The structures of benzimidazole derivatives and their potential as tuberculostatics

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.

Computing details

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)

Crystal data

2C17H18N2·H2O	Z = 4
Mr = 518.68	F(000) = 1112
Triclinic, P1	Dx = 1.216 Mg m^−3
a = 8.1685 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 11.4832 (2) Å	Cell parameters from 9960 reflections
c = 30.7638 (4) Å	θ = 2.9–72.2°
α = 99.9705 (5)°	µ = 0.58 mm^−1
β = 94.1047 (5)°	T = 105 K
γ = 90.9084 (6)°	Prism, colorless
V = 2833.62 (7) Å^3	0.73 × 0.15 × 0.04 mm

Data collection

Bruker SMART APEXII CCD diffractometer	9970 reflections with I > 2σ(I)
ωscan	Rint = 0.021
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 72.2°, θmin = 2.9°
Tmin = 0.657, Tmax = 0.754	h = −10→10
42329 measured reflections	k = −14→13
11147 independent reflections	l = −37→37

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 0.9457P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.112	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.31 e Å^−3
11147 reflections	Δρmin = −0.23 e Å^−3
801 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.00021 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C4A	0.59607 (15)	0.60871 (10)	0.30518 (4)	0.0233 (2)
C5A	0.66727 (15)	0.56393 (10)	0.34128 (4)	0.0243 (2)
H2A	0.722064	0.490941	0.336870	0.029*
C6A	0.65701 (14)	0.62740 (10)	0.38370 (4)	0.0225 (2)
C7A	0.57551 (14)	0.73692 (10)	0.39024 (4)	0.0237 (2)
C8A	0.50568 (14)	0.78218 (10)	0.35440 (4)	0.0248 (2)
H3A	0.451417	0.855401	0.358581	0.030*
C9A	0.51749 (14)	0.71714 (10)	0.31216 (4)	0.0228 (2)
C10A	0.73291 (16)	0.57993 (11)	0.42299 (4)	0.0285 (3)
H4A	0.780388	0.503026	0.412853	0.043*
H5A	0.648334	0.570616	0.443269	0.043*
H6A	0.819316	0.635309	0.438378	0.043*
C11A	0.56800 (17)	0.80601 (12)	0.43655 (4)	0.0320 (3)
H7A	0.508647	0.878991	0.435286	0.048*
H8A	0.679730	0.825754	0.449897	0.048*
H9A	0.510763	0.758075	0.454499	0.048*
C2A	0.51233 (17)	0.64394 (12)	0.24119 (3)	0.0319 (3)
C12A	0.4866 (2)	0.6463 (2)	0.19180 (4)	0.0284 (4)	0.755 (3)
H10A	0.513149	0.726667	0.186274	0.034*	0.755 (3)
H11A	0.561281	0.590458	0.175508	0.034*	0.755 (3)
C13A	0.3093 (2)	0.61215 (18)	0.17503 (5)	0.0327 (5)	0.755 (3)
H12A	0.286541	0.528745	0.177562	0.039*	0.755 (3)
H13A	0.234304	0.662350	0.193573	0.039*	0.755 (3)
C12B	0.4388 (7)	0.6059 (6)	0.19354 (9)	0.0283 (7)	0.245 (3)
H10B	0.527438	0.575294	0.174733	0.034*	0.245 (3)
H11B	0.357940	0.540325	0.192734	0.034*	0.245 (3)
C13B	0.3558 (7)	0.7033 (5)	0.17419 (17)	0.0303 (13)	0.245 (3)
H12B	0.432687	0.772616	0.179276	0.036*	0.245 (3)
H13B	0.259365	0.726318	0.191140	0.036*	0.245 (3)
C21A	0.2776 (2)	0.62720 (19)	0.12740 (5)	0.0288 (3)	0.755 (3)
C22A	0.2022 (2)	0.72817 (18)	0.11750 (6)	0.0299 (3)	0.755 (3)
H14A	0.170864	0.786961	0.140882	0.036*	0.755 (3)
C23A	0.1719 (2)	0.74447 (18)	0.07380 (6)	0.0306 (3)	0.755 (3)
H15A	0.119634	0.813732	0.067622	0.037*	0.755 (3)
C24A	0.2179 (3)	0.6599 (2)	0.03943 (7)	0.0308 (3)	0.755 (3)
H16A	0.198278	0.671076	0.009637	0.037*	0.755 (3)
C25A	0.2925 (3)	0.5588 (2)	0.04880 (8)	0.0312 (3)	0.755 (3)
H17A	0.322880	0.499897	0.025324	0.037*	0.755 (3)
C26A	0.3236 (2)	0.54302 (18)	0.09262 (6)	0.0302 (3)	0.755 (3)
H18A	0.376648	0.473964	0.098704	0.036*	0.755 (3)
C21B	0.2976 (6)	0.6788 (5)	0.12518 (16)	0.0295 (3)	0.245 (3)
C22B	0.2014 (6)	0.7581 (5)	0.10680 (19)	0.0297 (3)	0.245 (3)
H14B	0.164712	0.826086	0.125347	0.036*	0.245 (3)
C23B	0.1574 (7)	0.7403 (5)	0.06180 (19)	0.0303 (3)	0.245 (3)
H15B	0.090913	0.795857	0.049805	0.036*	0.245 (3)
C24B	0.2098 (9)	0.6423 (6)	0.0343 (2)	0.0308 (3)	0.245 (3)
H16B	0.179155	0.630238	0.003423	0.037*	0.245 (3)
C25B	0.3072 (10)	0.5612 (7)	0.0518 (2)	0.0308 (3)	0.245 (3)
H17B	0.345010	0.494198	0.033002	0.037*	0.245 (3)
C26B	0.3493 (7)	0.5788 (5)	0.09717 (19)	0.0302 (3)	0.245 (3)
H18B	0.413727	0.522322	0.109277	0.036*	0.245 (3)
N1A	0.46489 (13)	0.73709 (9)	0.27047 (3)	0.0270 (2)
H1A	0.410931	0.798494	0.264153	0.032*
N3A	0.58962 (14)	0.56385 (10)	0.25984 (3)	0.0317 (2)
C2C	0.96487 (16)	0.74385 (11)	0.25997 (4)	0.0261 (2)
C4C	0.86837 (16)	0.76411 (11)	0.19478 (4)	0.0270 (3)
C5C	0.79895 (16)	0.80490 (11)	0.15758 (4)	0.0278 (3)
H2C	0.769018	0.885124	0.159474	0.033*
C6C	0.77440 (15)	0.72644 (11)	0.11785 (4)	0.0260 (2)
C7C	0.82171 (15)	0.60712 (11)	0.11522 (4)	0.0256 (2)
C8C	0.88769 (16)	0.56602 (11)	0.15230 (4)	0.0274 (3)
H3C	0.917452	0.485804	0.150589	0.033*
C9C	0.90928 (16)	0.64543 (11)	0.19221 (4)	0.0268 (3)
C10C	0.69862 (17)	0.76852 (12)	0.07737 (4)	0.0322 (3)
H4C	0.676984	0.853081	0.084724	0.048*
H5C	0.595287	0.724352	0.067292	0.048*
H6C	0.774354	0.755474	0.053805	0.048*
C11C	0.80435 (17)	0.52485 (11)	0.07124 (4)	0.0299 (3)
H7C	0.833602	0.444871	0.075414	0.045*
H8C	0.877632	0.552349	0.051020	0.045*
H9C	0.690540	0.523798	0.058682	0.045*
C12C	1.02378 (16)	0.76714 (11)	0.30790 (4)	0.0262 (3)
H10C	1.144508	0.759753	0.310693	0.031*
H11C	0.974566	0.706723	0.322784	0.031*
C13C	0.97966 (17)	0.88962 (11)	0.33099 (4)	0.0300 (3)
H12C	1.019371	0.949424	0.314279	0.036*
H13C	0.858664	0.894190	0.330681	0.036*
C21C	1.05232 (15)	0.91888 (10)	0.37826 (4)	0.0234 (2)
C22C	1.16767 (16)	1.01084 (11)	0.39105 (4)	0.0274 (3)
H14C	1.201870	1.055048	0.369743	0.033*
