (3)0.003 (3)
C210.054 (4)0.044 (4)0.046 (3)0.016 (3)0.000 (3)0.007 (3)
C220.053 (4)0.064 (5)0.044 (4)0.002 (3)0.021 (3)0.006 (3)
N30.027 (2)0.043 (3)0.028 (2)0.000 (2)0.0033 (19)0.003 (2)
N40.035 (3)0.071 (4)0.033 (3)0.009 (3)0.011 (2)0.012 (3)
S20.0323 (7)0.0488 (10)0.0352 (8)0.0019 (7)0.0081 (6)0.0029 (7)
C230.033 (3)0.040 (4)0.035 (3)0.002 (3)0.008 (3)0.000 (3)
C240.032 (3)0.047 (4)0.040 (4)0.004 (3)0.011 (3)0.008 (3)
C250.035 (3)0.050 (4)0.031 (3)0.002 (3)0.011 (3)0.003 (3)
C260.036 (3)0.042 (4)0.032 (3)0.000 (3)0.004 (3)0.002 (3)
O10.036 (2)0.072 (3)0.031 (2)0.010 (2)0.0048 (17)0.019 (2)
O20.037 (2)0.108 (4)0.033 (2)0.007 (2)0.0091 (19)0.020 (2)
O30.037 (2)0.071 (3)0.033 (2)0.0045 (19)0.0055 (17)0.017 (2)
O40.035 (2)0.121 (4)0.039 (2)0.010 (2)0.013 (2)0.028 (2)
Geometric parameters (Å, º) top
C1—C61.344 (7)C12—C131.496 (7)
C1—C21.514 (7)C12—S21.761 (5)
C1—S11.744 (5)C13—C191.527 (8)
C2—C3A1.520 (9)C13—C141.532 (7)
C2—C81.524 (8)C13—C201.533 (8)
C2—C91.551 (9)C14—C151.526 (8)
C2—C3B1.66 (3)C14—H14A0.9900
C3A—C4A1.541 (14)C14—H14B0.9900
C3A—H3A10.9900C15—C161.542 (7)
C3A—H3A20.9900C15—H15A0.9900
C4A—C51.575 (10)C15—H15B0.9900
C4A—H4A10.9900C16—C171.513 (7)
C4A—H4A20.9900C16—C221.523 (7)
C3B—C4B1.53 (5)C16—C211.536 (7)
C3B—H3B10.9900C17—N31.404 (6)
C3B—H3B20.9900C18—N41.319 (7)
C4B—C51.47 (2)C18—N31.320 (6)
C4B—H4B10.9900C18—S21.723 (5)
C4B—H4B20.9900C19—H19A0.9800
C5—C61.504 (7)C19—H19B0.9800
C5—C101.526 (8)C19—H19C0.9800
C5—C111.540 (8)C20—H20A0.9800
C6—N11.401 (6)C20—H20B0.9800
C7—N21.318 (6)C20—H20C0.9800
C7—N11.325 (6)C21—H21A0.9800
C7—S11.721 (5)C21—H21B0.9800
C8—H8A0.9800C21—H21C0.9800
C8—H8B0.9800C22—H22A0.9800
C8—H8C0.9800C22—H22B0.9800
C9—H9A0.9800C22—H22C0.9800
C9—H9B0.9800N3—H4N0.96 (5)
C9—H9C0.9800N4—H5N1.00 (6)
C10—H10A0.9800N4—H6N0.81 (6)
C10—H10B0.9800C23—O11.251 (6)
C10—H10C0.9800C23—O21.258 (6)
C11—H11A0.9800C23—C241.484 (7)
C11—H11B0.9800C24—C251.321 (6)
C11—H11C0.9800C24—H240.9500
N1—H1N0.85 (5)C25—C261.483 (7)
N2—H2N0.94 (6)C25—H250.9500
N2—H3N0.91 (6)C26—O41.232 (6)
C12—C171.345 (7)C26—O31.267 (6)
C6—C1—C2126.7 (5)C7—N2—H3N119 (4)
C6—C1—S1111.2 (4)H2N—N2—H3N118 (5)
C2—C1—S1122.1 (4)C7—S1—C190.3 (2)
C1—C2—C3A106.1 (5)C17—C12—C13127.0 (5)
C1—C2—C8109.5 (5)C17—C12—S2110.0 (4)
C3A—C2—C8118.0 (6)C13—C12—S2122.9 (4)
C1—C2—C9109.7 (5)C12—C13—C19110.8 (5)
C3A—C2—C9105.5 (6)C12—C13—C14106.9 (4)
C8—C2—C9107.7 (5)C19—C13—C14111.1 (5)
C1—C2—C3B102.3 (11)C12—C13—C20110.9 (5)
C8—C2—C3B89.8 (15)C19—C13—C20108.2 (5)
C9—C2—C3B134.9 (15)C14—C13—C20108.8 (5)
C2—C3A—C4A111.1 (9)C15—C14—C13113.0 (5)
