







Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808016115/su2055sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808016115/su2055Isup2.hkl |
CCDC reference: 696481
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.113
- Data-to-parameter ratio = 20.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O10 .. N1 .. 2.85 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_4_C Check Cell Rounding: # of Values Ending with 0 = 6 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels .......... 8
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.08 From the CIF: _reflns_number_total 8874 Count of symmetry unique reflns 4772 Completeness (_total/calc) 185.96% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4102 Fraction of Friedel pairs measured 0.860 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 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.
Author Response: The authors FHK, SRJ and IAR were involved in the data collection, structure solution and preparation of publication material. The authors PSP, SMD and EDDS were involved in the synthesis of the compound in different phases. |
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
Compound (I) was synthesized by mixing solutions of the sodium salt of m-nitrobenzene sulfonic acid (0.5 g) in 5 ml of distilled water with 5 drops of 0.1 N HCl and S-benzylthiuronium chloride (1 g) in 5 ml of distilled water. The mixing immediately yielded a precipitate when the reaction container was placed in ice cold water. The resulting precipitate was filtered and dried. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of an ethanol solution at room temperature.
H atoms were positioned geometrically [C—H = 0.93 Å; N—H = 0.86 Å and CH2 = 0.97 Å] and refined using a riding model with Uiso(H) = 1.2Ueq(C, N).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
C8H11N2S+·C6H4NO5S− | Z = 2 |
Mr = 369.41 | F(000) = 384 |
Triclinic, P1 | Dx = 1.513 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0397 (1) Å | Cell parameters from 4354 reflections |
b = 7.7856 (1) Å | θ = 2.8–34.6° |
c = 17.4680 (2) Å | µ = 0.36 mm−1 |
α = 81.366 (1)° | T = 100 K |
β = 89.322 (1)° | Plate, colourless |
γ = 87.057 (1)° | 0.32 × 0.19 × 0.04 mm |
V = 811.01 (2) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 8874 independent reflections |
Radiation source: fine-focus sealed tube | 7378 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ϕ and ω scans | θmax = 30.1°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −7→8 |
Tmin = 0.894, Tmax = 0.986 | k = −10→10 |
19026 measured reflections | l = −24→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0534P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
8874 reflections | Δρmax = 0.38 e Å−3 |
433 parameters | Δρmin = −0.32 e Å−3 |