C23C	1.23371 (16)	1.03907 (11)	0.43456 (4)	0.0302 (3)
H15C	1.312827	1.101989	0.442840	0.036*
C24C	1.18415 (16)	0.97550 (11)	0.46579 (4)	0.0290 (3)
H16C	1.228623	0.994925	0.495614	0.035*
C25C	1.06938 (16)	0.88331 (11)	0.45350 (4)	0.0273 (3)
H17C	1.035077	0.839605	0.474948	0.033*
C26C	1.00448 (15)	0.85474 (10)	0.40993 (4)	0.0255 (2)
H18C	0.926794	0.790898	0.401642	0.031*
N1C	0.97087 (14)	0.63525 (9)	0.23443 (3)	0.0275 (2)
H1C	1.007098	0.570568	0.243089	0.033*
N3C	0.90546 (14)	0.82464 (9)	0.23780 (3)	0.0279 (2)
C2D	0.49420 (14)	0.23549 (11)	0.24663 (4)	0.0235 (2)
C4D	0.46929 (14)	0.14007 (10)	0.17952 (4)	0.0229 (2)
C5D	0.43928 (14)	0.05703 (11)	0.14070 (4)	0.0246 (2)
H2D	0.406499	−0.021984	0.141965	0.030*
C6D	0.45806 (14)	0.09163 (11)	0.10028 (4)	0.0243 (2)
C7D	0.51105 (14)	0.20893 (11)	0.09836 (4)	0.0239 (2)
C8D	0.54272 (14)	0.29125 (11)	0.13702 (4)	0.0240 (2)
H3D	0.579897	0.369487	0.136032	0.029*
C9D	0.51846 (14)	0.25591 (10)	0.17724 (4)	0.0224 (2)
C10D	0.41905 (17)	0.00517 (11)	0.05780 (4)	0.0301 (3)
H4D	0.386555	−0.071742	0.064667	0.045*
H5D	0.516391	−0.003629	0.040777	0.045*
H6D	0.328866	0.034725	0.040347	0.045*
C11D	0.53000 (17)	0.24411 (12)	0.05394 (4)	0.0302 (3)
H7D	0.565663	0.327461	0.058204	0.045*
H8D	0.424497	0.232831	0.036258	0.045*
H9D	0.612170	0.194894	0.038493	0.045*
C12D	0.51007 (16)	0.26862 (11)	0.29596 (4)	0.0268 (3)
H10D	0.450859	0.342654	0.304567	0.032*
H11D	0.627493	0.285020	0.305805	0.032*
C13D	0.44403 (17)	0.17471 (12)	0.32031 (4)	0.0313 (3)
H12D	0.323330	0.180524	0.320674	0.038*
H13D	0.468007	0.095235	0.304186	0.038*
C21D	0.51945 (15)	0.18896 (11)	0.36735 (4)	0.0255 (2)
C22D	0.62855 (16)	0.10674 (11)	0.37960 (4)	0.0287 (3)
H14D	0.654881	0.040918	0.358254	0.034*
C23D	0.69978 (16)	0.11930 (12)	0.42263 (4)	0.0307 (3)
H15D	0.774352	0.062384	0.430461	0.037*
C24D	0.66208 (16)	0.21478 (11)	0.45410 (4)	0.0287 (3)
H16D	0.709324	0.223047	0.483635	0.034*
C25D	0.55515 (16)	0.29791 (11)	0.44215 (4)	0.0297 (3)
H17D	0.529759	0.363925	0.463540	0.036*
C26D	0.48440 (16)	0.28561 (11)	0.39902 (4)	0.0285 (3)
H18D	0.411688	0.343576	0.391130	0.034*
N1D	0.53320 (12)	0.31482 (9)	0.22067 (3)	0.0236 (2)
H1D	0.562383	0.389663	0.229771	0.028*
N3D	0.45531 (12)	0.12880 (9)	0.22368 (3)	0.0247 (2)
C2E	−0.01801 (15)	0.32299 (11)	0.25458 (4)	0.0261 (2)
C4E	0.07942 (15)	0.42229 (10)	0.31725 (4)	0.0250 (2)
C5E	0.15287 (15)	0.50499 (10)	0.35227 (4)	0.0267 (3)
H2E	0.203942	0.575388	0.346787	0.032*
C6E	0.15002 (15)	0.48266 (11)	0.39511 (4)	0.0259 (2)
C7E	0.07614 (15)	0.37656 (11)	0.40346 (4)	0.0253 (2)
C8E	0.00561 (15)	0.29325 (11)	0.36867 (4)	0.0256 (2)
H3E	−0.043323	0.221817	0.373876	0.031*
C9E	0.00891 (14)	0.31774 (10)	0.32600 (4)	0.0239 (2)
C10E	0.22806 (17)	0.57177 (12)	0.43314 (4)	0.0323 (3)
H4E	0.267672	0.641131	0.421946	0.048*
H5E	0.320500	0.536029	0.447563	0.048*
H6E	0.146652	0.595997	0.454598	0.048*
C11E	0.07493 (17)	0.35318 (12)	0.45020 (4)	0.0328 (3)
H7E	0.025497	0.274651	0.449812	0.049*
H8E	0.010714	0.413275	0.467549	0.049*
H9E	0.187794	0.356416	0.463593	0.049*
C12E	−0.06336 (15)	0.28177 (12)	0.20638 (4)	0.0284 (3)
H10E	−0.113352	0.347354	0.193523	0.034*
H11E	−0.146034	0.216139	0.202653	0.034*
C13E	0.08680 (18)	0.23956 (16)	0.18151 (5)	0.0433 (4)
H12E	0.171723	0.303940	0.186803	0.052*
H13E	0.133096	0.171467	0.193513	0.052*
C21E	0.04696 (16)	0.20325 (13)	0.13222 (4)	0.0324 (3)
C22E	0.09371 (16)	0.27505 (12)	0.10324 (5)	0.0336 (3)
H14E	0.151638	0.347583	0.114571	0.040*
C23E	0.05756 (17)	0.24310 (12)	0.05788 (5)	0.0348 (3)
H15E	0.091178	0.293507	0.038526	0.042*
C24E	−0.02694 (18)	0.13849 (13)	0.04090 (5)	0.0363 (3)
H16E	−0.052001	0.116516	0.009893	0.044*
C25E	−0.0749 (2)	0.06588 (13)	0.06932 (5)	0.0420 (3)
H17E	−0.133344	−0.006339	0.057835	0.050*
C26E	−0.03802 (19)	0.09792 (14)	0.11466 (5)	0.0404 (3)
H18E	−0.071361	0.047140	0.133909	0.049*
N3E	0.05974 (13)	0.42424 (9)	0.27185 (3)	0.0282 (2)
N1E	−0.05056 (13)	0.25536 (9)	0.28517 (3)	0.0257 (2)
H1E	−0.100072	0.185179	0.280032	0.031*
O1W	0.28493 (14)	0.92370 (10)	0.24159 (4)	0.0466 (3)
H1W1	0.179 (2)	0.9342 (16)	0.2338 (6)	0.050 (5)*
H1W2	0.333 (2)	0.9882 (19)	0.2357 (6)	0.059 (6)*
O2W	0.77247 (14)	0.04454 (9)	0.26045 (4)	0.0429 (3)
H2W1	0.678 (3)	0.0484 (18)	0.2457 (7)	0.058 (6)*
H2W2	0.816 (3)	−0.0278 (19)	0.2532 (7)	0.061 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C4A	0.0272 (6)	0.0230 (6)	0.0186 (5)	0.0013 (4)	0.0014 (4)	0.0003 (4)
C5A	0.0279 (6)	0.0207 (5)	0.0235 (6)	0.0032 (4)	−0.0001 (5)	0.0021 (4)
C6A	0.0231 (5)	0.0232 (6)	0.0206 (6)	−0.0035 (4)	−0.0004 (4)	0.0035 (4)
C7A	0.0235 (6)	0.0238 (6)	0.0218 (6)	−0.0021 (4)	0.0019 (4)	−0.0011 (4)
C8A	0.0261 (6)	0.0199 (5)	0.0269 (6)	0.0015 (4)	0.0012 (5)	−0.0002 (4)
C9A	0.0243 (6)	0.0225 (6)	0.0219 (6)	−0.0004 (4)	0.0005 (4)	0.0054 (4)
C10A	0.0315 (6)	0.0310 (6)	0.0228 (6)	−0.0013 (5)	−0.0017 (5)	0.0062 (5)
C11A	0.0339 (7)	0.0344 (7)	0.0237 (6)	0.0018 (5)	0.0009 (5)	−0.0052 (5)
C2A	0.0370 (7)	0.0395 (7)	0.0193 (6)	0.0102 (5)	0.0028 (5)	0.0038 (5)
C12A	0.0288 (11)	0.0400 (12)	0.0187 (7)	−0.0024 (8)	0.0055 (6)	0.0107 (7)
C13A	0.0312 (9)	0.0474 (12)	0.0203 (8)	−0.0088 (8)	−0.0012 (6)	0.0104 (7)
C12B	0.0300 (15)	0.0397 (16)	0.0185 (10)	−0.0003 (12)	0.0078 (11)	0.0118 (11)
C13B	0.034 (3)	0.032 (3)	0.024 (3)	−0.003 (2)	0.004 (2)	0.000 (2)
