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Tuberculosis still remains a very important problem, especially its multidrug resistant varieties (MDR-TB). Among the potential tuberculostatics, there are two benzimidazole derivatives, namely 5,6-dimethyl-2-phenyl­ethyl­benzo[d]imidazole (1) and (E)-5,6-dimethyl-2-styryl-1H-benzo[d]imidazole (2) which showed significant tuberculostatic activities, better than those of Pyrazinamide and Isoniazyd. Also, the cytotoxicity of 1 appeared promising. The compounds were studied (with the use of X-ray diffraction) in the form of the hemihydrate of 1, C17H18N2·0.5H2O (1a), the methanol hemisolvate of 2, C17H16N2·0.5CH3OH (2a), and the acid oxalate salt of 2, namely (E)-5,6-dimethyl-2-styryl-1H-benzo[d]imidazolium hydrogen oxalate, C17H17N2+·C2HO4 (2b). All three structures reveal a similar extended conformation, despite the flexible linker between the two aromatic systems and the different types of strong inter­molecular hydrogen bonds. The mol­ecules of 2a are practically planar due to the double bond in the linker, which enables conjugation along the whole mol­ecule, while the mol­ecules of 1a exhibit the possibility of parallel orientations of their aromatic systems, despite the aliphatic (eth­yl) linker.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618014675/fp3059sup1.cif
Contains datablocks 1a, 2a, 2b, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014675/fp30591asup2.hkl
Contains datablock 1a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014675/fp30592asup3.hkl
Contains datablock 2a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014675/fp30592bsup4.hkl
Contains datablock 2b

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618014675/fp30591asup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618014675/fp30592asup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618014675/fp30592bsup7.cml
Supplementary material

CCDC references: 1873746; 1873745; 1873744

Computing details top

Data collection: APEX2 (Bruker, 2002) for (1a), (2b); CrysAlis PRO (Rigaku OD, 2015) for (2a). Cell refinement: SAINT-Plus (Bruker, 2003) for (1a), (2b); CrysAlis PRO (Rigaku OD 2015) for (2a). Data reduction: SAINT-Plus (Bruker, 2003) for (1a), (2b); CrysAlis PRO (Rigaku OD, 2015) for (2a). For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

5,6-Dimethyl-2-phenylethylbenzo[d]imidazole hemihydrate (1a) top
Crystal data top
2C17H18N2·H2OZ = 4
Mr = 518.68F(000) = 1112
Triclinic, P1Dx = 1.216 Mg m3
a = 8.1685 (1) ÅCu Kα radiation, λ = 1.54178 Å
b = 11.4832 (2) ÅCell parameters from 9960 reflections
c = 30.7638 (4) Åθ = 2.9–72.2°
α = 99.9705 (5)°µ = 0.58 mm1
β = 94.1047 (5)°T = 105 K
γ = 90.9084 (6)°Prism, colorless
V = 2833.62 (7) Å30.73 × 0.15 × 0.04 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
9970 reflections with I > 2σ(I)
ωscanRint = 0.021
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 72.2°, θmin = 2.9°
Tmin = 0.657, Tmax = 0.754h = 1010
42329 measured reflectionsk = 1413
11147 independent reflectionsl = 3737
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)] = 0.040 w = 1/[σ2(Fo2) + (0.0595P)2 + 0.9457P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.31 e Å3
11147 reflectionsΔρmin = 0.23 e Å3
801 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
206 restraintsExtinction coefficient: 0.00021 (8)
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)
C4A0.59607 (15)0.60871 (10)0.30518 (4)0.0233 (2)
C5A0.66727 (15)0.56393 (10)0.34128 (4)0.0243 (2)
H2A0.7220640.4909410.3368700.029*
C6A0.65701 (14)0.62740 (10)0.38370 (4)0.0225 (2)
C7A0.57551 (14)0.73692 (10)0.39024 (4)0.0237 (2)
C8A0.50568 (14)0.78218 (10)0.35440 (4)0.0248 (2)
H3A0.4514170.8554010.3585810.030*
C9A0.51749 (14)0.71714 (10)0.31216 (4)0.0228 (2)
C10A0.73291 (16)0.57993 (11)0.42299 (4)0.0285 (3)
H4A0.7803880.5030260.4128530.043*
H5A0.6483340.5706160.4432690.043*
H6A0.8193160.6353090.4383780.043*
C11A0.56800 (17)0.80601 (12)0.43655 (4)0.0320 (3)
H7A0.5086470.8789910.4352860.048*
H8A0.6797300.8257540.4498970.048*
H9A0.5107630.7580750.4544990.048*
C2A0.51233 (17)0.64394 (12)0.24119 (3)0.0319 (3)
C12A0.4866 (2)0.6463 (2)0.19180 (4)0.0284 (4)0.755 (3)
H10A0.5131490.7266670.1862740.034*0.755 (3)
H11A0.5612810.5904580.1755080.034*0.755 (3)
C13A0.3093 (2)0.61215 (18)0.17503 (5)0.0327 (5)0.755 (3)
H12A0.2865410.5287450.1775620.039*0.755 (3)
H13A0.2343040.6623500.1935730.039*0.755 (3)
C12B0.4388 (7)0.6059 (6)0.19354 (9)0.0283 (7)0.245 (3)
H10B0.5274380.5752940.1747330.034*0.245 (3)
H11B0.3579400.5403250.1927340.034*0.245 (3)
C13B0.3558 (7)0.7033 (5)0.17419 (17)0.0303 (13)0.245 (3)
H12B0.4326870.7726160.1792760.036*0.245 (3)
H13B0.2593650.7263180.1911400.036*0.245 (3)
C21A0.2776 (2)0.62720 (19)0.12740 (5)0.0288 (3)0.755 (3)
C22A0.2022 (2)0.72817 (18)0.11750 (6)0.0299 (3)0.755 (3)
H14A0.1708640.7869610.1408820.036*0.755 (3)
C23A0.1719 (2)0.74447 (18)0.07380 (6)0.0306 (3)0.755 (3)
H15A0.1196340.8137320.0676220.037*0.755 (3)
C24A0.2179 (3)0.6599 (2)0.03943 (7)0.0308 (3)0.755 (3)
H16A0.1982780.6710760.0096370.037*0.755 (3)
C25A0.2925 (3)0.5588 (2)0.04880 (8)0.0312 (3)0.755 (3)
H17A0.3228800.4998970.0253240.037*0.755 (3)
C26A0.3236 (2)0.54302 (18)0.09262 (6)0.0302 (3)0.755 (3)
H18A0.3766480.4739640.0987040.036*0.755 (3)
C21B0.2976 (6)0.6788 (5)0.12518 (16)0.0295 (3)0.245 (3)
C22B0.2014 (6)0.7581 (5)0.10680 (19)0.0297 (3)0.245 (3)
H14B0.1647120.8260860.1253470.036*0.245 (3)
C23B0.1574 (7)0.7403 (5)0.06180 (19)0.0303 (3)0.245 (3)
H15B0.0909130.7958570.0498050.036*0.245 (3)
C24B0.2098 (9)0.6423 (6)0.0343 (2)0.0308 (3)0.245 (3)
