


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811030583/lh5291sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536811030583/lh5291Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811030583/lh5291Isup3.cml |
CCDC reference: 845313
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean
() = 0.000 Å
- Disorder in main residue
- R factor = 0.058
- wR factor = 0.158
- Data-to-parameter ratio = 17.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.0 Ratio
Author Response: This is due to a full molecule disorder model with 78 non-hydrogen atoms. |
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N2B -- C14B .. 7.0 su PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C1X -C6X 1.37 Ang. PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 4 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 10 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 105
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 96 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT242_ALERT_2_G Check Low Ueq as Compared to Neighbors for C17X PLAT242_ALERT_2_G Check Low Ueq as Compared to Neighbors for C13Y PLAT242_ALERT_2_G Check Low Ueq as Compared to Neighbors for C20Y PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 100 Perc. PLAT432_ALERT_2_G Short Inter X...Y Contact N3X .. C9Y .. 2.88 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact N3X .. C10Y .. 2.99 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact N3Y .. C9X .. 2.93 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact N3Y .. C8X .. 2.95 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact C9X .. C9Y .. 2.98 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact C9X .. C10Y .. 3.10 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact C10X .. C10Y .. 3.00 Ang. PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 24 PLAT793_ALERT_4_G The Model has Chirality at C14A (Verify) .... S PLAT793_ALERT_4_G The Model has Chirality at C14B (Verify) .... S PLAT793_ALERT_4_G The Model has Chirality at C14X (Verify) .... R PLAT793_ALERT_4_G The Model has Chirality at C14Y (Verify) .... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 144
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 19 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 14 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The title compound was synthesized using Taha-Teoh's method (Eltayeb et al., 2011). To a solution of 2-(2-aminophenyl)-1H-benzimidazole (0.209 g, 1.0 mmol) in ethanol (30 mL) was added 2-hydroxybenzaldehyde (0.1 mL, 1.0 mmol). The color of the resulting solution is pale-yellow. Then on adding zinc chloride (0.136 g, 1.0 mmol), the color of the solution became golden-yellow. The mixture was refluxed with stirring for 3 h. Crystals suitable for XRD were formed after several days of slow evaporation of ethanol at room temperature.
The title compound is disordered over two positions with refined site-occupancies of 0.748 (1) : 0.252 (1). All minor disordered components were refined isotropically. The O-bound hydrogen atoms were located from difference Fourier map and refined as riding on their parent atom, with Uiso(H) = 1.2 Ueq(O). The rest of the hydrogen atoms were positioned geomatrically [C–H = 0.93 - 0.98 Å; N–H = 0.86 Å] and refined using a riding model, with Uiso(H) = 1.2 Ueq(C, N). The highest residual electron density peak and the deepest hole are located at 0.68 Å and 0.12 Å, respectively, from H3AB. The same Uij parameters were used for atom pair C16Y/C12Y.
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
C20H15N3O | F(000) = 1312 |
Mr = 313.35 | Dx = 1.383 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9430 reflections |
a = 17.1513 (10) Å | θ = 2.4–32.7° |
b = 19.1160 (11) Å | µ = 0.09 mm−1 |
c = 9.2630 (5) Å | T = 297 K |
β = 97.590 (1)° | Block, yellow |
V = 3010.4 (3) Å3 | 0.30 × 0.28 × 0.25 mm |
Z = 8 |
Bruker APEXII DUO CCD area-detector diffractometer | 11057 independent reflections |
Radiation source: fine-focus sealed tube | 8231 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ϕ and ω scans | θmax = 32.8°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −26→26 |
Tmin = 0.974, Tmax = 0.978 | k = −29→29 |
40861 measured reflections | l = −12→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0604P)2 + 1.3534P] where P = (Fo2 + 2Fc2)/3 |
11057 reflections | (Δ/σ)max = 0.001 |
625 parameters | Δρmax = 0.44 e Å−3 |
144 restraints | Δρmin = −0.42 e Å−3 |
C20H15N3O | V = 3010.4 (3) Å3 |
Mr = 313.35 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.1513 (10) Å | µ = 0.09 mm−1 |
b = 19.1160 (11) Å | T = 297 K |
c = 9.2630 (5) Å | 0.30 × 0.28 × 0.25 mm |
β = 97.590 (1)° |
Bruker APEXII DUO CCD area-detector diffractometer | 11057 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 8231 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.978 | Rint = 0.047 |
40861 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 144 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.44 e Å−3 |
11057 reflections | Δρmin = −0.42 e Å−3 |
625 parameters |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1A | 0.47310 (12) | 0.61154 (16) | 0.9445 (3) | 0.0161 (5) | 0.7479 (13) |
H1OA | 0.4159 | 0.6051 | 0.9253 | 0.019* | 0.7479 (13) |
N1A | 0.82502 (7) | 0.56968 (7) | 0.82493 (16) | 0.0190 (3) | 0.7479 (13) |