C21A	0.0308 (5)	0.0348 (6)	0.0208 (5)	−0.0043 (5)	−0.0012 (4)	0.0065 (5)
C22A	0.0325 (5)	0.0357 (6)	0.0214 (6)	−0.0034 (5)	−0.0001 (5)	0.0058 (5)
C23A	0.0344 (5)	0.0351 (5)	0.0223 (6)	−0.0038 (4)	−0.0010 (5)	0.0067 (5)
C24A	0.0355 (5)	0.0355 (6)	0.0212 (5)	−0.0043 (5)	−0.0020 (4)	0.0069 (5)
C25A	0.0348 (5)	0.0360 (5)	0.0218 (5)	−0.0031 (5)	−0.0026 (4)	0.0047 (4)
C26A	0.0327 (5)	0.0350 (6)	0.0222 (5)	−0.0029 (5)	−0.0025 (4)	0.0057 (5)
C21B	0.0321 (6)	0.0349 (7)	0.0212 (6)	−0.0031 (6)	−0.0015 (5)	0.0058 (6)
C22B	0.0326 (6)	0.0350 (6)	0.0215 (6)	−0.0034 (6)	−0.0008 (6)	0.0064 (6)
C23B	0.0341 (6)	0.0354 (6)	0.0212 (6)	−0.0040 (5)	−0.0015 (6)	0.0063 (6)
C24B	0.0350 (6)	0.0355 (6)	0.0215 (6)	−0.0039 (5)	−0.0018 (5)	0.0059 (5)
C25B	0.0343 (6)	0.0355 (6)	0.0219 (6)	−0.0033 (5)	−0.0024 (5)	0.0053 (5)
C26B	0.0328 (6)	0.0352 (6)	0.0218 (6)	−0.0032 (6)	−0.0025 (5)	0.0054 (6)
N1A	0.0322 (5)	0.0284 (5)	0.0216 (5)	0.0063 (4)	0.0006 (4)	0.0074 (4)
N3A	0.0399 (6)	0.0353 (6)	0.0181 (5)	0.0106 (5)	−0.0009 (4)	−0.0001 (4)
C2C	0.0336 (6)	0.0227 (6)	0.0210 (6)	0.0031 (5)	−0.0007 (5)	0.0022 (4)
C4C	0.0362 (7)	0.0222 (6)	0.0214 (6)	0.0029 (5)	−0.0016 (5)	0.0022 (4)
C5C	0.0352 (7)	0.0226 (6)	0.0256 (6)	0.0030 (5)	−0.0020 (5)	0.0059 (5)
C6C	0.0285 (6)	0.0280 (6)	0.0222 (6)	−0.0004 (5)	−0.0008 (5)	0.0074 (5)
C7C	0.0288 (6)	0.0268 (6)	0.0203 (6)	−0.0010 (5)	0.0002 (5)	0.0021 (5)
C8C	0.0369 (7)	0.0218 (6)	0.0223 (6)	0.0037 (5)	−0.0008 (5)	0.0021 (5)
C9C	0.0361 (7)	0.0237 (6)	0.0204 (6)	0.0040 (5)	−0.0026 (5)	0.0049 (5)
C10C	0.0380 (7)	0.0339 (7)	0.0251 (6)	−0.0005 (5)	−0.0048 (5)	0.0091 (5)
C11C	0.0370 (7)	0.0309 (6)	0.0201 (6)	−0.0012 (5)	−0.0006 (5)	0.0012 (5)
C12C	0.0341 (6)	0.0242 (6)	0.0196 (6)	0.0042 (5)	−0.0019 (5)	0.0027 (4)
C13C	0.0407 (7)	0.0273 (6)	0.0209 (6)	0.0089 (5)	−0.0025 (5)	0.0021 (5)
C21C	0.0283 (6)	0.0216 (5)	0.0198 (6)	0.0066 (4)	0.0015 (4)	0.0014 (4)
C22C	0.0336 (6)	0.0226 (6)	0.0272 (6)	0.0020 (5)	0.0048 (5)	0.0070 (5)
C23C	0.0324 (7)	0.0231 (6)	0.0328 (7)	−0.0027 (5)	−0.0021 (5)	0.0009 (5)
C24C	0.0366 (7)	0.0265 (6)	0.0213 (6)	0.0048 (5)	−0.0036 (5)	−0.0012 (5)
C25C	0.0354 (7)	0.0266 (6)	0.0205 (6)	0.0029 (5)	0.0051 (5)	0.0048 (5)
C26C	0.0279 (6)	0.0232 (6)	0.0244 (6)	−0.0014 (4)	0.0012 (5)	0.0017 (4)
N1C	0.0425 (6)	0.0198 (5)	0.0193 (5)	0.0065 (4)	−0.0032 (4)	0.0027 (4)
N3C	0.0386 (6)	0.0233 (5)	0.0206 (5)	0.0047 (4)	−0.0030 (4)	0.0024 (4)
C2D	0.0229 (6)	0.0286 (6)	0.0205 (6)	0.0062 (4)	0.0022 (4)	0.0074 (4)
C4D	0.0224 (5)	0.0265 (6)	0.0216 (6)	0.0041 (4)	0.0013 (4)	0.0086 (4)
C5D	0.0262 (6)	0.0237 (6)	0.0247 (6)	0.0016 (4)	0.0002 (5)	0.0071 (5)
C6D	0.0237 (6)	0.0264 (6)	0.0230 (6)	0.0034 (4)	0.0002 (4)	0.0052 (5)
C7D	0.0231 (6)	0.0282 (6)	0.0217 (6)	0.0039 (4)	0.0022 (4)	0.0075 (5)
C8D	0.0254 (6)	0.0246 (6)	0.0235 (6)	0.0019 (4)	0.0023 (4)	0.0075 (5)
C9D	0.0209 (5)	0.0253 (6)	0.0211 (6)	0.0038 (4)	0.0007 (4)	0.0047 (4)
C10D	0.0375 (7)	0.0286 (6)	0.0237 (6)	0.0006 (5)	−0.0025 (5)	0.0045 (5)
C11D	0.0386 (7)	0.0306 (6)	0.0224 (6)	0.0002 (5)	0.0045 (5)	0.0071 (5)
C12D	0.0314 (6)	0.0294 (6)	0.0205 (6)	0.0050 (5)	0.0031 (5)	0.0059 (5)
C13D	0.0335 (7)	0.0396 (7)	0.0216 (6)	−0.0048 (5)	0.0007 (5)	0.0089 (5)
C21D	0.0270 (6)	0.0295 (6)	0.0212 (6)	−0.0032 (5)	0.0038 (5)	0.0076 (5)
C22D	0.0349 (7)	0.0277 (6)	0.0245 (6)	0.0032 (5)	0.0090 (5)	0.0044 (5)
C23D	0.0319 (6)	0.0333 (7)	0.0303 (7)	0.0072 (5)	0.0049 (5)	0.0133 (5)
C24D	0.0312 (6)	0.0337 (7)	0.0220 (6)	−0.0038 (5)	−0.0007 (5)	0.0087 (5)
C25D	0.0379 (7)	0.0259 (6)	0.0245 (6)	0.0004 (5)	0.0047 (5)	0.0014 (5)
C26D	0.0315 (6)	0.0285 (6)	0.0272 (6)	0.0055 (5)	0.0030 (5)	0.0086 (5)
N1D	0.0273 (5)	0.0240 (5)	0.0198 (5)	0.0033 (4)	0.0021 (4)	0.0046 (4)
N3D	0.0270 (5)	0.0280 (5)	0.0206 (5)	0.0039 (4)	0.0010 (4)	0.0081 (4)
C2E	0.0270 (6)	0.0272 (6)	0.0244 (6)	0.0076 (5)	−0.0002 (5)	0.0055 (5)
C4E	0.0273 (6)	0.0237 (6)	0.0249 (6)	0.0063 (4)	0.0005 (5)	0.0069 (5)
C5E	0.0283 (6)	0.0208 (6)	0.0311 (6)	0.0020 (4)	−0.0011 (5)	0.0063 (5)
C6E	0.0252 (6)	0.0232 (6)	0.0278 (6)	0.0042 (4)	−0.0009 (5)	0.0012 (5)
C7E	0.0264 (6)	0.0258 (6)	0.0236 (6)	0.0049 (5)	0.0020 (5)	0.0031 (5)
C8E	0.0284 (6)	0.0221 (6)	0.0263 (6)	0.0019 (4)	0.0028 (5)	0.0042 (5)
C9E	0.0257 (6)	0.0216 (6)	0.0235 (6)	0.0051 (4)	−0.0002 (4)	0.0013 (4)
C10E	0.0356 (7)	0.0279 (6)	0.0307 (7)	0.0002 (5)	−0.0027 (5)	−0.0002 (5)
C11E	0.0391 (7)	0.0341 (7)	0.0247 (6)	−0.0013 (5)	0.0024 (5)	0.0042 (5)
C12E	0.0280 (6)	0.0343 (7)	0.0229 (6)	0.0069 (5)	−0.0010 (5)	0.0053 (5)
C13E	0.0287 (7)	0.0689 (11)	0.0289 (7)	0.0127 (7)	−0.0004 (5)	−0.0004 (7)
C21E	0.0261 (6)	0.0424 (7)	0.0268 (6)	0.0099 (5)	0.0018 (5)	0.0001 (5)
C22E	0.0304 (7)	0.0311 (7)	0.0363 (7)	0.0047 (5)	0.0009 (5)	−0.0025 (5)
C23E	0.0381 (7)	0.0342 (7)	0.0334 (7)	0.0093 (6)	0.0057 (6)	0.0077 (5)
C24E	0.0398 (7)	0.0395 (7)	0.0267 (7)	0.0097 (6)	0.0000 (5)	−0.0025 (5)
C25E	0.0475 (8)	0.0332 (7)	0.0413 (8)	−0.0030 (6)	0.0033 (6)	−0.0043 (6)
C26E	0.0451 (8)	0.0409 (8)	0.0371 (8)	0.0017 (6)	0.0079 (6)	0.0100 (6)
N3E	0.0329 (6)	0.0277 (5)	0.0248 (5)	0.0052 (4)	−0.0012 (4)	0.0078 (4)
N1E	0.0299 (5)	0.0228 (5)	0.0231 (5)	0.0024 (4)	−0.0009 (4)	0.0019 (4)
O1W	0.0380 (6)	0.0361 (6)	0.0721 (8)	0.0011 (4)	−0.0015 (5)	0.0293 (5)
O2W	0.0428 (6)	0.0222 (5)	0.0561 (7)	0.0084 (4)	−0.0212 (5)	−0.0049 (4)