H16B0.1791550.6302380.0034230.037*0.245 (3)
C25B0.3072 (10)0.5612 (7)0.0518 (2)0.0308 (3)0.245 (3)
H17B0.3450100.4941980.0330020.037*0.245 (3)
C26B0.3493 (7)0.5788 (5)0.09717 (19)0.0302 (3)0.245 (3)
H18B0.4137270.5223220.1092770.036*0.245 (3)
N1A0.46489 (13)0.73709 (9)0.27047 (3)0.0270 (2)
H1A0.4109310.7984940.2641530.032*
N3A0.58962 (14)0.56385 (10)0.25984 (3)0.0317 (2)
C2C0.96487 (16)0.74385 (11)0.25997 (4)0.0261 (2)
C4C0.86837 (16)0.76411 (11)0.19478 (4)0.0270 (3)
C5C0.79895 (16)0.80490 (11)0.15758 (4)0.0278 (3)
H2C0.7690180.8851240.1594740.033*
C6C0.77440 (15)0.72644 (11)0.11785 (4)0.0260 (2)
C7C0.82171 (15)0.60712 (11)0.11522 (4)0.0256 (2)
C8C0.88769 (16)0.56602 (11)0.15230 (4)0.0274 (3)
H3C0.9174520.4858040.1505890.033*
C9C0.90928 (16)0.64543 (11)0.19221 (4)0.0268 (3)
C10C0.69862 (17)0.76852 (12)0.07737 (4)0.0322 (3)
H4C0.6769840.8530810.0847240.048*
H5C0.5952870.7243520.0672920.048*
H6C0.7743540.7554740.0538050.048*
C11C0.80435 (17)0.52485 (11)0.07124 (4)0.0299 (3)
H7C0.8336020.4448710.0754140.045*
H8C0.8776320.5523490.0510200.045*
H9C0.6905400.5237980.0586820.045*
C12C1.02378 (16)0.76714 (11)0.30790 (4)0.0262 (3)
H10C1.1445080.7597530.3106930.031*
H11C0.9745660.7067230.3227840.031*
C13C0.97966 (17)0.88962 (11)0.33099 (4)0.0300 (3)
H12C1.0193710.9494240.3142790.036*
H13C0.8586640.8941900.3306810.036*
C21C1.05232 (15)0.91888 (10)0.37826 (4)0.0234 (2)
C22C1.16767 (16)1.01084 (11)0.39105 (4)0.0274 (3)
H14C1.2018701.0550480.3697430.033*
C23C1.23371 (16)1.03907 (11)0.43456 (4)0.0302 (3)
H15C1.3128271.1019890.4428400.036*
C24C1.18415 (16)0.97550 (11)0.46579 (4)0.0290 (3)
H16C1.2286230.9949250.4956140.035*
C25C1.06938 (16)0.88331 (11)0.45350 (4)0.0273 (3)
H17C1.0350770.8396050.4749480.033*
C26C1.00448 (15)0.85474 (10)0.40993 (4)0.0255 (2)
H18C0.9267940.7908980.4016420.031*
N1C0.97087 (14)0.63525 (9)0.23443 (3)0.0275 (2)
H1C1.0070980.5705680.2430890.033*
N3C0.90546 (14)0.82464 (9)0.23780 (3)0.0279 (2)
C2D0.49420 (14)0.23549 (11)0.24663 (4)0.0235 (2)
C4D0.46929 (14)0.14007 (10)0.17952 (4)0.0229 (2)
C5D0.43928 (14)0.05703 (11)0.14070 (4)0.0246 (2)
H2D0.4064990.0219840.1419650.030*
C6D0.45806 (14)0.09163 (11)0.10028 (4)0.0243 (2)
C7D0.51105 (14)0.20893 (11)0.09836 (4)0.0239 (2)
C8D0.54272 (14)0.29125 (11)0.13702 (4)0.0240 (2)
H3D0.5798970.3694870.1360320.029*
C9D0.51846 (14)0.25591 (10)0.17724 (4)0.0224 (2)
C10D0.41905 (17)0.00517 (11)0.05780 (4)0.0301 (3)
H4D0.3865550.0717420.0646670.045*
H5D0.5163910.0036290.0407770.045*
H6D0.3288660.0347250.0403470.045*
C11D0.53000 (17)0.24411 (12)0.05394 (4)0.0302 (3)
H7D0.5656630.3274610.0582040.045*
H8D0.4244970.2328310.0362580.045*
H9D0.6121700.1948940.0384930.045*
C12D0.51007 (16)0.26862 (11)0.29596 (4)0.0268 (3)
H10D0.4508590.3426540.3045670.032*
H11D0.6274930.2850200.3058050.032*
C13D0.44403 (17)0.17471 (12)0.32031 (4)0.0313 (3)
H12D0.3233300.1805240.3206740.038*
H13D0.4680070.0952350.3041860.038*
C21D0.51945 (15)0.18896 (11)0.36735 (4)0.0255 (2)
C22D0.62855 (16)0.10674 (11)0.37960 (4)0.0287 (3)
H14D0.6548810.0409180.3582540.034*
C23D0.69978 (16)0.11930 (12)0.42263 (4)0.0307 (3)
H15D0.7743520.0623840.4304610.037*
C24D0.66208 (16)0.21478 (11)0.45410 (4)0.0287 (3)
H16D0.7093240.2230470.4836350.034*
C25D0.55515 (16)0.29791 (11)0.44215 (4)0.0297 (3)
H17D0.5297590.3639250.4635400.036*
C26D0.48440 (16)0.28561 (11)0.39902 (4)0.0285 (3)
H18D0.4116880.3435760.3911300.034*
N1D0.53320 (12)0.31482 (9)0.22067 (3)0.0236 (2)
H1D0.5623830.3896630.2297710.028*
N3D0.45531 (12)0.12880 (9)0.22368 (3)0.0247 (2)
C2E0.01801 (15)0.32299 (11)0.25458 (4)0.0261 (2)
C4E0.07942 (15)0.42229 (10)0.31725 (4)0.0250 (2)
C5E0.15287 (15)0.50499 (10)0.35227 (4)0.0267 (3)
H2E0.2039420.5753880.3467870.032*
C6E0.15002 (15)0.48266 (11)0.39511 (4)0.0259 (2)
C7E0.07614 (15)0.37656 (11)0.40346 (4)0.0253 (2)
C8E0.00561 (15)0.29325 (11)0.36867 (4)0.0256 (2)
H3E0.0433230.2218170.3738760.031*
C9E0.00891 (14)0.31774 (10)0.32600 (4)0.0239 (2)
C10E0.22806 (17)0.57177 (12)0.43314 (4)0.0323 (3)
H4E0.2676720.6411310.4219460.048*
H5E0.3205000.5360290.4475630.048*
H6E0.1466520.5959970.4545980.048*
C11E0.07493 (17)0.35318 (12)0.45020 (4)0.0328 (3)
H7E0.0254970.2746510.4498120.049*
H8E0.0107140.4132750.4675490.049*
H9E0.1877940.3564160.4635930.049*
C12E0.06336 (15)0.28177 (12)0.20638 (4)0.0284 (3)
H10E0.1133520.3473540.1935230.034*
H11E0.1460340.2161390.2026530.034*
C13E0.08680 (18)0.23956 (16)0.18151 (5)0.0433 (4)
H12E0.1717230.3039400.1868030.052*
H13E0.1330960.1714670.1935130.052*
C21E0.04696 (16)0.20325 (13)0.13222 (4)0.0324 (3)
C22E0.09371 (16)0.27505 (12)0.10324 (5)0.0336 (3)
H14E0.1516380.3475830.1145710.040*
C23E0.05756 (17)0.24310 (12)0.05788 (5)0.0348 (3)
H15E0.0911780.2935070.0385260.042*
C24E0.02694 (18)0.13849 (13)0.04090 (5)0.0363 (3)
H16E0.0520010.1165160.0098930.044*
C25E0.0749 (2)0.06588 (13)0.06932 (5)0.0420 (3)
H17E0.1333440.0063390.0578350.050*
C26E0.03802 (19)0.09792 (14)0.11466 (5)0.0404 (3)
H18E0.0713610.0471400.1339090.049*
N3E0.05974 (13)0.42424 (9)0.27185 (3)0.0282 (2)
N1E0.05056 (13)0.25536 (9)0.28517 (3)0.0257 (2)
H1E0.1000720.1851790.2800320.031*
O1W0.28493 (14)0.92370 (10)0.24159 (4)0.0466 (3)
H1W10.179 (2)0.9342 (16)0.2338 (6)0.050 (5)*
H1W20.333 (2)0.9882 (19)0.2357 (6)0.059 (6)*
O2W0.77247 (14)0.04454 (9)0.26045 (4)0.0429 (3)
H2W10.678 (3)0.0484 (18)0.2457 (7)0.058 (6)*
H2W20.816 (3)0.0278 (19)0.2532 (7)0.061 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C4A0.0272 (6)0.0230 (6)0.0186 (5)0.0013 (4)0.0014 (4)0.0003 (4)
C5A0.0279 (6)0.0207 (5)0.0235 (6)0.0032 (4)0.0001 (5)0.0021 (4)