N2A | 0.71433 (7) | 0.59508 (7) | 0.91751 (15) | 0.0155 (2) | 0.7479 (13) |
N3A | 0.60604 (7) | 0.51973 (7) | 0.90775 (16) | 0.0166 (3) | 0.7479 (13) |
H3AB | 0.5745 | 0.5014 | 0.9620 | 0.020* | 0.7479 (13) |
C1A | 0.83777 (10) | 0.62752 (8) | 0.91544 (19) | 0.0184 (3) | 0.7479 (13) |
C2A | 0.90681 (10) | 0.66651 (10) | 0.9555 (2) | 0.0250 (4) | 0.7479 (13) |
H2AA | 0.9533 | 0.6560 | 0.9185 | 0.030* | 0.7479 (13) |
C3A | 0.90283 (12) | 0.72153 (12) | 1.0530 (3) | 0.0306 (5) | 0.7479 (13) |
H3AA | 0.9478 | 0.7478 | 1.0820 | 0.037* | 0.7479 (13) |
C4A | 0.83290 (15) | 0.73839 (12) | 1.1087 (3) | 0.0346 (5) | 0.7479 (13) |
H4AA | 0.8324 | 0.7755 | 1.1735 | 0.042* | 0.7479 (13) |
C5A | 0.76429 (11) | 0.70022 (11) | 1.0683 (3) | 0.0296 (4) | 0.7479 (13) |
H5AA | 0.7175 | 0.7114 | 1.1036 | 0.036* | 0.7479 (13) |
C6A | 0.76874 (9) | 0.64467 (9) | 0.9730 (2) | 0.0184 (3) | 0.7479 (13) |
C7A | 0.75068 (11) | 0.55190 (12) | 0.8291 (2) | 0.0153 (3) | 0.7479 (13) |
C8A | 0.70730 (9) | 0.49398 (8) | 0.75729 (18) | 0.0154 (3) | 0.7479 (13) |
C9A | 0.63282 (9) | 0.47982 (8) | 0.79902 (18) | 0.0151 (3) | 0.7479 (13) |
C10A | 0.59061 (10) | 0.42188 (10) | 0.7374 (2) | 0.0208 (3) | 0.7479 (13) |
H10A | 0.5413 | 0.4117 | 0.7632 | 0.025* | 0.7479 (13) |
C11A | 0.62240 (14) | 0.37973 (11) | 0.6380 (2) | 0.0261 (4) | 0.7479 (13) |
H11A | 0.5940 | 0.3415 | 0.5976 | 0.031* | 0.7479 (13) |
C12A | 0.69640 (14) | 0.39393 (11) | 0.5979 (2) | 0.0269 (4) | 0.7479 (13) |
H12A | 0.7173 | 0.3653 | 0.5315 | 0.032* | 0.7479 (13) |
C13A | 0.73847 (10) | 0.45117 (10) | 0.6579 (2) | 0.0212 (3) | 0.7479 (13) |
H13A | 0.7878 | 0.4610 | 0.6315 | 0.025* | 0.7479 (13) |
C14A | 0.63058 (13) | 0.59199 (16) | 0.9310 (3) | 0.0124 (6) | 0.7479 (13) |
H14A | 0.6237 | 0.6051 | 1.0308 | 0.015* | 0.7479 (13) |
C15A | 0.58296 (14) | 0.64264 (17) | 0.8268 (3) | 0.0125 (7) | 0.7479 (13) |
C16A | 0.61480 (14) | 0.68116 (17) | 0.7214 (3) | 0.0201 (6) | 0.7479 (13) |
H16A | 0.6674 | 0.6753 | 0.7092 | 0.024* | 0.7479 (13) |
C17A | 0.5679 (3) | 0.7286 (4) | 0.6337 (8) | 0.0340 (15) | 0.7479 (13) |
H17A | 0.5898 | 0.7551 | 0.5650 | 0.041* | 0.7479 (13) |
C18A | 0.48936 (16) | 0.73634 (19) | 0.6488 (4) | 0.0233 (8) | 0.7479 (13) |
H18A | 0.4583 | 0.7673 | 0.5889 | 0.028* | 0.7479 (13) |
C19A | 0.45662 (18) | 0.6981 (2) | 0.7532 (5) | 0.0178 (9) | 0.7479 (13) |
H19A | 0.4039 | 0.7041 | 0.7643 | 0.021* | 0.7479 (13) |
C20A | 0.50286 (14) | 0.65047 (16) | 0.8415 (3) | 0.0117 (6) | 0.7479 (13) |
O1B | 1.03721 (19) | 0.4897 (2) | 0.2130 (4) | 0.0231 (6) | 0.7479 (13) |
H1OB | 1.0934 | 0.4797 | 0.2233 | 0.028* | 0.7479 (13) |
N1B | 0.67513 (8) | 0.41530 (9) | 0.15645 (18) | 0.0253 (3) | 0.7479 (13) |
N2B | 0.79070 (8) | 0.47098 (8) | 0.16595 (18) | 0.0237 (3) | 0.7479 (13) |
N3B | 0.88892 (9) | 0.44281 (9) | 0.02448 (18) | 0.0261 (3) | 0.7479 (13) |
H3BB | 0.9205 | 0.4619 | −0.0286 | 0.031* | 0.7479 (13) |
C1B | 0.67384 (10) | 0.47560 (10) | 0.2429 (2) | 0.0243 (3) | 0.7479 (13) |
C2B | 0.61365 (12) | 0.50263 (11) | 0.3142 (2) | 0.0288 (4) | 0.7479 (13) |
H2BA | 0.5655 | 0.4799 | 0.3109 | 0.035* | 0.7479 (13) |
C3B | 0.62839 (19) | 0.5640 (2) | 0.3893 (5) | 0.0256 (7) | 0.7479 (13) |
H3BA | 0.5887 | 0.5831 | 0.4362 | 0.031* | 0.7479 (13) |
C4B | 0.70066 (18) | 0.59922 (17) | 0.3987 (4) | 0.0341 (6) | 0.7479 (13) |
H4BA | 0.7084 | 0.6404 | 0.4522 | 0.041* | 0.7479 (13) |
C5B | 0.76129 (11) | 0.57226 (12) | 0.3270 (3) | 0.0302 (4) | 0.7479 (13) |
H5BA | 0.8096 | 0.5947 | 0.3310 | 0.036* | 0.7479 (13) |
C6B | 0.74580 (12) | 0.51085 (10) | 0.2504 (2) | 0.0233 (3) | 0.7479 (13) |
C7B | 0.74581 (9) | 0.41479 (10) | 0.1156 (2) | 0.0216 (3) | 0.7479 (13) |
C8B | 0.77894 (10) | 0.36412 (10) | 0.0230 (2) | 0.0216 (3) | 0.7479 (13) |
C9B | 0.85229 (10) | 0.38073 (10) | −0.0204 (2) | 0.0227 (3) | 0.7479 (13) |
C10B | 0.88395 (10) | 0.33569 (11) | −0.1166 (2) | 0.0266 (4) | 0.7479 (13) |
H10B | 0.9325 | 0.3457 | −0.1461 | 0.032* | 0.7479 (13) |
C11B | 0.84375 (12) | 0.27688 (12) | −0.1674 (3) | 0.0265 (4) | 0.7479 (13) |
H11B | 0.8657 | 0.2480 | −0.2321 | 0.032* | 0.7479 (13) |
C12B | 0.7707 (2) | 0.25862 (17) | −0.1257 (4) | 0.0244 (6) | 0.7479 (13) |
H12B | 0.7446 | 0.2182 | −0.1606 | 0.029* | 0.7479 (13) |
C13B | 0.73862 (11) | 0.30330 (12) | −0.0298 (3) | 0.0262 (4) | 0.7479 (13) |
H13B | 0.6901 | 0.2927 | −0.0005 | 0.031* | 0.7479 (13) |
C14B | 0.87512 (14) | 0.4770 (2) | 0.1610 (5) | 0.0165 (8) | 0.7479 (13) |
H14B | 0.8893 | 0.5265 | 0.1570 | 0.020* | 0.7479 (13) |
C15B | 0.92214 (18) | 0.4436 (2) | 0.2945 (4) | 0.0144 (10) | 0.7479 (13) |
C16B | 0.88769 (15) | 0.40564 (16) | 0.3972 (3) | 0.0179 (5) | 0.7479 (13) |
H16B | 0.8333 | 0.4009 | 0.3868 | 0.022* | 0.7479 (13) |
C17B | 0.93327 (19) | 0.3747 (2) | 0.5154 (4) | 0.0224 (8) | 0.7479 (13) |
H17B | 0.9094 | 0.3492 | 0.5830 | 0.027* | 0.7479 (13) |
C18B | 1.0145 (2) | 0.3818 (2) | 0.5324 (5) | 0.0211 (7) | 0.7479 (13) |
H18B | 1.0448 | 0.3617 | 0.6124 | 0.025* | 0.7479 (13) |
C19B | 1.0507 (3) | 0.4187 (4) | 0.4312 (6) | 0.0222 (9) | 0.7479 (13) |
H19B | 1.1052 | 0.4234 | 0.4422 | 0.027* | 0.7479 (13) |
C20B | 1.0042 (3) | 0.4486 (3) | 0.3125 (6) | 0.0208 (9) | 0.7479 (13) |
O1X | 0.4731 (8) | 0.6132 (8) | 0.9421 (16) | 0.055 (4)* | 0.2521 (13) |
H1OX | 0.4254 | 0.6071 | 0.9301 | 0.066* | 0.2521 (13) |