Geometric parameters (Å, º)

C4A—C5A	1.3966 (16)	C23C—H15C	0.9500
C4A—N3A	1.3976 (15)	C24C—C25C	1.3863 (18)
C4A—C9A	1.4004 (16)	C24C—H16C	0.9500
C5A—C6A	1.3891 (16)	C25C—C26C	1.3878 (17)
C5A—H2A	0.9500	C25C—H17C	0.9500
C6A—C7A	1.4225 (17)	C26C—H18C	0.9500
C6A—C10A	1.5080 (16)	N1C—H1C	0.8800
C7A—C8A	1.3888 (17)	C2D—N3D	1.3253 (16)
C7A—C11A	1.5119 (16)	C2D—N1D	1.3594 (15)
C8A—C9A	1.3928 (16)	C2D—C12D	1.4951 (16)
C8A—H3A	0.9500	C4D—C5D	1.3972 (17)
C9A—N1A	1.3813 (15)	C4D—C9D	1.3983 (16)
C10A—H4A	0.9800	C4D—N3D	1.3992 (15)
C10A—H5A	0.9800	C5D—C6D	1.3869 (16)
C10A—H6A	0.9800	C5D—H2D	0.9500
C11A—H7A	0.9800	C6D—C7D	1.4206 (17)
C11A—H8A	0.9800	C6D—C10D	1.5089 (17)
C11A—H9A	0.9800	C7D—C8D	1.3905 (17)
C2A—N3A	1.3127 (16)	C7D—C11D	1.5081 (16)
C2A—N1A	1.3548 (16)	C8D—C9D	1.3933 (16)
C2A—C12A	1.5240 (9)	C8D—H3D	0.9500
C2A—C12B	1.5310 (10)	C9D—N1D	1.3853 (15)
C12A—C13A	1.524 (3)	C10D—H4D	0.9800
C12A—H10A	0.9900	C10D—H5D	0.9800
C12A—H11A	0.9900	C10D—H6D	0.9800
C13A—C21A	1.510 (2)	C11D—H7D	0.9800
C13A—H12A	0.9900	C11D—H8D	0.9800
C13A—H13A	0.9900	C11D—H9D	0.9800
C12B—C13B	1.503 (9)	C12D—C13D	1.5278 (17)
C12B—H10B	0.9900	C12D—H10D	0.9900
C12B—H11B	0.9900	C12D—H11D	0.9900
C13B—C21B	1.524 (7)	C13D—C21D	1.5125 (16)
C13B—H12B	0.9900	C13D—H12D	0.9900
C13B—H13B	0.9900	C13D—H13D	0.9900
C21A—C26A	1.390 (2)	C21D—C22D	1.3891 (18)
C21A—C22A	1.391 (3)	C21D—C26D	1.3923 (17)
C22A—C23A	1.394 (2)	C22D—C23D	1.3900 (18)
C22A—H14A	0.9500	C22D—H14D	0.9500
C23A—C24A	1.384 (3)	C23D—C24D	1.3856 (18)
C23A—H15A	0.9500	C23D—H15D	0.9500
C24A—C25A	1.384 (3)	C24D—C25D	1.3825 (18)
C24A—H16A	0.9500	C24D—H16D	0.9500
C25A—C26A	1.397 (3)	C25D—C26D	1.3919 (18)
C25A—H17A	0.9500	C25D—H17D	0.9500
C26A—H18A	0.9500	C26D—H18D	0.9500
C21B—C22B	1.380 (6)	N1D—H1D	0.8800
C21B—C26B	1.402 (6)	C2E—N3E	1.3236 (17)
C22B—C23B	1.384 (6)	C2E—N1E	1.3572 (16)
C22B—H14B	0.9500	C2E—C12E	1.4942 (17)
C23B—C24B	1.380 (6)	C4E—N3E	1.3984 (15)
C23B—H15B	0.9500	C4E—C5E	1.3991 (17)
C24B—C25B	1.388 (7)	C4E—C9E	1.3992 (17)
C24B—H16B	0.9500	C5E—C6E	1.3873 (18)
C25B—C26B	1.391 (6)	C5E—H2E	0.9500
C25B—H17B	0.9500	C6E—C7E	1.4219 (17)
C26B—H18B	0.9500	C6E—C10E	1.5101 (17)
N1A—H1A	0.8800	C7E—C8E	1.3899 (17)
C2C—N3C	1.3220 (16)	C7E—C11E	1.5083 (17)
C2C—N1C	1.3577 (15)	C8E—C9E	1.3914 (17)
C2C—C12C	1.4950 (16)	C8E—H3E	0.9500
C4C—N3C	1.3943 (15)	C9E—N1E	1.3845 (15)
C4C—C5C	1.3968 (17)	C10E—H4E	0.9800
C4C—C9C	1.3986 (17)	C10E—H5E	0.9800
C5C—C6C	1.3871 (17)	C10E—H6E	0.9800
C5C—H2C	0.9500	C11E—H7E	0.9800
C6C—C7C	1.4198 (17)	C11E—H8E	0.9800
C6C—C10C	1.5082 (16)	C11E—H9E	0.9800
C7C—C8C	1.3861 (17)	C12E—C13E	1.5328 (18)
C7C—C11C	1.5062 (16)	C12E—H10E	0.9900
C8C—C9C	1.3950 (17)	C12E—H11E	0.9900
C8C—H3C	0.9500	C13E—C21E	1.5117 (18)
C9C—N1C	1.3837 (15)	C13E—H12E	0.9900
C10C—H4C	0.9800	C13E—H13E	0.9900
C10C—H5C	0.9800	C21E—C22E	1.383 (2)
C10C—H6C	0.9800	C21E—C26E	1.389 (2)
C11C—H7C	0.9800	C22E—C23E	1.3890 (19)
C11C—H8C	0.9800	C22E—H14E	0.9500
C11C—H9C	0.9800	C23E—C24E	1.377 (2)
C12C—C13C	1.5229 (16)	C23E—H15E	0.9500
C12C—H10C	0.9900	C24E—C25E	1.380 (2)
C12C—H11C	0.9900	C24E—H16E	0.9500
C13C—C21C	1.5102 (16)	C25E—C26E	1.389 (2)
C13C—H12C	0.9900	C25E—H17E	0.9500
C13C—H13C	0.9900	C26E—H18E	0.9500
C21C—C22C	1.3890 (17)	N1E—H1E	0.8800
C21C—C26C	1.3922 (17)	O1W—H1W1	0.90 (2)
C22C—C23C	1.3887 (18)	O1W—H1W2	0.88 (2)
C22C—H14C	0.9500	O2W—H2W1	0.87 (2)
C23C—C24C	1.3815 (19)	O2W—H2W2	0.91 (2)
C5A—C4A—N3A	130.71 (11)	C24C—C23C—H15C	120.1
C5A—C4A—C9A	119.73 (11)	C22C—C23C—H15C	120.1
N3A—C4A—C9A	109.55 (10)	C23C—C24C—C25C	119.85 (11)
C6A—C5A—C4A	119.21 (11)	C23C—C24C—H16C	120.1
C6A—C5A—H2A	120.4	C25C—C24C—H16C	120.1
C4A—C5A—H2A	120.4	C24C—C25C—C26C	120.13 (11)
C5A—C6A—C7A	120.34 (11)	C24C—C25C—H17C	119.9
C5A—C6A—C10A	119.78 (11)	C26C—C25C—H17C	119.9
C7A—C6A—C10A	119.88 (10)	C25C—C26C—C21C	120.53 (11)
C8A—C7A—C6A	120.61 (11)	C25C—C26C—H18C	119.7
C8A—C7A—C11A	119.66 (11)	C21C—C26C—H18C	119.7
C6A—C7A—C11A	119.71 (11)	C2C—N1C—C9C	107.08 (10)
C7A—C8A—C9A	118.09 (11)	C2C—N1C—H1C	126.5
C7A—C8A—H3A	121.0	C9C—N1C—H1C	126.5
C9A—C8A—H3A	121.0	C2C—N3C—C4C	104.90 (10)
N1A—C9A—C8A	132.64 (11)	N3D—C2D—N1D	112.96 (10)
N1A—C9A—C4A	105.34 (10)	N3D—C2D—C12D	126.01 (11)
C8A—C9A—C4A	122.01 (11)	N1D—C2D—C12D	120.83 (11)
C6A—C10A—H4A	109.5	C5D—C4D—C9D	119.95 (11)
C6A—C10A—H5A	109.5	C5D—C4D—N3D	130.19 (11)
H4A—C10A—H5A	109.5	C9D—C4D—N3D	109.84 (10)
C6A—C10A—H6A	109.5	C6D—C5D—C4D	119.03 (11)
H4A—C10A—H6A	109.5	C6D—C5D—H2D	120.5
H5A—C10A—H6A	109.5	C4D—C5D—H2D	120.5
C7A—C11A—H7A	109.5	C5D—C6D—C7D	120.57 (11)
C7A—C11A—H8A	109.5	C5D—C6D—C10D	120.07 (11)
H7A—C11A—H8A	109.5	C7D—C6D—C10D	119.35 (11)
C7A—C11A—H9A	109.5	C8D—C7D—C6D	120.40 (11)
H7A—C11A—H9A	109.5	C8D—C7D—C11D	120.19 (11)
H8A—C11A—H9A	109.5	C6D—C7D—C11D	119.40 (11)
N3A—C2A—N1A	113.71 (10)	C7D—C8D—C9D	118.23 (11)
N3A—C2A—C12A	126.89 (13)	C7D—C8D—H3D	120.9
N1A—C2A—C12A	119.15 (13)	C9D—C8D—H3D	120.9
N3A—C2A—C12B	117.3 (3)	N1D—C9D—C8D	132.95 (11)
N1A—C2A—C12B	125.7 (3)	N1D—C9D—C4D	105.27 (10)
C13A—C12A—C2A	110.43 (14)	C8D—C9D—C4D	121.77 (11)
C13A—C12A—H10A	109.6	C6D—C10D—H4D	109.5
C2A—C12A—H10A	109.6	C6D—C10D—H5D	109.5
C13A—C12A—H11A	109.6	H4D—C10D—H5D	109.5
C2A—C12A—H11A	109.6	C6D—C10D—H6D	109.5
H10A—C12A—H11A	108.1	H4D—C10D—H6D	109.5
C21A—C13A—C12A	110.86 (13)	H5D—C10D—H6D	109.5
C21A—C13A—H12A	109.5	C7D—C11D—H7D	109.5