C6A0.0231 (5)0.0232 (6)0.0206 (6)0.0035 (4)0.0004 (4)0.0035 (4)
C7A0.0235 (6)0.0238 (6)0.0218 (6)0.0021 (4)0.0019 (4)0.0011 (4)
C8A0.0261 (6)0.0199 (5)0.0269 (6)0.0015 (4)0.0012 (5)0.0002 (4)
C9A0.0243 (6)0.0225 (6)0.0219 (6)0.0004 (4)0.0005 (4)0.0054 (4)
C10A0.0315 (6)0.0310 (6)0.0228 (6)0.0013 (5)0.0017 (5)0.0062 (5)
C11A0.0339 (7)0.0344 (7)0.0237 (6)0.0018 (5)0.0009 (5)0.0052 (5)
C2A0.0370 (7)0.0395 (7)0.0193 (6)0.0102 (5)0.0028 (5)0.0038 (5)
C12A0.0288 (11)0.0400 (12)0.0187 (7)0.0024 (8)0.0055 (6)0.0107 (7)
C13A0.0312 (9)0.0474 (12)0.0203 (8)0.0088 (8)0.0012 (6)0.0104 (7)
C12B0.0300 (15)0.0397 (16)0.0185 (10)0.0003 (12)0.0078 (11)0.0118 (11)
C13B0.034 (3)0.032 (3)0.024 (3)0.003 (2)0.004 (2)0.000 (2)
C21A0.0308 (5)0.0348 (6)0.0208 (5)0.0043 (5)0.0012 (4)0.0065 (5)
C22A0.0325 (5)0.0357 (6)0.0214 (6)0.0034 (5)0.0001 (5)0.0058 (5)
C23A0.0344 (5)0.0351 (5)0.0223 (6)0.0038 (4)0.0010 (5)0.0067 (5)
C24A0.0355 (5)0.0355 (6)0.0212 (5)0.0043 (5)0.0020 (4)0.0069 (5)
C25A0.0348 (5)0.0360 (5)0.0218 (5)0.0031 (5)0.0026 (4)0.0047 (4)
C26A0.0327 (5)0.0350 (6)0.0222 (5)0.0029 (5)0.0025 (4)0.0057 (5)
C21B0.0321 (6)0.0349 (7)0.0212 (6)0.0031 (6)0.0015 (5)0.0058 (6)
C22B0.0326 (6)0.0350 (6)0.0215 (6)0.0034 (6)0.0008 (6)0.0064 (6)
C23B0.0341 (6)0.0354 (6)0.0212 (6)0.0040 (5)0.0015 (6)0.0063 (6)
C24B0.0350 (6)0.0355 (6)0.0215 (6)0.0039 (5)0.0018 (5)0.0059 (5)
C25B0.0343 (6)0.0355 (6)0.0219 (6)0.0033 (5)0.0024 (5)0.0053 (5)
C26B0.0328 (6)0.0352 (6)0.0218 (6)0.0032 (6)0.0025 (5)0.0054 (6)
N1A0.0322 (5)0.0284 (5)0.0216 (5)0.0063 (4)0.0006 (4)0.0074 (4)
N3A0.0399 (6)0.0353 (6)0.0181 (5)0.0106 (5)0.0009 (4)0.0001 (4)
C2C0.0336 (6)0.0227 (6)0.0210 (6)0.0031 (5)0.0007 (5)0.0022 (4)
C4C0.0362 (7)0.0222 (6)0.0214 (6)0.0029 (5)0.0016 (5)0.0022 (4)
C5C0.0352 (7)0.0226 (6)0.0256 (6)0.0030 (5)0.0020 (5)0.0059 (5)
C6C0.0285 (6)0.0280 (6)0.0222 (6)0.0004 (5)0.0008 (5)0.0074 (5)
C7C0.0288 (6)0.0268 (6)0.0203 (6)0.0010 (5)0.0002 (5)0.0021 (5)
C8C0.0369 (7)0.0218 (6)0.0223 (6)0.0037 (5)0.0008 (5)0.0021 (5)
C9C0.0361 (7)0.0237 (6)0.0204 (6)0.0040 (5)0.0026 (5)0.0049 (5)
C10C0.0380 (7)0.0339 (7)0.0251 (6)0.0005 (5)0.0048 (5)0.0091 (5)
C11C0.0370 (7)0.0309 (6)0.0201 (6)0.0012 (5)0.0006 (5)0.0012 (5)
C12C0.0341 (6)0.0242 (6)0.0196 (6)0.0042 (5)0.0019 (5)0.0027 (4)
C13C0.0407 (7)0.0273 (6)0.0209 (6)0.0089 (5)0.0025 (5)0.0021 (5)
C21C0.0283 (6)0.0216 (5)0.0198 (6)0.0066 (4)0.0015 (4)0.0014 (4)
C22C0.0336 (6)0.0226 (6)0.0272 (6)0.0020 (5)0.0048 (5)0.0070 (5)
C23C0.0324 (7)0.0231 (6)0.0328 (7)0.0027 (5)0.0021 (5)0.0009 (5)
C24C0.0366 (7)0.0265 (6)0.0213 (6)0.0048 (5)0.0036 (5)0.0012 (5)
C25C0.0354 (7)0.0266 (6)0.0205 (6)0.0029 (5)0.0051 (5)0.0048 (5)
C26C0.0279 (6)0.0232 (6)0.0244 (6)0.0014 (4)0.0012 (5)0.0017 (4)
N1C0.0425 (6)0.0198 (5)0.0193 (5)0.0065 (4)0.0032 (4)0.0027 (4)
N3C0.0386 (6)0.0233 (5)0.0206 (5)0.0047 (4)0.0030 (4)0.0024 (4)
C2D0.0229 (6)0.0286 (6)0.0205 (6)0.0062 (4)0.0022 (4)0.0074 (4)
C4D0.0224 (5)0.0265 (6)0.0216 (6)0.0041 (4)0.0013 (4)0.0086 (4)
C5D0.0262 (6)0.0237 (6)0.0247 (6)0.0016 (4)0.0002 (5)0.0071 (5)
C6D0.0237 (6)0.0264 (6)0.0230 (6)0.0034 (4)0.0002 (4)0.0052 (5)
C7D0.0231 (6)0.0282 (6)0.0217 (6)0.0039 (4)0.0022 (4)0.0075 (5)
C8D0.0254 (6)0.0246 (6)0.0235 (6)0.0019 (4)0.0023 (4)0.0075 (5)
C9D0.0209 (5)0.0253 (6)0.0211 (6)0.0038 (4)0.0007 (4)0.0047 (4)
C10D0.0375 (7)0.0286 (6)0.0237 (6)0.0006 (5)0.0025 (5)0.0045 (5)
C11D0.0386 (7)0.0306 (6)0.0224 (6)0.0002 (5)0.0045 (5)0.0071 (5)
C12D0.0314 (6)0.0294 (6)0.0205 (6)0.0050 (5)0.0031 (5)0.0059 (5)
C13D0.0335 (7)0.0396 (7)0.0216 (6)0.0048 (5)0.0007 (5)0.0089 (5)
C21D0.0270 (6)0.0295 (6)0.0212 (6)0.0032 (5)0.0038 (5)0.0076 (5)
C22D0.0349 (7)0.0277 (6)0.0245 (6)0.0032 (5)0.0090 (5)0.0044 (5)
C23D0.0319 (6)0.0333 (7)0.0303 (7)0.0072 (5)0.0049 (5)0.0133 (5)
C24D0.0312 (6)0.0337 (7)0.0220 (6)0.0038 (5)0.0007 (5)0.0087 (5)
C25D0.0379 (7)0.0259 (6)0.0245 (6)0.0004 (5)0.0047 (5)0.0014 (5)
C26D0.0315 (6)0.0285 (6)0.0272 (6)0.0055 (5)0.0030 (5)0.0086 (5)
N1D0.0273 (5)0.0240 (5)0.0198 (5)0.0033 (4)0.0021 (4)0.0046 (4)
N3D0.0270 (5)0.0280 (5)0.0206 (5)0.0039 (4)0.0010 (4)0.0081 (4)
C2E0.0270 (6)0.0272 (6)0.0244 (6)0.0076 (5)0.0002 (5)0.0055 (5)
C4E0.0273 (6)0.0237 (6)0.0249 (6)0.0063 (4)0.0005 (5)0.0069 (5)
C5E0.0283 (6)0.0208 (6)0.0311 (6)0.0020 (4)0.0011 (5)0.0063 (5)
C6E0.0252 (6)0.0232 (6)0.0278 (6)0.0042 (4)0.0009 (5)0.0012 (5)
C7E0.0264 (6)0.0258 (6)0.0236 (6)0.0049 (5)0.0020 (5)0.0031 (5)
C8E0.0284 (6)0.0221 (6)0.0263 (6)0.0019 (4)0.0028 (5)0.0042 (5)
C9E0.0257 (6)0.0216 (6)0.0235 (6)0.0051 (4)0.0002 (4)0.0013 (4)
C10E0.0356 (7)0.0279 (6)0.0307 (7)0.0002 (5)0.0027 (5)0.0002 (5)
C11E0.0391 (7)0.0341 (7)0.0247 (6)0.0013 (5)0.0024 (5)0.0042 (5)
C12E0.0280 (6)0.0343 (7)0.0229 (6)0.0069 (5)0.0010 (5)0.0053 (5)
C13E0.0287 (7)0.0689 (11)0.0289 (7)0.0127 (7)0.0004 (5)0.0004 (7)
C21E0.0261 (6)0.0424 (7)0.0268 (6)0.0099 (5)0.0018 (5)0.0001 (5)
C22E0.0304 (7)0.0311 (7)0.0363 (7)0.0047 (5)0.0009 (5)0.0025 (5)
C23E0.0381 (7)0.0342 (7)0.0334 (7)0.0093 (6)0.0057 (6)0.0077 (5)
C24E0.0398 (7)0.0395 (7)0.0267 (7)0.0097 (6)0.0000 (5)0.0025 (5)
C25E0.0475 (8)0.0332 (7)0.0413 (8)0.0030 (6)0.0033 (6)0.0043 (6)
C26E0.0451 (8)0.0409 (8)0.0371 (8)0.0017 (6)0.0079 (6)0.0100 (6)
N3E0.0329 (6)0.0277 (5)0.0248 (5)0.0052 (4)0.0012 (4)0.0078 (4)
N1E0.0299 (5)0.0228 (5)0.0231 (5)0.0024 (4)0.0009 (4)0.0019 (4)
O1W0.0380 (6)0.0361 (6)0.0721 (8)0.0011 (4)0.0015 (5)0.0293 (5)
O2W0.0428 (6)0.0222 (5)0.0561 (7)0.0084 (4)0.0212 (5)0.0049 (4)
Geometric parameters (Å, º) top
C4A—C5A1.3966 (16)C23C—H15C0.9500
C4A—N3A1.3976 (15)C24C—C25C1.3863 (18)
C4A—C9A1.4004 (16)C24C—H16C0.9500