C2—C3A—H3A1109.4C15—C14—H14A109.0
C4A—C3A—H3A1109.4C13—C14—H14A109.0
C2—C3A—H3A2109.4C15—C14—H14B109.0
C4A—C3A—H3A2109.4C13—C14—H14B109.0
H3A1—C3A—H3A2108.0H14A—C14—H14B107.8
C3A—C4A—C5111.7 (8)C14—C15—C16114.5 (5)
C3A—C4A—H4A1109.3C14—C15—H15A108.6
C5—C4A—H4A1109.3C16—C15—H15A108.6
C3A—C4A—H4A2109.3C14—C15—H15B108.6
C5—C4A—H4A2109.3C16—C15—H15B108.6
H4A1—C4A—H4A2107.9H15A—C15—H15B107.6
C4B—C3B—C2114 (3)C17—C16—C22109.7 (4)
C4B—C3B—H3B1108.7C17—C16—C21110.2 (4)
C2—C3B—H3B1108.7C22—C16—C21109.8 (5)
C4B—C3B—H3B2108.7C17—C16—C15106.8 (4)
C2—C3B—H3B2108.7C22—C16—C15111.4 (4)
H3B1—C3B—H3B2107.6C21—C16—C15108.9 (5)
C5—C4B—C3B112 (3)C12—C17—N3113.5 (4)
C5—C4B—H4B1109.3C12—C17—C16125.6 (4)
C3B—C4B—H4B1109.3N3—C17—C16120.9 (4)
C5—C4B—H4B2109.3N4—C18—N3122.9 (5)
C3B—C4B—H4B2109.3N4—C18—S2124.9 (4)
H4B1—C4B—H4B2107.9N3—C18—S2112.1 (4)
C4B—C5—C6112.1 (10)C13—C19—H19A109.5
C4B—C5—C10121.4 (12)C13—C19—H19B109.5
C6—C5—C10110.5 (5)H19A—C19—H19B109.5
C4B—C5—C1192.1 (15)C13—C19—H19C109.5
C6—C5—C11110.1 (4)H19A—C19—H19C109.5
C10—C5—C11108.9 (5)H19B—C19—H19C109.5
C6—C5—C4A105.1 (5)C13—C20—H20A109.5
C10—C5—C4A106.4 (5)C13—C20—H20B109.5
C11—C5—C4A115.8 (6)H20A—C20—H20B109.5
C1—C6—N1112.5 (4)C13—C20—H20C109.5
C1—C6—C5126.0 (4)H20A—C20—H20C109.5
N1—C6—C5121.5 (4)H20B—C20—H20C109.5
N2—C7—N1123.7 (5)C16—C21—H21A109.5
N2—C7—S1124.4 (4)C16—C21—H21B109.5
N1—C7—S1111.8 (4)H21A—C21—H21B109.5
C2—C8—H8A109.5C16—C21—H21C109.5
C2—C8—H8B109.5H21A—C21—H21C109.5
H8A—C8—H8B109.5H21B—C21—H21C109.5
C2—C8—H8C109.5C16—C22—H22A109.5
H8A—C8—H8C109.5C16—C22—H22B109.5
H8B—C8—H8C109.5H22A—C22—H22B109.5
C2—C9—H9A109.5C16—C22—H22C109.5
C2—C9—H9B109.5H22A—C22—H22C109.5
H9A—C9—H9B109.5H22B—C22—H22C109.5
C2—C9—H9C109.5C18—N3—C17113.9 (4)
H9A—C9—H9C109.5C18—N3—H4N123 (3)
H9B—C9—H9C109.5C17—N3—H4N123 (3)
C5—C10—H10A109.5C18—N4—H5N112 (3)
C5—C10—H10B109.5C18—N4—H6N115 (4)
H10A—C10—H10B109.5H5N—N4—H6N130 (5)
C5—C10—H10C109.5C18—S2—C1290.5 (2)
H10A—C10—H10C109.5O1—C23—O2124.2 (5)
H10B—C10—H10C109.5O1—C23—C24118.1 (5)
C5—C11—H11A109.5O2—C23—C24117.7 (5)
C5—C11—H11B109.5C25—C24—C23124.6 (5)
H11A—C11—H11B109.5C25—C24—H24117.7
C5—C11—H11C109.5C23—C24—H24117.7
H11A—C11—H11C109.5C24—C25—C26124.6 (5)
H11B—C11—H11C109.5C24—C25—H25117.7
C7—N1—C6114.1 (4)C26—C25—H25117.7
C7—N1—H1N119 (3)O4—C26—O3124.4 (5)
C6—N1—H1N126 (3)O4—C26—C25119.2 (5)
C7—N2—H2N117 (4)O3—C26—C25116.3 (5)
C6—C1—C2—C3A15.4 (9)N1—C7—S1—C10.6 (4)
S1—C1—C2—C3A165.0 (6)C6—C1—S1—C70.8 (4)
C6—C1—C2—C8113.1 (6)C2—C1—S1—C7179.5 (5)
S1—C1—C2—C866.6 (6)C17—C12—C13—C19107.5 (6)
C6—C1—C2—C9128.9 (6)S2—C12—C13—C1975.3 (6)