C12A—C13A—H12A	109.5	C7D—C11D—H8D	109.5
C21A—C13A—H13A	109.5	H7D—C11D—H8D	109.5
C12A—C13A—H13A	109.5	C7D—C11D—H9D	109.5
H12A—C13A—H13A	108.1	H7D—C11D—H9D	109.5
C13B—C12B—C2A	114.1 (4)	H8D—C11D—H9D	109.5
C13B—C12B—H10B	108.7	C2D—C12D—C13D	114.51 (11)
C2A—C12B—H10B	108.7	C2D—C12D—H10D	108.6
C13B—C12B—H11B	108.7	C13D—C12D—H10D	108.6
C2A—C12B—H11B	108.7	C2D—C12D—H11D	108.6
H10B—C12B—H11B	107.6	C13D—C12D—H11D	108.6
C12B—C13B—C21B	118.1 (4)	H10D—C12D—H11D	107.6
C12B—C13B—H12B	107.8	C21D—C13D—C12D	111.82 (10)
C21B—C13B—H12B	107.8	C21D—C13D—H12D	109.3
C12B—C13B—H13B	107.8	C12D—C13D—H12D	109.3
C21B—C13B—H13B	107.8	C21D—C13D—H13D	109.3
H12B—C13B—H13B	107.1	C12D—C13D—H13D	109.3
C26A—C21A—C22A	118.35 (15)	H12D—C13D—H13D	107.9
C26A—C21A—C13A	121.79 (18)	C22D—C21D—C26D	118.51 (11)
C22A—C21A—C13A	119.86 (17)	C22D—C21D—C13D	120.43 (11)
C21A—C22A—C23A	121.05 (17)	C26D—C21D—C13D	121.05 (11)
C21A—C22A—H14A	119.5	C21D—C22D—C23D	121.02 (12)
C23A—C22A—H14A	119.5	C21D—C22D—H14D	119.5
C24A—C23A—C22A	120.08 (18)	C23D—C22D—H14D	119.5
C24A—C23A—H15A	120.0	C24D—C23D—C22D	120.04 (12)
C22A—C23A—H15A	120.0	C24D—C23D—H15D	120.0
C25A—C24A—C23A	119.46 (19)	C22D—C23D—H15D	120.0
C25A—C24A—H16A	120.3	C25D—C24D—C23D	119.45 (12)
C23A—C24A—H16A	120.3	C25D—C24D—H16D	120.3
C24A—C25A—C26A	120.3 (2)	C23D—C24D—H16D	120.3
C24A—C25A—H17A	119.8	C24D—C25D—C26D	120.50 (12)
C26A—C25A—H17A	119.8	C24D—C25D—H17D	119.8
C21A—C26A—C25A	120.72 (18)	C26D—C25D—H17D	119.8
C21A—C26A—H18A	119.6	C25D—C26D—C21D	120.47 (12)
C25A—C26A—H18A	119.6	C25D—C26D—H18D	119.8
C22B—C21B—C26B	118.4 (4)	C21D—C26D—H18D	119.8
C22B—C21B—C13B	120.9 (5)	C2D—N1D—C9D	107.25 (10)
C26B—C21B—C13B	120.6 (5)	C2D—N1D—H1D	126.4
C21B—C22B—C23B	121.1 (5)	C9D—N1D—H1D	126.4
C21B—C22B—H14B	119.4	C2D—N3D—C4D	104.68 (10)
C23B—C22B—H14B	119.4	N3E—C2E—N1E	113.26 (11)
C24B—C23B—C22B	120.3 (5)	N3E—C2E—C12E	125.15 (11)
C24B—C23B—H15B	119.8	N1E—C2E—C12E	121.57 (11)
C22B—C23B—H15B	119.8	N3E—C4E—C5E	130.85 (11)
C23B—C24B—C25B	119.8 (5)	N3E—C4E—C9E	109.68 (11)
C23B—C24B—H16B	120.1	C5E—C4E—C9E	119.48 (11)
C25B—C24B—H16B	120.1	C6E—C5E—C4E	119.01 (11)
C24B—C25B—C26B	119.6 (5)	C6E—C5E—H2E	120.5
C24B—C25B—H17B	120.2	C4E—C5E—H2E	120.5
C26B—C25B—H17B	120.2	C5E—C6E—C7E	120.76 (11)
C25B—C26B—C21B	120.7 (5)	C5E—C6E—C10E	119.39 (11)
C25B—C26B—H18B	119.6	C7E—C6E—C10E	119.85 (11)
C21B—C26B—H18B	119.6	C8E—C7E—C6E	120.37 (11)
C2A—N1A—C9A	106.82 (10)	C8E—C7E—C11E	119.48 (11)
C2A—N1A—H1A	126.6	C6E—C7E—C11E	120.15 (11)
C9A—N1A—H1A	126.6	C7E—C8E—C9E	117.93 (11)
C2A—N3A—C4A	104.56 (10)	C7E—C8E—H3E	121.0
N3C—C2C—N1C	112.99 (11)	C9E—C8E—H3E	121.0
N3C—C2C—C12C	124.76 (11)	N1E—C9E—C8E	132.12 (11)
N1C—C2C—C12C	122.24 (11)	N1E—C9E—C4E	105.44 (10)
N3C—C4C—C5C	129.84 (11)	C8E—C9E—C4E	122.43 (11)
N3C—C4C—C9C	109.65 (10)	C6E—C10E—H4E	109.5
C5C—C4C—C9C	120.50 (11)	C6E—C10E—H5E	109.5
C6C—C5C—C4C	118.97 (11)	H4E—C10E—H5E	109.5
C6C—C5C—H2C	120.5	C6E—C10E—H6E	109.5
C4C—C5C—H2C	120.5	H4E—C10E—H6E	109.5
C5C—C6C—C7C	120.08 (11)	H5E—C10E—H6E	109.5
C5C—C6C—C10C	119.79 (11)	C7E—C11E—H7E	109.5
C7C—C6C—C10C	120.13 (11)	C7E—C11E—H8E	109.5
C8C—C7C—C6C	120.98 (11)	H7E—C11E—H8E	109.5
C8C—C7C—C11C	119.47 (11)	C7E—C11E—H9E	109.5
C6C—C7C—C11C	119.53 (11)	H7E—C11E—H9E	109.5
C7C—C8C—C9C	118.31 (11)	H8E—C11E—H9E	109.5
C7C—C8C—H3C	120.8	C2E—C12E—C13E	111.47 (10)
C9C—C8C—H3C	120.8	C2E—C12E—H10E	109.3
N1C—C9C—C8C	133.50 (11)	C13E—C12E—H10E	109.3
N1C—C9C—C4C	105.38 (10)	C2E—C12E—H11E	109.3
C8C—C9C—C4C	121.11 (11)	C13E—C12E—H11E	109.3
C6C—C10C—H4C	109.5	H10E—C12E—H11E	108.0
C6C—C10C—H5C	109.5	C21E—C13E—C12E	112.89 (11)
H4C—C10C—H5C	109.5	C21E—C13E—H12E	109.0
C6C—C10C—H6C	109.5	C12E—C13E—H12E	109.0
H4C—C10C—H6C	109.5	C21E—C13E—H13E	109.0
H5C—C10C—H6C	109.5	C12E—C13E—H13E	109.0
C7C—C11C—H7C	109.5	H12E—C13E—H13E	107.8
C7C—C11C—H8C	109.5	C22E—C21E—C26E	118.04 (13)
H7C—C11C—H8C	109.5	C22E—C21E—C13E	120.57 (13)
C7C—C11C—H9C	109.5	C26E—C21E—C13E	121.39 (14)
H7C—C11C—H9C	109.5	C21E—C22E—C23E	121.25 (13)
H8C—C11C—H9C	109.5	C21E—C22E—H14E	119.4
C2C—C12C—C13C	112.26 (10)	C23E—C22E—H14E	119.4
C2C—C12C—H10C	109.2	C24E—C23E—C22E	120.13 (13)
C13C—C12C—H10C	109.2	C24E—C23E—H15E	119.9
C2C—C12C—H11C	109.2	C22E—C23E—H15E	119.9
C13C—C12C—H11C	109.2	C23E—C24E—C25E	119.42 (13)
H10C—C12C—H11C	107.9	C23E—C24E—H16E	120.3
C21C—C13C—C12C	112.82 (10)	C25E—C24E—H16E	120.3
C21C—C13C—H12C	109.0	C24E—C25E—C26E	120.29 (14)
C12C—C13C—H12C	109.0	C24E—C25E—H17E	119.9
C21C—C13C—H13C	109.0	C26E—C25E—H17E	119.9
C12C—C13C—H13C	109.0	C21E—C26E—C25E	120.87 (14)
H12C—C13C—H13C	107.8	C21E—C26E—H18E	119.6
C22C—C21C—C26C	118.66 (11)	C25E—C26E—H18E	119.6
C22C—C21C—C13C	120.61 (11)	C2E—N3E—C4E	104.61 (10)
C26C—C21C—C13C	120.73 (11)	C2E—N1E—C9E	106.99 (10)
C23C—C22C—C21C	120.93 (11)	C2E—N1E—H1E	126.5
C23C—C22C—H14C	119.5	C9E—N1E—H1E	126.5
C21C—C22C—H14C	119.5	H1W1—O1W—H1W2	102.2 (17)
C24C—C23C—C22C	119.89 (12)	H2W1—O2W—H2W2	111.0 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1W	0.88	1.97	2.8486 (15)	172
N1C—H1C···N3E^i	0.88	2.07	2.9370 (14)	169
N1D—H1D···N3A	0.88	2.05	2.9201 (15)	168
N1E—H1E···O2W^ii	0.88	1.89	2.7610 (15)	170
O1W—H1W1···N3C^ii	0.90 (2)	2.57 (2)	3.2720 (16)	135.9 (15)
O1W—H1W2···N3D^iii	0.88 (2)	1.99 (2)	2.8711 (15)	176.1 (19)
O2W—H2W1···N3D	0.87 (2)	2.17 (2)	2.9945 (14)	157.2 (18)
O2W—H2W2···N3C^iv	0.91 (2)	1.86 (2)	2.7619 (14)	179 (2)

