Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030395/bt2405sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030395/bt2405Isup2.hkl |
CCDC reference: 655045
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.119
- Data-to-parameter ratio = 17.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C2 - C9 .. 9.21 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C33 .. 7.65 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C34 - C37 .. 7.10 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C34 - C38 .. 7.59 su
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 100 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C6 .. 5.15 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C10 .. 6.31 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C13 .. 6.16 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C14 .. 5.53 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C24 .. 5.46 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C25 .. 5.95 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.13
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Gowda et al. (2004, 2007); Gowda, Foro & Fuess (2007a, 2007b); Gowda, Kožíšek, Tokarčík & Fuess (2007a, 2007b).
The title compound was prepared according to the literature method (Gowda et al., 2004). The purity of the compound was checked by determining its melting point. The compound was further characterized by recording its infrared and NMR spectra (Gowda et al., 2004). Single crystals of the title compound were obtained from a slow evaporation of an ethanolic solution.
H atoms bonded to C were refined using a riding model with C—H ranging from 0.95 to 0.98Å and Uiso(H) = 1.2 Ueq(C). The methyl groups were allowed to rotate but not to tip. H atoms bonded to N were located in difference map and their positions were refined with Uiso(H) = 1.2 Ueq(N).
In the present work, the structure of N-(2,6-dimethylphenyl)-2,2,2- trimethylacetamide has been determined, as part of our study of the effect of ring and side chain substitutions on the solid state structures of chemically and biologically significant compounds such as acetanilides (Gowda, Foro, & Fuess, 2007a; Gowda, Foro, & Fuess, 2007b; Gowda et al., 2007; Gowda, Kožíšek, Tokarčík & Fuess, 2007a, 2007b). The title compound crystallizes with four molecules in the asymmetric unit (Figs. 1 & 2). The structure of resembles those of N-(2,6-dimethylphenyl)-acetamide (Gowda, Foro, & Fuess, 2007a, b), N-(2-methylphenyl)- 2,2,2-trimethylacetamide (Gowda, Kožíšek, Tokarčík & Fuess, 2007b), N-(3,5-dimethylphenyl)-2,2,2-trimethylacetamide (Gowda, Kožíšek, Tokarčík & Fuess, 2007a), N-(2,6-dimethylphenyl)-2,2,2-trichloroacetamide (Gowda, Foro, & Fuess, 2007a) and other closely related acetanilides (Gowda et al., 2007), with somewhat slightly different bond parameters. The molecules are linked into chains through N—H···O hydrogen bonds (Table 1).