S1—C1—C2—C951.4 (6)C17—C12—C13—C1413.7 (7)
C6—C1—C2—C3B18.8 (17)S2—C12—C13—C14163.5 (4)
S1—C1—C2—C3B160.8 (16)C17—C12—C13—C20132.2 (6)
C1—C2—C3A—C4A47.8 (10)S2—C12—C13—C2045.0 (6)
C8—C2—C3A—C4A75.5 (9)C12—C13—C14—C1544.1 (6)
C9—C2—C3A—C4A164.1 (8)C19—C13—C14—C1577.0 (6)
C2—C3A—C4A—C569.2 (12)C20—C13—C14—C15163.9 (5)
C1—C2—C3B—C4B48 (3)C13—C14—C15—C1662.5 (7)
C8—C2—C3B—C4B158 (3)C14—C15—C16—C1740.9 (6)
C9—C2—C3B—C4B87 (3)C14—C15—C16—C2278.9 (6)
C2—C3B—C4B—C562 (4)C14—C15—C16—C21159.9 (5)
C3B—C4B—C5—C638 (3)C13—C12—C17—N3176.7 (5)
C3B—C4B—C5—C1095 (3)S2—C12—C17—N30.8 (6)
C3B—C4B—C5—C11151 (3)C13—C12—C17—C163.4 (8)
C3A—C4A—C5—C647.3 (10)S2—C12—C17—C16179.1 (4)
C3A—C4A—C5—C10164.5 (8)C22—C16—C17—C12111.1 (6)
C3A—C4A—C5—C1174.4 (10)C21—C16—C17—C12127.9 (5)
C2—C1—C6—N1179.6 (5)C15—C16—C17—C129.8 (7)
S1—C1—C6—N10.7 (5)C22—C16—C17—N369.1 (6)
C2—C1—C6—C50.9 (9)C21—C16—C17—N351.9 (6)
S1—C1—C6—C5178.8 (4)C15—C16—C17—N3170.1 (5)
C4B—C5—C6—C19.7 (17)N4—C18—N3—C17178.6 (5)
C10—C5—C6—C1129.1 (5)S2—C18—N3—C171.4 (6)
C11—C5—C6—C1110.6 (6)C12—C17—N3—C181.5 (6)
C4A—C5—C6—C114.7 (8)C16—C17—N3—C18178.4 (4)
C4B—C5—C6—N1170.9 (16)N4—C18—S2—C12177.9 (5)
C10—C5—C6—N150.4 (6)N3—C18—S2—C120.8 (4)
C11—C5—C6—N169.9 (6)C17—C12—S2—C180.0 (4)
C4A—C5—C6—N1164.7 (6)C13—C12—S2—C18177.6 (4)
N2—C7—N1—C6177.7 (5)O1—C23—C24—C25177.5 (5)
S1—C7—N1—C60.3 (6)O2—C23—C24—C252.4 (8)
C1—C6—N1—C70.3 (6)C23—C24—C25—C26177.5 (5)
C5—C6—N1—C7179.2 (5)C24—C25—C26—O40.8 (8)
N2—C7—S1—C1177.9 (5)C24—C25—C26—O3179.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.85 (5)1.84 (5)2.670 (5)167 (5)
N2—H2N···O20.94 (6)1.77 (6)2.704 (6)177 (5)
N2—H3N···O4i0.91 (6)1.90 (6)2.746 (6)153 (5)
N3—H4N···O30.96 (5)1.67 (5)2.617 (5)169 (5)
N4—H5N···O41.00 (6)1.75 (6)2.754 (7)178 (5)
N4—H6N···O2ii0.81 (6)2.09 (6)2.763 (6)141 (6)
Symmetry codes: (i) x+1, y, z; (ii) x1, 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+·0.5C4H4O42·0.5C4H5O4·0.5C11H18N2SF(000) = 580
Mr = 538.75Dx = 1.226 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.9437 (3) ÅCell parameters from 9613 reflections
b = 14.7253 (4) Åθ = 2.3–28.0°
c = 11.2676 (4) ŵ = 0.22 mm1
β = 100.493 (3)°T = 173 K
V = 1459.11 (8) Å3Plate, colourless
Z = 20.32 × 0.15 × 0.02 mm
Data collection top
Rigaku XtaLAB P200 HPC
diffractometer
6272 independent reflections
Radiation source: rotating anode, Rigaku FR-X5511 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromatorRint = 0.034
ω scansθmax = 29.1°, θmin = 2.3°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku, 2017)
h = 1012
Tmin = 0.779, Tmax = 1.000k = 1919
