



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808019995/hb2737sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808019995/hb2737Isup2.hkl |
CCDC reference: 702570
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.031
- wR factor = 0.079
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT063_ALERT_4_C Crystal Probably too Large for Beam Size ....... 0.75 mm 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 = 4 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C2S PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels .......... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a solution of 1,10-phenanthroline (50 mg, 0.20 mmol) in 5 ml CHCl3, 2-mercaptoaniline (0.60 µL, 0.40 mmol) was added followed by the addition of p-toluene sulfonic acid mono hydrate (76 mg, 0.40 mmol) in a Pyrex tube under argon. The tube was placed in a CEM microwave. The reaction conditions were set up as follows: power: 300 W, ramp time: 20 min, hold time: 20 min, and temperature: 373 K. When the reaction vessel was opened, a yellow precipitate was observed, which was filtered off and washed with cold CHCl3 and dried under vacuum. [y: 30 mg, 40%]. IR: ν= 1597 cm-1 (C=N), 1550 cm-1 (C=C). 1H-NMR([D3],CDCl3, 300 MHz): δ=8.74 (d, 4J= 9.0 Hz,, 8-H, 3-H), 8.41 (d, 3J=9.0 Hz,2H, H-4, H-7), 7.88 (s, 2H, H-5, and H-6), 8.169 (t, 4H, 2 J= 8.1 Hz, 1J=8.7 Hz,H-16, H-16', H-13, H-13'), 7.53 (m, 4H, H-14, H-14', H-15, H-15').13 C: NMR([D3], CDCl3, 75.5 MHz): δ= 155 (C-2, C-9), δ= 146 (C-11,C-12), δ=137.48 (C-3, C-8). δ=127.591 (C-4, C-7,), δ=126.60 (C-5, C-6), δ= 172 (C-13, C-13'), δ= 152 (C-14, C-14'), δ= 130.26 (C-15, C-15'), δ=137.0 (C-19, C-19') δ=126.18 (C-19, C-19'). δ=124.04 (C-18, C-18'). δ=122.54 (C-17, C-17'). δ=120.51 (C-16, C-16').
Yellow needles of (I) were grown from CH2Cl2/hexane at 253 K.
The H atoms were located in difference maps and their positions and Uiso values were freely refined.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 2005); software used to prepare material for publication: XCIF (Bruker, 2005).
![]() | Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids for the non-hydrogen atoms. |
![]() | Fig. 2. The formation of the title compound. |
C26H14N4S2·2CH2Cl2 | Z = 2 |
Mr = 616.38 | F(000) = 628 |
Triclinic, P1 | Dx = 1.522 Mg m−3 |
Hall symbol: -P 1 | Melting point > 573 K |