For related literature, see: Gowda et al. (2004, 2007); Gowda, Foro & Fuess (2007a, 2007b); Gowda, Kožíšek, Tokarčík & Fuess (2007a, 2007b).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C13H19NO | Z = 8 |
Mr = 205.29 | F(000) = 896 |
Triclinic, P1 | Dx = 1.097 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.799 (1) Å | Cell parameters from 4489 reflections |
b = 15.330 (1) Å | θ = 2.2–21.9° |
c = 16.173 (1) Å | µ = 0.07 mm−1 |
α = 70.004 (8)° | T = 100 K |
β = 89.800 (7)° | Prism, colourless |
γ = 81.487 (7)° | 0.36 × 0.16 × 0.16 mm |
V = 2485.1 (3) Å3 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 10127 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4638 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 8.4012 pixels mm-1 | θmax = 26.4°, θmin = 2.4° |
Rotation method data acquisition using ω and φ scans | h = −12→13 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −19→19 |
Tmin = 0.976, Tmax = 0.989 | l = −20→19 |
26845 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0492P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
10127 reflections | Δρmax = 0.21 e Å−3 |
571 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0018 (4) |
C13H19NO | γ = 81.487 (7)° |
Mr = 205.29 | V = 2485.1 (3) Å3 |
Triclinic, P1 | Z = 8 |
a = 10.799 (1) Å | Mo Kα radiation |
b = 15.330 (1) Å | µ = 0.07 mm−1 |
c = 16.173 (1) Å | T = 100 K |
α = 70.004 (8)° | 0.36 × 0.16 × 0.16 mm |
β = 89.800 (7)° |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 10127 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 4638 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.989 | Rint = 0.056 |
26845 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.21 e Å−3 |
10127 reflections | Δρmin = −0.22 e Å−3 |
571 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0649 (2) | 0.14871 (14) | 0.78936 (14) | 0.0315 (6) | |
C2 | 0.0007 (2) | 0.12608 (15) | 0.86686 (16) | 0.0389 (6) | |
C3 | 0.0677 (3) | 0.11314 (16) | 0.94468 (15) | 0.0488 (7) | |
H3 | 0.0267 | 0.0973 | 0.9987 | 0.059* | |
C4 | 0.1927 (3) | 0.12295 (16) | 0.94443 (18) | 0.0518 (8) | |
H4 | 0.2368 | 0.1151 | 0.9979 | 0.062* | |
C5 | 0.2535 (3) | 0.14408 (15) | 0.86678 (18) | 0.0465 (7) | |
H5 | 0.3399 | 0.1497 | 0.8674 | 0.056* | |
C6 | 0.1912 (2) | 0.15735 (14) | 0.78768 (15) | 0.0332 (6) | |