C5A—C6A1.3891 (16)C25C—C26C1.3878 (17)
C5A—H2A0.9500C25C—H17C0.9500
C6A—C7A1.4225 (17)C26C—H18C0.9500
C6A—C10A1.5080 (16)N1C—H1C0.8800
C7A—C8A1.3888 (17)C2D—N3D1.3253 (16)
C7A—C11A1.5119 (16)C2D—N1D1.3594 (15)
C8A—C9A1.3928 (16)C2D—C12D1.4951 (16)
C8A—H3A0.9500C4D—C5D1.3972 (17)
C9A—N1A1.3813 (15)C4D—C9D1.3983 (16)
C10A—H4A0.9800C4D—N3D1.3992 (15)
C10A—H5A0.9800C5D—C6D1.3869 (16)
C10A—H6A0.9800C5D—H2D0.9500
C11A—H7A0.9800C6D—C7D1.4206 (17)
C11A—H8A0.9800C6D—C10D1.5089 (17)
C11A—H9A0.9800C7D—C8D1.3905 (17)
C2A—N3A1.3127 (16)C7D—C11D1.5081 (16)
C2A—N1A1.3548 (16)C8D—C9D1.3933 (16)
C2A—C12A1.5240 (9)C8D—H3D0.9500
C2A—C12B1.5310 (10)C9D—N1D1.3853 (15)
C12A—C13A1.524 (3)C10D—H4D0.9800
C12A—H10A0.9900C10D—H5D0.9800
C12A—H11A0.9900C10D—H6D0.9800
C13A—C21A1.510 (2)C11D—H7D0.9800
C13A—H12A0.9900C11D—H8D0.9800
C13A—H13A0.9900C11D—H9D0.9800
C12B—C13B1.503 (9)C12D—C13D1.5278 (17)
C12B—H10B0.9900C12D—H10D0.9900
C12B—H11B0.9900C12D—H11D0.9900
C13B—C21B1.524 (7)C13D—C21D1.5125 (16)
C13B—H12B0.9900C13D—H12D0.9900
C13B—H13B0.9900C13D—H13D0.9900
C21A—C26A1.390 (2)C21D—C22D1.3891 (18)
C21A—C22A1.391 (3)C21D—C26D1.3923 (17)
C22A—C23A1.394 (2)C22D—C23D1.3900 (18)
C22A—H14A0.9500C22D—H14D0.9500
C23A—C24A1.384 (3)C23D—C24D1.3856 (18)
C23A—H15A0.9500C23D—H15D0.9500
C24A—C25A1.384 (3)C24D—C25D1.3825 (18)
C24A—H16A0.9500C24D—H16D0.9500
C25A—C26A1.397 (3)C25D—C26D1.3919 (18)
C25A—H17A0.9500C25D—H17D0.9500
C26A—H18A0.9500C26D—H18D0.9500
C21B—C22B1.380 (6)N1D—H1D0.8800
C21B—C26B1.402 (6)C2E—N3E1.3236 (17)
C22B—C23B1.384 (6)C2E—N1E1.3572 (16)
C22B—H14B0.9500C2E—C12E1.4942 (17)
C23B—C24B1.380 (6)C4E—N3E1.3984 (15)
C23B—H15B0.9500C4E—C5E1.3991 (17)
C24B—C25B1.388 (7)C4E—C9E1.3992 (17)
C24B—H16B0.9500C5E—C6E1.3873 (18)
C25B—C26B1.391 (6)C5E—H2E0.9500
C25B—H17B0.9500C6E—C7E1.4219 (17)
C26B—H18B0.9500C6E—C10E1.5101 (17)
N1A—H1A0.8800C7E—C8E1.3899 (17)
C2C—N3C1.3220 (16)C7E—C11E1.5083 (17)
C2C—N1C1.3577 (15)C8E—C9E1.3914 (17)
C2C—C12C1.4950 (16)C8E—H3E0.9500
C4C—N3C1.3943 (15)C9E—N1E1.3845 (15)
C4C—C5C1.3968 (17)C10E—H4E0.9800
C4C—C9C1.3986 (17)C10E—H5E0.9800
C5C—C6C1.3871 (17)C10E—H6E0.9800
C5C—H2C0.9500C11E—H7E0.9800
C6C—C7C1.4198 (17)C11E—H8E0.9800
C6C—C10C1.5082 (16)C11E—H9E0.9800
C7C—C8C1.3861 (17)C12E—C13E1.5328 (18)
C7C—C11C1.5062 (16)C12E—H10E0.9900
C8C—C9C1.3950 (17)C12E—H11E0.9900
C8C—H3C0.9500C13E—C21E1.5117 (18)
C9C—N1C1.3837 (15)C13E—H12E0.9900
C10C—H4C0.9800C13E—H13E0.9900
C10C—H5C0.9800C21E—C22E1.383 (2)
C10C—H6C0.9800C21E—C26E1.389 (2)
C11C—H7C0.9800C22E—C23E1.3890 (19)
C11C—H8C0.9800C22E—H14E0.9500
C11C—H9C0.9800C23E—C24E1.377 (2)
C12C—C13C1.5229 (16)C23E—H15E0.9500
C12C—H10C0.9900C24E—C25E1.380 (2)
C12C—H11C0.9900C24E—H16E0.9500
C13C—C21C1.5102 (16)C25E—C26E1.389 (2)
C13C—H12C0.9900C25E—H17E0.9500
C13C—H13C0.9900C26E—H18E0.9500
C21C—C22C1.3890 (17)N1E—H1E0.8800
C21C—C26C1.3922 (17)O1W—H1W10.90 (2)
C22C—C23C1.3887 (18)O1W—H1W20.88 (2)
C22C—H14C0.9500O2W—H2W10.87 (2)
C23C—C24C1.3815 (19)O2W—H2W20.91 (2)
C5A—C4A—N3A130.71 (11)C24C—C23C—H15C120.1
C5A—C4A—C9A119.73 (11)C22C—C23C—H15C120.1
N3A—C4A—C9A109.55 (10)C23C—C24C—C25C119.85 (11)
C6A—C5A—C4A119.21 (11)C23C—C24C—H16C120.1
C6A—C5A—H2A120.4C25C—C24C—H16C120.1
C4A—C5A—H2A120.4C24C—C25C—C26C120.13 (11)
C5A—C6A—C7A120.34 (11)C24C—C25C—H17C119.9
C5A—C6A—C10A119.78 (11)C26C—C25C—H17C119.9
C7A—C6A—C10A119.88 (10)C25C—C26C—C21C120.53 (11)
C8A—C7A—C6A120.61 (11)C25C—C26C—H18C119.7
C8A—C7A—C11A119.66 (11)C21C—C26C—H18C119.7
C6A—C7A—C11A119.71 (11)C2C—N1C—C9C107.08 (10)
C7A—C8A—C9A118.09 (11)C2C—N1C—H1C126.5
C7A—C8A—H3A121.0C9C—N1C—H1C126.5
C9A—C8A—H3A121.0C2C—N3C—C4C104.90 (10)
N1A—C9A—C8A132.64 (11)N3D—C2D—N1D112.96 (10)
N1A—C9A—C4A105.34 (10)N3D—C2D—C12D126.01 (11)
C8A—C9A—C4A122.01 (11)N1D—C2D—C12D120.83 (11)
C6A—C10A—H4A109.5C5D—C4D—C9D119.95 (11)
C6A—C10A—H5A109.5C5D—C4D—N3D130.19 (11)
H4A—C10A—H5A109.5C9D—C4D—N3D109.84 (10)
C6A—C10A—H6A109.5C6D—C5D—C4D119.03 (11)
H4A—C10A—H6A109.5C6D—C5D—H2D120.5
H5A—C10A—H6A109.5C4D—C5D—H2D120.5
C7A—C11A—H7A109.5C5D—C6D—C7D120.57 (11)
C7A—C11A—H8A109.5C5D—C6D—C10D120.07 (11)
H7A—C11A—H8A109.5C7D—C6D—C10D119.35 (11)
C7A—C11A—H9A109.5C8D—C7D—C6D120.40 (11)
H7A—C11A—H9A109.5C8D—C7D—C11D120.19 (11)
H8A—C11A—H9A109.5C6D—C7D—C11D119.40 (11)
N3A—C2A—N1A113.71 (10)C7D—C8D—C9D118.23 (11)
N3A—C2A—C12A126.89 (13)C7D—C8D—H3D120.9
N1A—C2A—C12A119.15 (13)C9D—C8D—H3D120.9
N3A—C2A—C12B117.3 (3)N1D—C9D—C8D132.95 (11)
N1A—C2A—C12B125.7 (3)N1D—C9D—C4D105.27 (10)
C13A—C12A—C2A110.43 (14)C8D—C9D—C4D121.77 (11)
C13A—C12A—H10A109.6C6D—C10D—H4D109.5
C2A—C12A—H10A109.6C6D—C10D—H5D109.5
C13A—C12A—H11A109.6H4D—C10D—H5D109.5
C2A—C12A—H11A109.6C6D—C10D—H6D109.5
H10A—C12A—H11A108.1H4D—C10D—H6D109.5
C21A—C13A—C12A110.86 (13)H5D—C10D—H6D109.5
C21A—C13A—H12A109.5C7D—C11D—H7D109.5
C12A—C13A—H12A109.5C7D—C11D—H8D109.5
C21A—C13A—H13A109.5H7D—C11D—H8D109.5
C12A—C13A—H13A109.5C7D—C11D—H9D109.5
H12A—C13A—H13A108.1H7D—C11D—H9D109.5
C13B—C12B—C2A114.1 (4)H8D—C11D—H9D109.5
C13B—C12B—H10B108.7C2D—C12D—C13D114.51 (11)
C2A—C12B—H10B108.7C2D—C12D—H10D108.6
C13B—C12B—H11B108.7C13D—C12D—H10D108.6
C2A—C12B—H11B108.7C2D—C12D—H11D108.6
H10B—C12B—H11B107.6C13D—C12D—H11D108.6
C12B—C13B—C21B118.1 (4)H10D—C12D—H11D107.6
C12B—C13B—H12B107.8C21D—C13D—C12D111.82 (10)
C21B—C13B—H12B107.8C21D—C13D—H12D109.3
C12B—C13B—H13B107.8C12D—C13D—H12D109.3
C21B—C13B—H13B107.8C21D—C13D—H13D109.3
H12B—C13B—H13B107.1C12D—C13D—H13D109.3
C26A—C21A—C22A118.35 (15)H12D—C13D—H13D107.9
C26A—C21A—C13A121.79 (18)C22D—C21D—C26D118.51 (11)
C22A—C21A—C13A119.86 (17)C22D—C21D—C13D120.43 (11)
C21A—C22A—C23A121.05 (17)C26D—C21D—C13D121.05 (11)