3 restraints | Absolute structure: Flack (1983), with how many Friedel pairs? |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (5) |
C8H11N2S+·C6H4NO5S− | γ = 87.057 (1)° |
Mr = 369.41 | V = 811.01 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.0397 (1) Å | Mo Kα radiation |
b = 7.7856 (1) Å | µ = 0.36 mm−1 |
c = 17.4680 (2) Å | T = 100 K |
α = 81.366 (1)° | 0.32 × 0.19 × 0.04 mm |
β = 89.322 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 8874 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 7378 reflections with I > 2σ(I) |
Tmin = 0.894, Tmax = 0.986 | Rint = 0.043 |
19026 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.112 | Δρmax = 0.38 e Å−3 |
S = 1.03 | Δρmin = −0.32 e Å−3 |
8874 reflections | Absolute structure: Flack (1983), with how many Friedel pairs? |
433 parameters | Absolute structure parameter: −0.03 (5) |
3 restraints |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.37546 (10) | 0.53723 (8) | 0.82205 (4) | 0.01444 (14) | |
O1 | 0.4811 (4) | 0.4607 (3) | 0.47221 (12) | 0.0252 (5) | |
O2 | 0.1931 (4) | 0.4114 (3) | 0.54531 (12) | 0.0241 (5) | |
O3 | 0.4577 (3) | 0.3635 (3) | 0.85663 (11) | 0.0180 (4) | |
O4 | 0.1377 (3) | 0.5430 (3) | 0.80849 (11) | 0.0184 (4) | |
O5 | 0.4448 (3) | 0.6737 (3) | 0.86311 (12) | 0.0206 (4) | |
N1 | 0.3820 (4) | 0.4617 (3) | 0.53419 (14) | 0.0193 (5) | |
C1 | 0.4988 (4) | 0.5723 (3) | 0.72854 (15) | 0.0147 (5) | |
C2 | 0.7020 (4) | 0.6478 (4) | 0.71677 (16) | 0.0167 (5) | |
H2A | 0.7710 | 0.6903 | 0.7569 | 0.020* | |
C3 | 0.8017 (5) | 0.6590 (4) | 0.64337 (18) | 0.0207 (6) | |
H3A | 0.9384 | 0.7085 | 0.6351 | 0.025* | |
C4 | 0.7004 (5) | 0.5977 (4) | 0.58323 (17) | 0.0184 (6) | |
H4A | 0.7673 | 0.6044 | 0.5347 | 0.022* | |
C5 | 0.4953 (5) | 0.5255 (4) | 0.59719 (16) | 0.0163 (5) | |
C6 | 0.3912 (5) | 0.5112 (3) | 0.66886 (15) | 0.0154 (5) | |
H6A | 0.2539 | 0.4623 | 0.6767 | 0.018* | |
S2 | 0.31950 (11) | −0.08507 (8) | 0.41082 (4) | 0.01834 (15) | |
O6 | 0.5275 (5) | 0.1046 (3) | 0.73759 (13) | 0.0379 (6) | |
O7 | 0.2256 (5) | 0.0097 (4) | 0.69863 (14) | 0.0493 (8) | |
O8 | 0.1789 (4) | 0.0611 (3) | 0.37490 (12) | 0.0231 (5) | |
O9 | 0.4738 (4) | −0.1484 (3) | 0.35681 (13) | 0.0301 (5) | |
O10 | 0.1907 (4) | −0.2203 (3) | 0.45482 (13) | 0.0282 (5) | |
N2 | 0.4156 (5) | 0.0558 (4) | 0.68796 (15) | 0.0285 (6) | |
C7 | 0.4798 (5) | −0.0078 (4) | 0.48202 (16) | 0.0168 (5) | |
C8 | 0.3892 (5) | −0.0087 (4) | 0.55576 (17) | 0.0185 (6) | |
H8A | 0.2493 | −0.0502 | 0.5677 | 0.022* | |
C9 | 0.5124 (5) | 0.0534 (4) | 0.61044 (17) | 0.0215 (6) | |
C10 | 0.7218 (5) | 0.1167 (4) | 0.59464 (18) | 0.0227 (6) | |
H10A | 0.8017 | 0.1578 | 0.6327 | 0.027* | |
C11 | 0.8082 (5) | 0.1169 (4) | 0.52112 (19) | 0.0239 (6) | |
H11A | 0.9479 | 0.1590 | 0.5094 | 0.029* | |