a = 8.0969 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 12.3990 (2) Å | Cell parameters from 5710 reflections |
c = 14.6006 (3) Å | θ = 3–65° |
α = 108.234 (1)° | µ = 5.67 mm−1 |
β = 102.181 (1)° | T = 100 K |
γ = 94.335 (1)° | Needle, yellow |
V = 1344.93 (5) Å3 | 0.75 × 0.07 × 0.05 mm |
Bruker APEXII CCD diffractometer | 4352 independent reflections |
Radiation source: fine-focus sealed tube | 3831 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 66.5°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −9→9 |
Tmin = 0.101, Tmax = 0.765 | k = −14→13 |
10764 measured reflections | l = 0→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.079 | All H-atom parameters refined |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.6095P] where P = (Fo2 + 2Fc2)/3 |
4352 reflections | (Δ/σ)max = 0.001 |
415 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C26H14N4S2·2CH2Cl2 | γ = 94.335 (1)° |
Mr = 616.38 | V = 1344.93 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.0969 (2) Å | Cu Kα radiation |
b = 12.3990 (2) Å | µ = 5.67 mm−1 |
c = 14.6006 (3) Å | T = 100 K |
α = 108.234 (1)° | 0.75 × 0.07 × 0.05 mm |
β = 102.181 (1)° |
Bruker APEXII CCD diffractometer | 4352 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3831 reflections with I > 2σ(I) |
Tmin = 0.101, Tmax = 0.765 | Rint = 0.021 |
10764 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.079 | All H-atom parameters refined |
S = 1.00 | Δρmax = 0.37 e Å−3 |
4352 reflections | Δρmin = −0.38 e Å−3 |
415 parameters |
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 | −0.16197 (6) | 0.64055 (4) | 0.22928 (3) | 0.02003 (12) | |
S2 | 0.22351 (6) | 0.40021 (4) | 0.33879 (3) | 0.01732 (12) | |
N1 | −0.02010 (19) | 0.73385 (13) | 0.44545 (11) | 0.0161 (3) | |
N2 | 0.17914 (18) | 0.58715 (12) | 0.50867 (11) | 0.0155 (3) | |
N3 | −0.2641 (2) | 0.84086 (13) | 0.26682 (12) | 0.0211 (4) | |
N4 | 0.39069 (19) | 0.33830 (12) | 0.48236 (11) | 0.0167 (3) | |
C1 | −0.1189 (2) | 0.80420 (15) | 0.41677 (14) | 0.0172 (4) | |
C2 | −0.1611 (2) | 0.90203 (16) | 0.48337 (14) | 0.0195 (4) | |
C3 | −0.0951 (2) | 0.92663 (16) | 0.58255 (14) | 0.0195 (4) | |
C4 | 0.0093 (2) | 0.85441 (15) | 0.61687 (13) | 0.0164 (4) | |
C5 | 0.0753 (2) | 0.87447 (16) | 0.72043 (14) | 0.0186 (4) | |
C6 | 0.1658 (2) | 0.79970 (16) | 0.75169 (14) | 0.0196 (4) | |
C7 | 0.2011 (2) | 0.69974 (15) | 0.68113 (13) | 0.0167 (4) | |