19079 measured reflectionsl = 1414
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0529P)2 + 0.1056P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.26 e Å3
6272 reflectionsΔρmin = 0.25 e Å3
354 parametersAbsolute structure: Flack x determined using 2211 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.00 (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
xyzUiso*/UeqOcc. (<1)
C11.2888 (3)0.39542 (19)0.6860 (2)0.0263 (6)
C21.3946 (3)0.4407 (2)0.7881 (3)0.0357 (7)
C3A1.2962 (6)0.5069 (4)0.8461 (5)0.0365 (17)*0.593 (11)
H3A11.26890.55980.79230.044*0.593 (11)
H3A21.35480.52930.92370.044*0.593 (11)
C4A1.1500 (6)0.4594 (5)0.8685 (6)0.0366 (16)*0.593 (11)
H4A11.09790.49850.91980.044*0.593 (11)
H4A21.17680.40150.91180.044*0.593 (11)
C3B1.2917 (10)0.4598 (8)0.8865 (9)0.049 (3)*0.407 (11)
H3B11.27540.40200.92710.059*0.407 (11)
H3B21.34680.50150.94830.059*0.407 (11)
C4B1.1399 (9)0.5005 (7)0.8353 (8)0.038 (2)*0.407 (11)
H4B11.15640.55860.79540.046*0.407 (11)
H4B21.08600.51430.90250.046*0.407 (11)
C51.0393 (3)0.4400 (2)0.7449 (3)0.0308 (6)
C61.1354 (3)0.39467 (18)0.6659 (2)0.0236 (6)
C71.1723 (3)0.30960 (19)0.5050 (2)0.0265 (6)
C81.4933 (5)0.3708 (3)0.8639 (4)0.0612 (11)
H8A1.55740.40100.93240.092*
H8B1.55790.34040.81460.092*
H8C1.42850.32580.89390.092*
C91.5000 (5)0.5061 (3)0.7370 (4)0.0690 (12)
H9A1.55920.54140.80300.103*
H9B1.43900.54740.67930.103*
H9C1.56910.47140.69610.103*
C100.9296 (4)0.3719 (2)0.7834 (3)0.0480 (9)
H10A0.87150.40140.83850.072*
H10B0.98690.32070.82450.072*
H10C0.85960.34990.71210.072*
C110.9468 (5)0.5170 (3)0.6769 (4)0.0669 (13)
H11A0.88200.54440.72850.100*
H11B0.88300.49280.60360.100*
H11C1.01580.56310.65470.100*
N11.0710 (3)0.34631 (16)0.5629 (2)0.0246 (5)
H1N0.968 (4)0.335 (2)0.534 (3)0.030*
N21.1368 (3)0.2592 (2)0.4072 (2)0.0397 (7)
H2N1.209 (4)0.241 (3)0.369 (3)0.048*
H3N1.047 (4)0.257 (3)0.374 (3)0.048*
S11.35670 (7)0.33342 (5)0.57387 (6)0.03090 (18)
C120.1518 (3)0.11232 (19)0.1824 (3)0.0261 (6)
C130.2459 (4)0.0700 (2)0.2927 (3)0.0345 (7)
C140.1355 (4)0.0472 (2)0.3784 (3)0.0405 (8)
H14A0.18710.00660.44310.049*
H14B0.10810.10380.41670.049*
C150.0097 (4)0.0011 (2)0.3133 (3)0.0426 (8)
H15A0.07150.01720.37380.051*
H15B0.01830.05470.27360.051*
C160.1071 (3)0.06150 (19)0.2180 (3)0.0295 (6)
C170.0007 (3)0.11035 (18)0.1495 (2)0.0245 (6)
C180.0513 (3)0.19535 (18)0.0048 (2)0.0263 (6)
C190.3270 (5)0.0149 (3)0.2585 (4)0.0581 (10)
H19A0.38660.04210.33150.087*
H19B0.39500.00180.20300.087*
H19C0.25160.05880.21930.087*
C200.3652 (4)0.1381 (2)0.3552 (3)0.0459 (8)