C12 | 0.6880 (5) | 0.0546 (4) | 0.46421 (17) | 0.0195 (6) | |
H12A | 0.7471 | 0.0549 | 0.4148 | 0.023* | |
S3 | 0.77990 (11) | 0.92863 (9) | 0.89784 (5) | 0.02185 (17) | |
N3 | 0.9177 (4) | 1.2377 (3) | 0.85658 (14) | 0.0211 (5) | |
H1N3 | 1.0112 | 1.3173 | 0.8448 | 0.025* | |
H2N3 | 0.7778 | 1.2643 | 0.8544 | 0.025* | |
N4 | 1.1997 (4) | 1.0283 (3) | 0.88215 (14) | 0.0199 (5) | |
H1N4 | 1.2973 | 1.1048 | 0.8708 | 0.024* | |
H2N4 | 1.2408 | 0.9209 | 0.8963 | 0.024* | |
C13 | 0.8638 (5) | 0.8126 (4) | 1.08658 (18) | 0.0229 (6) | |
H13A | 0.7231 | 0.8611 | 1.0730 | 0.027* | |
C14 | 0.9388 (6) | 0.8053 (4) | 1.16156 (19) | 0.0292 (7) | |
H14A | 0.8479 | 0.8490 | 1.1982 | 0.035* | |
C15 | 1.1470 (6) | 0.7337 (4) | 1.18259 (18) | 0.0294 (7) | |
H15A | 1.1961 | 0.7290 | 1.2332 | 0.035* | |
C16 | 1.2827 (6) | 0.6688 (4) | 1.12789 (19) | 0.0274 (7) | |
H16A | 1.4234 | 0.6208 | 1.1417 | 0.033* | |
C17 | 1.2086 (5) | 0.6754 (4) | 1.05282 (17) | 0.0217 (6) | |
H17A | 1.3000 | 0.6312 | 1.0164 | 0.026* | |
C18 | 0.9993 (5) | 0.7473 (4) | 1.03121 (17) | 0.0178 (6) | |
C19 | 0.9156 (5) | 0.7358 (4) | 0.95108 (18) | 0.0216 (6) | |
H19A | 0.8127 | 0.6432 | 0.9556 | 0.026* | |
H19B | 1.0406 | 0.7015 | 0.9204 | 0.026* | |
C20 | 0.9890 (5) | 1.0752 (4) | 0.87791 (15) | 0.0165 (5) | |
S4 | 0.70823 (11) | 0.42238 (9) | 0.29521 (4) | 0.02029 (15) | |
N5 | 0.8675 (4) | 0.6477 (3) | 0.37270 (14) | 0.0205 (5) | |
H1N5 | 0.9647 | 0.6932 | 0.3980 | 0.025* | |
H2N5 | 0.7379 | 0.6980 | 0.3650 | 0.025* | |
N6 | 1.1136 (4) | 0.4218 (3) | 0.35682 (14) | 0.0209 (5) | |
H1N6 | 1.2132 | 0.4650 | 0.3819 | 0.025* | |
H2N6 | 1.1425 | 0.3262 | 0.3388 | 0.025* | |
C21 | 0.7614 (5) | 0.3251 (4) | 0.09917 (17) | 0.0211 (6) | |
H21A | 0.8905 | 0.3852 | 0.0900 | 0.025* | |
C22 | 0.6228 (5) | 0.3107 (4) | 0.03818 (17) | 0.0241 (6) | |
H22A | 0.6595 | 0.3609 | −0.0118 | 0.029* | |
C23 | 0.4305 (5) | 0.2224 (4) | 0.05098 (18) | 0.0258 (7) | |
H23A | 0.3378 | 0.2128 | 0.0099 | 0.031* | |
C24 | 0.3766 (5) | 0.1484 (4) | 0.12517 (19) | 0.0266 (7) | |
H24A | 0.2463 | 0.0897 | 0.1341 | 0.032* | |
C25 | 0.5157 (5) | 0.1608 (4) | 0.18650 (17) | 0.0228 (6) | |
H25A | 0.4794 | 0.1091 | 0.2362 | 0.027* | |
C26 | 0.7088 (5) | 0.2503 (4) | 0.17390 (16) | 0.0180 (6) | |
C27 | 0.8588 (5) | 0.2713 (4) | 0.23962 (17) | 0.0242 (6) | |
H27A | 0.9976 | 0.3182 | 0.2200 | 0.029* | |
H27B | 0.8905 | 0.1601 | 0.2718 | 0.029* | |
C28 | 0.9169 (5) | 0.5019 (4) | 0.34598 (16) | 0.0175 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0132 (3) | 0.0156 (3) | 0.0147 (3) | −0.0010 (2) | −0.0006 (2) | −0.0028 (2) |
O1 | 0.0274 (12) | 0.0322 (12) | 0.0163 (10) | 0.0034 (9) | 0.0009 (9) | −0.0061 (9) |
O2 | 0.0218 (11) | 0.0285 (12) | 0.0236 (11) | −0.0070 (9) | −0.0016 (9) | −0.0066 (9) |
O3 | 0.0197 (10) | 0.0164 (10) | 0.0169 (9) | 0.0018 (8) | −0.0002 (8) | 0.0000 (8) |