N1X | 0.7962 (3) | 0.5228 (3) | 0.7655 (6) | 0.0338 (11)* | 0.2521 (13) |
N2X | 0.6853 (3) | 0.5492 (3) | 0.8586 (6) | 0.0356 (12)* | 0.2521 (13) |
N3X | 0.6784 (3) | 0.6299 (3) | 1.0464 (7) | 0.0429 (14)* | 0.2521 (13) |
H3XB | 0.6602 | 0.6361 | 1.1276 | 0.051* | 0.2521 (13) |
C1X | 0.7358 (3) | 0.4754 (3) | 0.7172 (7) | 0.0264 (11)* | 0.2521 (13) |
C2X | 0.7366 (4) | 0.4182 (4) | 0.6289 (8) | 0.0351 (14)* | 0.2521 (13) |
H2XA | 0.7824 | 0.4057 | 0.5914 | 0.042* | 0.2521 (13) |
C3X | 0.6704 (5) | 0.3800 (4) | 0.5966 (10) | 0.0367 (19)* | 0.2521 (13) |
H3XA | 0.6703 | 0.3425 | 0.5327 | 0.044* | 0.2521 (13) |
C4X | 0.6027 (5) | 0.3954 (4) | 0.6564 (10) | 0.0344 (19)* | 0.2521 (13) |
H4XA | 0.5587 | 0.3669 | 0.6360 | 0.041* | 0.2521 (13) |
C5X | 0.5998 (4) | 0.4525 (4) | 0.7459 (8) | 0.0331 (14)* | 0.2521 (13) |
H5XA | 0.5545 | 0.4640 | 0.7856 | 0.040* | 0.2521 (13) |
C6X | 0.6674 (4) | 0.4919 (3) | 0.7740 (7) | 0.0255 (10)* | 0.2521 (13) |
C7X | 0.7623 (5) | 0.5673 (4) | 0.8464 (11) | 0.034 (3)* | 0.2521 (13) |
C8X | 0.7975 (4) | 0.6267 (3) | 0.9330 (7) | 0.0300 (12)* | 0.2521 (13) |
C9X | 0.7530 (4) | 0.6565 (4) | 1.0300 (8) | 0.0351 (14)* | 0.2521 (13) |
C10X | 0.7850 (5) | 0.7112 (4) | 1.1162 (10) | 0.0420 (19)* | 0.2521 (13) |
H10C | 0.7557 | 0.7328 | 1.1810 | 0.050* | 0.2521 (13) |
C11X | 0.8593 (6) | 0.7332 (5) | 1.1061 (11) | 0.045 (3)* | 0.2521 (13) |
H11C | 0.8804 | 0.7688 | 1.1675 | 0.054* | 0.2521 (13) |
C12X | 0.9049 (5) | 0.7050 (5) | 1.0090 (9) | 0.035 (2)* | 0.2521 (13) |
H12C | 0.9548 | 0.7223 | 1.0008 | 0.042* | 0.2521 (13) |
C13X | 0.8731 (5) | 0.6502 (4) | 0.9245 (8) | 0.0334 (13)* | 0.2521 (13) |
H13C | 0.9029 | 0.6285 | 0.8606 | 0.040* | 0.2521 (13) |
C14X | 0.6312 (8) | 0.5922 (9) | 0.9299 (16) | 0.049 (5)* | 0.2521 (13) |
H14C | 0.5958 | 0.5608 | 0.9740 | 0.058* | 0.2521 (13) |
C15X | 0.5812 (8) | 0.6416 (9) | 0.8288 (18) | 0.044 (5)* | 0.2521 (13) |
C16X | 0.6105 (10) | 0.6770 (9) | 0.7192 (19) | 0.065 (6)* | 0.2521 (13) |
H16C | 0.6634 | 0.6704 | 0.7103 | 0.079* | 0.2521 (13) |
C17X | 0.5687 (11) | 0.7214 (11) | 0.621 (2) | 0.028 (3)* | 0.2521 (13) |
H17C | 0.5901 | 0.7410 | 0.5436 | 0.033* | 0.2521 (13) |
C18X | 0.4932 (10) | 0.7351 (11) | 0.647 (2) | 0.063 (6)* | 0.2521 (13) |
H18C | 0.4646 | 0.7695 | 0.5919 | 0.076* | 0.2521 (13) |
C19X | 0.4586 (10) | 0.6994 (11) | 0.750 (2) | 0.046 (6)* | 0.2521 (13) |
H19C | 0.4061 | 0.7072 | 0.7602 | 0.055* | 0.2521 (13) |
C20X | 0.5018 (8) | 0.6524 (10) | 0.838 (2) | 0.048 (5)* | 0.2521 (13) |
O1Y | 1.0330 (7) | 0.4857 (7) | 0.1895 (12) | 0.024 (2)* | 0.2521 (13) |
H1OY | 1.0840 | 0.4785 | 0.2002 | 0.028* | 0.2521 (13) |
N1Y | 0.6910 (2) | 0.38802 (19) | 0.0948 (4) | 0.0128 (7)* | 0.2521 (13) |
N2Y | 0.8087 (2) | 0.43856 (19) | 0.1044 (4) | 0.0132 (7)* | 0.2521 (13) |
N3Y | 0.8417 (2) | 0.5488 (2) | 0.2063 (4) | 0.0174 (7)* | 0.2521 (13) |
H3YB | 0.8655 | 0.5872 | 0.1907 | 0.021* | 0.2521 (13) |
C1Y | 0.7373 (2) | 0.3489 (2) | 0.0136 (5) | 0.0116 (7)* | 0.2521 (13) |
C2Y | 0.7211 (4) | 0.2875 (3) | −0.0681 (7) | 0.0241 (14)* | 0.2521 (13) |
H2YA | 0.6729 | 0.2645 | −0.0750 | 0.029* | 0.2521 (13) |
C3Y | 0.7835 (6) | 0.2639 (6) | −0.1384 (14) | 0.025 (3)* | 0.2521 (13) |
H3YA | 0.7748 | 0.2245 | −0.1974 | 0.030* | 0.2521 (13) |
C4Y | 0.8562 (4) | 0.2940 (3) | −0.1270 (7) | 0.0218 (13)* | 0.2521 (13) |
H4YA | 0.8954 | 0.2732 | −0.1727 | 0.026* | 0.2521 (13) |
C5Y | 0.8719 (3) | 0.3535 (3) | −0.0503 (6) | 0.0152 (8)* | 0.2521 (13) |
H5YA | 0.9206 | 0.3754 | −0.0448 | 0.018* | 0.2521 (13) |
C6Y | 0.8125 (3) | 0.3803 (2) | 0.0192 (5) | 0.0105 (7)* | 0.2521 (13) |
C7Y | 0.7352 (3) | 0.4417 (2) | 0.1501 (5) | 0.0138 (8)* | 0.2521 (13) |
C8Y | 0.7164 (3) | 0.4979 (2) | 0.2431 (5) | 0.0131 (9)* | 0.2521 (13) |
C9Y | 0.7740 (3) | 0.5507 (3) | 0.2677 (6) | 0.0195 (9)* | 0.2521 (13) |
C10Y | 0.7561 (3) | 0.6108 (3) | 0.3521 (6) | 0.0258 (10)* | 0.2521 (13) |
H10D | 0.7921 | 0.6472 | 0.3698 | 0.031* | 0.2521 (13) |
C11Y | 0.6862 (6) | 0.6133 (5) | 0.4052 (14) | 0.036 (3)* | 0.2521 (13) |
H11D | 0.6745 | 0.6529 | 0.4565 | 0.043* | 0.2521 (13) |
C12Y | 0.6304 (11) | 0.5587 (9) | 0.386 (3) | 0.056 (4)* | 0.2521 (13) |
H12D | 0.5845 | 0.5603 | 0.4297 | 0.067* | 0.2521 (13) |
C13Y | 0.6468 (3) | 0.5023 (3) | 0.3001 (6) | 0.0192 (9)* | 0.2521 (13) |
H13D | 0.6097 | 0.4668 | 0.2808 | 0.023* | 0.2521 (13) |
C14Y | 0.8749 (8) | 0.4810 (7) | 0.166 (2) | 0.041 (5)* | 0.2521 (13) |
H14D | 0.9078 | 0.4900 | 0.0892 | 0.050* | 0.2521 (13) |
C15Y | 0.9251 (8) | 0.4442 (10) | 0.2900 (19) | 0.036 (6)* | 0.2521 (13) |
C16Y | 0.8933 (9) | 0.4054 (9) | 0.3928 (19) | 0.056 (4)* | 0.2521 (13) |
H16D | 0.8392 | 0.3985 | 0.3813 | 0.067* | 0.2521 (13) |
C17Y | 0.9389 (10) | 0.3760 (11) | 0.514 (2) | 0.057 (6)* | 0.2521 (13) |
H17D | 0.9171 | 0.3522 | 0.5862 | 0.069* | 0.2521 (13) |
C18Y | 1.0187 (10) | 0.3851 (11) | 0.517 (2) | 0.046 (5)* | 0.2521 (13) |
H18D | 1.0524 | 0.3627 | 0.5895 | 0.055* | 0.2521 (13) |
C19Y | 1.0504 (10) | 0.4253 (12) | 0.419 (2) | 0.026 (4)* | 0.2521 (13) |
H19D | 1.1047 | 0.4316 | 0.4304 | 0.031* | 0.2521 (13) |
C20Y | 1.0060 (7) | 0.4567 (8) | 0.3046 (14) | 0.0095 (19)* | 0.2521 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0074 (5) | 0.0250 (8) | 0.0163 (7) | 0.0011 (4) | 0.0035 (3) | 0.0049 (5) |
N1A | 0.0115 (5) | 0.0228 (6) | 0.0231 (7) | 0.0008 (4) | 0.0033 (4) | 0.0029 (6) |