C8 | 0.2901 (2) | 0.61883 (16) | 0.71135 (14) | 0.0188 (4) | |
C9 | 0.3234 (2) | 0.52576 (16) | 0.64199 (14) | 0.0180 (4) | |
C10 | 0.2672 (2) | 0.51431 (15) | 0.54114 (14) | 0.0160 (4) | |
C11 | 0.0425 (2) | 0.75722 (15) | 0.54414 (13) | 0.0156 (4) | |
C12 | 0.1452 (2) | 0.67863 (15) | 0.57772 (13) | 0.0159 (4) | |
C13 | −0.1855 (2) | 0.77490 (15) | 0.30927 (14) | 0.0174 (4) | |
C14 | −0.2697 (2) | 0.67676 (16) | 0.12950 (14) | 0.0198 (4) | |
C15 | −0.3127 (2) | 0.78754 (16) | 0.16477 (14) | 0.0202 (4) | |
C16 | −0.3991 (3) | 0.83493 (19) | 0.09613 (15) | 0.0274 (5) | |
C17 | −0.4411 (3) | 0.77107 (19) | −0.00363 (16) | 0.0295 (5) | |
C18 | −0.3985 (3) | 0.66055 (19) | −0.03754 (16) | 0.0280 (5) | |
C19 | −0.3121 (3) | 0.61241 (18) | 0.02860 (15) | 0.0247 (4) | |
C20 | 0.3034 (2) | 0.41652 (15) | 0.46417 (13) | 0.0154 (4) | |
C21 | 0.3131 (2) | 0.27520 (15) | 0.30739 (14) | 0.0177 (4) | |
C22 | 0.3991 (2) | 0.25688 (15) | 0.39417 (14) | 0.0171 (4) | |
C23 | 0.4800 (2) | 0.15927 (16) | 0.38635 (15) | 0.0196 (4) | |
C24 | 0.4739 (2) | 0.08355 (16) | 0.29330 (15) | 0.0221 (4) | |
C25 | 0.3865 (3) | 0.10262 (17) | 0.20755 (15) | 0.0245 (4) | |
C26 | 0.3058 (2) | 0.19776 (17) | 0.21311 (15) | 0.0219 (4) | |
H2 | −0.233 (3) | 0.9445 (19) | 0.4549 (16) | 0.028 (6)* | |
H3 | −0.118 (2) | 0.9906 (18) | 0.6279 (15) | 0.017 (5)* | |
H5 | 0.054 (2) | 0.9395 (18) | 0.7645 (15) | 0.016 (5)* | |
H6 | 0.207 (2) | 0.8083 (16) | 0.8204 (15) | 0.015 (5)* | |
H8 | 0.328 (2) | 0.6297 (17) | 0.7835 (16) | 0.021 (5)* | |
H9 | 0.380 (3) | 0.4734 (18) | 0.6609 (15) | 0.022 (5)* | |
H16 | −0.425 (3) | 0.909 (2) | 0.1181 (16) | 0.029 (6)* | |
H17 | −0.504 (3) | 0.803 (2) | −0.0520 (17) | 0.034 (6)* | |
H18 | −0.429 (2) | 0.6211 (17) | −0.1043 (16) | 0.019 (5)* | |
H19 | −0.286 (3) | 0.535 (2) | 0.0041 (16) | 0.029 (6)* | |
H23 | 0.535 (3) | 0.1458 (18) | 0.4413 (16) | 0.021 (5)* | |
H24 | 0.528 (3) | 0.0190 (19) | 0.2872 (15) | 0.023 (5)* | |
H25 | 0.381 (3) | 0.0496 (19) | 0.1426 (16) | 0.025 (6)* | |
H26 | 0.245 (3) | 0.2090 (17) | 0.1567 (16) | 0.021 (5)* | |
Cl1S | 0.32173 (7) | 0.83312 (4) | 0.34294 (4) | 0.03355 (14) | |
Cl2S | 0.32540 (7) | 0.60371 (4) | 0.20953 (4) | 0.03418 (14) | |
C1S | 0.3093 (3) | 0.68551 (17) | 0.33012 (15) | 0.0217 (4) | |
H1SA | 0.201 (3) | 0.6616 (17) | 0.3398 (14) | 0.020 (5)* | |
H1SB | 0.403 (3) | 0.6741 (18) | 0.3742 (16) | 0.026 (6)* | |