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

5,6-Dimethyl-2-phenylethylbenzo[d]imidazole methanol hemisolvate (2a)

Crystal data

2C17H16N2·CH4O	F(000) = 1128
Mr = 528.63	Dx = 1.220 Mg m^−3
Monoclinic, Cc	Cu Kα radiation, λ = 1.54184 Å
a = 13.095 (3) Å	Cell parameters from 4004 reflections
b = 9.2984 (19) Å	θ = 3.7–75.6°
c = 23.685 (5) Å	µ = 0.58 mm^−1
β = 93.95 (3)°	T = 293 K
V = 2877.1 (11) Å^3	Prism, yellow
Z = 4	0.43 × 0.28 × 0.22 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 300K diffractometer	3033 reflections with I > 2σ(I)
ω scan	Rint = 0.022
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	θmax = 78.8°, θmin = 3.7°
Tmin = 0.653, Tmax = 1.000	h = −12→16
7321 measured reflections	k = −11→11
3571 independent reflections	l = −29→22

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.1084P)^2 + 0.1424P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.156	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.21 e Å^−3
3571 reflections	Δρmin = −0.25 e Å^−3
367 parameters	Absolute structure: Flack x determined using 591 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraints	Absolute structure parameter: 0.1 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C2A	0.4774 (3)	0.8916 (4)	0.35430 (15)	0.0697 (8)
C4A	0.4418 (3)	0.6881 (4)	0.31217 (15)	0.0638 (8)
C5A	0.4328 (3)	0.5671 (4)	0.27716 (16)	0.0701 (8)
H2A	0.4658	0.5647	0.2436	0.084*
C6A	0.3757 (3)	0.4527 (4)	0.29223 (16)	0.0710 (9)
C7A	0.3250 (3)	0.4543 (4)	0.34378 (17)	0.0718 (9)
C8A	0.3348 (3)	0.5736 (4)	0.37908 (17)	0.0728 (9)
H3A	0.3022	0.5763	0.4127	0.087*
C9A	0.3940 (3)	0.6889 (4)	0.36319 (15)	0.0657 (8)
C10A	0.3658 (4)	0.3215 (5)	0.2552 (2)	0.0939 (13)
H6A	0.4071	0.3332	0.2236	0.141*
H4A	0.2955	0.3092	0.2417	0.141*
H5A	0.3883	0.2384	0.2766	0.141*
C11A	0.2634 (3)	0.3277 (5)	0.3605 (2)	0.0862 (11)
H9A	0.2295	0.3507	0.3941	0.129*
H8A	0.3078	0.2468	0.3679	0.129*
H7A	0.2132	0.3046	0.3304	0.129*
C12A	0.5165 (3)	1.0326 (4)	0.36531 (16)	0.0725 (9)
H10A	0.5589	1.0720	0.3395	0.087*
C13A	0.4962 (3)	1.1129 (4)	0.41075 (16)	0.0719 (9)
H11A	0.4557	1.0694	0.4367	0.086*
C21A	0.5296 (3)	1.2589 (4)	0.42421 (18)	0.0800 (10)
C22A	0.4931 (4)	1.3237 (6)	0.4707 (2)	0.0979 (14)
H12A	0.4512	1.2713	0.4933	0.118*
C23A	0.5165 (7)	1.4633 (8)	0.4851 (3)	0.129 (2)
H13A	0.4906	1.5048	0.5169	0.155*
C24A	0.5787 (7)	1.5413 (7)	0.4521 (4)	0.141 (3)
H14A	0.5945	1.6364	0.4612	0.169*
C25A	0.6176 (6)	1.4787 (7)	0.4057 (4)	0.132 (2)
H15A	0.6605	1.5311	0.3837	0.159*
C26A	0.5930 (5)	1.3377 (5)	0.3914 (2)	0.1010 (14)
H16A	0.6192	1.2959	0.3598	0.121*
N1A	0.4184 (3)	0.8186 (3)	0.38904 (14)	0.0737 (8)
H1A	0.3996	0.8475	0.4212	0.088*
N3A	0.4938 (2)	0.8169 (3)	0.30712 (13)	0.0689 (7)
C2B	0.4716 (3)	1.0377 (4)	0.65581 (15)	0.0681 (8)
C4B	0.5332 (3)	0.8203 (4)	0.64907 (15)	0.0664 (8)
C5B	0.5572 (3)	0.6804 (4)	0.63341 (17)	0.0778 (10)
H2B	0.5296	0.6421	0.5994	0.093*
C6B	0.6214 (3)	0.6006 (4)	0.66836 (18)	0.0752 (9)
C7B	0.6662 (3)	0.6593 (4)	0.72012 (17)	0.0705 (8)
C8B	0.6425 (3)	0.7977 (4)	0.73512 (16)	0.0699 (8)
H3B	0.6715	0.8375	0.7685	0.084*
C9B	0.5750 (3)	0.8770 (4)	0.70000 (15)	0.0663 (8)
C10B	0.6486 (4)	0.4468 (5)	0.6525 (2)	0.0969 (14)
H4B	0.6260	0.4291	0.6137	0.145*
H5B	0.6156	0.3805	0.6765	0.145*
H6B	0.7214	0.4339	0.6575	0.145*
C11B	0.7362 (3)	0.5690 (5)	0.7580 (2)	0.0873 (11)
H9B	0.7622	0.6254	0.7898	0.131*
H8B	0.7922	0.5356	0.7374	0.131*
H7B	0.6991	0.4880	0.7712	0.131*
C12B	0.4167 (3)	1.1684 (4)	0.64617 (17)	0.0745 (9)
H10B	0.4226	1.2390	0.6741	0.089*
C13B	0.3572 (3)	1.1956 (4)	0.59948 (17)	0.0744 (9)
H11B	0.3541	1.1244	0.5718	0.089*
C21B	0.2960 (3)	1.3255 (5)	0.58684 (18)	0.0775 (10)
C22B	0.2358 (4)	1.3341 (6)	0.5377 (2)	0.0980 (14)
H12B	0.2357	1.2568	0.5129	0.118*
C23B	0.1755 (4)	1.4500 (8)	0.5230 (3)	0.1119 (18)
H13B	0.1362	1.4513	0.4887	0.134*
C24B	0.1738 (6)	1.5620 (9)	0.5587 (3)	0.131 (2)
H14B	0.1320	1.6406	0.5496	0.157*
C25B	0.2341 (6)	1.5609 (7)	0.6091 (3)	0.128 (2)
H15B	0.2341	1.6390	0.6337	0.153*
C26B	0.2942 (4)	1.4417 (5)	0.6222 (2)	0.0958 (14)
H16B	0.3347	1.4404	0.6561	0.115*
N1B	0.5347 (2)	1.0147 (3)	0.70379 (13)	0.0698 (7)
H1B	0.5470	1.0744	0.7311	0.084*
N3B	0.4695 (3)	0.9212 (3)	0.62176 (13)	0.0735 (8)
O1S	0.3909 (3)	0.8798 (5)	0.50739 (13)	0.1082 (11)
H1S	0.4191	0.9063	0.5376	0.162*
C1S	0.3080 (5)	0.8202 (13)	0.5161 (4)	0.186 (5)
H4S	0.2641	0.8214	0.4819	0.280*
H3S	0.2755	0.8710	0.5453	0.280*
H2S	0.3205	0.7226	0.5277	0.280*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2A	0.074 (2)	0.077 (2)	0.0562 (17)	−0.0041 (16)	−0.0068 (14)	0.0104 (16)
C4A	0.0671 (17)	0.0656 (18)	0.0576 (17)	−0.0040 (14)	−0.0046 (13)	0.0073 (14)
C5A	0.074 (2)	0.075 (2)	0.0596 (17)	0.0024 (17)	−0.0021 (15)	−0.0009 (15)
C6A	0.075 (2)	0.0688 (19)	0.068 (2)	0.0030 (16)	−0.0067 (16)	−0.0011 (16)
C7A	0.072 (2)	0.0658 (19)	0.075 (2)	−0.0025 (15)	−0.0112 (16)	0.0092 (17)
C8A	0.079 (2)	0.074 (2)	0.0643 (19)	−0.0026 (17)	0.0033 (16)	0.0051 (16)
C9A	0.0750 (19)	0.0639 (18)	0.0572 (16)	−0.0023 (15)	−0.0030 (14)	0.0040 (14)
C10A	0.108 (3)	0.074 (2)	0.100 (3)	−0.005 (2)	0.003 (3)	−0.011 (2)
C11A	0.082 (3)	0.078 (2)	0.098 (3)	−0.0131 (19)	0.000 (2)	0.003 (2)
C12A	0.081 (2)	0.073 (2)	0.0626 (19)	−0.0069 (17)	−0.0029 (16)	0.0075 (16)
C13A	0.077 (2)	0.0715 (19)	0.0655 (19)	−0.0021 (16)	−0.0086 (16)	0.0105 (17)
C21A	0.091 (2)	0.071 (2)	0.074 (2)	0.0020 (18)	−0.0241 (19)	0.0016 (18)
C22A	0.118 (4)	0.102 (3)	0.070 (2)	0.014 (3)	−0.018 (2)	−0.010 (2)
C23A	0.159 (6)	0.110 (4)	0.110 (4)	0.028 (4)	−0.041 (4)	−0.040 (4)
C24A	0.165 (6)	0.086 (3)	0.160 (7)	−0.002 (4)	−0.072 (6)	−0.037 (4)
C25A	0.163 (6)	0.088 (3)	0.141 (5)	−0.034 (4)	−0.022 (5)	−0.007 (4)
C26A	0.121 (4)	0.082 (3)	0.100 (3)	−0.025 (3)	0.002 (3)	0.005 (2)
N1A	0.088 (2)	0.0744 (18)	0.0584 (15)	−0.0080 (14)	0.0048 (14)	0.0021 (13)
N3A	0.0741 (17)	0.0728 (17)	0.0587 (15)	−0.0056 (13)	−0.0033 (12)	0.0073 (13)
C2B	0.079 (2)	0.071 (2)	0.0546 (16)	0.0029 (16)	0.0021 (14)	−0.0060 (15)
C4B	0.078 (2)	0.0621 (17)	0.0584 (17)	0.0030 (15)	0.0038 (15)	−0.0083 (14)
C5B	0.095 (3)	0.072 (2)	0.065 (2)	0.0040 (19)	0.0008 (18)	−0.0132 (17)
C6B	0.084 (2)	0.067 (2)	0.075 (2)	0.0059 (17)	0.0106 (17)	−0.0058 (17)
C7B	0.071 (2)	0.0686 (19)	0.072 (2)	0.0047 (15)	0.0024 (15)	−0.0005 (16)
C8B	0.073 (2)	0.0701 (18)	0.0653 (19)	0.0013 (16)	−0.0032 (15)	−0.0037 (15)
C9B	0.0752 (19)	0.0634 (17)	0.0600 (17)	0.0041 (15)	0.0029 (14)	−0.0045 (14)
C10B	0.118 (4)	0.072 (2)	0.101 (3)	0.017 (2)	0.008 (3)	−0.016 (2)
C11B	0.085 (3)	0.078 (2)	0.097 (3)	0.012 (2)	−0.007 (2)	0.003 (2)
C12B	0.085 (2)	0.073 (2)	0.0647 (19)	0.0027 (17)	0.0004 (17)	−0.0069 (16)
C13B	0.084 (2)	0.072 (2)	0.067 (2)	0.0066 (17)	−0.0016 (16)	0.0025 (16)
C21B	0.079 (2)	0.083 (2)	0.070 (2)	0.0057 (18)	0.0012 (17)	0.0060 (18)
C22B	0.093 (3)	0.115 (3)	0.082 (3)	0.013 (3)	−0.018 (2)	0.008 (2)
C23B	0.099 (3)	0.137 (5)	0.096 (4)	0.021 (3)	−0.019 (3)	0.024 (3)
C24B	0.140 (5)	0.142 (5)	0.109 (4)	0.066 (4)	−0.002 (4)	0.035 (4)
C25B	0.160 (5)	0.112 (4)	0.109 (4)	0.063 (4)	−0.009 (4)	0.003 (3)
C26B	0.120 (4)	0.087 (3)	0.078 (3)	0.032 (2)	−0.010 (2)	−0.001 (2)
N1B	0.0840 (18)	0.0671 (16)	0.0567 (14)	0.0056 (14)	−0.0066 (13)	−0.0076 (13)
N3B	0.087 (2)	0.0758 (18)	0.0560 (15)	0.0036 (15)	−0.0086 (13)	−0.0082 (13)
O1S	0.124 (3)	0.136 (3)	0.0637 (16)	−0.019 (2)	0.0014 (17)	−0.0102 (18)
C1S	0.167 (8)	0.267 (13)	0.127 (6)	−0.057 (8)	0.018 (5)	−0.043 (7)

Geometric parameters (Å, º)