C21A—C22A—H14A119.5C21D—C22D—C23D121.02 (12)
C23A—C22A—H14A119.5C21D—C22D—H14D119.5
C24A—C23A—C22A120.08 (18)C23D—C22D—H14D119.5
C24A—C23A—H15A120.0C24D—C23D—C22D120.04 (12)
C22A—C23A—H15A120.0C24D—C23D—H15D120.0
C25A—C24A—C23A119.46 (19)C22D—C23D—H15D120.0
C25A—C24A—H16A120.3C25D—C24D—C23D119.45 (12)
C23A—C24A—H16A120.3C25D—C24D—H16D120.3
C24A—C25A—C26A120.3 (2)C23D—C24D—H16D120.3
C24A—C25A—H17A119.8C24D—C25D—C26D120.50 (12)
C26A—C25A—H17A119.8C24D—C25D—H17D119.8
C21A—C26A—C25A120.72 (18)C26D—C25D—H17D119.8
C21A—C26A—H18A119.6C25D—C26D—C21D120.47 (12)
C25A—C26A—H18A119.6C25D—C26D—H18D119.8
C22B—C21B—C26B118.4 (4)C21D—C26D—H18D119.8
C22B—C21B—C13B120.9 (5)C2D—N1D—C9D107.25 (10)
C26B—C21B—C13B120.6 (5)C2D—N1D—H1D126.4
C21B—C22B—C23B121.1 (5)C9D—N1D—H1D126.4
C21B—C22B—H14B119.4C2D—N3D—C4D104.68 (10)
C23B—C22B—H14B119.4N3E—C2E—N1E113.26 (11)
C24B—C23B—C22B120.3 (5)N3E—C2E—C12E125.15 (11)
C24B—C23B—H15B119.8N1E—C2E—C12E121.57 (11)
C22B—C23B—H15B119.8N3E—C4E—C5E130.85 (11)
C23B—C24B—C25B119.8 (5)N3E—C4E—C9E109.68 (11)
C23B—C24B—H16B120.1C5E—C4E—C9E119.48 (11)
C25B—C24B—H16B120.1C6E—C5E—C4E119.01 (11)
C24B—C25B—C26B119.6 (5)C6E—C5E—H2E120.5
C24B—C25B—H17B120.2C4E—C5E—H2E120.5
C26B—C25B—H17B120.2C5E—C6E—C7E120.76 (11)
C25B—C26B—C21B120.7 (5)C5E—C6E—C10E119.39 (11)
C25B—C26B—H18B119.6C7E—C6E—C10E119.85 (11)
C21B—C26B—H18B119.6C8E—C7E—C6E120.37 (11)
C2A—N1A—C9A106.82 (10)C8E—C7E—C11E119.48 (11)
C2A—N1A—H1A126.6C6E—C7E—C11E120.15 (11)
C9A—N1A—H1A126.6C7E—C8E—C9E117.93 (11)
C2A—N3A—C4A104.56 (10)C7E—C8E—H3E121.0
N3C—C2C—N1C112.99 (11)C9E—C8E—H3E121.0
N3C—C2C—C12C124.76 (11)N1E—C9E—C8E132.12 (11)
N1C—C2C—C12C122.24 (11)N1E—C9E—C4E105.44 (10)
N3C—C4C—C5C129.84 (11)C8E—C9E—C4E122.43 (11)
N3C—C4C—C9C109.65 (10)C6E—C10E—H4E109.5
C5C—C4C—C9C120.50 (11)C6E—C10E—H5E109.5
C6C—C5C—C4C118.97 (11)H4E—C10E—H5E109.5
C6C—C5C—H2C120.5C6E—C10E—H6E109.5
C4C—C5C—H2C120.5H4E—C10E—H6E109.5
C5C—C6C—C7C120.08 (11)H5E—C10E—H6E109.5
C5C—C6C—C10C119.79 (11)C7E—C11E—H7E109.5
C7C—C6C—C10C120.13 (11)C7E—C11E—H8E109.5
C8C—C7C—C6C120.98 (11)H7E—C11E—H8E109.5
C8C—C7C—C11C119.47 (11)C7E—C11E—H9E109.5
C6C—C7C—C11C119.53 (11)H7E—C11E—H9E109.5
C7C—C8C—C9C118.31 (11)H8E—C11E—H9E109.5
C7C—C8C—H3C120.8C2E—C12E—C13E111.47 (10)
C9C—C8C—H3C120.8C2E—C12E—H10E109.3
N1C—C9C—C8C133.50 (11)C13E—C12E—H10E109.3
N1C—C9C—C4C105.38 (10)C2E—C12E—H11E109.3
C8C—C9C—C4C121.11 (11)C13E—C12E—H11E109.3
C6C—C10C—H4C109.5H10E—C12E—H11E108.0
C6C—C10C—H5C109.5C21E—C13E—C12E112.89 (11)
H4C—C10C—H5C109.5C21E—C13E—H12E109.0
C6C—C10C—H6C109.5C12E—C13E—H12E109.0
H4C—C10C—H6C109.5C21E—C13E—H13E109.0
H5C—C10C—H6C109.5C12E—C13E—H13E109.0
C7C—C11C—H7C109.5H12E—C13E—H13E107.8
C7C—C11C—H8C109.5C22E—C21E—C26E118.04 (13)
H7C—C11C—H8C109.5C22E—C21E—C13E120.57 (13)
C7C—C11C—H9C109.5C26E—C21E—C13E121.39 (14)
H7C—C11C—H9C109.5C21E—C22E—C23E121.25 (13)
H8C—C11C—H9C109.5C21E—C22E—H14E119.4
C2C—C12C—C13C112.26 (10)C23E—C22E—H14E119.4
C2C—C12C—H10C109.2C24E—C23E—C22E120.13 (13)
C13C—C12C—H10C109.2C24E—C23E—H15E119.9
C2C—C12C—H11C109.2C22E—C23E—H15E119.9
C13C—C12C—H11C109.2C23E—C24E—C25E119.42 (13)
H10C—C12C—H11C107.9C23E—C24E—H16E120.3
C21C—C13C—C12C112.82 (10)C25E—C24E—H16E120.3
C21C—C13C—H12C109.0C24E—C25E—C26E120.29 (14)
C12C—C13C—H12C109.0C24E—C25E—H17E119.9
C21C—C13C—H13C109.0C26E—C25E—H17E119.9
C12C—C13C—H13C109.0C21E—C26E—C25E120.87 (14)
H12C—C13C—H13C107.8C21E—C26E—H18E119.6
C22C—C21C—C26C118.66 (11)C25E—C26E—H18E119.6
C22C—C21C—C13C120.61 (11)C2E—N3E—C4E104.61 (10)
C26C—C21C—C13C120.73 (11)C2E—N1E—C9E106.99 (10)
C23C—C22C—C21C120.93 (11)C2E—N1E—H1E126.5
C23C—C22C—H14C119.5C9E—N1E—H1E126.5
C21C—C22C—H14C119.5H1W1—O1W—H1W2102.2 (17)
C24C—C23C—C22C119.89 (12)H2W1—O2W—H2W2111.0 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1W0.881.972.8486 (15)172
N1C—H1C···N3Ei0.882.072.9370 (14)169
N1D—H1D···N3A0.882.052.9201 (15)168
N1E—H1E···O2Wii0.881.892.7610 (15)170
O1W—H1W1···N3Cii0.90 (2)2.57 (2)3.2720 (16)135.9 (15)
O1W—H1W2···N3Diii0.88 (2)1.99 (2)2.8711 (15)176.1 (19)
O2W—H2W1···N3D0.87 (2)2.17 (2)2.9945 (14)157.2 (18)
O2W—H2W2···N3Civ0.91 (2)1.86 (2)2.7619 (14)179 (2)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x, y+1, z; (iv) x, y1, z.
5,6-Dimethyl-2-phenylethylbenzo[d]imidazole methanol hemisolvate (2a) top
Crystal data top
2C17H16N2·CH4OF(000) = 1128
Mr = 528.63Dx = 1.220 Mg m3
Monoclinic, CcCu Kα radiation, λ = 1.54184 Å
a = 13.095 (3) ÅCell parameters from 4004 reflections
b = 9.2984 (19) Åθ = 3.7–75.6°
c = 23.685 (5) ŵ = 0.58 mm1
β = 93.95 (3)°T = 293 K
V = 2877.1 (11) Å3Prism, yellow
Z = 40.43 × 0.28 × 0.22 mm
Data collection top
XtaLAB Synergy, Dualflex, Pilatus 300K
diffractometer
3033 reflections with I > 2σ(I)
ω scanRint = 0.022
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
θmax = 78.8°, θmin = 3.7°
Tmin = 0.653, Tmax = 1.000h = 1216
7321 measured reflectionsk = 1111
3571 independent reflectionsl = 2922
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055 w = 1/[σ2(Fo2) + (0.1084P)2 + 0.1424P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.156(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.21 e Å3
3571 reflectionsΔρmin = 0.25 e Å3
367 parametersAbsolute structure: Flack x determined using 591 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraintsAbsolute structure parameter: 0.1 (4)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C2A0.4774 (3)0.8916 (4)0.35430 (15)0.0697 (8)
C4A0.4418 (3)0.6881 (4)0.31217 (15)0.0638 (8)
C5A0.4328 (3)0.5671 (4)0.27716 (16)0.0701 (8)
H2A0.46580.56470.24360.084*
C6A0.3757 (3)0.4527 (4)0.29223 (16)0.0710 (9)
C7A0.3250 (3)0.4543 (4)0.34378 (17)0.0718 (9)