C7 | −0.00024 (19) | 0.10499 (15) | 0.66636 (13) | 0.0256 (5) | |
C8 | −0.07001 (19) | 0.13618 (14) | 0.57685 (13) | 0.0249 (5) | |
C9 | −0.1353 (2) | 0.11504 (17) | 0.86599 (15) | 0.0536 (7) | |
H9A | −0.1451 | 0.0640 | 0.8442 | 0.064* | |
H9B | −0.1846 | 0.1738 | 0.8273 | 0.064* | |
H9C | −0.1648 | 0.1001 | 0.9259 | 0.064* | |
C10 | 0.2571 (2) | 0.17881 (15) | 0.70316 (15) | 0.0462 (7) | |
H10A | 0.2171 | 0.2394 | 0.6614 | 0.055* | |
H10B | 0.2521 | 0.1294 | 0.6782 | 0.055* | |
H10C | 0.3453 | 0.1816 | 0.7145 | 0.055* | |
C11 | 0.0291 (2) | 0.15985 (15) | 0.50841 (13) | 0.0400 (6) | |
H11A | 0.0941 | 0.1048 | 0.5189 | 0.048* | |
H11B | 0.0672 | 0.2123 | 0.5132 | 0.048* | |
H11C | −0.0102 | 0.1777 | 0.4493 | 0.048* | |
C12 | −0.1291 (2) | 0.05423 (14) | 0.57049 (14) | 0.0369 (6) | |
H12A | −0.1917 | 0.0389 | 0.6151 | 0.044* | |
H12B | −0.0639 | −0.0006 | 0.5805 | 0.044* | |
H12C | −0.1697 | 0.0717 | 0.5118 | 0.044* | |
C13 | −0.1715 (2) | 0.22187 (15) | 0.56060 (15) | 0.0435 (7) | |
H13A | −0.1327 | 0.2756 | 0.5610 | 0.052* | |
H13B | −0.2316 | 0.2081 | 0.6071 | 0.052* | |
H13C | −0.2151 | 0.2368 | 0.5033 | 0.052* | |
C14 | 0.61128 (18) | 0.06586 (13) | 0.22279 (14) | 0.0250 (5) | |
C15 | 0.5538 (2) | 0.05535 (14) | 0.15060 (14) | 0.0281 (6) | |
C16 | 0.4501 (2) | 0.00871 (14) | 0.16555 (15) | 0.0355 (6) | |
H16 | 0.4090 | 0.0007 | 0.1174 | 0.043* | |
C17 | 0.4061 (2) | −0.02609 (15) | 0.24876 (16) | 0.0403 (6) | |
H17 | 0.3360 | −0.0585 | 0.2577 | 0.048* | |
C18 | 0.4640 (2) | −0.01373 (15) | 0.31906 (15) | 0.0355 (6) | |
H18 | 0.4330 | −0.0376 | 0.3762 | 0.043* | |
C19 | 0.5669 (2) | 0.03308 (14) | 0.30732 (14) | 0.0291 (6) | |
C20 | 0.7244 (2) | 0.20128 (15) | 0.17613 (13) | 0.0230 (5) | |
C21 | 0.85034 (19) | 0.23408 (13) | 0.18171 (13) | 0.0231 (5) | |
C22 | 0.6029 (2) | 0.09186 (14) | 0.06028 (13) | 0.0375 (6) | |
H22A | 0.6910 | 0.0641 | 0.0617 | 0.045* | |
H22B | 0.5961 | 0.1604 | 0.0413 | 0.045* | |
H22C | 0.5537 | 0.0750 | 0.0189 | 0.045* | |
C23 | 0.6297 (2) | 0.04825 (15) | 0.38334 (13) | 0.0362 (6) | |
H23A | 0.6244 | 0.1158 | 0.3717 | 0.043* | |
H23B | 0.7179 | 0.0191 | 0.3902 | 0.043* | |
H23C | 0.5875 | 0.0197 | 0.4375 | 0.043* | |
C24 | 0.88453 (19) | 0.21409 (14) | 0.27880 (13) | 0.0327 (6) | |
H24A | 0.8987 | 0.1461 | 0.3103 | 0.039* | |
H24B | 0.8158 | 0.2436 | 0.3047 | 0.039* | |
H24C | 0.9610 | 0.2398 | 0.2837 | 0.039* | |
C25 | 0.9524 (2) | 0.18120 (15) | 0.14211 (14) | 0.0402 (6) | |
H25A | 0.9301 | 0.1950 | 0.0797 | 0.048* | |
H25B | 0.9590 | 0.1135 | 0.1738 | 0.048* | |
H25C | 1.0329 | 0.2014 | 0.1476 | 0.048* | |
C26 | 0.83978 (19) | 0.33891 (13) | 0.13096 (13) | 0.0308 (6) | |