Cl3S | 0.07322 (8) | 0.63525 (5) | 0.93119 (5) | 0.04547 (17) | |
Cl4S | 0.05564 (10) | 0.87470 (6) | 1.03272 (6) | 0.0674 (2) | |
C2S | 0.1165 (3) | 0.7470 (2) | 1.04721 (19) | 0.0406 (6) | |
H2SA | 0.241 (4) | 0.763 (2) | 1.0784 (19) | 0.049 (7)* | |
H2SB | 0.047 (3) | 0.726 (2) | 1.087 (2) | 0.049 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0242 (3) | 0.0178 (2) | 0.0193 (2) | 0.00770 (18) | 0.00485 (18) | 0.00731 (19) |
S2 | 0.0174 (2) | 0.0169 (2) | 0.0178 (2) | 0.00438 (17) | 0.00378 (17) | 0.00611 (18) |
N1 | 0.0145 (8) | 0.0172 (8) | 0.0189 (8) | 0.0021 (6) | 0.0067 (6) | 0.0076 (6) |
N2 | 0.0128 (8) | 0.0152 (8) | 0.0189 (8) | 0.0011 (6) | 0.0053 (6) | 0.0058 (6) |
N3 | 0.0232 (9) | 0.0223 (9) | 0.0222 (9) | 0.0082 (7) | 0.0080 (7) | 0.0109 (7) |
N4 | 0.0146 (8) | 0.0159 (8) | 0.0204 (8) | 0.0020 (6) | 0.0054 (6) | 0.0066 (6) |
C1 | 0.0142 (9) | 0.0175 (9) | 0.0226 (10) | 0.0019 (7) | 0.0076 (7) | 0.0085 (8) |
C2 | 0.0198 (10) | 0.0174 (9) | 0.0251 (10) | 0.0062 (8) | 0.0087 (8) | 0.0097 (8) |
C3 | 0.0205 (10) | 0.0154 (10) | 0.0241 (10) | 0.0028 (8) | 0.0100 (8) | 0.0057 (8) |
C4 | 0.0136 (9) | 0.0153 (9) | 0.0210 (10) | 0.0000 (7) | 0.0073 (7) | 0.0055 (7) |
C5 | 0.0174 (10) | 0.0163 (10) | 0.0206 (10) | 0.0009 (7) | 0.0079 (7) | 0.0025 (8) |
C6 | 0.0180 (10) | 0.0232 (10) | 0.0168 (10) | 0.0010 (8) | 0.0053 (7) | 0.0054 (8) |
C7 | 0.0124 (9) | 0.0185 (9) | 0.0185 (9) | −0.0010 (7) | 0.0041 (7) | 0.0059 (8) |
C8 | 0.0144 (9) | 0.0225 (10) | 0.0203 (10) | 0.0009 (7) | 0.0045 (7) | 0.0086 (8) |
C9 | 0.0149 (10) | 0.0186 (10) | 0.0224 (10) | 0.0038 (8) | 0.0040 (7) | 0.0098 (8) |
C10 | 0.0104 (9) | 0.0148 (9) | 0.0233 (10) | 0.0002 (7) | 0.0054 (7) | 0.0069 (8) |
C11 | 0.0121 (9) | 0.0162 (9) | 0.0201 (10) | −0.0005 (7) | 0.0060 (7) | 0.0076 (7) |
C12 | 0.0119 (9) | 0.0155 (9) | 0.0209 (10) | −0.0006 (7) | 0.0063 (7) | 0.0062 (8) |
C13 | 0.0161 (10) | 0.0169 (9) | 0.0222 (10) | 0.0032 (7) | 0.0093 (7) | 0.0078 (8) |
C14 | 0.0163 (10) | 0.0237 (10) | 0.0228 (10) | 0.0051 (8) | 0.0065 (7) | 0.0110 (8) |
C15 | 0.0203 (10) | 0.0228 (10) | 0.0206 (10) | 0.0065 (8) | 0.0077 (7) | 0.0089 (8) |
C16 | 0.0330 (12) | 0.0290 (12) | 0.0264 (11) | 0.0177 (9) | 0.0105 (9) | 0.0128 (9) |
C17 | 0.0310 (12) | 0.0381 (13) | 0.0238 (11) | 0.0151 (10) | 0.0061 (9) | 0.0145 (10) |
C18 | 0.0301 (12) | 0.0337 (12) | 0.0187 (11) | 0.0105 (9) | 0.0040 (8) | 0.0069 (9) |