O4 | 0.0138 (10) | 0.0201 (10) | 0.0209 (10) | −0.0010 (8) | 0.0001 (8) | −0.0019 (8) |
O5 | 0.0202 (10) | 0.0223 (10) | 0.0222 (10) | −0.0061 (8) | 0.0008 (8) | −0.0111 (8) |
N1 | 0.0229 (14) | 0.0157 (12) | 0.0188 (12) | 0.0024 (10) | −0.0025 (10) | −0.0019 (9) |
C1 | 0.0144 (13) | 0.0126 (13) | 0.0167 (13) | 0.0009 (10) | −0.0022 (10) | −0.0018 (10) |
C2 | 0.0130 (13) | 0.0167 (13) | 0.0199 (13) | −0.0007 (10) | −0.0032 (10) | −0.0012 (11) |
C3 | 0.0128 (13) | 0.0199 (14) | 0.0273 (15) | −0.0018 (10) | 0.0006 (11) | 0.0034 (12) |
C4 | 0.0167 (14) | 0.0195 (14) | 0.0182 (13) | 0.0018 (11) | 0.0020 (11) | −0.0008 (11) |
C5 | 0.0176 (13) | 0.0149 (13) | 0.0166 (12) | 0.0015 (10) | −0.0048 (10) | −0.0031 (10) |
C6 | 0.0141 (13) | 0.0144 (13) | 0.0170 (13) | −0.0010 (10) | −0.0017 (10) | −0.0002 (10) |
S2 | 0.0198 (4) | 0.0174 (3) | 0.0176 (3) | 0.0013 (3) | −0.0044 (3) | −0.0023 (3) |
O6 | 0.0591 (18) | 0.0348 (14) | 0.0216 (12) | −0.0018 (12) | −0.0106 (11) | −0.0094 (10) |
O7 | 0.0337 (15) | 0.092 (2) | 0.0243 (13) | −0.0050 (15) | 0.0061 (11) | −0.0138 (14) |
O8 | 0.0235 (11) | 0.0209 (11) | 0.0232 (10) | 0.0045 (8) | −0.0055 (9) | 0.0004 (9) |
O9 | 0.0310 (13) | 0.0378 (13) | 0.0224 (11) | 0.0120 (10) | −0.0038 (9) | −0.0118 (10) |
O10 | 0.0330 (13) | 0.0221 (11) | 0.0284 (11) | −0.0104 (9) | −0.0110 (10) | 0.0035 (9) |
N2 | 0.0390 (18) | 0.0263 (14) | 0.0199 (13) | 0.0067 (12) | −0.0021 (12) | −0.0052 (11) |
C7 | 0.0169 (14) | 0.0150 (13) | 0.0175 (13) | 0.0034 (10) | −0.0031 (10) | −0.0003 (10) |
C8 | 0.0172 (14) | 0.0171 (13) | 0.0205 (13) | 0.0024 (11) | −0.0019 (11) | −0.0019 (11) |
C9 | 0.0232 (16) | 0.0201 (15) | 0.0206 (14) | 0.0059 (11) | −0.0056 (11) | −0.0036 (11) |
C10 | 0.0206 (15) | 0.0202 (15) | 0.0276 (15) | 0.0037 (11) | −0.0091 (12) | −0.0055 (12) |
C11 | 0.0149 (14) | 0.0199 (15) | 0.0363 (17) | −0.0018 (11) | −0.0032 (12) | −0.0021 (13) |
C12 | 0.0178 (14) | 0.0164 (14) | 0.0235 (14) | 0.0011 (11) | −0.0009 (11) | −0.0013 (11) |
S3 | 0.0150 (4) | 0.0199 (4) | 0.0292 (4) | −0.0045 (3) | −0.0034 (3) | 0.0025 (3) |
N3 | 0.0147 (12) | 0.0189 (12) | 0.0294 (13) | −0.0045 (9) | −0.0001 (10) | −0.0012 (10) |
N4 | 0.0142 (12) | 0.0211 (13) | 0.0241 (12) | −0.0025 (9) | 0.0002 (10) | −0.0016 (10) |
C13 | 0.0206 (15) | 0.0208 (15) | 0.0268 (15) | −0.0007 (11) | 0.0053 (12) | −0.0024 (12) |
C14 | 0.0363 (19) | 0.0219 (16) | 0.0287 (16) | −0.0027 (13) | 0.0097 (14) | −0.0010 (13) |
C15 | 0.038 (2) | 0.0278 (18) | 0.0200 (15) | −0.0090 (14) | −0.0013 (13) | 0.0053 (13) |
C16 | 0.0228 (16) | 0.0265 (17) | 0.0298 (17) | −0.0019 (12) | −0.0054 (13) | 0.0067 (13) |
C17 | 0.0192 (15) | 0.0220 (15) | 0.0224 (14) | 0.0022 (11) | 0.0039 (12) | −0.0002 (12) |
C18 | 0.0176 (14) | 0.0130 (13) | 0.0224 (14) | −0.0041 (10) | 0.0024 (11) | −0.0004 (11) |