N2A | 0.0098 (5) | 0.0170 (5) | 0.0197 (6) | 0.0012 (4) | 0.0019 (4) | −0.0012 (5) |
N3A | 0.0134 (5) | 0.0164 (5) | 0.0212 (7) | −0.0001 (4) | 0.0070 (4) | 0.0019 (5) |
C1A | 0.0105 (6) | 0.0198 (7) | 0.0243 (8) | −0.0009 (5) | 0.0008 (5) | 0.0052 (6) |
C2A | 0.0134 (7) | 0.0249 (8) | 0.0350 (10) | −0.0046 (6) | −0.0030 (6) | 0.0057 (8) |
C3A | 0.0214 (9) | 0.0263 (10) | 0.0410 (13) | −0.0029 (7) | −0.0069 (8) | −0.0022 (10) |
C4A | 0.0244 (10) | 0.0264 (10) | 0.0504 (15) | 0.0004 (8) | −0.0053 (9) | −0.0125 (9) |
C5A | 0.0179 (7) | 0.0259 (9) | 0.0428 (12) | 0.0018 (6) | −0.0037 (8) | −0.0117 (9) |
C6A | 0.0130 (6) | 0.0198 (7) | 0.0220 (8) | 0.0015 (5) | 0.0005 (6) | −0.0020 (6) |
C7A | 0.0113 (6) | 0.0175 (8) | 0.0176 (8) | 0.0030 (7) | 0.0040 (6) | 0.0033 (7) |
C8A | 0.0118 (6) | 0.0172 (6) | 0.0179 (7) | 0.0027 (5) | 0.0047 (5) | 0.0005 (6) |
C9A | 0.0128 (6) | 0.0154 (6) | 0.0175 (7) | 0.0001 (5) | 0.0032 (5) | 0.0032 (6) |
C10A | 0.0199 (7) | 0.0184 (8) | 0.0239 (9) | −0.0046 (6) | 0.0021 (6) | 0.0003 (7) |
C11A | 0.0342 (10) | 0.0186 (8) | 0.0261 (10) | −0.0038 (8) | 0.0063 (8) | −0.0036 (7) |
C12A | 0.0318 (10) | 0.0218 (8) | 0.0287 (10) | 0.0001 (8) | 0.0100 (8) | −0.0042 (7) |
C13A | 0.0229 (7) | 0.0196 (8) | 0.0223 (8) | 0.0020 (6) | 0.0075 (6) | −0.0037 (7) |
C14A | 0.0073 (7) | 0.0168 (9) | 0.0134 (9) | 0.0026 (4) | 0.0027 (4) | 0.0008 (5) |
C15A | 0.0076 (7) | 0.0157 (9) | 0.0141 (10) | 0.0018 (4) | 0.0012 (4) | 0.0005 (5) |
C16A | 0.0084 (6) | 0.0285 (10) | 0.0235 (10) | 0.0003 (5) | 0.0031 (5) | 0.0113 (7) |
C17A | 0.0188 (11) | 0.040 (3) | 0.043 (3) | −0.0027 (11) | 0.0015 (10) | 0.024 (2) |
C18A | 0.0134 (7) | 0.0226 (10) | 0.0319 (13) | 0.0004 (5) | −0.0042 (6) | 0.0144 (8) |
C19A | 0.0090 (8) | 0.0189 (11) | 0.0244 (13) | 0.0020 (5) | −0.0017 (5) | 0.0021 (6) |
C20A | 0.0090 (7) | 0.0133 (8) | 0.0127 (9) | 0.0005 (4) | 0.0006 (4) | −0.0006 (5) |
O1B | 0.0110 (7) | 0.0381 (13) | 0.0213 (12) | 0.0031 (6) | 0.0060 (8) | 0.0082 (11) |
N1B | 0.0152 (6) | 0.0329 (8) | 0.0274 (8) | −0.0009 (5) | 0.0016 (5) | 0.0018 (7) |
N2B | 0.0157 (6) | 0.0257 (7) | 0.0298 (8) | 0.0000 (5) | 0.0032 (5) | 0.0058 (6) |
N3B | 0.0201 (6) | 0.0335 (8) | 0.0257 (8) | −0.0034 (5) | 0.0070 (5) | 0.0063 (7) |
C1B | 0.0165 (7) | 0.0318 (9) | 0.0246 (9) | 0.0031 (6) | 0.0022 (6) | 0.0032 (7) |
C2B | 0.0180 (8) | 0.0399 (11) | 0.0288 (10) | 0.0018 (7) | 0.0036 (7) | −0.0006 (8) |
C3B | 0.0170 (8) | 0.0360 (12) | 0.0236 (10) | 0.0059 (7) | 0.0023 (6) | −0.0044 (8) |
C4B | 0.0307 (12) | 0.0370 (14) | 0.0336 (13) | −0.0007 (11) | 0.0004 (10) | −0.0056 (11) |
C5B | 0.0219 (8) | 0.0321 (10) | 0.0360 (11) | −0.0007 (7) | 0.0013 (7) | 0.0034 (9) |
C6B | 0.0176 (8) | 0.0260 (8) | 0.0261 (9) | 0.0010 (7) | 0.0025 (6) | 0.0043 (7) |
C7B | 0.0149 (6) | 0.0263 (8) | 0.0230 (8) | −0.0002 (6) | 0.0002 (6) | 0.0066 (7) |
C8B | 0.0169 (8) | 0.0257 (8) | 0.0224 (8) | 0.0021 (6) | 0.0027 (6) | 0.0057 (7) |
C9B | 0.0175 (7) | 0.0288 (9) | 0.0216 (8) | 0.0021 (6) | 0.0024 (6) | 0.0056 (7) |
C10B | 0.0192 (7) | 0.0368 (10) | 0.0238 (9) | 0.0016 (7) | 0.0025 (6) | 0.0036 (8) |
C11B | 0.0220 (8) | 0.0311 (10) | 0.0263 (10) | 0.0047 (7) | 0.0029 (7) | 0.0019 (9) |
C12B | 0.0187 (11) | 0.0263 (11) | 0.0281 (13) | −0.0032 (9) | 0.0028 (10) | 0.0016 (9) |
C13B | 0.0187 (8) | 0.0318 (10) | 0.0284 (10) | 0.0026 (7) | 0.0047 (7) | 0.0048 (9) |
C14B | 0.0076 (8) | 0.0203 (10) | 0.0216 (12) | −0.0010 (5) | 0.0027 (5) | 0.0065 (7) |
C15B | 0.0099 (9) | 0.0158 (12) | 0.0177 (13) | −0.0001 (5) | 0.0023 (5) | 0.0022 (6) |
C16B | 0.0110 (7) | 0.0216 (9) | 0.0212 (9) | −0.0043 (5) | 0.0019 (5) | 0.0069 (6) |
C17B | 0.0165 (8) | 0.0280 (12) | 0.0227 (12) | −0.0035 (6) | 0.0017 (6) | 0.0109 (7) |
C18B | 0.0177 (10) | 0.0263 (13) | 0.0188 (11) | 0.0033 (6) | 0.0007 (7) | 0.0082 (9) |
C19B | 0.0140 (10) | 0.0296 (19) | 0.0228 (16) | 0.0054 (8) | 0.0019 (7) | 0.0060 (11) |
C20B | 0.0186 (11) | 0.0198 (18) | 0.0254 (14) | 0.0007 (9) | 0.0084 (7) | 0.0045 (10) |
O1A—C20A | 1.361 (3) | O1X—C20X | 1.362 (13) |
O1A—H1OA | 0.9812 | O1X—H1OX | 0.8201 |
N1A—C7A | 1.325 (2) | N1X—C7X | 1.318 (9) |
N1A—C1A | 1.387 (2) | N1X—C1X | 1.405 (7) |
N2A—C7A | 1.370 (2) | N2X—C6X | 1.358 (7) |
N2A—C6A | 1.381 (2) | N2X—C7X | 1.385 (9) |
N2A—C14A | 1.460 (3) | N2X—C14X | 1.461 (12) |
N3A—C9A | 1.389 (2) | N3X—C9X | 1.404 (8) |
N3A—C14A | 1.452 (3) | N3X—C14X | 1.453 (15) |
N3A—H3AB | 0.8600 | N3X—H3XB | 0.8600 |
C1A—C6A | 1.400 (2) | C1X—C2X | 1.367 (9) |
C1A—C2A | 1.407 (2) | C1X—C6X | 1.383 (9) |
C2A—C3A | 1.394 (3) | C2X—C3X | 1.350 (9) |
C2A—H2AA | 0.9300 | C2X—H2XA | 0.9300 |
C3A—C4A | 1.404 (4) | C3X—C4X | 1.383 (10) |
C3A—H3AA | 0.9300 | C3X—H3XA | 0.9300 |
C4A—C5A | 1.393 (3) | C4X—C5X | 1.375 (10) |
C4A—H4AA | 0.9300 | C4X—H4XA | 0.9300 |
C5A—C6A | 1.390 (3) | C5X—C6X | 1.378 (9) |
C5A—H5AA | 0.9300 | C5X—H5XA | 0.9300 |
C7A—C8A | 1.446 (3) | C7X—C8X | 1.473 (9) |
C8A—C13A | 1.390 (2) | C8X—C9X | 1.376 (9) |
C8A—C9A | 1.409 (2) | C8X—C13X | 1.384 (9) |
C9A—C10A | 1.403 (2) | C9X—C10X | 1.385 (10) |
C10A—C11A | 1.388 (3) | C10X—C11X | 1.356 (11) |
C10A—H10A | 0.9300 | C10X—H10C | 0.9300 |
C11A—C12A | 1.395 (3) | C11X—C12X | 1.377 (11) |
C11A—H11A | 0.9300 | C11X—H11C | 0.9300 |
C12A—C13A | 1.386 (3) | C12X—C13X | 1.378 (10) |
C12A—H12A | 0.9300 | C12X—H12C | 0.9300 |