C19 | 0.0260 (11) | 0.0233 (11) | 0.0239 (11) | 0.0069 (8) | 0.0048 (8) | 0.0068 (9) |
C20 | 0.0109 (9) | 0.0163 (9) | 0.0199 (9) | −0.0003 (7) | 0.0042 (7) | 0.0077 (7) |
C21 | 0.0136 (9) | 0.0165 (9) | 0.0235 (10) | 0.0017 (7) | 0.0053 (7) | 0.0072 (8) |
C22 | 0.0141 (9) | 0.0163 (9) | 0.0209 (10) | −0.0011 (7) | 0.0057 (7) | 0.0062 (8) |
C23 | 0.0174 (10) | 0.0185 (10) | 0.0271 (11) | 0.0030 (7) | 0.0080 (8) | 0.0116 (8) |
C24 | 0.0206 (10) | 0.0155 (10) | 0.0323 (12) | 0.0028 (8) | 0.0115 (8) | 0.0077 (8) |
C25 | 0.0237 (11) | 0.0199 (10) | 0.0254 (11) | 0.0005 (8) | 0.0086 (8) | 0.0005 (9) |
C26 | 0.0182 (10) | 0.0241 (10) | 0.0201 (10) | 0.0017 (8) | 0.0027 (8) | 0.0045 (8) |
Cl1S | 0.0412 (3) | 0.0209 (3) | 0.0436 (3) | 0.0111 (2) | 0.0151 (2) | 0.0133 (2) |
Cl2S | 0.0537 (4) | 0.0306 (3) | 0.0227 (3) | 0.0168 (2) | 0.0146 (2) | 0.0094 (2) |
C1S | 0.0249 (11) | 0.0205 (10) | 0.0228 (11) | 0.0081 (8) | 0.0076 (8) | 0.0095 (8) |
Cl3S | 0.0506 (4) | 0.0385 (3) | 0.0509 (4) | 0.0138 (3) | 0.0195 (3) | 0.0139 (3) |
Cl4S | 0.0650 (5) | 0.0360 (4) | 0.0686 (5) | 0.0069 (3) | −0.0205 (4) | −0.0029 (3) |
C2S | 0.0348 (14) | 0.0513 (15) | 0.0376 (14) | 0.0033 (11) | 0.0082 (11) | 0.0187 (12) |
S1—C14 | 1.7370 (19) | C10—C20 | 1.469 (2) |
S1—C13 | 1.7607 (18) | C11—C12 | 1.460 (2) |
S2—C21 | 1.7334 (18) | C14—C19 | 1.391 (3) |
S2—C20 | 1.7491 (18) | C14—C15 | 1.407 (3) |
N1—C1 | 1.330 (2) | C15—C16 | 1.405 (3) |
N1—C11 | 1.351 (2) | C16—C17 | 1.376 (3) |
N2—C10 | 1.331 (2) | C16—H16 | 0.94 (2) |
N2—C12 | 1.352 (2) | C17—C18 | 1.400 (3) |
N3—C13 | 1.299 (2) | C17—H17 | 0.98 (2) |
N3—C15 | 1.382 (2) | C18—C19 | 1.385 (3) |
N4—C20 | 1.303 (2) | C18—H18 | 0.91 (2) |
N4—C22 | 1.384 (2) | C19—H19 | 0.97 (2) |
C1—C2 | 1.414 (3) | C21—C26 | 1.397 (3) |
C1—C13 | 1.464 (3) | C21—C22 | 1.405 (3) |
C2—C3 | 1.359 (3) | C22—C23 | 1.404 (3) |
C2—H2 | 0.93 (2) | C23—C24 | 1.377 (3) |
C3—C4 | 1.408 (3) | C23—H23 | 0.90 (2) |
C3—H3 | 0.92 (2) | C24—C25 | 1.400 (3) |
C4—C11 | 1.422 (3) | C24—H24 | 0.93 (2) |
C4—C5 | 1.427 (3) | C25—C26 | 1.380 (3) |
C5—C6 | 1.353 (3) | C25—H25 | 0.96 (2) |
C5—H5 | 0.92 (2) | C26—H26 | 0.92 (2) |
C6—C7 | 1.435 (3) | Cl1S—C1S | 1.7733 (19) |
C6—H6 | 0.96 (2) | Cl2S—C1S | 1.773 (2) |
C7—C8 | 1.405 (3) | C1S—H1SA | 0.95 (2) |
C7—C12 | 1.414 (3) | C1S—H1SB | 0.94 (2) |
C8—C9 | 1.364 (3) | Cl3S—C2S | 1.766 (3) |