C19 | 0.0195 (15) | 0.0150 (14) | 0.0298 (16) | −0.0016 (11) | 0.0014 (12) | −0.0017 (12) |
C20 | 0.0156 (13) | 0.0207 (14) | 0.0136 (12) | −0.0031 (10) | 0.0007 (10) | −0.0027 (10) |
S4 | 0.0170 (4) | 0.0252 (4) | 0.0202 (3) | −0.0003 (3) | −0.0022 (3) | −0.0082 (3) |
N5 | 0.0177 (12) | 0.0222 (13) | 0.0228 (12) | −0.0013 (9) | −0.0009 (10) | −0.0067 (10) |
N6 | 0.0187 (13) | 0.0233 (13) | 0.0212 (12) | 0.0006 (10) | −0.0056 (10) | −0.0050 (10) |
C21 | 0.0222 (15) | 0.0188 (14) | 0.0224 (14) | −0.0025 (11) | 0.0019 (12) | −0.0027 (12) |
C22 | 0.0329 (18) | 0.0236 (16) | 0.0157 (13) | −0.0003 (13) | −0.0014 (12) | −0.0027 (12) |
C23 | 0.0283 (17) | 0.0249 (16) | 0.0265 (16) | 0.0023 (13) | −0.0125 (13) | −0.0116 (13) |
C24 | 0.0242 (16) | 0.0241 (16) | 0.0335 (17) | −0.0064 (12) | −0.0009 (13) | −0.0087 (13) |
C25 | 0.0269 (16) | 0.0221 (15) | 0.0185 (14) | −0.0005 (12) | 0.0036 (12) | −0.0001 (12) |
C26 | 0.0215 (15) | 0.0182 (14) | 0.0149 (12) | 0.0013 (11) | −0.0023 (11) | −0.0047 (11) |
C27 | 0.0256 (16) | 0.0286 (16) | 0.0197 (14) | 0.0069 (12) | −0.0035 (12) | −0.0103 (12) |
C28 | 0.0163 (14) | 0.0215 (15) | 0.0144 (12) | −0.0026 (11) | 0.0008 (11) | −0.0011 (11) |
S1—O5 | 1.449 (2) | N4—C20 | 1.306 (4) |
S1—O4 | 1.456 (2) | N4—H1N4 | 0.8600 |
S1—O3 | 1.461 (2) | N4—H2N4 | 0.8600 |
S1—C1 | 1.776 (3) | C13—C14 | 1.383 (5) |
O1—N1 | 1.232 (3) | C13—C18 | 1.396 (4) |
O2—N1 | 1.229 (3) | C13—H13A | 0.9300 |
N1—C5 | 1.464 (4) | C14—C15 | 1.380 (5) |
C1—C2 | 1.388 (4) | C14—H14A | 0.9300 |
C1—C6 | 1.390 (4) | C15—C16 | 1.387 (5) |
C2—C3 | 1.403 (4) | C15—H15A | 0.9300 |
C2—H2A | 0.9300 | C16—C17 | 1.383 (4) |
C3—C4 | 1.379 (4) | C16—H16A | 0.9300 |
C3—H3A | 0.9300 | C17—C18 | 1.389 (4) |
C4—C5 | 1.390 (4) | C17—H17A | 0.9300 |
C4—H4A | 0.9300 | C18—C19 | 1.510 (4) |
C5—C6 | 1.386 (4) | C19—H19A | 0.9700 |
C6—H6A | 0.9300 | C19—H19B | 0.9700 |
S2—O9 | 1.440 (2) | S4—C28 | 1.740 (3) |
S2—O8 | 1.452 (2) | S4—C27 | 1.835 (3) |
S2—O10 | 1.460 (2) | N5—C28 | 1.310 (4) |
S2—C7 | 1.778 (3) | N5—H1N5 | 0.8600 |
O6—N2 | 1.222 (4) | N5—H2N5 | 0.8600 |
O7—N2 | 1.224 (4) | N6—C28 | 1.315 (4) |
N2—C9 | 1.471 (4) | N6—H1N6 | 0.8600 |
C7—C12 | 1.386 (4) | N6—H2N6 | 0.8600 |
C7—C8 | 1.393 (4) | C21—C22 | 1.384 (4) |
C8—C9 | 1.376 (4) | C21—C26 | 1.387 (4) |
C8—H8A | 0.9300 | C21—H21A | 0.9300 |
C9—C10 | 1.390 (4) | C22—C23 | 1.379 (5) |
C10—C11 | 1.380 (5) | C22—H22A | 0.9300 |
C10—H10A | 0.9300 | C23—C24 | 1.379 (4) |
C11—C12 | 1.396 (4) | C23—H23A | 0.9300 |
C11—H11A | 0.9300 | C24—C25 | 1.387 (4) |
C12—H12A | 0.9300 | C24—H24A | 0.9300 |
S3—C20 | 1.742 (3) | C25—C26 | 1.388 (4) |
S3—C19 | 1.806 (3) | C25—H25A | 0.9300 |
N3—C20 | 1.316 (4) | C26—C27 | 1.504 (4) |
N3—H1N3 | 0.8600 | C27—H27A | 0.9700 |
N3—H2N3 | 0.8600 | C27—H27B | 0.9700 |