H20A0.42160.11120.42950.069*
H20B0.31410.19360.37480.069*
H20C0.43580.15300.30100.069*
C210.2173 (4)0.0007 (2)0.1322 (3)0.0446 (8)
H21A0.27850.03510.17890.067*
H21B0.15930.04010.08900.067*
H21C0.28440.03880.07390.067*
C220.1982 (4)0.1307 (2)0.2773 (3)0.0426 (8)
H22A0.26810.09860.32030.064*
H22B0.25640.16970.21500.064*
H22C0.12830.16800.33440.064*
N30.0575 (3)0.15834 (16)0.0442 (2)0.0248 (5)
H4N0.153 (9)0.165 (5)0.011 (6)0.030*0.50 (5)
N40.0255 (3)0.2469 (2)0.1041 (2)0.0387 (7)
H5N0.096 (4)0.249 (3)0.142 (3)0.046*
H6N0.073 (4)0.245 (2)0.147 (3)0.046*
S20.23122 (8)0.17442 (5)0.07649 (6)0.02918 (18)
C260.3743 (3)0.22426 (19)0.1462 (3)0.0271 (6)
C250.5352 (3)0.2536 (2)0.1889 (3)0.0298 (6)
H25A0.55380.30960.14510.036*
H25B0.60390.20600.16760.036*
C240.5760 (3)0.2717 (2)0.3238 (3)0.0300 (7)
H24A0.52020.32640.34270.036*
H24B0.54060.21990.36720.036*
C230.7441 (3)0.2859 (2)0.3709 (3)0.0284 (6)
O10.7810 (2)0.32184 (16)0.47272 (18)0.0379 (5)
O20.8363 (2)0.2585 (2)0.3079 (2)0.0575 (7)
O30.3395 (3)0.20074 (16)0.03486 (19)0.0388 (6)
H1O0.249 (11)0.191 (5)0.008 (7)0.047*0.50 (5)
O40.2832 (2)0.2213 (2)0.21545 (19)0.0500 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0280 (14)0.0258 (13)0.0253 (14)0.0017 (11)0.0051 (11)0.0003 (12)
C20.0308 (15)0.0380 (16)0.0364 (17)0.0002 (13)0.0009 (13)0.0095 (15)
C50.0322 (15)0.0316 (15)0.0295 (15)0.0011 (13)0.0082 (13)0.0073 (13)
C60.0287 (14)0.0218 (12)0.0207 (13)0.0020 (11)0.0050 (11)0.0005 (11)
C70.0236 (14)0.0331 (15)0.0223 (14)0.0018 (11)0.0032 (11)0.0001 (12)
C80.063 (2)0.059 (2)0.048 (2)0.019 (2)0.0263 (19)0.0101 (19)
C90.069 (3)0.047 (2)0.079 (3)0.026 (2)0.018 (2)0.003 (2)
C100.054 (2)0.0462 (19)0.053 (2)0.0011 (17)0.0319 (18)0.0051 (17)
C110.079 (3)0.048 (2)0.088 (3)0.031 (2)0.052 (3)0.023 (2)
N10.0226 (12)0.0286 (12)0.0226 (12)0.0009 (10)0.0037 (9)0.0015 (10)
N20.0287 (14)0.0613 (19)0.0288 (15)0.0056 (13)0.0044 (12)0.0156 (14)
S10.0231 (3)0.0400 (4)0.0290 (4)0.0043 (3)0.0032 (3)0.0045 (3)
C120.0266 (14)0.0253 (13)0.0267 (14)0.0014 (11)0.0058 (12)0.0007 (12)
C130.0337 (16)0.0343 (15)0.0331 (16)0.0093 (13)0.0005 (13)0.0047 (14)
C140.0425 (18)0.0461 (18)0.0305 (16)0.0013 (14)0.0000 (14)0.0137 (15)
C150.0437 (18)0.0420 (17)0.0408 (18)0.0018 (15)0.0044 (15)0.0170 (15)
C160.0303 (14)0.0295 (14)0.0287 (15)0.0027 (12)0.0052 (12)0.0028 (13)
C170.0276 (14)0.0231 (12)0.0225 (14)0.0007 (11)0.0038 (11)0.0016 (11)
C180.0262 (14)0.0297 (15)0.0225 (14)0.0023 (11)0.0032 (12)0.0017 (11)
C190.062 (2)0.048 (2)0.061 (2)0.0282 (18)0.004 (2)0.0068 (19)
C200.0333 (17)0.060 (2)0.0387 (19)0.0004 (16)0.0078 (14)0.0049 (17)