C8—H8 | 0.99 (2) | Cl4S—C2S | 1.754 (3) |
C9—C10 | 1.404 (3) | C2S—H2SA | 0.99 (3) |
C9—H9 | 0.90 (2) | C2S—H2SB | 0.97 (3) |
C14—S1—C13 | 88.49 (9) | N3—C15—C16 | 125.46 (18) |
C21—S2—C20 | 88.48 (9) | N3—C15—C14 | 115.44 (17) |
C1—N1—C11 | 117.85 (15) | C16—C15—C14 | 119.10 (18) |
C10—N2—C12 | 117.47 (15) | C17—C16—C15 | 119.06 (19) |
C13—N3—C15 | 110.46 (16) | C17—C16—H16 | 120.7 (14) |
C20—N4—C22 | 110.30 (15) | C15—C16—H16 | 120.3 (14) |
N1—C1—C2 | 123.86 (17) | C16—C17—C18 | 121.17 (19) |
N1—C1—C13 | 116.02 (16) | C16—C17—H17 | 119.5 (13) |
C2—C1—C13 | 120.12 (16) | C18—C17—H17 | 119.3 (13) |
C3—C2—C1 | 118.15 (18) | C19—C18—C17 | 120.83 (19) |
C3—C2—H2 | 125.4 (14) | C19—C18—H18 | 120.8 (13) |
C1—C2—H2 | 116.4 (14) | C17—C18—H18 | 118.4 (13) |
C2—C3—C4 | 120.23 (18) | C18—C19—C14 | 118.09 (19) |
C2—C3—H3 | 120.3 (12) | C18—C19—H19 | 119.8 (13) |
C4—C3—H3 | 119.5 (12) | C14—C19—H19 | 122.1 (13) |
C3—C4—C11 | 117.41 (17) | N4—C20—C10 | 124.42 (16) |
C3—C4—C5 | 122.00 (17) | N4—C20—S2 | 116.40 (14) |
C11—C4—C5 | 120.56 (17) | C10—C20—S2 | 119.17 (13) |
C6—C5—C4 | 120.92 (17) | C26—C21—C22 | 121.22 (17) |
C6—C5—H5 | 121.6 (12) | C26—C21—S2 | 128.96 (15) |
C4—C5—H5 | 117.4 (12) | C22—C21—S2 | 109.82 (14) |
C5—C6—C7 | 120.55 (17) | N4—C22—C23 | 125.39 (17) |
C5—C6—H6 | 123.3 (12) | N4—C22—C21 | 114.98 (16) |
C7—C6—H6 | 116.1 (12) | C23—C22—C21 | 119.60 (17) |
C8—C7—C12 | 117.46 (16) | C24—C23—C22 | 119.06 (19) |
C8—C7—C6 | 121.80 (17) | C24—C23—H23 | 120.1 (13) |
C12—C7—C6 | 120.73 (16) | C22—C23—H23 | 120.9 (13) |
C9—C8—C7 | 120.03 (17) | C23—C24—C25 | 120.61 (18) |
C9—C8—H8 | 120.5 (12) | C23—C24—H24 | 119.8 (13) |
C7—C8—H8 | 119.5 (12) | C25—C24—H24 | 119.6 (13) |
C8—C9—C10 | 118.20 (17) | C26—C25—C24 | 121.51 (19) |
C8—C9—H9 | 120.5 (13) | C26—C25—H25 | 117.7 (13) |
C10—C9—H9 | 121.3 (13) | C24—C25—H25 | 120.8 (13) |
N2—C10—C9 | 124.03 (17) | C25—C26—C21 | 117.99 (19) |
N2—C10—C20 | 116.04 (16) | C25—C26—H26 | 121.5 (13) |
C9—C10—C20 | 119.93 (16) | C21—C26—H26 | 120.4 (13) |
N1—C11—C4 | 122.47 (16) | Cl2S—C1S—Cl1S | 110.15 (11) |
N1—C11—C12 | 118.95 (16) | Cl2S—C1S—H1SA | 109.8 (12) |
C4—C11—C12 | 118.57 (16) | Cl1S—C1S—H1SA | 107.6 (12) |
N2—C12—C7 | 122.76 (16) | Cl2S—C1S—H1SB | 105.3 (13) |
N2—C12—C11 | 118.65 (16) | Cl1S—C1S—H1SB | 110.1 (13) |
C7—C12—C11 | 118.56 (16) | H1SA—C1S—H1SB | 113.8 (18) |