C13A—H13A | 0.9300 | C13X—H13C | 0.9300 |
C14A—C15A | 1.526 (3) | C14X—C15X | 1.514 (14) |
C14A—H14A | 0.9800 | C14X—H14C | 0.9800 |
C15A—C16A | 1.391 (3) | C15X—C16X | 1.370 (14) |
C15A—C20A | 1.406 (3) | C15X—C20X | 1.392 (13) |
C16A—C17A | 1.399 (5) | C16X—C17X | 1.372 (14) |
C16A—H16A | 0.9300 | C16X—H16C | 0.9300 |
C17A—C18A | 1.381 (5) | C17X—C18X | 1.371 (15) |
C17A—H17A | 0.9300 | C17X—H17C | 0.9300 |
C18A—C19A | 1.389 (3) | C18X—C19X | 1.375 (14) |
C18A—H18A | 0.9300 | C18X—H18C | 0.9300 |
C19A—C20A | 1.398 (3) | C19X—C20X | 1.364 (14) |
C19A—H19A | 0.9300 | C19X—H19C | 0.9300 |
O1B—C20B | 1.387 (4) | O1Y—C20Y | 1.337 (12) |
O1B—H1OB | 0.9754 | O1Y—H1OY | 0.8786 |
N1B—C7B | 1.317 (2) | N1Y—C7Y | 1.337 (6) |
N1B—C1B | 1.405 (3) | N1Y—C1Y | 1.382 (5) |
N2B—C7B | 1.367 (2) | N2Y—C6Y | 1.371 (5) |
N2B—C6B | 1.395 (2) | N2Y—C7Y | 1.384 (6) |
N2B—C14B | 1.459 (3) | N2Y—C14Y | 1.451 (12) |
N3B—C9B | 1.381 (2) | N3Y—C9Y | 1.359 (6) |
N3B—C14B | 1.470 (5) | N3Y—C14Y | 1.483 (16) |
N3B—H3BB | 0.8600 | N3Y—H3YB | 0.8600 |
C1B—C2B | 1.396 (3) | C1Y—C2Y | 1.404 (7) |
C1B—C6B | 1.400 (3) | C1Y—C6Y | 1.417 (7) |
C2B—C3B | 1.369 (4) | C2Y—C3Y | 1.399 (11) |
C2B—H2BA | 0.9300 | C2Y—H2YA | 0.9300 |
C3B—C4B | 1.403 (4) | C3Y—C4Y | 1.364 (10) |
C3B—H3BA | 0.9300 | C3Y—H3YA | 0.9300 |
C4B—C5B | 1.404 (4) | C4Y—C5Y | 1.350 (8) |
C4B—H4BA | 0.9300 | C4Y—H4YA | 0.9300 |
C5B—C6B | 1.379 (3) | C5Y—C6Y | 1.374 (7) |
C5B—H5BA | 0.9300 | C5Y—H5YA | 0.9300 |
C7B—C8B | 1.458 (3) | C7Y—C8Y | 1.439 (6) |
C8B—C9B | 1.407 (2) | C8Y—C13Y | 1.371 (7) |
C8B—C13B | 1.407 (3) | C8Y—C9Y | 1.409 (7) |
C9B—C10B | 1.399 (3) | C9Y—C10Y | 1.445 (8) |
C10B—C11B | 1.370 (3) | C10Y—C11Y | 1.356 (10) |
C10B—H10B | 0.9300 | C10Y—H10D | 0.9300 |
C11B—C12B | 1.403 (4) | C11Y—C12Y | 1.412 (16) |
C11B—H11B | 0.9300 | C11Y—H11D | 0.9300 |
C12B—C13B | 1.397 (4) | C12Y—C13Y | 1.393 (15) |
C12B—H12B | 0.9300 | C12Y—H12D | 0.9300 |
C13B—H13B | 0.9300 | C13Y—H13D | 0.9300 |
C14B—C15B | 1.524 (3) | C14Y—C15Y | 1.515 (14) |
C14B—H14B | 0.9800 | C14Y—H14D | 0.9800 |
C15B—C16B | 1.389 (3) | C15Y—C16Y | 1.376 (14) |
C15B—C20B | 1.398 (4) | C15Y—C20Y | 1.396 (13) |
C16B—C17B | 1.390 (3) | C16Y—C17Y | 1.397 (14) |
C16B—H16B | 0.9300 | C16Y—H16D | 0.9300 |
C17B—C18B | 1.389 (4) | C17Y—C18Y | 1.376 (14) |
C17B—H17B | 0.9300 | C17Y—H17D | 0.9300 |
C18B—C19B | 1.384 (5) | C18Y—C19Y | 1.356 (14) |
C18B—H18B | 0.9300 | C18Y—H18D | 0.9300 |
C19B—C20B | 1.394 (5) | C19Y—C20Y | 1.360 (13) |
C19B—H19B | 0.9300 | C19Y—H19D | 0.9300 |
C20A—O1A—H1OA | 113.6 | C20X—O1X—H1OA | 114.8 |
C20A—O1A—H1OX | 113.8 | C20X—O1X—H1OX | 115.4 |
C7A—N1A—C1A | 105.22 (16) | C7X—N1X—C1X | 103.6 (6) |
C7A—N2A—C6A | 107.32 (15) | C6X—N2X—C7X | 107.4 (6) |
C7A—N2A—C14A | 123.90 (18) | C6X—N2X—C14X | 127.3 (8) |
C6A—N2A—C14A | 128.34 (16) | C7X—N2X—C14X | 124.5 (8) |
C9A—N3A—C14A | 120.86 (15) | C9X—N3X—C14X | 121.7 (8) |
C9A—N3A—H3AB | 119.6 | C9X—N3X—H3XB | 119.1 |
C14A—N3A—H3AB | 119.6 | C14X—N3X—H3XB | 119.1 |
N1A—C1A—C6A | 110.06 (15) | C2X—C1X—C6X | 119.1 (6) |
N1A—C1A—C2A | 129.92 (16) | C2X—C1X—N1X | 129.9 (6) |
C6A—C1A—C2A | 120.00 (16) | C6X—C1X—N1X | 111.0 (6) |
C3A—C2A—C1A | 117.34 (17) | C3X—C2X—C1X | 119.3 (7) |
C3A—C2A—H2AA | 121.3 | C3X—C2X—H2XA | 120.3 |
C1A—C2A—H2AA | 121.3 | C1X—C2X—H2XA | 120.3 |
C2A—C3A—C4A | 121.92 (18) | C2X—C3X—C4X | 121.5 (8) |
C2A—C3A—H3AA | 119.0 | C2X—C3X—H3XA | 119.2 |
C4A—C3A—H3AA | 119.0 | C4X—C3X—H3XA | 119.2 |
C5A—C4A—C3A | 120.9 (2) | C5X—C4X—C3X | 120.6 (7) |
C5A—C4A—H4AA | 119.6 | C5X—C4X—H4XA | 119.7 |
C3A—C4A—H4AA | 119.6 | C3X—C4X—H4XA | 119.7 |
C6A—C5A—C4A | 117.10 (19) | C4X—C5X—C6X | 116.8 (6) |
C6A—C5A—H5AA | 121.5 | C4X—C5X—H5XA | 121.6 |
C4A—C5A—H5AA | 121.5 | C6X—C5X—H5XA | 121.6 |
N2A—C6A—C5A | 132.06 (17) | N2X—C6X—C5X | 132.0 (7) |
N2A—C6A—C1A | 105.16 (15) | N2X—C6X—C1X | 105.4 (6) |
C5A—C6A—C1A | 122.76 (16) | C5X—C6X—C1X | 122.5 (6) |
N1A—C7A—N2A | 112.2 (2) | N1X—C7X—N2X | 112.5 (6) |
N1A—C7A—C8A | 128.45 (17) | N1X—C7X—C8X | 128.8 (7) |
N2A—C7A—C8A | 119.30 (16) | N2X—C7X—C8X | 118.3 (7) |
C13A—C8A—C9A | 120.70 (15) | C9X—C8X—C13X | 120.6 (6) |
C13A—C8A—C7A | 122.39 (15) | C9X—C8X—C7X | 116.8 (7) |
C9A—C8A—C7A | 116.81 (15) | C13X—C8X—C7X | 122.5 (7) |
N3A—C9A—C10A | 121.76 (15) | C8X—C9X—C10X | 118.5 (6) |
N3A—C9A—C8A | 119.48 (14) | C8X—C9X—N3X | 120.9 (7) |
C10A—C9A—C8A | 118.55 (15) | C10X—C9X—N3X | 120.6 (7) |
C11A—C10A—C9A | 120.09 (16) | C11X—C10X—C9X | 119.9 (8) |
C11A—C10A—H10A | 120.0 | C11X—C10X—H10C | 120.0 |
C9A—C10A—H10A | 120.0 | C9X—C10X—H10C | 120.0 |
C10A—C11A—C12A | 120.97 (18) | C10X—C11X—C12X | 122.9 (9) |
C10A—C11A—H11A | 119.5 | C10X—C11X—H11C | 118.5 |
C12A—C11A—H11A | 119.5 | C12X—C11X—H11C | 118.5 |
C13A—C12A—C11A | 119.37 (18) | C11X—C12X—C13X | 116.9 (8) |
C13A—C12A—H12A | 120.3 | C11X—C12X—H12C | 121.5 |
C11A—C12A—H12A | 120.3 | C13X—C12X—H12C | 121.5 |
C12A—C13A—C8A | 120.32 (16) | C12X—C13X—C8X | 121.1 (7) |
C12A—C13A—H13A | 119.8 | C12X—C13X—H13C | 119.4 |
C8A—C13A—H13A | 119.8 | C8X—C13X—H13C | 119.4 |
N3A—C14A—N2A | 107.16 (16) | N3X—C14X—N2X | 106.8 (9) |
N3A—C14A—C15A | 112.9 (2) | N3X—C14X—C15X | 111.3 (13) |
N2A—C14A—C15A | 111.8 (2) | N2X—C14X—C15X | 114.4 (11) |
N3A—C14A—H14A | 108.3 | N3X—C14X—H14C | 108.0 |
N2A—C14A—H14A | 108.3 | N2X—C14X—H14C | 108.0 |
C15A—C14A—H14A | 108.3 | C15X—C14X—H14C | 108.0 |