C210.0418 (18)0.0429 (18)0.0472 (19)0.0173 (15)0.0028 (16)0.0068 (16)
C220.0396 (18)0.0499 (19)0.0433 (19)0.0023 (15)0.0206 (16)0.0042 (16)
N30.0218 (11)0.0306 (13)0.0210 (12)0.0003 (10)0.0015 (9)0.0004 (10)
N40.0286 (14)0.0594 (17)0.0277 (15)0.0047 (13)0.0038 (12)0.0121 (13)
S20.0230 (3)0.0361 (4)0.0287 (4)0.0008 (3)0.0053 (3)0.0016 (3)
C260.0268 (14)0.0289 (14)0.0248 (14)0.0020 (12)0.0021 (12)0.0022 (12)
C250.0281 (15)0.0363 (15)0.0243 (15)0.0015 (12)0.0031 (12)0.0019 (13)
C240.0250 (14)0.0386 (16)0.0256 (15)0.0016 (12)0.0025 (12)0.0064 (13)
C230.0279 (15)0.0321 (14)0.0251 (15)0.0012 (12)0.0045 (12)0.0019 (13)
O10.0275 (10)0.0581 (14)0.0274 (11)0.0050 (10)0.0029 (8)0.0178 (11)
O20.0259 (12)0.109 (2)0.0368 (13)0.0003 (13)0.0035 (10)0.0313 (14)
O30.0263 (11)0.0618 (16)0.0273 (12)0.0077 (10)0.0022 (9)0.0105 (10)
O40.0280 (11)0.0919 (19)0.0312 (12)0.0076 (12)0.0084 (10)0.0186 (13)
Geometric parameters (Å, º) top
C1—C61.349 (4)C13—C191.530 (4)
C1—C21.506 (4)C13—C201.538 (5)
C1—S11.754 (3)C13—C141.538 (4)
C2—C81.515 (5)C14—C151.528 (5)
C2—C91.531 (5)C14—H14A0.9900
C2—C3A1.537 (6)C14—H14B0.9900
C2—C3B1.589 (10)C15—C161.536 (4)
C3A—C4A1.544 (9)C15—H15A0.9900
C3A—H3A10.9900C15—H15B0.9900
C3A—H3A20.9900C16—C171.512 (4)
C4A—C51.581 (6)C16—C221.532 (4)
C4A—H4A10.9900C16—C211.536 (4)
C4A—H4A20.9900C17—N31.395 (4)
C3B—C4B1.499 (14)C18—N31.321 (3)
C3B—H3B10.9900C18—N41.337 (4)
C3B—H3B20.9900C18—S21.728 (3)
C4B—C51.519 (8)C19—H19A0.9800
C4B—H4B10.9900C19—H19B0.9800
C4B—H4B20.9900C19—H19C0.9800
C5—C61.502 (4)C20—H20A0.9800
C5—C101.520 (4)C20—H20B0.9800
C5—C111.525 (5)C20—H20C0.9800
C6—N11.394 (3)C21—H21A0.9800
C7—N21.319 (4)C21—H21B0.9800
C7—N11.325 (3)C21—H21C0.9800
C7—S11.726 (3)C22—H22A0.9800
C8—H8A0.9800C22—H22B0.9800
C8—H8B0.9800C22—H22C0.9800
C8—H8C0.9800N3—H4N0.87 (8)
C9—H9A0.9800N4—H5N0.82 (4)
C9—H9B0.9800N4—H6N0.92 (4)
C9—H9C0.9800C26—O41.228 (3)
C10—H10A0.9800C26—O31.283 (4)
C10—H10B0.9800C26—C251.496 (4)
C10—H10C0.9800C25—C241.521 (4)
C11—H11A0.9800C25—H25A0.9900
C11—H11B0.9800C25—H25B0.9900
C11—H11C0.9800C24—C231.515 (4)
N1—H1N0.93 (3)C24—H24A0.9900
N2—H2N0.89 (4)C24—H24B0.9900
N2—H3N0.82 (4)C23—O21.249 (4)
C12—C171.348 (4)C23—O11.252 (3)
C12—C131.503 (4)O3—H1O0.82 (10)
C12—S21.753 (3)
C6—C1—C2127.6 (3)C17—C12—S2109.8 (2)
C6—C1—S1110.5 (2)C13—C12—S2123.0 (2)
C2—C1—S1122.0 (2)C12—C13—C19110.5 (3)
C1—C2—C8110.5 (3)C12—C13—C20110.2 (3)
C1—C2—C9109.6 (3)C19—C13—C20109.1 (3)
C8—C2—C9107.7 (3)C12—C13—C14106.4 (2)
C1—C2—C3A106.1 (3)C19—C13—C14111.6 (3)
C8—C2—C3A120.8 (4)C20—C13—C14109.1 (3)