N3—C13—C1 | 124.79 (16) | Cl4S—C2S—Cl3S | 111.12 (14) |
N3—C13—S1 | 116.14 (14) | Cl4S—C2S—H2SA | 106.9 (15) |
C1—C13—S1 | 119.06 (13) | Cl3S—C2S—H2SA | 109.9 (15) |
C19—C14—C15 | 121.75 (18) | Cl4S—C2S—H2SB | 106.1 (16) |
C19—C14—S1 | 128.78 (15) | Cl3S—C2S—H2SB | 108.2 (16) |
C15—C14—S1 | 109.46 (14) | H2SA—C2S—H2SB | 115 (2) |
C11—N1—C1—C2 | 0.4 (3) | C14—S1—C13—N3 | −0.46 (15) |
C11—N1—C1—C13 | −179.31 (15) | C14—S1—C13—C1 | 178.90 (14) |
N1—C1—C2—C3 | 0.9 (3) | C13—S1—C14—C19 | −179.45 (19) |
C13—C1—C2—C3 | −179.40 (16) | C13—S1—C14—C15 | 0.63 (14) |
C1—C2—C3—C4 | −1.3 (3) | C13—N3—C15—C16 | −179.48 (19) |
C2—C3—C4—C11 | 0.5 (3) | C13—N3—C15—C14 | 0.4 (2) |
C2—C3—C4—C5 | −177.33 (17) | C19—C14—C15—N3 | 179.34 (17) |
C3—C4—C5—C6 | 175.55 (18) | S1—C14—C15—N3 | −0.7 (2) |
C11—C4—C5—C6 | −2.2 (3) | C19—C14—C15—C16 | −0.8 (3) |
C4—C5—C6—C7 | 1.5 (3) | S1—C14—C15—C16 | 179.16 (15) |
C5—C6—C7—C8 | −177.99 (17) | N3—C15—C16—C17 | −179.27 (19) |
C5—C6—C7—C12 | 1.3 (3) | C14—C15—C16—C17 | 0.8 (3) |
C12—C7—C8—C9 | 1.7 (3) | C15—C16—C17—C18 | −0.4 (3) |
C6—C7—C8—C9 | −179.01 (17) | C16—C17—C18—C19 | −0.2 (3) |
C7—C8—C9—C10 | 0.3 (3) | C17—C18—C19—C14 | 0.3 (3) |
C12—N2—C10—C9 | 1.2 (2) | C15—C14—C19—C18 | 0.2 (3) |
C12—N2—C10—C20 | −179.38 (15) | S1—C14—C19—C18 | −179.70 (16) |
C8—C9—C10—N2 | −1.8 (3) | C22—N4—C20—C10 | 178.79 (16) |
C8—C9—C10—C20 | 178.81 (16) | C22—N4—C20—S2 | −0.35 (19) |
C1—N1—C11—C4 | −1.3 (2) | N2—C10—C20—N4 | 178.51 (16) |
C1—N1—C11—C12 | 177.38 (16) | C9—C10—C20—N4 | −2.1 (3) |
C3—C4—C11—N1 | 0.9 (3) | N2—C10—C20—S2 | −2.4 (2) |
C5—C4—C11—N1 | 178.72 (16) | C9—C10—C20—S2 | 177.03 (13) |
C3—C4—C11—C12 | −177.81 (16) | C21—S2—C20—N4 | 0.89 (14) |
C5—C4—C11—C12 | 0.0 (2) | C21—S2—C20—C10 | −178.30 (14) |
C10—N2—C12—C7 | 0.9 (2) | C20—S2—C21—C26 | 177.75 (18) |
C10—N2—C12—C11 | −177.37 (15) | C20—S2—C21—C22 | −1.12 (13) |
C8—C7—C12—N2 | −2.3 (3) | C20—N4—C22—C23 | −178.48 (17) |
C6—C7—C12—N2 | 178.33 (16) | C20—N4—C22—C21 | −0.6 (2) |
C8—C7—C12—C11 | 175.94 (16) | C26—C21—C22—N4 | −177.75 (16) |
C6—C7—C12—C11 | −3.4 (2) | S2—C21—C22—N4 | 1.22 (19) |
N1—C11—C12—N2 | 2.3 (2) | C26—C21—C22—C23 | 0.3 (3) |
C4—C11—C12—N2 | −178.98 (15) | S2—C21—C22—C23 | 179.26 (14) |
N1—C11—C12—C7 | −176.04 (15) | N4—C22—C23—C24 | 178.07 (17) |
C4—C11—C12—C7 | 2.7 (2) | C21—C22—C23—C24 | 0.3 (3) |
C15—N3—C13—C1 | −179.20 (16) | C22—C23—C24—C25 | −0.8 (3) |