C8A0.3348 (3)0.5736 (4)0.37908 (17)0.0728 (9)
H3A0.30220.57630.41270.087*
C9A0.3940 (3)0.6889 (4)0.36319 (15)0.0657 (8)
C10A0.3658 (4)0.3215 (5)0.2552 (2)0.0939 (13)
H6A0.40710.33320.22360.141*
H4A0.29550.30920.24170.141*
H5A0.38830.23840.27660.141*
C11A0.2634 (3)0.3277 (5)0.3605 (2)0.0862 (11)
H9A0.22950.35070.39410.129*
H8A0.30780.24680.36790.129*
H7A0.21320.30460.33040.129*
C12A0.5165 (3)1.0326 (4)0.36531 (16)0.0725 (9)
H10A0.55891.07200.33950.087*
C13A0.4962 (3)1.1129 (4)0.41075 (16)0.0719 (9)
H11A0.45571.06940.43670.086*
C21A0.5296 (3)1.2589 (4)0.42421 (18)0.0800 (10)
C22A0.4931 (4)1.3237 (6)0.4707 (2)0.0979 (14)
H12A0.45121.27130.49330.118*
C23A0.5165 (7)1.4633 (8)0.4851 (3)0.129 (2)
H13A0.49061.50480.51690.155*
C24A0.5787 (7)1.5413 (7)0.4521 (4)0.141 (3)
H14A0.59451.63640.46120.169*
C25A0.6176 (6)1.4787 (7)0.4057 (4)0.132 (2)
H15A0.66051.53110.38370.159*
C26A0.5930 (5)1.3377 (5)0.3914 (2)0.1010 (14)
H16A0.61921.29590.35980.121*
N1A0.4184 (3)0.8186 (3)0.38904 (14)0.0737 (8)
H1A0.39960.84750.42120.088*
N3A0.4938 (2)0.8169 (3)0.30712 (13)0.0689 (7)
C2B0.4716 (3)1.0377 (4)0.65581 (15)0.0681 (8)
C4B0.5332 (3)0.8203 (4)0.64907 (15)0.0664 (8)
C5B0.5572 (3)0.6804 (4)0.63341 (17)0.0778 (10)
H2B0.52960.64210.59940.093*
C6B0.6214 (3)0.6006 (4)0.66836 (18)0.0752 (9)
C7B0.6662 (3)0.6593 (4)0.72012 (17)0.0705 (8)
C8B0.6425 (3)0.7977 (4)0.73512 (16)0.0699 (8)
H3B0.67150.83750.76850.084*
C9B0.5750 (3)0.8770 (4)0.70000 (15)0.0663 (8)
C10B0.6486 (4)0.4468 (5)0.6525 (2)0.0969 (14)
H4B0.62600.42910.61370.145*
H5B0.61560.38050.67650.145*
H6B0.72140.43390.65750.145*
C11B0.7362 (3)0.5690 (5)0.7580 (2)0.0873 (11)
H9B0.76220.62540.78980.131*
H8B0.79220.53560.73740.131*
H7B0.69910.48800.77120.131*
C12B0.4167 (3)1.1684 (4)0.64617 (17)0.0745 (9)
H10B0.42261.23900.67410.089*
C13B0.3572 (3)1.1956 (4)0.59948 (17)0.0744 (9)
H11B0.35411.12440.57180.089*
C21B0.2960 (3)1.3255 (5)0.58684 (18)0.0775 (10)
C22B0.2358 (4)1.3341 (6)0.5377 (2)0.0980 (14)
H12B0.23571.25680.51290.118*
C23B0.1755 (4)1.4500 (8)0.5230 (3)0.1119 (18)
H13B0.13621.45130.48870.134*
C24B0.1738 (6)1.5620 (9)0.5587 (3)0.131 (2)
H14B0.13201.64060.54960.157*
C25B0.2341 (6)1.5609 (7)0.6091 (3)0.128 (2)
H15B0.23411.63900.63370.153*
C26B0.2942 (4)1.4417 (5)0.6222 (2)0.0958 (14)
H16B0.33471.44040.65610.115*
N1B0.5347 (2)1.0147 (3)0.70379 (13)0.0698 (7)
H1B0.54701.07440.73110.084*
N3B0.4695 (3)0.9212 (3)0.62176 (13)0.0735 (8)
O1S0.3909 (3)0.8798 (5)0.50739 (13)0.1082 (11)
H1S0.41910.90630.53760.162*
C1S0.3080 (5)0.8202 (13)0.5161 (4)0.186 (5)
H4S0.26410.82140.48190.280*
H3S0.27550.87100.54530.280*
H2S0.32050.72260.52770.280*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C2A0.074 (2)0.077 (2)0.0562 (17)0.0041 (16)0.0068 (14)0.0104 (16)
C4A0.0671 (17)0.0656 (18)0.0576 (17)0.0040 (14)0.0046 (13)0.0073 (14)
C5A0.074 (2)0.075 (2)0.0596 (17)0.0024 (17)0.0021 (15)0.0009 (15)
C6A0.075 (2)0.0688 (19)0.068 (2)0.0030 (16)0.0067 (16)0.0011 (16)
C7A0.072 (2)0.0658 (19)0.075 (2)0.0025 (15)0.0112 (16)0.0092 (17)
C8A0.079 (2)0.074 (2)0.0643 (19)0.0026 (17)0.0033 (16)0.0051 (16)
C9A0.0750 (19)0.0639 (18)0.0572 (16)0.0023 (15)0.0030 (14)0.0040 (14)
C10A0.108 (3)0.074 (2)0.100 (3)0.005 (2)0.003 (3)0.011 (2)
C11A0.082 (3)0.078 (2)0.098 (3)0.0131 (19)0.000 (2)0.003 (2)
C12A0.081 (2)0.073 (2)0.0626 (19)0.0069 (17)0.0029 (16)0.0075 (16)
C13A0.077 (2)0.0715 (19)0.0655 (19)0.0021 (16)0.0086 (16)0.0105 (17)
C21A0.091 (2)0.071 (2)0.074 (2)0.0020 (18)0.0241 (19)0.0016 (18)
C22A0.118 (4)0.102 (3)0.070 (2)0.014 (3)0.018 (2)0.010 (2)
C23A0.159 (6)0.110 (4)0.110 (4)0.028 (4)0.041 (4)0.040 (4)
C24A0.165 (6)0.086 (3)0.160 (7)0.002 (4)0.072 (6)0.037 (4)
C25A0.163 (6)0.088 (3)0.141 (5)0.034 (4)0.022 (5)0.007 (4)
C26A0.121 (4)0.082 (3)0.100 (3)0.025 (3)0.002 (3)0.005 (2)
N1A0.088 (2)0.0744 (18)0.0584 (15)0.0080 (14)0.0048 (14)0.0021 (13)
N3A0.0741 (17)0.0728 (17)0.0587 (15)0.0056 (13)0.0033 (12)0.0073 (13)
C2B0.079 (2)0.071 (2)0.0546 (16)0.0029 (16)0.0021 (14)0.0060 (15)
C4B0.078 (2)0.0621 (17)0.0584 (17)0.0030 (15)0.0038 (15)0.0083 (14)
C5B0.095 (3)0.072 (2)0.065 (2)0.0040 (19)0.0008 (18)0.0132 (17)
C6B0.084 (2)0.067 (2)0.075 (2)0.0059 (17)0.0106 (17)0.0058 (17)
C7B0.071 (2)0.0686 (19)0.072 (2)0.0047 (15)0.0024 (15)0.0005 (16)
C8B0.073 (2)0.0701 (18)0.0653 (19)0.0013 (16)0.0032 (15)0.0037 (15)
C9B0.0752 (19)0.0634 (17)0.0600 (17)0.0041 (15)0.0029 (14)0.0045 (14)
C10B0.118 (4)0.072 (2)0.101 (3)0.017 (2)0.008 (3)0.016 (2)
C11B0.085 (3)0.078 (2)0.097 (3)0.012 (2)0.007 (2)0.003 (2)
C12B0.085 (2)0.073 (2)0.0647 (19)0.0027 (17)0.0004 (17)0.0069 (16)
C13B0.084 (2)0.072 (2)0.067 (2)0.0066 (17)0.0016 (16)0.0025 (16)
C21B0.079 (2)0.083 (2)0.070 (2)0.0057 (18)0.0012 (17)0.0060 (18)
C22B0.093 (3)0.115 (3)0.082 (3)0.013 (3)0.018 (2)0.008 (2)
C23B0.099 (3)0.137 (5)0.096 (4)0.021 (3)0.019 (3)0.024 (3)
C24B0.140 (5)0.142 (5)0.109 (4)0.066 (4)0.002 (4)0.035 (4)
C25B0.160 (5)0.112 (4)0.109 (4)0.063 (4)0.009 (4)0.003 (3)
C26B0.120 (4)0.087 (3)0.078 (3)0.032 (2)0.010 (2)0.001 (2)
N1B0.0840 (18)0.0671 (16)0.0567 (14)0.0056 (14)0.0066 (13)0.0076 (13)
N3B0.087 (2)0.0758 (18)0.0560 (15)0.0036 (15)0.0086 (13)0.0082 (13)
O1S0.124 (3)0.136 (3)0.0637 (16)0.019 (2)0.0014 (17)0.0102 (18)
C1S0.167 (8)0.267 (13)0.127 (6)0.057 (8)0.018 (5)0.043 (7)
Geometric parameters (Å, º) top
C2A—N3A1.345 (5)C4B—N3B1.386 (5)
C2A—N1A1.349 (5)C4B—C9B1.393 (5)
C2A—C12A1.425 (5)C4B—C5B1.395 (5)
C4A—N3A1.387 (4)C5B—C6B1.359 (6)
C4A—C5A1.398 (5)C5B—H2B0.9300
C4A—C9A1.399 (5)C6B—C7B1.431 (6)
C5A—C6A1.362 (5)C6B—C10B1.527 (6)
C5A—H2A0.9300C7B—C8B1.376 (5)
C6A—C7A1.429 (6)C7B—C11B1.495 (5)