O5—S1—O4 | 113.68 (12) | C14—C13—C18 | 120.0 (3) |
O5—S1—O3 | 113.38 (12) | C14—C13—H13A | 120.0 |
O4—S1—O3 | 111.39 (12) | C18—C13—H13A | 120.0 |
O5—S1—C1 | 107.07 (12) | C15—C14—C13 | 120.7 (3) |
O4—S1—C1 | 105.35 (12) | C15—C14—H14A | 119.6 |
O3—S1—C1 | 105.17 (12) | C13—C14—H14A | 119.6 |
O2—N1—O1 | 122.9 (2) | C14—C15—C16 | 119.6 (3) |
O2—N1—C5 | 118.8 (2) | C14—C15—H15A | 120.2 |
O1—N1—C5 | 118.3 (2) | C16—C15—H15A | 120.2 |
C2—C1—C6 | 121.3 (3) | C17—C16—C15 | 120.0 (3) |
C2—C1—S1 | 121.1 (2) | C17—C16—H16A | 120.0 |
C6—C1—S1 | 117.5 (2) | C15—C16—H16A | 120.0 |
C1—C2—C3 | 118.9 (3) | C16—C17—C18 | 120.7 (3) |
C1—C2—H2A | 120.5 | C16—C17—H17A | 119.6 |
C3—C2—H2A | 120.5 | C18—C17—H17A | 119.6 |
C4—C3—C2 | 121.1 (3) | C17—C18—C13 | 119.0 (3) |
C4—C3—H3A | 119.4 | C17—C18—C19 | 119.0 (3) |
C2—C3—H3A | 119.4 | C13—C18—C19 | 121.7 (3) |
C3—C4—C5 | 118.1 (3) | C18—C19—S3 | 117.6 (2) |
C3—C4—H4A | 121.0 | C18—C19—H19A | 107.9 |
C5—C4—H4A | 121.0 | S3—C19—H19A | 107.9 |
C6—C5—C4 | 122.7 (3) | C18—C19—H19B | 107.9 |
C6—C5—N1 | 117.9 (2) | S3—C19—H19B | 107.9 |
C4—C5—N1 | 119.4 (2) | H19A—C19—H19B | 107.2 |
C5—C6—C1 | 117.8 (3) | N4—C20—N3 | 122.3 (3) |
C5—C6—H6A | 121.1 | N4—C20—S3 | 123.1 (2) |
C1—C6—H6A | 121.1 | N3—C20—S3 | 114.6 (2) |
O9—S2—O8 | 112.40 (13) | C28—S4—C27 | 103.46 (14) |
O9—S2—O10 | 113.93 (15) | C28—N5—H1N5 | 120.0 |
O8—S2—O10 | 111.89 (14) | C28—N5—H2N5 | 120.0 |
O9—S2—C7 | 106.75 (14) | H1N5—N5—H2N5 | 120.0 |
O8—S2—C7 | 106.93 (13) | C28—N6—H1N6 | 120.0 |
O10—S2—C7 | 104.21 (13) | C28—N6—H2N6 | 120.0 |
O6—N2—O7 | 123.8 (3) | H1N6—N6—H2N6 | 120.0 |
O6—N2—C9 | 118.6 (3) | C22—C21—C26 | 120.4 (3) |
O7—N2—C9 | 117.6 (3) | C22—C21—H21A | 119.8 |
C12—C7—C8 | 120.9 (3) | C26—C21—H21A | 119.8 |
C12—C7—S2 | 120.8 (2) | C23—C22—C21 | 120.4 (3) |
C8—C7—S2 | 118.3 (2) | C23—C22—H22A | 119.8 |
C9—C8—C7 | 118.1 (3) | C21—C22—H22A | 119.8 |
C9—C8—H8A | 120.9 | C22—C23—C24 | 119.6 (3) |
C7—C8—H8A | 120.9 | C22—C23—H23A | 120.2 |
C8—C9—C10 | 122.5 (3) | C24—C23—H23A | 120.2 |
C8—C9—N2 | 118.3 (3) | C23—C24—C25 | 120.4 (3) |
C10—C9—N2 | 119.2 (3) | C23—C24—H24A | 119.8 |
C11—C10—C9 | 118.4 (3) | C25—C24—H24A | 119.8 |
C11—C10—H10A | 120.8 | C24—C25—C26 | 120.2 (3) |
C9—C10—H10A | 120.8 | C24—C25—H25A | 119.9 |
C10—C11—C12 | 120.6 (3) | C26—C25—H25A | 119.9 |
C10—C11—H11A | 119.7 | C21—C26—C25 | 119.0 (3) |
C12—C11—H11A | 119.7 | C21—C26—C27 | 119.5 (3) |
C7—C12—C11 | 119.4 (3) | C25—C26—C27 | 121.4 (3) |
C7—C12—H12A | 120.3 | C26—C27—S4 | 105.9 (2) |
C11—C12—H12A | 120.3 | C26—C27—H27A | 110.6 |
C20—S3—C19 | 104.77 (14) | S4—C27—H27A | 110.6 |
C20—N3—H1N3 | 120.0 | C26—C27—H27B | 110.6 |
C20—N3—H2N3 | 120.0 | S4—C27—H27B | 110.6 |
H1N3—N3—H2N3 | 120.0 | H27A—C27—H27B | 108.7 |
C20—N4—H1N4 | 120.0 | N5—C28—N6 | 121.5 (3) |