C15—N3—C13—S1 | 0.1 (2) | C23—C24—C25—C26 | 0.8 (3) |
N1—C1—C13—N3 | −170.20 (17) | C24—C25—C26—C21 | −0.2 (3) |
C2—C1—C13—N3 | 10.1 (3) | C22—C21—C26—C25 | −0.3 (3) |
N1—C1—C13—S1 | 10.5 (2) | S2—C21—C26—C25 | −179.07 (15) |
C2—C1—C13—S1 | −169.22 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1S—H1SB···N4i | 0.94 (2) | 2.44 (2) | 3.360 (3) | 166.7 (19) |
C3—H3···Cl1Sii | 0.92 (2) | 2.82 (2) | 3.615 (2) | 145.6 (16) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C26H14N4S2·2CH2Cl2 |
Mr | 616.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 8.0969 (2), 12.3990 (2), 14.6006 (3) |
α, β, γ (°) | 108.234 (1), 102.181 (1), 94.335 (1) |
V (Å3) | 1344.93 (5) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 5.67 |
Crystal size (mm) | 0.75 × 0.07 × 0.05 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.101, 0.765 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10764, 4352, 3831 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.079, 1.00 |
No. of reflections | 4352 |
No. of parameters | 415 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.37, −0.38 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 2005), XCIF (Bruker, 2005).
D—H···A | D—H | H···A | D···A | D—H···A |
C1S—H1SB···N4i | 0.94 (2) | 2.44 (2) | 3.360 (3) | 166.7 (19) |
C3—H3···Cl1Sii | 0.92 (2) | 2.82 (2) | 3.615 (2) | 145.6 (16) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1. |
As part of our studies of the biological properties of Schiff bases, we attempted to synthesize Schiff bases from 1,10-phenanthroline. It has been found in the literature that Schiff bases formed from S-alkyl and S-aryl substituted amines contain both hard nitrogen and soft sulfur donor atoms. (e.g. Kerbs, 2003). Consequently, these compounds are capable of forming stable complexes with a wide variety of metal ions. These complexes have interesting physio-chemical properties and potential chemotherapeutic effets (e.g. Gude et al.2005). In this paper the synthesis and structure of the title compound, (I), are reported.
The main molecule is close to planar, with dihedral angles of 9.05 (5)° and 1.03 (7)° for the S1 and S2 benzothiazolyl moieties respectively, with respect to the phenanthroline core. There are two dichloromethane solvent molecules in the asymmetric unit (Fig. 1).
Weak intermolecular C—H···N and C—H···Cl interactions (Table 1) may help to stabilise the packing.