C6A—C10A1.504 (6)C8B—C9B1.384 (5)
C7A—C8A1.389 (5)C8B—H3B0.9300
C7A—C11A1.497 (5)C9B—N1B1.390 (5)
C8A—C9A1.390 (5)C10B—H4B0.9600
C8A—H3A0.9300C10B—H5B0.9600
C9A—N1A1.381 (5)C10B—H6B0.9600
C10A—H6A0.9600C11B—H9B0.9600
C10A—H4A0.9600C11B—H8B0.9600
C10A—H5A0.9600C11B—H7B0.9600
C11A—H9A0.9600C12B—C13B1.332 (5)
C11A—H8A0.9600C12B—H10B0.9300
C11A—H7A0.9600C13B—C21B1.469 (5)
C12A—C13A1.352 (6)C13B—H11B0.9300
C12A—H10A0.9300C21B—C22B1.361 (6)
C13A—C21A1.455 (6)C21B—C26B1.368 (6)
C13A—H11A0.9300C22B—C23B1.367 (8)
C21A—C22A1.370 (7)C22B—H12B0.9300
C21A—C26A1.385 (7)C23B—C24B1.344 (10)
C22A—C23A1.372 (9)C23B—H13B0.9300
C22A—H12A0.9300C24B—C25B1.384 (9)
C23A—C24A1.373 (12)C24B—H14B0.9300
C23A—H13A0.9300C25B—C26B1.383 (7)
C24A—C25A1.372 (13)C25B—H15B0.9300
C24A—H14A0.9300C26B—H16B0.9300
C25A—C26A1.386 (8)N1B—H1B0.8600
C25A—H15A0.9300O1S—C1S1.2492 (12)
C26A—H16A0.9300O1S—H1S0.8200
N1A—H1A0.8600C1S—H4S0.9600
C2B—N3B1.350 (5)C1S—H3S0.9600
C2B—N1B1.375 (5)C1S—H2S0.9600
C2B—C12B1.423 (5)
N3A—C2A—N1A112.2 (3)N3B—C4B—C5B130.3 (3)
N3A—C2A—C12A123.4 (3)C9B—C4B—C5B120.0 (3)
N1A—C2A—C12A124.4 (4)C6B—C5B—C4B119.3 (4)
N3A—C4A—C5A131.7 (3)C6B—C5B—H2B120.4
N3A—C4A—C9A108.8 (3)C4B—C5B—H2B120.4
C5A—C4A—C9A119.5 (3)C5B—C6B—C7B120.9 (3)
C6A—C5A—C4A119.9 (4)C5B—C6B—C10B120.5 (4)
C6A—C5A—H2A120.1C7B—C6B—C10B118.6 (4)
C4A—C5A—H2A120.1C8B—C7B—C6B119.4 (3)
C5A—C6A—C7A120.8 (3)C8B—C7B—C11B120.7 (4)
C5A—C6A—C10A120.5 (4)C6B—C7B—C11B119.9 (3)
C7A—C6A—C10A118.8 (4)C7B—C8B—C9B119.3 (3)
C8A—C7A—C6A119.6 (3)C7B—C8B—H3B120.4
C8A—C7A—C11A119.8 (4)C9B—C8B—H3B120.4
C6A—C7A—C11A120.6 (4)C8B—C9B—N1B132.9 (3)
C9A—C8A—C7A118.8 (4)C8B—C9B—C4B121.0 (3)
C9A—C8A—H3A120.6N1B—C9B—C4B106.0 (3)
C7A—C8A—H3A120.6C6B—C10B—H4B109.5
N1A—C9A—C8A132.1 (4)C6B—C10B—H5B109.5
N1A—C9A—C4A106.5 (3)H4B—C10B—H5B109.5
C8A—C9A—C4A121.4 (3)C6B—C10B—H6B109.5
C6A—C10A—H6A109.5H4B—C10B—H6B109.5
C6A—C10A—H4A109.5H5B—C10B—H6B109.5
H6A—C10A—H4A109.5C7B—C11B—H9B109.5
C6A—C10A—H5A109.5C7B—C11B—H8B109.5
H6A—C10A—H5A109.5H9B—C11B—H8B109.5
H4A—C10A—H5A109.5C7B—C11B—H7B109.5
C7A—C11A—H9A109.5H9B—C11B—H7B109.5
C7A—C11A—H8A109.5H8B—C11B—H7B109.5
H9A—C11A—H8A109.5C13B—C12B—C2B123.7 (4)
C7A—C11A—H7A109.5C13B—C12B—H10B118.1
H9A—C11A—H7A109.5C2B—C12B—H10B118.1
H8A—C11A—H7A109.5C12B—C13B—C21B127.2 (4)
C13A—C12A—C2A124.5 (4)C12B—C13B—H11B116.4
C13A—C12A—H10A117.8C21B—C13B—H11B116.4
C2A—C12A—H10A117.8C22B—C21B—C26B116.3 (4)
C12A—C13A—C21A128.1 (4)C22B—C21B—C13B119.9 (4)
C12A—C13A—H11A115.9C26B—C21B—C13B123.8 (4)
C21A—C13A—H11A115.9C21B—C22B—C23B123.7 (5)
C22A—C21A—C26A118.3 (5)C21B—C22B—H12B118.1
C22A—C21A—C13A118.0 (5)C23B—C22B—H12B118.1
C26A—C21A—C13A123.6 (4)C24B—C23B—C22B118.9 (5)
C21A—C22A—C23A122.1 (7)C24B—C23B—H13B120.5
C21A—C22A—H12A119.0C22B—C23B—H13B120.5
C23A—C22A—H12A119.0C23B—C24B—C25B120.3 (5)
C22A—C23A—C24A119.3 (7)C23B—C24B—H14B119.8
C22A—C23A—H13A120.3C25B—C24B—H14B119.8
C24A—C23A—H13A120.3C24B—C25B—C26B118.8 (6)
C25A—C24A—C23A119.9 (5)C24B—C25B—H15B120.6
C25A—C24A—H14A120.0C26B—C25B—H15B120.6
C23A—C24A—H14A120.0C21B—C26B—C25B121.9 (5)
C24A—C25A—C26A120.2 (8)C21B—C26B—H16B119.0
C24A—C25A—H15A119.9C25B—C26B—H16B119.0
C26A—C25A—H15A119.9C2B—N1B—C9B107.4 (3)
C21A—C26A—C25A120.1 (6)C2B—N1B—H1B126.3
C21A—C26A—H16A119.9C9B—N1B—H1B126.3
C25A—C26A—H16A119.9C2B—N3B—C4B106.1 (3)
C2A—N1A—C9A107.1 (3)C1S—O1S—H1S109.5
C2A—N1A—H1A126.5O1S—C1S—H4S109.5
C9A—N1A—H1A126.5O1S—C1S—H3S109.5
C2A—N3A—C4A105.5 (3)H4S—C1S—H3S109.5
N3B—C2B—N1B110.8 (3)O1S—C1S—H2S109.5
N3B—C2B—C12B126.9 (3)H4S—C1S—H2S109.5
N1B—C2B—C12B122.3 (3)H3S—C1S—H2S109.5
N3B—C4B—C9B109.6 (3)
N3A—C4A—C5A—C6A179.8 (3)N3B—C4B—C5B—C6B178.8 (4)
C9A—C4A—C5A—C6A1.7 (5)C9B—C4B—C5B—C6B0.1 (6)
C4A—C5A—C6A—C7A0.4 (5)C4B—C5B—C6B—C7B1.5 (6)
C4A—C5A—C6A—C10A179.7 (4)C4B—C5B—C6B—C10B179.7 (4)
C5A—C6A—C7A—C8A0.4 (5)C5B—C6B—C7B—C8B1.2 (6)
C10A—C6A—C7A—C8A178.9 (4)C10B—C6B—C7B—C8B179.9 (4)
C5A—C6A—C7A—C11A179.3 (4)C5B—C6B—C7B—C11B179.7 (4)
C10A—C6A—C7A—C11A0.0 (5)C10B—C6B—C7B—C11B1.4 (6)
C6A—C7A—C8A—C9A0.1 (5)C6B—C7B—C8B—C9B0.5 (6)
C11A—C7A—C8A—C9A178.8 (3)C11B—C7B—C8B—C9B178.0 (4)
C7A—C8A—C9A—N1A179.2 (4)C7B—C8B—C9B—N1B178.3 (4)
C7A—C8A—C9A—C4A1.4 (5)C7B—C8B—C9B—C4B1.9 (6)
N3A—C4A—C9A—N1A0.5 (4)N3B—C4B—C9B—C8B179.2 (4)
C5A—C4A—C9A—N1A178.3 (3)C5B—C4B—C9B—C8B1.6 (6)
N3A—C4A—C9A—C8A179.0 (3)N3B—C4B—C9B—N1B0.6 (4)
C5A—C4A—C9A—C8A2.2 (5)C5B—C4B—C9B—N1B178.5 (4)
N3A—C2A—C12A—C13A175.9 (3)N3B—C2B—C12B—C13B2.9 (7)
N1A—C2A—C12A—C13A2.7 (6)N1B—C2B—C12B—C13B178.1 (4)
C2A—C12A—C13A—C21A177.6 (3)C2B—C12B—C13B—C21B178.3 (4)
C12A—C13A—C21A—C22A175.1 (4)C12B—C13B—C21B—C22B177.4 (5)
C12A—C13A—C21A—C26A2.3 (6)C12B—C13B—C21B—C26B1.8 (7)
C26A—C21A—C22A—C23A0.8 (7)C26B—C21B—C22B—C23B0.2 (8)
C13A—C21A—C22A—C23A176.8 (5)C13B—C21B—C22B—C23B179.1 (5)
C21A—C22A—C23A—C24A0.2 (9)C21B—C22B—C23B—C24B0.7 (10)
C22A—C23A—C24A—C25A0.7 (10)C22B—C23B—C24B—C25B1.4 (11)
C23A—C24A—C25A—C26A1.0 (11)C23B—C24B—C25B—C26B1.2 (12)
C22A—C21A—C26A—C25A0.5 (8)C22B—C21B—C26B—C25B0.5 (8)
C13A—C21A—C26A—C25A177.0 (5)C13B—C21B—C26B—C25B178.8 (6)
C24A—C25A—C26A—C21A0.4 (10)C24B—C25B—C26B—C21B0.2 (11)
N3A—C2A—N1A—C9A0.4 (4)N3B—C2B—N1B—C9B0.2 (4)
C12A—C2A—N1A—C9A178.4 (3)C12B—C2B—N1B—C9B179.4 (4)
C8A—C9A—N1A—C2A178.9 (4)C8B—C9B—N1B—C2B179.4 (4)
C4A—C9A—N1A—C2A0.5 (4)C4B—C9B—N1B—C2B0.5 (4)
N1A—C2A—N3A—C4A0.0 (4)N1B—C2B—N3B—C4B0.2 (4)
C12A—C2A—N3A—C4A178.8 (3)C12B—C2B—N3B—C4B178.9 (4)
C5A—C4A—N3A—C2A178.3 (4)C9B—C4B—N3B—C2B0.5 (4)
C9A—C4A—N3A—C2A0.3 (4)C5B—C4B—N3B—C2B178.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1S—H1S···N3B0.822.062.857 (4)164
N1B—H1B···N3Ai0.862.222.985 (4)149
N1A—H1A···O1S0.862.072.907 (5)163
Symmetry code: (i) x, y+2, z+1/2.