C16A—C15A—C20A | 119.4 (2) | C16X—C15X—C20X | 115.6 (12) |
C16A—C15A—C14A | 123.6 (2) | C16X—C15X—C14X | 122.2 (13) |
C20A—C15A—C14A | 117.0 (2) | C20X—C15X—C14X | 122.2 (12) |
C15A—C16A—C17A | 120.1 (3) | C15X—C16X—C17X | 125.7 (15) |
C15A—C16A—H16A | 119.9 | C15X—C16X—H16C | 117.2 |
C17A—C16A—H16A | 119.9 | C17X—C16X—H16C | 117.2 |
C18A—C17A—C16A | 120.3 (4) | C18X—C17X—C16X | 115.4 (15) |
C18A—C17A—H17A | 119.9 | C18X—C17X—H17C | 122.3 |
C16A—C17A—H17A | 119.9 | C16X—C17X—H17C | 122.3 |
C17A—C18A—C19A | 120.3 (3) | C17X—C18X—C19X | 122.0 (15) |
C17A—C18A—H18A | 119.9 | C17X—C18X—H18C | 119.0 |
C19A—C18A—H18A | 119.9 | C19X—C18X—H18C | 119.0 |
C18A—C19A—C20A | 120.0 (3) | C20X—C19X—C18X | 119.6 (15) |
C18A—C19A—H19A | 120.0 | C20X—C19X—H19C | 120.2 |
C20A—C19A—H19A | 120.0 | C18X—C19X—H19C | 120.2 |
O1A—C20A—C19A | 122.0 (2) | O1X—C20X—C19X | 124.6 (14) |
O1A—C20A—C15A | 118.1 (2) | O1X—C20X—C15X | 114.2 (13) |
C19A—C20A—C15A | 119.9 (2) | C19X—C20X—C15X | 121.2 (13) |
C20B—O1B—H1OB | 108.0 | C20Y—O1Y—H1OB | 98.5 |
C20B—O1B—H1OY | 115.2 | C20Y—O1Y—H1OY | 106.8 |
C7B—N1B—C1B | 104.73 (15) | C7Y—N1Y—C1Y | 106.7 (4) |
C7B—N2B—C6B | 107.03 (15) | C6Y—N2Y—C7Y | 109.0 (4) |
C7B—N2B—C14B | 124.6 (2) | C6Y—N2Y—C14Y | 125.9 (8) |
C6B—N2B—C14B | 126.8 (2) | C7Y—N2Y—C14Y | 123.6 (8) |
C9B—N3B—C14B | 121.47 (17) | C9Y—N3Y—C14Y | 120.4 (7) |
C9B—N3B—H3BB | 119.3 | C9Y—N3Y—H3YB | 119.8 |
C14B—N3B—H3BB | 119.3 | C14Y—N3Y—H3YB | 119.8 |
C2B—C1B—C6B | 120.02 (18) | N1Y—C1Y—C2Y | 131.2 (4) |
C2B—C1B—N1B | 129.91 (17) | N1Y—C1Y—C6Y | 109.6 (4) |
C6B—C1B—N1B | 110.07 (15) | C2Y—C1Y—C6Y | 119.2 (4) |
C3B—C2B—C1B | 117.3 (2) | C3Y—C2Y—C1Y | 114.3 (6) |
C3B—C2B—H2BA | 121.3 | C3Y—C2Y—H2YA | 122.8 |
C1B—C2B—H2BA | 121.3 | C1Y—C2Y—H2YA | 122.8 |
C2B—C3B—C4B | 123.0 (3) | C4Y—C3Y—C2Y | 125.1 (9) |
C2B—C3B—H3BA | 118.5 | C4Y—C3Y—H3YA | 117.4 |
C4B—C3B—H3BA | 118.5 | C2Y—C3Y—H3YA | 117.4 |
C3B—C4B—C5B | 119.9 (3) | C5Y—C4Y—C3Y | 120.9 (7) |
C3B—C4B—H4BA | 120.1 | C5Y—C4Y—H4YA | 119.6 |
C5B—C4B—H4BA | 120.1 | C3Y—C4Y—H4YA | 119.6 |
C6B—C5B—C4B | 116.8 (2) | C4Y—C5Y—C6Y | 116.9 (5) |
C6B—C5B—H5BA | 121.6 | C4Y—C5Y—H5YA | 121.6 |
C4B—C5B—H5BA | 121.6 | C6Y—C5Y—H5YA | 121.6 |
C5B—C6B—N2B | 132.11 (19) | N2Y—C6Y—C5Y | 131.8 (4) |
C5B—C6B—C1B | 122.96 (18) | N2Y—C6Y—C1Y | 104.7 (4) |
N2B—C6B—C1B | 104.92 (17) | C5Y—C6Y—C1Y | 123.5 (4) |
N1B—C7B—N2B | 113.23 (18) | N1Y—C7Y—N2Y | 110.0 (4) |
N1B—C7B—C8B | 128.25 (17) | N1Y—C7Y—C8Y | 130.0 (4) |
N2B—C7B—C8B | 118.49 (15) | N2Y—C7Y—C8Y | 120.0 (4) |
C9B—C8B—C13B | 120.29 (17) | C13Y—C8Y—C9Y | 121.5 (4) |
C9B—C8B—C7B | 116.80 (17) | C13Y—C8Y—C7Y | 123.4 (5) |
C13B—C8B—C7B | 122.79 (16) | C9Y—C8Y—C7Y | 115.1 (5) |
N3B—C9B—C10B | 121.40 (16) | N3Y—C9Y—C8Y | 122.1 (5) |
N3B—C9B—C8B | 119.77 (18) | N3Y—C9Y—C10Y | 120.2 (4) |
C10B—C9B—C8B | 118.70 (17) | C8Y—C9Y—C10Y | 117.5 (5) |
C11B—C10B—C9B | 120.27 (17) | C11Y—C10Y—C9Y | 119.1 (6) |
C11B—C10B—H10B | 119.9 | C11Y—C10Y—H10D | 120.4 |
C9B—C10B—H10B | 119.9 | C9Y—C10Y—H10D | 120.4 |
C10B—C11B—C12B | 122.4 (2) | C10Y—C11Y—C12Y | 123.1 (10) |
C10B—C11B—H11B | 118.8 | C10Y—C11Y—H11D | 118.4 |
C12B—C11B—H11B | 118.8 | C12Y—C11Y—H11D | 118.4 |
C13B—C12B—C11B | 117.7 (3) | C13Y—C12Y—C11Y | 117.3 (13) |
C13B—C12B—H12B | 121.2 | C13Y—C12Y—H12D | 121.4 |
C11B—C12B—H12B | 121.2 | C11Y—C12Y—H12D | 121.4 |
C12B—C13B—C8B | 120.6 (2) | C8Y—C13Y—C12Y | 121.3 (8) |
C12B—C13B—H13B | 119.7 | C8Y—C13Y—H13D | 119.3 |
C8B—C13B—H13B | 119.7 | C12Y—C13Y—H13D | 119.3 |
N2B—C14B—N3B | 105.4 (2) | N2Y—C14Y—N3Y | 106.3 (9) |
N2B—C14B—C15B | 111.3 (3) | N2Y—C14Y—C15Y | 112.1 (11) |
N3B—C14B—C15B | 112.6 (3) | N3Y—C14Y—C15Y | 114.5 (15) |
N2B—C14B—H14B | 109.2 | N2Y—C14Y—H14D | 107.9 |
N3B—C14B—H14B | 109.2 | N3Y—C14Y—H14D | 107.9 |
C15B—C14B—H14B | 109.2 | C15Y—C14Y—H14D | 107.9 |
C16B—C15B—C20B | 117.8 (3) | C16Y—C15Y—C20Y | 120.4 (12) |
C16B—C15B—C14B | 123.2 (3) | C16Y—C15Y—C14Y | 122.5 (13) |
C20B—C15B—C14B | 119.0 (3) | C20Y—C15Y—C14Y | 116.9 (11) |
C15B—C16B—C17B | 121.1 (2) | C15Y—C16Y—C17Y | 122.7 (14) |
C15B—C16B—H16B | 119.5 | C15Y—C16Y—H16D | 118.7 |
C17B—C16B—H16B | 119.5 | C17Y—C16Y—H16D | 118.7 |
C18B—C17B—C16B | 119.9 (3) | C18Y—C17Y—C16Y | 114.7 (14) |
C18B—C17B—H17B | 120.0 | C18Y—C17Y—H17D | 122.7 |
C16B—C17B—H17B | 120.0 | C16Y—C17Y—H17D | 122.7 |
C19B—C18B—C17B | 120.4 (3) | C19Y—C18Y—C17Y | 122.8 (15) |
C19B—C18B—H18B | 119.8 | C19Y—C18Y—H18D | 118.6 |
C17B—C18B—H18B | 119.8 | C17Y—C18Y—H18D | 118.6 |
C18B—C19B—C20B | 118.8 (4) | C18Y—C19Y—C20Y | 122.6 (15) |
C18B—C19B—H19B | 120.6 | C18Y—C19Y—H19D | 118.7 |
C20B—C19B—H19B | 120.6 | C20Y—C19Y—H19D | 118.7 |
O1B—C20B—C19B | 121.0 (4) | O1Y—C20Y—C19Y | 126.0 (12) |
O1B—C20B—C15B | 116.9 (4) | O1Y—C20Y—C15Y | 115.9 (11) |
C19B—C20B—C15B | 121.9 (4) | C19Y—C20Y—C15Y | 116.5 (12) |
C7A—N1A—C1A—C6A | −0.70 (19) | C7X—N1X—C1X—C2X | 179.6 (8) |
C7A—N1A—C1A—C2A | 177.60 (18) | C7X—N1X—C1X—C6X | −1.6 (8) |
N1A—C1A—C2A—C3A | −178.11 (18) | C6X—C1X—C2X—C3X | 1.4 (10) |
C6A—C1A—C2A—C3A | 0.0 (3) | N1X—C1X—C2X—C3X | −179.8 (7) |
C1A—C2A—C3A—C4A | −0.6 (3) | C1X—C2X—C3X—C4X | −3.1 (12) |
C2A—C3A—C4A—C5A | 0.1 (4) | C2X—C3X—C4X—C5X | 3.0 (13) |
C3A—C4A—C5A—C6A | 0.9 (4) | C3X—C4X—C5X—C6X | −1.1 (12) |
C7A—N2A—C6A—C5A | −179.3 (2) | C7X—N2X—C6X—C5X | −180.0 (8) |
C14A—N2A—C6A—C5A | 8.2 (3) | C14X—N2X—C6X—C5X | −9.8 (13) |