C20—N4—H2N4 | 120.0 | N5—C28—S4 | 116.1 (2) |
H1N4—N4—H2N4 | 120.0 | N6—C28—S4 | 122.4 (2) |
O5—S1—C1—C2 | 30.8 (3) | O7—N2—C9—C10 | 175.5 (3) |
O4—S1—C1—C2 | 152.1 (2) | C8—C9—C10—C11 | 0.1 (4) |
O3—S1—C1—C2 | −90.1 (2) | N2—C9—C10—C11 | −178.6 (3) |
O5—S1—C1—C6 | −153.3 (2) | C9—C10—C11—C12 | −0.2 (4) |
O4—S1—C1—C6 | −32.0 (2) | C8—C7—C12—C11 | 0.1 (4) |
O3—S1—C1—C6 | 85.8 (2) | S2—C7—C12—C11 | 179.0 (2) |
C6—C1—C2—C3 | −1.3 (4) | C10—C11—C12—C7 | 0.1 (4) |
S1—C1—C2—C3 | 174.5 (2) | C18—C13—C14—C15 | 0.0 (5) |
C1—C2—C3—C4 | 0.5 (4) | C13—C14—C15—C16 | 0.1 (5) |
C2—C3—C4—C5 | 0.5 (4) | C14—C15—C16—C17 | −0.2 (5) |
C3—C4—C5—C6 | −0.8 (4) | C15—C16—C17—C18 | 0.3 (5) |
C3—C4—C5—N1 | 179.1 (2) | C16—C17—C18—C13 | −0.2 (4) |
O2—N1—C5—C6 | 5.8 (4) | C16—C17—C18—C19 | −173.9 (3) |
O1—N1—C5—C6 | −174.1 (2) | C14—C13—C18—C17 | 0.1 (4) |
O2—N1—C5—C4 | −174.1 (3) | C14—C13—C18—C19 | 173.6 (3) |
O1—N1—C5—C4 | 6.0 (4) | C17—C18—C19—S3 | −135.9 (2) |
C4—C5—C6—C1 | 0.0 (4) | C13—C18—C19—S3 | 50.5 (4) |
N1—C5—C6—C1 | −179.8 (2) | C20—S3—C19—C18 | 67.8 (2) |
C2—C1—C6—C5 | 1.0 (4) | C19—S3—C20—N4 | 17.4 (3) |
S1—C1—C6—C5 | −174.9 (2) | C19—S3—C20—N3 | −163.9 (2) |
O9—S2—C7—C12 | 28.0 (3) | C26—C21—C22—C23 | 0.2 (5) |
O8—S2—C7—C12 | −92.5 (2) | C21—C22—C23—C24 | 0.1 (5) |
O10—S2—C7—C12 | 148.9 (2) | C22—C23—C24—C25 | −0.7 (5) |
O9—S2—C7—C8 | −153.1 (2) | C23—C24—C25—C26 | 1.0 (5) |
O8—S2—C7—C8 | 86.4 (2) | C22—C21—C26—C25 | 0.1 (4) |
O10—S2—C7—C8 | −32.2 (3) | C22—C21—C26—C27 | −178.5 (3) |
C12—C7—C8—C9 | −0.2 (4) | C24—C25—C26—C21 | −0.7 (4) |
S2—C7—C8—C9 | −179.1 (2) | C24—C25—C26—C27 | 177.9 (3) |
C7—C8—C9—C10 | 0.1 (4) | C21—C26—C27—S4 | 108.2 (3) |
C7—C8—C9—N2 | 178.8 (3) | C25—C26—C27—S4 | −70.4 (3) |
O6—N2—C9—C8 | 177.2 (3) | C28—S4—C27—C26 | −159.2 (2) |
O7—N2—C9—C8 | −3.3 (4) | C27—S4—C28—N5 | 160.8 (2) |
O6—N2—C9—C10 | −4.0 (4) | C27—S4—C28—N6 | −18.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N3···O4i | 0.86 | 1.97 | 2.796 (3) | 162 |
N3—H1N3···S1i | 0.86 | 2.84 | 3.694 (3) | 170 |
N3—H2N3···O3ii | 0.86 | 2.05 | 2.898 (3) | 171 |
N4—H1N4···O3i | 0.86 | 2.26 | 3.080 (3) | 160 |
N4—H2N4···O5iii | 0.86 | 2.37 | 3.126 (3) | 146 |
N5—H1N5···O10i | 0.86 | 1.91 | 2.764 (3) | 176 |
N5—H1N5···S2i | 0.86 | 2.85 | 3.642 (3) | 154 |
N5—H2N5···O9ii | 0.86 | 1.94 | 2.783 (3) | 168 |
N6—H1N6···O1iii | 0.86 | 2.27 | 3.072 (3) | 156 |
N6—H2N6···O8iii | 0.86 | 2.07 | 2.787 (3) | 141 |
C6—H6A···O4 | 0.93 | 2.56 | 2.900 (3) | 102 |
C8—H8A···O10 | 0.93 | 2.57 | 2.896 (4) | 101 |
C19—H19B···O4iii | 0.97 | 2.51 | 3.331 (4) | 142 |
C27—H27B···O8iii | 0.97 | 2.53 | 3.259 (4) | 132 |
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C8H11N2S+·C6H4NO5S− |
Mr | 369.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 6.0397 (1), 7.7856 (1), 17.4680 (2) |
α, β, γ (°) | 81.366 (1), 89.322 (1), 87.057 (1) |