C2A—N3A	1.345 (5)	C4B—N3B	1.386 (5)
C2A—N1A	1.349 (5)	C4B—C9B	1.393 (5)
C2A—C12A	1.425 (5)	C4B—C5B	1.395 (5)
C4A—N3A	1.387 (4)	C5B—C6B	1.359 (6)
C4A—C5A	1.398 (5)	C5B—H2B	0.9300
C4A—C9A	1.399 (5)	C6B—C7B	1.431 (6)
C5A—C6A	1.362 (5)	C6B—C10B	1.527 (6)
C5A—H2A	0.9300	C7B—C8B	1.376 (5)
C6A—C7A	1.429 (6)	C7B—C11B	1.495 (5)
C6A—C10A	1.504 (6)	C8B—C9B	1.384 (5)
C7A—C8A	1.389 (5)	C8B—H3B	0.9300
C7A—C11A	1.497 (5)	C9B—N1B	1.390 (5)
C8A—C9A	1.390 (5)	C10B—H4B	0.9600
C8A—H3A	0.9300	C10B—H5B	0.9600
C9A—N1A	1.381 (5)	C10B—H6B	0.9600
C10A—H6A	0.9600	C11B—H9B	0.9600
C10A—H4A	0.9600	C11B—H8B	0.9600
C10A—H5A	0.9600	C11B—H7B	0.9600
C11A—H9A	0.9600	C12B—C13B	1.332 (5)
C11A—H8A	0.9600	C12B—H10B	0.9300
C11A—H7A	0.9600	C13B—C21B	1.469 (5)
C12A—C13A	1.352 (6)	C13B—H11B	0.9300
C12A—H10A	0.9300	C21B—C22B	1.361 (6)
C13A—C21A	1.455 (6)	C21B—C26B	1.368 (6)
C13A—H11A	0.9300	C22B—C23B	1.367 (8)
C21A—C22A	1.370 (7)	C22B—H12B	0.9300
C21A—C26A	1.385 (7)	C23B—C24B	1.344 (10)
C22A—C23A	1.372 (9)	C23B—H13B	0.9300
C22A—H12A	0.9300	C24B—C25B	1.384 (9)
C23A—C24A	1.373 (12)	C24B—H14B	0.9300
C23A—H13A	0.9300	C25B—C26B	1.383 (7)
C24A—C25A	1.372 (13)	C25B—H15B	0.9300
C24A—H14A	0.9300	C26B—H16B	0.9300
C25A—C26A	1.386 (8)	N1B—H1B	0.8600
C25A—H15A	0.9300	O1S—C1S	1.2492 (12)
C26A—H16A	0.9300	O1S—H1S	0.8200
N1A—H1A	0.8600	C1S—H4S	0.9600
C2B—N3B	1.350 (5)	C1S—H3S	0.9600
C2B—N1B	1.375 (5)	C1S—H2S	0.9600
C2B—C12B	1.423 (5)
N3A—C2A—N1A	112.2 (3)	N3B—C4B—C5B	130.3 (3)
N3A—C2A—C12A	123.4 (3)	C9B—C4B—C5B	120.0 (3)
N1A—C2A—C12A	124.4 (4)	C6B—C5B—C4B	119.3 (4)
N3A—C4A—C5A	131.7 (3)	C6B—C5B—H2B	120.4
N3A—C4A—C9A	108.8 (3)	C4B—C5B—H2B	120.4
C5A—C4A—C9A	119.5 (3)	C5B—C6B—C7B	120.9 (3)
C6A—C5A—C4A	119.9 (4)	C5B—C6B—C10B	120.5 (4)
C6A—C5A—H2A	120.1	C7B—C6B—C10B	118.6 (4)
C4A—C5A—H2A	120.1	C8B—C7B—C6B	119.4 (3)
C5A—C6A—C7A	120.8 (3)	C8B—C7B—C11B	120.7 (4)
C5A—C6A—C10A	120.5 (4)	C6B—C7B—C11B	119.9 (3)
C7A—C6A—C10A	118.8 (4)	C7B—C8B—C9B	119.3 (3)
C8A—C7A—C6A	119.6 (3)	C7B—C8B—H3B	120.4
C8A—C7A—C11A	119.8 (4)	C9B—C8B—H3B	120.4
C6A—C7A—C11A	120.6 (4)	C8B—C9B—N1B	132.9 (3)
C9A—C8A—C7A	118.8 (4)	C8B—C9B—C4B	121.0 (3)
C9A—C8A—H3A	120.6	N1B—C9B—C4B	106.0 (3)
C7A—C8A—H3A	120.6	C6B—C10B—H4B	109.5
N1A—C9A—C8A	132.1 (4)	C6B—C10B—H5B	109.5
N1A—C9A—C4A	106.5 (3)	H4B—C10B—H5B	109.5
C8A—C9A—C4A	121.4 (3)	C6B—C10B—H6B	109.5
C6A—C10A—H6A	109.5	H4B—C10B—H6B	109.5
C6A—C10A—H4A	109.5	H5B—C10B—H6B	109.5
H6A—C10A—H4A	109.5	C7B—C11B—H9B	109.5
C6A—C10A—H5A	109.5	C7B—C11B—H8B	109.5
H6A—C10A—H5A	109.5	H9B—C11B—H8B	109.5
H4A—C10A—H5A	109.5	C7B—C11B—H7B	109.5
C7A—C11A—H9A	109.5	H9B—C11B—H7B	109.5
C7A—C11A—H8A	109.5	H8B—C11B—H7B	109.5
H9A—C11A—H8A	109.5	C13B—C12B—C2B	123.7 (4)
C7A—C11A—H7A	109.5	C13B—C12B—H10B	118.1
H9A—C11A—H7A	109.5	C2B—C12B—H10B	118.1
H8A—C11A—H7A	109.5	C12B—C13B—C21B	127.2 (4)
C13A—C12A—C2A	124.5 (4)	C12B—C13B—H11B	116.4
C13A—C12A—H10A	117.8	C21B—C13B—H11B	116.4
C2A—C12A—H10A	117.8	C22B—C21B—C26B	116.3 (4)
C12A—C13A—C21A	128.1 (4)	C22B—C21B—C13B	119.9 (4)
C12A—C13A—H11A	115.9	C26B—C21B—C13B	123.8 (4)
C21A—C13A—H11A	115.9	C21B—C22B—C23B	123.7 (5)
C22A—C21A—C26A	118.3 (5)	C21B—C22B—H12B	118.1
C22A—C21A—C13A	118.0 (5)	C23B—C22B—H12B	118.1
C26A—C21A—C13A	123.6 (4)	C24B—C23B—C22B	118.9 (5)
C21A—C22A—C23A	122.1 (7)	C24B—C23B—H13B	120.5
C21A—C22A—H12A	119.0	C22B—C23B—H13B	120.5
C23A—C22A—H12A	119.0	C23B—C24B—C25B	120.3 (5)
C22A—C23A—C24A	119.3 (7)	C23B—C24B—H14B	119.8
C22A—C23A—H13A	120.3	C25B—C24B—H14B	119.8
C24A—C23A—H13A	120.3	C24B—C25B—C26B	118.8 (6)
C25A—C24A—C23A	119.9 (5)	C24B—C25B—H15B	120.6
C25A—C24A—H14A	120.0	C26B—C25B—H15B	120.6
C23A—C24A—H14A	120.0	C21B—C26B—C25B	121.9 (5)
C24A—C25A—C26A	120.2 (8)	C21B—C26B—H16B	119.0
C24A—C25A—H15A	119.9	C25B—C26B—H16B	119.0
C26A—C25A—H15A	119.9	C2B—N1B—C9B	107.4 (3)
C21A—C26A—C25A	120.1 (6)	C2B—N1B—H1B	126.3
C21A—C26A—H16A	119.9	C9B—N1B—H1B	126.3
C25A—C26A—H16A	119.9	C2B—N3B—C4B	106.1 (3)
C2A—N1A—C9A	107.1 (3)	C1S—O1S—H1S	109.5
C2A—N1A—H1A	126.5	O1S—C1S—H4S	109.5
C9A—N1A—H1A	126.5	O1S—C1S—H3S	109.5
C2A—N3A—C4A	105.5 (3)	H4S—C1S—H3S	109.5
N3B—C2B—N1B	110.8 (3)	O1S—C1S—H2S	109.5
N3B—C2B—C12B	126.9 (3)	H4S—C1S—H2S	109.5
N1B—C2B—C12B	122.3 (3)	H3S—C1S—H2S	109.5
N3B—C4B—C9B	109.6 (3)
N3A—C4A—C5A—C6A	−179.8 (3)	N3B—C4B—C5B—C6B	−178.8 (4)
C9A—C4A—C5A—C6A	1.7 (5)	C9B—C4B—C5B—C6B	0.1 (6)
C4A—C5A—C6A—C7A	−0.4 (5)	C4B—C5B—C6B—C7B	−1.5 (6)
C4A—C5A—C6A—C10A	−179.7 (4)	C4B—C5B—C6B—C10B	179.7 (4)
C5A—C6A—C7A—C8A	−0.4 (5)	C5B—C6B—C7B—C8B	1.2 (6)
C10A—C6A—C7A—C8A	178.9 (4)	C10B—C6B—C7B—C8B	−179.9 (4)
C5A—C6A—C7A—C11A	−179.3 (4)	C5B—C6B—C7B—C11B	179.7 (4)
C10A—C6A—C7A—C11A	0.0 (5)	C10B—C6B—C7B—C11B	−1.4 (6)
C6A—C7A—C8A—C9A	−0.1 (5)	C6B—C7B—C8B—C9B	0.5 (6)
C11A—C7A—C8A—C9A	178.8 (3)	C11B—C7B—C8B—C9B	−178.0 (4)
C7A—C8A—C9A—N1A	−179.2 (4)	C7B—C8B—C9B—N1B	178.3 (4)
C7A—C8A—C9A—C4A	1.4 (5)	C7B—C8B—C9B—C4B	−1.9 (6)
N3A—C4A—C9A—N1A	−0.5 (4)	N3B—C4B—C9B—C8B	−179.2 (4)
C5A—C4A—C9A—N1A	178.3 (3)	C5B—C4B—C9B—C8B	1.6 (6)
N3A—C4A—C9A—C8A	179.0 (3)	N3B—C4B—C9B—N1B	0.6 (4)
C5A—C4A—C9A—C8A	−2.2 (5)	C5B—C4B—C9B—N1B	−178.5 (4)
N3A—C2A—C12A—C13A	175.9 (3)	N3B—C2B—C12B—C13B	−2.9 (7)
N1A—C2A—C12A—C13A	−2.7 (6)	N1B—C2B—C12B—C13B	178.1 (4)
C2A—C12A—C13A—C21A	−177.6 (3)	C2B—C12B—C13B—C21B	178.3 (4)
C12A—C13A—C21A—C22A	175.1 (4)	C12B—C13B—C21B—C22B	−177.4 (5)
C12A—C13A—C21A—C26A	−2.3 (6)	C12B—C13B—C21B—C26B	1.8 (7)
C26A—C21A—C22A—C23A	0.8 (7)	C26B—C21B—C22B—C23B	−0.2 (8)
C13A—C21A—C22A—C23A	−176.8 (5)	C13B—C21B—C22B—C23B	179.1 (5)
C21A—C22A—C23A—C24A	−0.2 (9)	C21B—C22B—C23B—C24B	−0.7 (10)
C22A—C23A—C24A—C25A	−0.7 (10)	C22B—C23B—C24B—C25B	1.4 (11)
C23A—C24A—C25A—C26A	1.0 (11)	C23B—C24B—C25B—C26B	−1.2 (12)
C22A—C21A—C26A—C25A	−0.5 (8)	C22B—C21B—C26B—C25B	0.5 (8)
C13A—C21A—C26A—C25A	177.0 (5)	C13B—C21B—C26B—C25B	−178.8 (6)
C24A—C25A—C26A—C21A	−0.4 (10)	C24B—C25B—C26B—C21B	0.2 (11)
N3A—C2A—N1A—C9A	−0.4 (4)	N3B—C2B—N1B—C9B	0.2 (4)
C12A—C2A—N1A—C9A	178.4 (3)	C12B—C2B—N1B—C9B	179.4 (4)
C8A—C9A—N1A—C2A	−178.9 (4)	C8B—C9B—N1B—C2B	179.4 (4)
C4A—C9A—N1A—C2A	0.5 (4)	C4B—C9B—N1B—C2B	−0.5 (4)
N1A—C2A—N3A—C4A	0.0 (4)	N1B—C2B—N3B—C4B	0.2 (4)
C12A—C2A—N3A—C4A	−178.8 (3)	C12B—C2B—N3B—C4B	−178.9 (4)
C5A—C4A—N3A—C2A	−178.3 (4)	C9B—C4B—N3B—C2B	−0.5 (4)
C9A—C4A—N3A—C2A	0.3 (4)	C5B—C4B—N3B—C2B	178.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1S···N3B	0.82	2.06	2.857 (4)	164
N1B—H1B···N3A^i	0.86	2.22	2.985 (4)	149
N1A—H1A···O1S	0.86	2.07	2.907 (5)	163

Symmetry code: (i) x, −y+2, z+1/2.

(E)-5,6-Dimethyl-2-styryl-1H-benzo[d]imidazolium hydrogen oxalate (2b)

Crystal data

C17H17N2^+·C2HO4^−	F(000) = 712
Mr = 338.35	Dx = 1.319 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 5.56861 (9) Å	Cell parameters from 9985 reflections
b = 18.0016 (3) Å	θ = 5.2–72.3°
c = 17.1528 (3) Å	µ = 0.77 mm^−1
β = 97.8415 (7)°	T = 110 K
V = 1703.39 (5) Å^3	Prism, yellow
Z = 4	0.75 × 0.07 × 0.06 mm