C9—C2—C3A101.6 (4)C15—C14—C13112.5 (3)
C1—C2—C3B104.4 (4)C15—C14—H14A109.1
C8—C2—C3B94.5 (5)C13—C14—H14A109.1
C9—C2—C3B128.7 (5)C15—C14—H14B109.1
C2—C3A—C4A110.5 (5)C13—C14—H14B109.1
C2—C3A—H3A1109.6H14A—C14—H14B107.8
C4A—C3A—H3A1109.6C14—C15—C16113.7 (3)
C2—C3A—H3A2109.6C14—C15—H15A108.8
C4A—C3A—H3A2109.6C16—C15—H15A108.8
H3A1—C3A—H3A2108.1C14—C15—H15B108.8
C3A—C4A—C5110.5 (5)C16—C15—H15B108.8
C3A—C4A—H4A1109.5H15A—C15—H15B107.7
C5—C4A—H4A1109.5C17—C16—C22109.9 (2)
C3A—C4A—H4A2109.5C17—C16—C21110.3 (2)
C5—C4A—H4A2109.5C22—C16—C21109.3 (3)
H4A1—C4A—H4A2108.1C17—C16—C15107.6 (2)
C4B—C3B—C2113.6 (8)C22—C16—C15111.0 (3)
C4B—C3B—H3B1108.8C21—C16—C15108.7 (3)
C2—C3B—H3B1108.8C12—C17—N3114.6 (2)
C4B—C3B—H3B2108.8C12—C17—C16124.7 (2)
C2—C3B—H3B2108.8N3—C17—C16120.7 (2)
H3B1—C3B—H3B2107.7N3—C18—N4123.8 (3)
C3B—C4B—C5114.1 (8)N3—C18—S2113.0 (2)
C3B—C4B—H4B1108.7N4—C18—S2123.2 (2)
C5—C4B—H4B1108.7C13—C19—H19A109.5
C3B—C4B—H4B2108.7C13—C19—H19B109.5
C5—C4B—H4B2108.7H19A—C19—H19B109.5
H4B1—C4B—H4B2107.6C13—C19—H19C109.5
C6—C5—C4B109.0 (4)H19A—C19—H19C109.5
C6—C5—C10110.2 (2)H19B—C19—H19C109.5
C4B—C5—C10122.0 (4)C13—C20—H20A109.5
C6—C5—C11110.4 (3)C13—C20—H20B109.5
C4B—C5—C1195.9 (5)H20A—C20—H20B109.5
C10—C5—C11108.3 (3)C13—C20—H20C109.5
C6—C5—C4A105.6 (3)H20A—C20—H20C109.5
C10—C5—C4A101.6 (3)H20B—C20—H20C109.5
C11—C5—C4A120.2 (4)C16—C21—H21A109.5
C1—C6—N1113.4 (2)C16—C21—H21B109.5
C1—C6—C5124.8 (3)H21A—C21—H21B109.5
N1—C6—C5121.7 (2)C16—C21—H21C109.5
N2—C7—N1124.0 (3)H21A—C21—H21C109.5
N2—C7—S1123.7 (2)H21B—C21—H21C109.5
N1—C7—S1112.3 (2)C16—C22—H22A109.5
C2—C8—H8A109.5C16—C22—H22B109.5
C2—C8—H8B109.5H22A—C22—H22B109.5
H8A—C8—H8B109.5C16—C22—H22C109.5
C2—C8—H8C109.5H22A—C22—H22C109.5
H8A—C8—H8C109.5H22B—C22—H22C109.5
H8B—C8—H8C109.5C18—N3—C17112.5 (2)
C2—C9—H9A109.5C18—N3—H4N121 (4)
C2—C9—H9B109.5C17—N3—H4N127 (4)
H9A—C9—H9B109.5C18—N4—H5N115 (3)
C2—C9—H9C109.5C18—N4—H6N115 (2)
H9A—C9—H9C109.5H5N—N4—H6N118 (3)
H9B—C9—H9C109.5C18—S2—C1290.03 (13)
C5—C10—H10A109.5O4—C26—O3122.7 (3)
C5—C10—H10B109.5O4—C26—C25121.1 (3)
H10A—C10—H10B109.5O3—C26—C25116.1 (2)
C5—C10—H10C109.5C26—C25—C24114.4 (2)
H10A—C10—H10C109.5C26—C25—H25A108.7
H10B—C10—H10C109.5C24—C25—H25A108.7
C5—C11—H11A109.5C26—C25—H25B108.7
C5—C11—H11B109.5C24—C25—H25B108.7
H11A—C11—H11B109.5H25A—C25—H25B107.6
C5—C11—H11C109.5C23—C24—C25114.6 (2)
H11A—C11—H11C109.5C23—C24—H24A108.6
H11B—C11—H11C109.5C25—C24—H24A108.6
C7—N1—C6113.7 (2)C23—C24—H24B108.6
C7—N1—H1N118.6 (18)C25—C24—H24B108.6
C6—N1—H1N127.6 (18)H24A—C24—H24B107.6
C7—N2—H2N120 (2)O2—C23—O1124.5 (3)