H26A | 0.7719 | 0.3730 | 0.1536 | 0.037* | |
H26B | 0.8217 | 0.3511 | 0.0683 | 0.037* | |
H26C | 0.9190 | 0.3601 | 0.1383 | 0.037* | |
C27 | 0.41393 (18) | 0.29916 (14) | 0.30430 (13) | 0.0228 (5) | |
C28 | 0.34897 (19) | 0.23532 (14) | 0.36472 (14) | 0.0273 (5) | |
C29 | 0.3737 (2) | 0.21754 (15) | 0.45409 (14) | 0.0356 (6) | |
H29 | 0.3305 | 0.1747 | 0.4967 | 0.043* | |
C30 | 0.4598 (2) | 0.26134 (16) | 0.48133 (15) | 0.0400 (6) | |
H30 | 0.4764 | 0.2478 | 0.5425 | 0.048* | |
C31 | 0.5220 (2) | 0.32462 (15) | 0.42045 (15) | 0.0343 (6) | |
H31 | 0.5808 | 0.3547 | 0.4400 | 0.041* | |
C32 | 0.49984 (19) | 0.34489 (14) | 0.33076 (14) | 0.0267 (5) | |
C33 | 0.2896 (2) | 0.36453 (14) | 0.16344 (14) | 0.0245 (5) | |
C34 | 0.28635 (18) | 0.37096 (13) | 0.06697 (13) | 0.0220 (5) | |
C35 | 0.25744 (19) | 0.18665 (14) | 0.33497 (14) | 0.0371 (6) | |
H35A | 0.2944 | 0.1625 | 0.2901 | 0.045* | |
H35B | 0.1808 | 0.2312 | 0.3099 | 0.045* | |
H35C | 0.2370 | 0.1343 | 0.3853 | 0.045* | |
C36 | 0.5656 (2) | 0.41565 (15) | 0.26390 (14) | 0.0391 (6) | |
H36A | 0.5053 | 0.4723 | 0.2338 | 0.047* | |
H36B | 0.6017 | 0.3886 | 0.2207 | 0.047* | |
H36C | 0.6326 | 0.4321 | 0.2938 | 0.047* | |
C37 | 0.3138 (2) | 0.27300 (14) | 0.06025 (13) | 0.0352 (6) | |
H37A | 0.2541 | 0.2342 | 0.0944 | 0.042* | |
H37B | 0.3993 | 0.2439 | 0.0837 | 0.042* | |
H37C | 0.3056 | 0.2781 | −0.0016 | 0.042* | |
C38 | 0.38569 (19) | 0.42933 (14) | 0.01940 (13) | 0.0353 (6) | |
H38A | 0.4688 | 0.3985 | 0.0470 | 0.042* | |
H38B | 0.3679 | 0.4922 | 0.0235 | 0.042* | |
H38C | 0.3839 | 0.4345 | −0.0427 | 0.042* | |
C39 | 0.15722 (18) | 0.41861 (14) | 0.02437 (13) | 0.0313 (6) | |
H39A | 0.1372 | 0.4800 | 0.0316 | 0.038* | |
H39B | 0.0945 | 0.3793 | 0.0526 | 0.038* | |
H39C | 0.1567 | 0.4272 | −0.0385 | 0.038* | |
C40 | 0.2864 (2) | 0.58984 (14) | 0.27000 (15) | 0.0304 (6) | |
C41 | 0.3581 (2) | 0.58250 (14) | 0.34470 (14) | 0.0304 (6) | |
C42 | 0.4648 (2) | 0.62495 (15) | 0.33164 (16) | 0.0408 (6) | |
H42 | 0.5150 | 0.6212 | 0.3813 | 0.049* | |
C43 | 0.4999 (2) | 0.67262 (16) | 0.24805 (18) | 0.0510 (7) | |
H43 | 0.5735 | 0.7011 | 0.2405 | 0.061* | |
C44 | 0.4275 (2) | 0.67875 (15) | 0.17535 (16) | 0.0443 (7) | |
H44 | 0.4526 | 0.7109 | 0.1179 | 0.053* | |
C45 | 0.3193 (2) | 0.63888 (14) | 0.18489 (15) | 0.0360 (6) | |
C46 | 0.0722 (2) | 0.57113 (15) | 0.31516 (14) | 0.0288 (6) | |
C47 | −0.0358 (2) | 0.51674 (14) | 0.31754 (14) | 0.0291 (6) | |
C48 | 0.3221 (2) | 0.52920 (15) | 0.43530 (13) | 0.0363 (6) | |
H48A | 0.3061 | 0.4671 | 0.4377 | 0.044* | |
H48B | 0.2461 | 0.5638 | 0.4495 | 0.044* | |