C7A—N2A—C6A—C1A | −1.11 (18) | C7X—N2X—C6X—C1X | 2.2 (8) |
C14A—N2A—C6A—C1A | −173.61 (19) | C14X—N2X—C6X—C1X | 172.4 (9) |
C4A—C5A—C6A—N2A | 176.4 (2) | C4X—C5X—C6X—N2X | −178.1 (7) |
C4A—C5A—C6A—C1A | −1.5 (3) | C4X—C5X—C6X—C1X | −0.6 (10) |
N1A—C1A—C6A—N2A | 1.13 (18) | C2X—C1X—C6X—N2X | 178.5 (6) |
C2A—C1A—C6A—N2A | −177.36 (15) | N1X—C1X—C6X—N2X | −0.5 (7) |
N1A—C1A—C6A—C5A | 179.53 (17) | C2X—C1X—C6X—C5X | 0.5 (10) |
C2A—C1A—C6A—C5A | 1.0 (3) | N1X—C1X—C6X—C5X | −178.5 (6) |
C1A—N1A—C7A—N2A | 0.0 (2) | C1X—N1X—C7X—N2X | 3.0 (9) |
C1A—N1A—C7A—C8A | −178.26 (18) | C1X—N1X—C7X—C8X | 176.3 (9) |
C6A—N2A—C7A—N1A | 0.7 (2) | C6X—N2X—C7X—N1X | −3.5 (10) |
C14A—N2A—C7A—N1A | 173.66 (18) | C14X—N2X—C7X—N1X | −174.0 (9) |
C6A—N2A—C7A—C8A | 179.15 (15) | C6X—N2X—C7X—C8X | −177.6 (7) |
C14A—N2A—C7A—C8A | −7.9 (3) | C14X—N2X—C7X—C8X | 11.9 (14) |
N1A—C7A—C8A—C13A | −6.7 (3) | N1X—C7X—C8X—C9X | −167.6 (9) |
N2A—C7A—C8A—C13A | 175.20 (16) | N2X—C7X—C8X—C9X | 5.4 (12) |
N1A—C7A—C8A—C9A | 169.64 (17) | N1X—C7X—C8X—C13X | 9.2 (14) |
N2A—C7A—C8A—C9A | −8.5 (2) | N2X—C7X—C8X—C13X | −177.8 (7) |
C14A—N3A—C9A—C10A | −155.79 (17) | C13X—C8X—C9X—C10X | 1.4 (11) |
C14A—N3A—C9A—C8A | 29.6 (2) | C7X—C8X—C9X—C10X | 178.2 (8) |
C13A—C8A—C9A—N3A | 174.43 (15) | C13X—C8X—C9X—N3X | −175.6 (6) |
C7A—C8A—C9A—N3A | −2.0 (2) | C7X—C8X—C9X—N3X | 1.2 (10) |
C13A—C8A—C9A—C10A | −0.4 (2) | C14X—N3X—C9X—C8X | −25.8 (12) |
C7A—C8A—C9A—C10A | −176.78 (15) | C14X—N3X—C9X—C10X | 157.3 (9) |
N3A—C9A—C10A—C11A | −174.50 (17) | C8X—C9X—C10X—C11X | −1.5 (12) |
C8A—C9A—C10A—C11A | 0.2 (3) | N3X—C9X—C10X—C11X | 175.5 (8) |
C9A—C10A—C11A—C12A | 0.1 (3) | C9X—C10X—C11X—C12X | 2.3 (15) |
C10A—C11A—C12A—C13A | −0.3 (3) | C10X—C11X—C12X—C13X | −2.9 (14) |
C11A—C12A—C13A—C8A | 0.1 (3) | C11X—C12X—C13X—C8X | 2.7 (12) |
C9A—C8A—C13A—C12A | 0.2 (3) | C9X—C8X—C13X—C12X | −2.1 (11) |
C7A—C8A—C13A—C12A | 176.42 (18) | C7X—C8X—C13X—C12X | −178.8 (8) |
C9A—N3A—C14A—N2A | −41.4 (2) | C9X—N3X—C14X—N2X | 38.1 (14) |
C9A—N3A—C14A—C15A | 82.0 (2) | C9X—N3X—C14X—C15X | −87.5 (11) |
C7A—N2A—C14A—N3A | 30.8 (3) | C6X—N2X—C14X—N3X | 159.8 (8) |
C6A—N2A—C14A—N3A | −157.78 (16) | C7X—N2X—C14X—N3X | −31.6 (15) |
C7A—N2A—C14A—C15A | −93.4 (3) | C6X—N2X—C14X—C15X | −76.5 (16) |
C6A—N2A—C14A—C15A | 78.0 (3) | C7X—N2X—C14X—C15X | 92.1 (14) |
N3A—C14A—C15A—C16A | −114.4 (3) | N3X—C14X—C15X—C16X | 81.8 (17) |
N2A—C14A—C15A—C16A | 6.5 (4) | N2X—C14X—C15X—C16X | −39 (2) |
N3A—C14A—C15A—C20A | 66.4 (3) | N3X—C14X—C15X—C20X | −100.2 (19) |
N2A—C14A—C15A—C20A | −172.7 (3) | N2X—C14X—C15X—C20X | 138.5 (17) |
C20A—C15A—C16A—C17A | 1.8 (5) | C20X—C15X—C16X—C17X | 0.4 (18) |
C14A—C15A—C16A—C17A | −177.5 (5) | C14X—C15X—C16X—C17X | 178.5 (19) |
C15A—C16A—C17A—C18A | −1.6 (8) | C15X—C16X—C17X—C18X | 6.0 (19) |
C16A—C17A—C18A—C19A | 1.3 (9) | C16X—C17X—C18X—C19X | −8 (3) |
C17A—C18A—C19A—C20A | −1.3 (8) | C17X—C18X—C19X—C20X | 5 (4) |
C18A—C19A—C20A—O1A | −179.6 (4) | C18X—C19X—C20X—O1X | −178 (2) |
C18A—C19A—C20A—C15A | 1.5 (6) | C18X—C19X—C20X—C15X | 2 (3) |
C16A—C15A—C20A—O1A | 179.3 (3) | C16X—C15X—C20X—O1X | 176.0 (17) |
C14A—C15A—C20A—O1A | −1.5 (5) | C14X—C15X—C20X—O1X | −2 (3) |
C16A—C15A—C20A—C19A | −1.7 (5) | C16X—C15X—C20X—C19X | −5 (3) |
C14A—C15A—C20A—C19A | 177.6 (3) | C14X—C15X—C20X—C19X | 177 (2) |
C7B—N1B—C1B—C2B | 179.5 (2) | C7Y—N1Y—C1Y—C2Y | −179.7 (5) |
C7B—N1B—C1B—C6B | 0.5 (2) | C7Y—N1Y—C1Y—C6Y | −0.3 (5) |
C6B—C1B—C2B—C3B | 0.3 (4) | N1Y—C1Y—C2Y—C3Y | 178.9 (7) |
N1B—C1B—C2B—C3B | −178.6 (3) | C6Y—C1Y—C2Y—C3Y | −0.5 (9) |
C1B—C2B—C3B—C4B | −1.0 (6) | C1Y—C2Y—C3Y—C4Y | 2.8 (15) |
C2B—C3B—C4B—C5B | 1.1 (6) | C2Y—C3Y—C4Y—C5Y | −3.9 (16) |
C3B—C4B—C5B—C6B | −0.4 (4) | C3Y—C4Y—C5Y—C6Y | 2.3 (10) |
C4B—C5B—C6B—N2B | 178.5 (2) | C7Y—N2Y—C6Y—C5Y | −179.2 (5) |
C4B—C5B—C6B—C1B | −0.3 (3) | C14Y—N2Y—C6Y—C5Y | −12.7 (11) |
C7B—N2B—C6B—C5B | 179.9 (2) | C7Y—N2Y—C6Y—C1Y | 0.9 (5) |
C14B—N2B—C6B—C5B | 14.1 (3) | C14Y—N2Y—C6Y—C1Y | 167.4 (9) |
C7B—N2B—C6B—C1B | −1.15 (19) | C4Y—C5Y—C6Y—N2Y | 180.0 (5) |
C14B—N2B—C6B—C1B | −166.9 (2) | C4Y—C5Y—C6Y—C1Y | −0.1 (7) |
C2B—C1B—C6B—C5B | 0.3 (3) | N1Y—C1Y—C6Y—N2Y | −0.4 (5) |
N1B—C1B—C6B—C5B | 179.45 (18) | C2Y—C1Y—C6Y—N2Y | 179.1 (4) |
C2B—C1B—C6B—N2B | −178.71 (17) | N1Y—C1Y—C6Y—C5Y | 179.7 (4) |
N1B—C1B—C6B—N2B | 0.4 (2) | C2Y—C1Y—C6Y—C5Y | −0.8 (7) |
C1B—N1B—C7B—N2B | −1.3 (2) | C1Y—N1Y—C7Y—N2Y | 0.9 (5) |
C1B—N1B—C7B—C8B | −179.37 (17) | C1Y—N1Y—C7Y—C8Y | −179.6 (5) |
C6B—N2B—C7B—N1B | 1.6 (2) | C6Y—N2Y—C7Y—N1Y | −1.1 (5) |
C14B—N2B—C7B—N1B | 167.8 (2) | C14Y—N2Y—C7Y—N1Y | −168.0 (8) |
C6B—N2B—C7B—C8B | 179.87 (15) | C6Y—N2Y—C7Y—C8Y | 179.2 (4) |
C14B—N2B—C7B—C8B | −13.9 (3) | C14Y—N2Y—C7Y—C8Y | 12.3 (10) |
N1B—C7B—C8B—C9B | 171.53 (17) | N1Y—C7Y—C8Y—C13Y | 4.7 (8) |
N2B—C7B—C8B—C9B | −6.4 (2) | N2Y—C7Y—C8Y—C13Y | −175.8 (5) |
N1B—C7B—C8B—C13B | −4.5 (3) | N1Y—C7Y—C8Y—C9Y | −172.9 (5) |
N2B—C7B—C8B—C13B | 177.58 (17) | N2Y—C7Y—C8Y—C9Y | 6.6 (7) |
C14B—N3B—C9B—C10B | −156.83 (19) | C14Y—N3Y—C9Y—C8Y | −26.8 (10) |
C14B—N3B—C9B—C8B | 27.5 (3) | C14Y—N3Y—C9Y—C10Y | 158.2 (8) |
C13B—C8B—C9B—N3B | 175.78 (17) | C13Y—C8Y—C9Y—N3Y | −176.8 (5) |
C7B—C8B—C9B—N3B | −0.3 (2) | C7Y—C8Y—C9Y—N3Y | 0.8 (7) |
C13B—C8B—C9B—C10B | 0.0 (3) | C13Y—C8Y—C9Y—C10Y | −1.7 (8) |
C7B—C8B—C9B—C10B | −176.08 (16) | C7Y—C8Y—C9Y—C10Y | 175.9 (5) |