V (Å3) | 811.01 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.32 × 0.19 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.894, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19026, 8874, 7378 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.112, 1.03 |
No. of reflections | 8874 |
No. of parameters | 433 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.32 |
Absolute structure | Flack (1983), with how many Friedel pairs? |
Absolute structure parameter | −0.03 (5) |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N3···O4i | 0.86 | 1.97 | 2.796 (3) | 161.8 |
N3—H1N3···S1i | 0.86 | 2.84 | 3.694 (3) | 169.6 |
N3—H2N3···O3ii | 0.86 | 2.05 | 2.898 (3) | 170.5 |
N4—H1N4···O3i | 0.86 | 2.26 | 3.080 (3) | 159.9 |
N4—H2N4···O5iii | 0.86 | 2.37 | 3.126 (3) | 146.3 |
N5—H1N5···O10i | 0.86 | 1.91 | 2.764 (3) | 176.3 |
N5—H1N5···S2i | 0.86 | 2.85 | 3.642 (3) | 153.7 |
N5—H2N5···O9ii | 0.86 | 1.94 | 2.783 (3) | 167.6 |
N6—H1N6···O1iii | 0.86 | 2.27 | 3.072 (3) | 155.8 |
N6—H2N6···O8iii | 0.86 | 2.07 | 2.787 (3) | 140.8 |
C6—H6A···O4 | 0.93 | 2.56 | 2.900 (3) | 102 |
C8—H8A···O10 | 0.93 | 2.57 | 2.896 (4) | 101 |
C19—H19B···O4iii | 0.97 | 2.51 | 3.331 (4) | 142 |
C27—H27B···O8iii | 0.97 | 2.53 | 3.259 (4) | 132 |
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z; (iii) x+1, y, z. |
In continuation of our research on nonlinear optical (NLO) materials (Chantrapromma et al., 2005, 2006; Fun et al., 2006; Patil, Dharmaprakash et al. (2007); Patil, Fun et al. (2007), the crystal structure determination of the title compound, (I), was undertaken in order to obtain detailed information on its three-dimensional structure and crystal packing. Since the title compound crystallizes in a non-centrosymmetric space group, it should exhibit second-order nonlinear optical properties.
In the asymmetric unit of (I) there are two crystallographically independent s-benzylthiuronium cations and two independent m-nitrobenzene sulfonate anions (Fig. 1). Bond lengths and angles are found to have normal values (Allen et al., 1987). The dihedral angle formed by the mean plane of ring (C13–C18) with the mean planes through rings (C21–C26), (C1–C6) and (C7–C12) are 57.6 (2)°, 49.9 (2)° and 46.98 (1)°, respectively. The dihedral angle formed by the mean planes of rings (C1–C6) and (C7–C12) are 3.07 (1)°, indicating that they are almost coplanar.
An intramolecular hydrogen bond generates a S(5)S(5) ring motif (Bernstein et al., 1995). The crystal packing (Fig. 2) is stabilized by intramolecular C—H···O, intermolecular C—H···O, N—H···O and N—H···S hydrogen bonds which together with short S···O and N···O contacts, in the range 2.796 (3)–3.282 (3) Å [symmetry code: x, 1+y, z; 1+x, 1+y, z], form a two-dimensional network parrallel to the ab plane.