C7—N2—H3N117 (3)O2—C23—C24118.2 (2)
H2N—N2—H3N121 (4)O1—C23—C24117.3 (2)
C7—S1—C190.11 (13)C26—O3—H1O117 (5)
C17—C12—C13127.2 (3)
C6—C1—C2—C8117.8 (4)N1—C7—S1—C10.3 (2)
S1—C1—C2—C861.8 (3)C6—C1—S1—C70.1 (2)
C6—C1—C2—C9123.7 (3)C2—C1—S1—C7179.7 (2)
S1—C1—C2—C956.7 (3)C17—C12—C13—C19105.9 (4)
C6—C1—C2—C3A14.8 (5)S2—C12—C13—C1974.9 (3)
S1—C1—C2—C3A165.7 (3)C17—C12—C13—C20133.5 (3)
C6—C1—C2—C3B17.2 (6)S2—C12—C13—C2045.7 (3)
S1—C1—C2—C3B162.3 (5)C17—C12—C13—C1415.3 (4)
C1—C2—C3A—C4A47.7 (6)S2—C12—C13—C14163.9 (2)
C8—C2—C3A—C4A78.9 (5)C12—C13—C14—C1545.6 (3)
C9—C2—C3A—C4A162.2 (5)C19—C13—C14—C1574.9 (3)
C2—C3A—C4A—C570.2 (6)C20—C13—C14—C15164.5 (3)
C1—C2—C3B—C4B46.1 (9)C13—C14—C15—C1663.9 (4)
C8—C2—C3B—C4B158.7 (8)C14—C15—C16—C1742.2 (3)
C9—C2—C3B—C4B84.4 (9)C14—C15—C16—C2278.1 (3)
C2—C3B—C4B—C562.4 (12)C14—C15—C16—C21161.6 (3)
C3B—C4B—C5—C640.4 (10)C13—C12—C17—N3177.9 (3)
C3B—C4B—C5—C1089.8 (8)S2—C12—C17—N31.4 (3)
C3B—C4B—C5—C11154.4 (8)C13—C12—C17—C161.9 (4)
C3A—C4A—C5—C649.7 (6)S2—C12—C17—C16178.8 (2)
C3A—C4A—C5—C10164.7 (5)C22—C16—C17—C12110.0 (3)
C3A—C4A—C5—C1175.9 (5)C21—C16—C17—C12129.4 (3)
C2—C1—C6—N1179.9 (3)C15—C16—C17—C1211.0 (4)
S1—C1—C6—N10.4 (3)C22—C16—C17—N369.8 (3)
C2—C1—C6—C50.4 (5)C21—C16—C17—N350.8 (3)
S1—C1—C6—C5179.2 (2)C15—C16—C17—N3169.2 (3)
C4B—C5—C6—C110.6 (6)N4—C18—N3—C17177.9 (3)
C10—C5—C6—C1125.7 (3)S2—C18—N3—C170.6 (3)
C11—C5—C6—C1114.7 (3)C12—C17—N3—C181.3 (3)
C4A—C5—C6—C116.8 (4)C16—C17—N3—C18178.9 (2)
C4B—C5—C6—N1169.9 (5)N3—C18—S2—C120.2 (2)
C10—C5—C6—N153.8 (4)N4—C18—S2—C12177.2 (3)
C11—C5—C6—N165.8 (4)C17—C12—S2—C180.9 (2)
C4A—C5—C6—N1162.8 (4)C13—C12—S2—C18178.4 (2)
N2—C7—N1—C6178.3 (3)O4—C26—C25—C244.3 (4)
S1—C7—N1—C60.5 (3)O3—C26—C25—C24174.1 (3)
C1—C6—N1—C70.6 (3)C26—C25—C24—C23170.2 (3)
C5—C6—N1—C7179.0 (2)C25—C24—C23—O218.9 (4)
N2—C7—S1—C1178.5 (3)C25—C24—C23—O1163.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.93 (3)1.70 (3)2.632 (3)175 (3)
N2—H2N···O4i0.89 (4)1.98 (4)2.779 (3)149 (3)
N2—H3N···O20.82 (4)1.89 (4)2.716 (4)176 (4)
N3—H4N···O30.87 (8)1.73 (8)2.594 (3)166 (6)
N4—H5N···O2ii0.82 (4)2.07 (4)2.804 (4)148 (4)
N4—H6N···O40.92 (4)1.93 (4)2.842 (4)169 (3)
O3—H1O···N30.82 (10)1.78 (10)2.594 (3)174 (8)
Symmetry codes: (i) x+1, y, z; (ii) x1, 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···H68.760.947.662.263.365.265.4
H···Br6.2
H···O10.912.029.113.513.013.412.0
H···C5.96.76.66.05.53.74.2
H···S2.11.81.63.53.03.32.6
C···all2.82.92.93.13.13.13.0
N···all2.72.72.73.02.92.83.2
S···all6.56.36.46.26.46.26.5
 

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