N3B—C9B—C10B—C11B | −175.40 (18) | N3Y—C9Y—C10Y—C11Y | 176.2 (7) |
C8B—C9B—C10B—C11B | 0.3 (3) | C8Y—C9Y—C10Y—C11Y | 1.0 (10) |
C9B—C10B—C11B—C12B | −0.7 (3) | C9Y—C10Y—C11Y—C12Y | 2.2 (19) |
C10B—C11B—C12B—C13B | 0.7 (4) | C10Y—C11Y—C12Y—C13Y | −5 (3) |
C11B—C12B—C13B—C8B | −0.4 (4) | C9Y—C8Y—C13Y—C12Y | −0.8 (15) |
C9B—C8B—C13B—C12B | 0.0 (3) | C7Y—C8Y—C13Y—C12Y | −178.2 (13) |
C7B—C8B—C13B—C12B | 175.9 (2) | C11Y—C12Y—C13Y—C8Y | 4 (3) |
C7B—N2B—C14B—N3B | 35.6 (3) | C6Y—N2Y—C14Y—N3Y | 161.8 (7) |
C6B—N2B—C14B—N3B | −160.96 (18) | C7Y—N2Y—C14Y—N3Y | −33.5 (14) |
C7B—N2B—C14B—C15B | −86.7 (4) | C6Y—N2Y—C14Y—C15Y | −72.4 (17) |
C6B—N2B—C14B—C15B | 76.7 (4) | C7Y—N2Y—C14Y—C15Y | 92.3 (14) |
C9B—N3B—C14B—N2B | −42.1 (3) | C9Y—N3Y—C14Y—N2Y | 40.4 (14) |
C9B—N3B—C14B—C15B | 79.4 (3) | C9Y—N3Y—C14Y—C15Y | −83.9 (11) |
N2B—C14B—C15B—C16B | 6.9 (6) | N2Y—C14Y—C15Y—C16Y | −41 (2) |
N3B—C14B—C15B—C16B | −111.1 (4) | N3Y—C14Y—C15Y—C16Y | 80.5 (18) |
N2B—C14B—C15B—C20B | −175.8 (4) | N2Y—C14Y—C15Y—C20Y | 145.4 (16) |
N3B—C14B—C15B—C20B | 66.1 (5) | N3Y—C14Y—C15Y—C20Y | −93.4 (19) |
C20B—C15B—C16B—C17B | 1.1 (5) | C20Y—C15Y—C16Y—C17Y | −1.0 (18) |
C14B—C15B—C16B—C17B | 178.4 (4) | C14Y—C15Y—C16Y—C17Y | −175 (2) |
C15B—C16B—C17B—C18B | 0.4 (4) | C15Y—C16Y—C17Y—C18Y | −4.0 (17) |
C16B—C17B—C18B—C19B | −1.1 (7) | C16Y—C17Y—C18Y—C19Y | 6 (3) |
C17B—C18B—C19B—C20B | 0.3 (9) | C17Y—C18Y—C19Y—C20Y | −4 (4) |
C18B—C19B—C20B—O1B | 176.0 (6) | C18Y—C19Y—C20Y—O1Y | −167 (2) |
C18B—C19B—C20B—C15B | 1.3 (10) | C18Y—C19Y—C20Y—C15Y | −2 (3) |
C16B—C15B—C20B—O1B | −176.8 (4) | C16Y—C15Y—C20Y—O1Y | 170.4 (15) |
C14B—C15B—C20B—O1B | 5.8 (7) | C14Y—C15Y—C20Y—O1Y | −16 (2) |
C16B—C15B—C20B—C19B | −1.9 (8) | C16Y—C15Y—C20Y—C19Y | 4 (3) |
C14B—C15B—C20B—C19B | −179.3 (6) | C14Y—C15Y—C20Y—C19Y | 177.9 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···N1Bi | 0.98 | 1.69 | 2.641 (3) | 162 |
N3A—H3AB···O1Aii | 0.86 | 2.50 | 3.241 (3) | 144 |
O1B—H1OB···N1Aiii | 0.97 | 1.79 | 2.686 (4) | 151 |
N3B—H3BB···O1Biv | 0.86 | 2.15 | 2.974 (4) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C20H15N3O |
Mr | 313.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 297 |
a, b, c (Å) | 17.1513 (10), 19.1160 (11), 9.2630 (5) |
β (°) | 97.590 (1) |
V (Å3) | 3010.4 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.28 × 0.25 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.974, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40861, 11057, 8231 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.763 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.158, 1.05 |
No. of reflections | 11057 |
No. of parameters | 625 |
No. of restraints | 144 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.42 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···N1Bi | 0.98 | 1.69 | 2.641 (3) | 162 |
N3A—H3AB···O1Aii | 0.86 | 2.50 | 3.241 (3) | 144 |
O1B—H1OB···N1Aiii | 0.97 | 1.79 | 2.686 (4) | 151 |
N3B—H3BB···O1Biv | 0.86 | 2.15 | 2.974 (4) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+1, −z. |
The synthesis of benzimidazoles has received much attention owing to the varied biological activity such as antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), antiHIV (Barreca et al., 2003) and anticancer (Demirayak et al., 2002) properties exhibited by a number of derivatives of these compounds. Previously we reported the crystal structures of 4-allyl-2-[1-(5-allyl-2-hydroxy-3-methoxybenzyl) -1H-benzimidazol-2-yl]-6-methoxyphenol (Eltayeb et al., 2007a), 2-(2-methoxynaphthalen-1-yl)-1-[(2-methoxynaphthalen-1-yl)methyl] -1H-benzimidazole (Eltayeb et al., 2007b), 2-(benzimidazol-2-yl) -6-methoxyphenol (Eltayeb et al., 2007c) and 2-methoxy-6-(6-methyl -1H-benzimidazol-2-yl)phenol (Eltayeb et al., 2009). Considering the biological importance of the included benzimidazole ring, we describe in this paper the single crystal X-ray diffraction study of 2-(5,6- dihydrobenzimidazo[1,2-c]quinazolin-6-yl)phenol.
The asymmetric unit contains two independent molecules (Fig. 1), A and B. In each molecule, the benzimidazole fused ring system is disordered over two sets of sites with refined site occupancies of 0.748 (1) : 0.252 (1), suggesting 180° rotational disorder for the benzimidazole fused ring system. The conformations for pyrimidine rings are close to a sofa conformation (Cremer & Pople, 1975), puckering parameters Q = 0.330 (2) Å, Θ = 61.9 (3)° and ϕ = 277.5 (4)° (major component of molecule A), Q = 0.305 (12) Å, Θ = 120.6 (19)° and ϕ = 103.9 (19)° (minor component of molecule A), Q = 0.343 (3) Å, Θ = 60.4 (4)° and ϕ = 285.8 (4)° (major component of molecule B) and Q = 0.331 (11) Å, Θ = 119.3 (14)° and ϕ = 104.7 (14)° (minor component of molecule B). Bond lengths (Allen et al., 1987) and angles are within normal ranges. In molecule A (Fig. 2), the hydroxyphenyl ring (C15-C20) is almost perpendicular to the mean plane of benzimidazole ring (N1/N2/C1-C7) with the dihedral angles of 83.9 (3) and 82.4 (4)° for major and minor components, respectively. The corresponding dihedral angles for molecule B are 88.31 (14) and 85.8 (6)°.
In the crystal structure, Fig. 3, the molecules are linked via intermolecular O1A–H10A···N1Bi, N3A–H3AB···O1Aii, O1B–H10B···N1Aiii and N3B–H3BB..O1Biv hydrogen bonds (Table 1) into infinite one-dimensional chains along [100].