(E)-5,6-Dimethyl-2-styryl-1H-benzo[d]imidazolium hydrogen oxalate (2b) top
Crystal data top
C17H17N2+·C2HO4F(000) = 712
Mr = 338.35Dx = 1.319 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 5.56861 (9) ÅCell parameters from 9985 reflections
b = 18.0016 (3) Åθ = 5.2–72.3°
c = 17.1528 (3) ŵ = 0.77 mm1
β = 97.8415 (7)°T = 110 K
V = 1703.39 (5) Å3Prism, yellow
Z = 40.75 × 0.07 × 0.06 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3124 reflections with I > 2σ(I)
ω scanRint = 0.031
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008b)
θmax = 72.3°, θmin = 3.6°
Tmin = 0.673, Tmax = 0.754h = 66
3349 measured reflectionsk = 022
3349 independent reflectionsl = 021
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0525P)2 + 0.3027P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3349 reflectionsΔρmax = 0.24 e Å3
231 parametersΔρmin = 0.15 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C20.0652 (3)0.40505 (8)0.76988 (8)0.0263 (3)
C40.3059 (2)0.38397 (7)0.67930 (8)0.0234 (3)
C50.4355 (3)0.35485 (8)0.62208 (8)0.0248 (3)
H30.41090.30510.60430.030*
C60.5998 (3)0.40009 (8)0.59213 (8)0.0265 (3)
C70.6361 (3)0.47492 (8)0.61884 (9)0.0280 (3)
C80.5100 (3)0.50292 (8)0.67623 (9)0.0281 (3)
H40.53460.55250.69450.034*
C90.3458 (3)0.45645 (7)0.70657 (8)0.0249 (3)
C100.7418 (3)0.37007 (9)0.52992 (9)0.0324 (3)
H50.70410.31730.52110.049*
H60.91570.37590.54760.049*
H70.69770.39750.48070.049*
C110.8121 (3)0.52453 (9)0.58409 (10)0.0352 (4)
H90.97190.50080.58970.053*
H100.82430.57230.61180.053*
H80.75470.53280.52820.053*
C120.1091 (3)0.39727 (8)0.82420 (8)0.0292 (3)
H110.12450.43710.85950.035*
C130.2509 (3)0.33766 (8)0.82838 (8)0.0289 (3)
H120.23740.29840.79220.035*
C210.4250 (3)0.32824 (8)0.88434 (8)0.0304 (3)
C220.5753 (3)0.26627 (9)0.87807 (9)0.0329 (3)
H130.56120.23060.83810.039*
C230.7455 (3)0.25539 (9)0.92895 (9)0.0368 (4)
H140.84750.21290.92340.044*
C240.7664 (3)0.30659 (10)0.98777 (9)0.0381 (4)
H150.88300.29941.02270.046*
C250.6172 (4)0.36809 (11)0.99550 (10)0.0455 (4)
H160.63090.40301.03620.055*
C260.4473 (4)0.37962 (10)0.94452 (10)0.0417 (4)
H170.34610.42230.95040.050*
N30.1297 (2)0.35405 (6)0.71942 (7)0.0243 (2)
H20.06950.30890.71300.029*
N10.1949 (2)0.46681 (6)0.76335 (7)0.0271 (3)
H10.18550.50770.79090.032*
C1S0.8674 (2)0.62971 (7)0.82263 (8)0.0214 (3)
C2S1.1190 (2)0.66258 (8)0.81548 (8)0.0222 (3)
O1S0.69029 (18)0.67687 (5)0.80515 (6)0.0266 (2)
H1S0.540 (3)0.6528 (6)0.8087 (10)0.040*
O2S0.84578 (19)0.56580 (6)0.84260 (7)0.0340 (3)
O3S1.28124 (17)0.61507 (6)0.80966 (7)0.0295 (2)
O4S1.14404 (18)0.73080 (5)0.81726 (7)0.0309 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0284 (7)0.0205 (6)0.0282 (7)0.0052 (6)0.0023 (6)0.0010 (5)
C40.0217 (6)0.0184 (6)0.0280 (6)0.0001 (5)0.0042 (5)0.0024 (5)
C50.0232 (7)0.0214 (6)0.0277 (7)0.0015 (5)0.0040 (5)0.0010 (5)
C60.0227 (7)0.0283 (7)0.0263 (7)0.0019 (6)0.0052 (5)0.0017 (5)
C70.0239 (7)0.0254 (7)0.0319 (7)0.0011 (6)0.0070 (6)0.0059 (6)
C80.0267 (7)0.0197 (6)0.0349 (7)0.0007 (6)0.0057 (6)0.0019 (5)
C90.0257 (7)0.0195 (6)0.0275 (7)0.0043 (5)0.0037 (5)0.0008 (5)
C100.0260 (7)0.0370 (8)0.0336 (8)0.0023 (6)0.0020 (6)0.0007 (6)
C110.0308 (8)0.0325 (8)0.0407 (8)0.0046 (7)0.0009 (7)0.0067 (6)
C120.0344 (8)0.0245 (7)0.0282 (7)0.0088 (6)0.0023 (6)0.0017 (5)
C130.0327 (8)0.0277 (7)0.0256 (7)0.0072 (6)0.0009 (6)0.0009 (5)
C210.0342 (8)0.0309 (7)0.0259 (7)0.0090 (6)0.0026 (6)0.0026 (6)
C220.0372 (9)0.0310 (7)0.0299 (7)0.0075 (7)0.0024 (6)0.0030 (6)
C230.0385 (9)0.0375 (9)0.0347 (8)0.0054 (7)0.0058 (7)0.0078 (6)
C240.0388 (9)0.0459 (9)0.0309 (8)0.0080 (8)0.0093 (7)0.0081 (7)
C250.0559 (12)0.0474 (10)0.0353 (8)0.0037 (9)0.0143 (8)0.0060 (7)
C260.0487 (10)0.0412 (9)0.0370 (9)0.0003 (8)0.0125 (7)0.0068 (7)
N30.0247 (6)0.0183 (5)0.0289 (6)0.0009 (5)0.0003 (5)0.0006 (4)
N10.0309 (6)0.0193 (6)0.0298 (6)0.0036 (5)0.0000 (5)0.0014 (4)
C1S0.0191 (6)0.0206 (6)0.0252 (6)0.0003 (5)0.0055 (5)0.0040 (5)
C2S0.0180 (6)0.0232 (6)0.0256 (6)0.0001 (5)0.0038 (5)0.0008 (5)
O1S0.0160 (4)0.0243 (5)0.0399 (6)0.0006 (4)0.0056 (4)0.0027 (4)
O2S0.0275 (5)0.0198 (5)0.0570 (7)0.0006 (4)0.0135 (5)0.0026 (5)
O3S0.0174 (5)0.0233 (5)0.0485 (6)0.0002 (4)0.0075 (4)0.0072 (4)
O4S0.0214 (5)0.0191 (5)0.0527 (6)0.0012 (4)0.0065 (4)0.0020 (4)
Geometric parameters (Å, º) top
C2—N11.3385 (19)C12—H110.9500
C2—N31.3438 (18)C13—C211.464 (2)
C2—C121.441 (2)C13—H120.9500
C4—N31.3818 (19)C21—C221.390 (2)
C4—C91.3937 (18)C21—C261.404 (2)
C4—C51.398 (2)C22—C231.387 (2)
C5—C61.375 (2)C22—H130.9500
C5—H30.9500C23—C241.383 (2)
C6—C71.428 (2)C23—H140.9500
C6—C101.512 (2)C24—C251.380 (3)
C7—C81.380 (2)C24—H150.9500
C7—C111.508 (2)C25—C261.389 (3)
C8—C91.392 (2)C25—H160.9500
C8—H40.9500C26—H170.9500
C9—N11.383 (2)N3—H20.8800
C10—H50.9800N1—H10.8800
C10—H60.9800C1S—O2S1.2109 (17)
C10—H70.9800C1S—O1S1.3048 (16)
C11—H90.9800C1S—C2S1.5410 (19)
C11—H100.9800C2S—O4S1.2358 (17)
C11—H80.9800C2S—O3S1.2581 (17)
C12—C131.340 (2)O1S—H1S0.95 (2)
N1—C2—N3108.60 (13)C2—C12—H11117.8
N1—C2—C12123.60 (13)C12—C13—C21125.14 (14)
N3—C2—C12127.80 (13)C12—C13—H12117.4
N3—C4—C9106.82 (12)C21—C13—H12117.4
N3—C4—C5132.33 (12)C22—C21—C26118.21 (15)
C9—C4—C5120.85 (13)C22—C21—C13119.19 (14)
C6—C5—C4118.28 (13)C26—C21—C13122.60 (15)
C6—C5—H3120.9C23—C22—C21121.37 (15)
C4—C5—H3120.9C23—C22—H13119.3
C5—C6—C7120.73 (14)C21—C22—H13119.3
C5—C6—C10119.37 (13)C24—C23—C22119.84 (16)
C7—C6—C10119.90 (14)C24—C23—H14120.1
C8—C7—C6120.64 (14)C22—C23—H14120.1
C8—C7—C11119.15 (14)C25—C24—C23119.69 (16)
C6—C7—C11120.21 (14)C25—C24—H15120.2
C7—C8—C9118.12 (13)C23—C24—H15120.2
C7—C8—H4120.9C24—C25—C26120.83 (16)
C9—C8—H4120.9C24—C25—H16119.6
N1—C9—C8132.51 (13)C26—C25—H16119.6
N1—C9—C4106.14 (12)C25—C26—C21120.05 (17)
C8—C9—C4121.35 (14)C25—C26—H17120.0
C6—C10—H5109.5C21—C26—H17120.0
C6—C10—H6109.5C2—N3—C4108.95 (12)
H5—C10—H6109.5C2—N3—H2125.5
C6—C10—H7109.5C4—N3—H2125.5
H5—C10—H7109.5C2—N1—C9109.48 (11)
H6—C10—H7109.5C2—N1—H1125.3
C7—C11—H9109.5C9—N1—H1125.3
C7—C11—H10109.5O2S—C1S—O1S125.60 (12)
H9—C11—H10109.5O2S—C1S—C2S120.91 (12)
C7—C11—H8109.5O1S—C1S—C2S113.49 (11)
H9—C11—H8109.5O4S—C2S—O3S126.69 (12)
H10—C11—H8109.5O4S—C2S—C1S118.72 (12)
C13—C12—C2124.49 (14)O3S—C2S—C1S114.58 (11)
C13—C12—H11117.8C1S—O1S—H1S109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3Si0.882.022.8074 (15)148
N1—H1···O2Si0.882.433.0860 (16)131
O1S—H1S···O3Si0.951.592.5456 (14)176
N3—H2···O4Sii0.881.872.7169 (15)161
Symmetry codes: (i) x1, y, z; (ii) x+1, y1/2, z+3/2.
Interplanar angles (%) in 1a–2b top
MoleculeAngleMoleculeAngle
1 Mol. A6.8 (8)1 Mol. E2.1 (1)
1 Part B5.2 (2)2 Mol. A7.6 (3)
1 Mol. C53.54 (3)2 Mol. B3.9 (3)
1 Mol. D55.44 (3)2a12.02 (8)
Percentage of interactions betweent types of atoms for structures 1–2a top
1 Mol. A1 Part A1 Part B1 Mol. C1 Mol. D1 mol. E2 Mol. A2 Mol. B2a
C···C1.51.51.91.52.02.05.36.38.0
C···H26.827.526.927.324.725.826.023.422.0
C···N0.50.50.60.5---1.22.5
C···O--------0.3
H···H62.261.261.66263.162.97.78.92.5
H···N5.35.55.37.28.97.0---
H···O2.82.92.70.71.32.22.80.419.0
N···N0.90.90.90.8-0.1---
N···O---------
O···O------58.259.745.7
 

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