Data collection

Bruker SMART APEXII CCD diffractometer	3124 reflections with I > 2σ(I)
ω scan	Rint = 0.031
Absorption correction: multi-scan (TWINABS; Sheldrick, 2008b)	θmax = 72.3°, θmin = 3.6°
Tmin = 0.673, Tmax = 0.754	h = −6→6
3349 measured reflections	k = 0→22
3349 independent reflections	l = 0→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.3027P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3349 reflections	Δρmax = 0.24 e Å^−3
231 parameters	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C2	0.0652 (3)	0.40505 (8)	0.76988 (8)	0.0263 (3)
C4	0.3059 (2)	0.38397 (7)	0.67930 (8)	0.0234 (3)
C5	0.4355 (3)	0.35485 (8)	0.62208 (8)	0.0248 (3)
H3	0.4109	0.3051	0.6043	0.030*
C6	0.5998 (3)	0.40009 (8)	0.59213 (8)	0.0265 (3)
C7	0.6361 (3)	0.47492 (8)	0.61884 (9)	0.0280 (3)
C8	0.5100 (3)	0.50292 (8)	0.67623 (9)	0.0281 (3)
H4	0.5346	0.5525	0.6945	0.034*
C9	0.3458 (3)	0.45645 (7)	0.70657 (8)	0.0249 (3)
C10	0.7418 (3)	0.37007 (9)	0.52992 (9)	0.0324 (3)
H5	0.7041	0.3173	0.5211	0.049*
H6	0.9157	0.3759	0.5476	0.049*
H7	0.6977	0.3975	0.4807	0.049*
C11	0.8121 (3)	0.52453 (9)	0.58409 (10)	0.0352 (4)
H9	0.9719	0.5008	0.5897	0.053*
H10	0.8243	0.5723	0.6118	0.053*
H8	0.7547	0.5328	0.5282	0.053*
C12	−0.1091 (3)	0.39727 (8)	0.82420 (8)	0.0292 (3)
H11	−0.1245	0.4371	0.8595	0.035*
C13	−0.2509 (3)	0.33766 (8)	0.82838 (8)	0.0289 (3)
H12	−0.2374	0.2984	0.7922	0.035*
C21	−0.4250 (3)	0.32824 (8)	0.88434 (8)	0.0304 (3)
C22	−0.5753 (3)	0.26627 (9)	0.87807 (9)	0.0329 (3)
H13	−0.5612	0.2306	0.8381	0.039*
C23	−0.7455 (3)	0.25539 (9)	0.92895 (9)	0.0368 (4)
H14	−0.8475	0.2129	0.9234	0.044*
C24	−0.7664 (3)	0.30659 (10)	0.98777 (9)	0.0381 (4)
H15	−0.8830	0.2994	1.0227	0.046*
C25	−0.6172 (4)	0.36809 (11)	0.99550 (10)	0.0455 (4)
H16	−0.6309	0.4030	1.0362	0.055*
C26	−0.4473 (4)	0.37962 (10)	0.94452 (10)	0.0417 (4)
H17	−0.3461	0.4223	0.9504	0.050*
N3	0.1297 (2)	0.35405 (6)	0.71942 (7)	0.0243 (2)
H2	0.0695	0.3089	0.7130	0.029*
N1	0.1949 (2)	0.46681 (6)	0.76335 (7)	0.0271 (3)
H1	0.1855	0.5077	0.7909	0.032*
C1S	0.8674 (2)	0.62971 (7)	0.82263 (8)	0.0214 (3)
C2S	1.1190 (2)	0.66258 (8)	0.81548 (8)	0.0222 (3)
O1S	0.69029 (18)	0.67687 (5)	0.80515 (6)	0.0266 (2)
H1S	0.540 (3)	0.6528 (6)	0.8087 (10)	0.040*
O2S	0.84578 (19)	0.56580 (6)	0.84260 (7)	0.0340 (3)
O3S	1.28124 (17)	0.61507 (6)	0.80966 (7)	0.0295 (2)
O4S	1.14404 (18)	0.73080 (5)	0.81726 (7)	0.0309 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0284 (7)	0.0205 (6)	0.0282 (7)	0.0052 (6)	−0.0023 (6)	0.0010 (5)
C4	0.0217 (6)	0.0184 (6)	0.0280 (6)	0.0001 (5)	−0.0042 (5)	0.0024 (5)
C5	0.0232 (7)	0.0214 (6)	0.0277 (7)	0.0015 (5)	−0.0040 (5)	−0.0010 (5)
C6	0.0227 (7)	0.0283 (7)	0.0263 (7)	0.0019 (6)	−0.0052 (5)	0.0017 (5)
C7	0.0239 (7)	0.0254 (7)	0.0319 (7)	−0.0011 (6)	−0.0070 (6)	0.0059 (6)
C8	0.0267 (7)	0.0197 (6)	0.0349 (7)	−0.0007 (6)	−0.0057 (6)	0.0019 (5)
C9	0.0257 (7)	0.0195 (6)	0.0275 (7)	0.0043 (5)	−0.0037 (5)	0.0008 (5)
C10	0.0260 (7)	0.0370 (8)	0.0336 (8)	−0.0023 (6)	0.0020 (6)	−0.0007 (6)
C11	0.0308 (8)	0.0325 (8)	0.0407 (8)	−0.0046 (7)	−0.0009 (7)	0.0067 (6)
C12	0.0344 (8)	0.0245 (7)	0.0282 (7)	0.0088 (6)	0.0023 (6)	0.0017 (5)
C13	0.0327 (8)	0.0277 (7)	0.0256 (7)	0.0072 (6)	0.0009 (6)	0.0009 (5)
C21	0.0342 (8)	0.0309 (7)	0.0259 (7)	0.0090 (6)	0.0026 (6)	0.0026 (6)
C22	0.0372 (9)	0.0310 (7)	0.0299 (7)	0.0075 (7)	0.0024 (6)	0.0030 (6)
C23	0.0385 (9)	0.0375 (9)	0.0347 (8)	0.0054 (7)	0.0058 (7)	0.0078 (6)
C24	0.0388 (9)	0.0459 (9)	0.0309 (8)	0.0080 (8)	0.0093 (7)	0.0081 (7)
C25	0.0559 (12)	0.0474 (10)	0.0353 (8)	0.0037 (9)	0.0143 (8)	−0.0060 (7)
C26	0.0487 (10)	0.0412 (9)	0.0370 (9)	−0.0003 (8)	0.0125 (7)	−0.0068 (7)
N3	0.0247 (6)	0.0183 (5)	0.0289 (6)	0.0009 (5)	0.0003 (5)	0.0006 (4)
N1	0.0309 (6)	0.0193 (6)	0.0298 (6)	0.0036 (5)	0.0000 (5)	−0.0014 (4)
C1S	0.0191 (6)	0.0206 (6)	0.0252 (6)	−0.0003 (5)	0.0055 (5)	−0.0040 (5)
C2S	0.0180 (6)	0.0232 (6)	0.0256 (6)	−0.0001 (5)	0.0038 (5)	−0.0008 (5)
O1S	0.0160 (4)	0.0243 (5)	0.0399 (6)	0.0006 (4)	0.0056 (4)	0.0027 (4)
O2S	0.0275 (5)	0.0198 (5)	0.0570 (7)	−0.0006 (4)	0.0135 (5)	0.0026 (5)
O3S	0.0174 (5)	0.0233 (5)	0.0485 (6)	−0.0002 (4)	0.0075 (4)	−0.0072 (4)
O4S	0.0214 (5)	0.0191 (5)	0.0527 (6)	−0.0012 (4)	0.0065 (4)	0.0020 (4)

Geometric parameters (Å, º)

C2—N1	1.3385 (19)	C12—H11	0.9500
C2—N3	1.3438 (18)	C13—C21	1.464 (2)
C2—C12	1.441 (2)	C13—H12	0.9500
C4—N3	1.3818 (19)	C21—C22	1.390 (2)
C4—C9	1.3937 (18)	C21—C26	1.404 (2)
C4—C5	1.398 (2)	C22—C23	1.387 (2)
C5—C6	1.375 (2)	C22—H13	0.9500
C5—H3	0.9500	C23—C24	1.383 (2)
C6—C7	1.428 (2)	C23—H14	0.9500
C6—C10	1.512 (2)	C24—C25	1.380 (3)
C7—C8	1.380 (2)	C24—H15	0.9500
C7—C11	1.508 (2)	C25—C26	1.389 (3)
C8—C9	1.392 (2)	C25—H16	0.9500
C8—H4	0.9500	C26—H17	0.9500
C9—N1	1.383 (2)	N3—H2	0.8800
C10—H5	0.9800	N1—H1	0.8800
C10—H6	0.9800	C1S—O2S	1.2109 (17)
C10—H7	0.9800	C1S—O1S	1.3048 (16)
C11—H9	0.9800	C1S—C2S	1.5410 (19)
C11—H10	0.9800	C2S—O4S	1.2358 (17)
C11—H8	0.9800	C2S—O3S	1.2581 (17)
C12—C13	1.340 (2)	O1S—H1S	0.95 (2)
N1—C2—N3	108.60 (13)	C2—C12—H11	117.8
N1—C2—C12	123.60 (13)	C12—C13—C21	125.14 (14)
N3—C2—C12	127.80 (13)	C12—C13—H12	117.4
N3—C4—C9	106.82 (12)	C21—C13—H12	117.4
N3—C4—C5	132.33 (12)	C22—C21—C26	118.21 (15)
C9—C4—C5	120.85 (13)	C22—C21—C13	119.19 (14)
C6—C5—C4	118.28 (13)	C26—C21—C13	122.60 (15)
C6—C5—H3	120.9	C23—C22—C21	121.37 (15)
C4—C5—H3	120.9	C23—C22—H13	119.3
C5—C6—C7	120.73 (14)	C21—C22—H13	119.3
C5—C6—C10	119.37 (13)	C24—C23—C22	119.84 (16)
C7—C6—C10	119.90 (14)	C24—C23—H14	120.1
C8—C7—C6	120.64 (14)	C22—C23—H14	120.1
C8—C7—C11	119.15 (14)	C25—C24—C23	119.69 (16)
C6—C7—C11	120.21 (14)	C25—C24—H15	120.2
C7—C8—C9	118.12 (13)	C23—C24—H15	120.2
C7—C8—H4	120.9	C24—C25—C26	120.83 (16)
C9—C8—H4	120.9	C24—C25—H16	119.6
N1—C9—C8	132.51 (13)	C26—C25—H16	119.6
N1—C9—C4	106.14 (12)	C25—C26—C21	120.05 (17)
C8—C9—C4	121.35 (14)	C25—C26—H17	120.0
C6—C10—H5	109.5	C21—C26—H17	120.0
C6—C10—H6	109.5	C2—N3—C4	108.95 (12)
H5—C10—H6	109.5	C2—N3—H2	125.5
C6—C10—H7	109.5	C4—N3—H2	125.5
H5—C10—H7	109.5	C2—N1—C9	109.48 (11)
H6—C10—H7	109.5	C2—N1—H1	125.3
C7—C11—H9	109.5	C9—N1—H1	125.3
C7—C11—H10	109.5	O2S—C1S—O1S	125.60 (12)
H9—C11—H10	109.5	O2S—C1S—C2S	120.91 (12)
C7—C11—H8	109.5	O1S—C1S—C2S	113.49 (11)
H9—C11—H8	109.5	O4S—C2S—O3S	126.69 (12)
H10—C11—H8	109.5	O4S—C2S—C1S	118.72 (12)
C13—C12—C2	124.49 (14)	O3S—C2S—C1S	114.58 (11)
C13—C12—H11	117.8	C1S—O1S—H1S	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3S^i	0.88	2.02	2.8074 (15)	148
N1—H1···O2S^i	0.88	2.43	3.0860 (16)	131
O1S—H1S···O3S^i	0.95	1.59	2.5456 (14)	176
N3—H2···O4S^ii	0.88	1.87	2.7169 (15)	161

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2.