H48C | 0.3904 | 0.5218 | 0.4780 | 0.044* | |
C49 | 0.2376 (2) | 0.64833 (16) | 0.10600 (14) | 0.0472 (7) | |
H49A | 0.1558 | 0.6849 | 0.1077 | 0.057* | |
H49B | 0.2262 | 0.5858 | 0.1070 | 0.057* | |
H49C | 0.2778 | 0.6804 | 0.0520 | 0.057* | |
C50 | −0.0809 (2) | 0.53427 (16) | 0.22283 (14) | 0.0463 (7) | |
H50A | −0.0118 | 0.5129 | 0.1915 | 0.056* | |
H50B | −0.1095 | 0.6016 | 0.1929 | 0.056* | |
H50C | −0.1503 | 0.4995 | 0.2234 | 0.056* | |
C51 | −0.1421 (2) | 0.55081 (18) | 0.36546 (17) | 0.0558 (8) | |
H51A | −0.1702 | 0.6181 | 0.3350 | 0.067* | |
H51B | −0.1132 | 0.5401 | 0.4260 | 0.067* | |
H51C | −0.2120 | 0.5163 | 0.3664 | 0.067* | |
C52 | 0.0073 (2) | 0.41170 (14) | 0.36543 (15) | 0.0461 (7) | |
H52A | 0.0357 | 0.4011 | 0.4261 | 0.055* | |
H52B | 0.0766 | 0.3893 | 0.3348 | 0.055* | |
H52C | −0.0626 | 0.3774 | 0.3661 | 0.055* | |
N1 | −0.00496 (17) | 0.16643 (12) | 0.70878 (12) | 0.0296 (5) | |
H1A | −0.0395 (18) | 0.2230 (13) | 0.6835 (13) | 0.036* | |
N2 | 0.72269 (16) | 0.10847 (12) | 0.21176 (11) | 0.0252 (5) | |
H2A | 0.7912 (18) | 0.0703 (13) | 0.2367 (12) | 0.030* | |
N3 | 0.39556 (17) | 0.31548 (12) | 0.21201 (12) | 0.0257 (5) | |
H3A | 0.4578 (18) | 0.2954 (14) | 0.1876 (12) | 0.031* | |
N4 | 0.17862 (18) | 0.54433 (12) | 0.28008 (11) | 0.0294 (5) | |
H4A | 0.1836 (18) | 0.4990 (13) | 0.2583 (12) | 0.035* | |
O1 | 0.06421 (13) | 0.02588 (9) | 0.69633 (9) | 0.0342 (4) | |
O2 | 0.62806 (13) | 0.25735 (9) | 0.14412 (9) | 0.0283 (4) | |
O3 | 0.20194 (13) | 0.40129 (9) | 0.19555 (9) | 0.0301 (4) | |
O4 | 0.06294 (14) | 0.63754 (10) | 0.34287 (9) | 0.0392 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0514 (18) | 0.0205 (13) | 0.0228 (15) | 0.0053 (12) | −0.0123 (13) | −0.0119 (11) |
C2 | 0.0454 (18) | 0.0364 (15) | 0.0342 (17) | 0.0095 (12) | −0.0102 (14) | −0.0175 (13) |
C3 | 0.078 (2) | 0.0408 (16) | 0.0255 (16) | 0.0170 (15) | −0.0076 (15) | −0.0195 (12) |
C4 | 0.079 (2) | 0.0352 (16) | 0.043 (2) | 0.0090 (15) | −0.0288 (17) | −0.0223 (14) |
C5 | 0.0647 (19) | 0.0283 (15) | 0.0482 (18) | −0.0031 (13) | −0.0219 (16) | −0.0168 (13) |
C6 | 0.0444 (17) | 0.0227 (13) | 0.0339 (16) | −0.0035 (12) | −0.0091 (13) | −0.0122 (11) |
C7 | 0.0280 (14) | 0.0232 (13) | 0.0262 (14) | −0.0066 (11) | 0.0020 (11) | −0.0084 (11) |
C8 | 0.0314 (14) | 0.0220 (12) | 0.0216 (13) | 0.0026 (11) | −0.0053 (11) | −0.0106 (10) |
C9 | 0.062 (2) | 0.0597 (18) | 0.0350 (16) | 0.0135 (15) | 0.0100 (14) | −0.0200 (14) |
C10 | 0.0508 (18) | 0.0342 (15) | 0.0525 (18) | −0.0076 (13) | −0.0069 (14) | −0.0132 (13) |
C11 | 0.0494 (17) | 0.0419 (15) | 0.0237 (14) | −0.0095 (13) | −0.0054 (12) | −0.0039 (12) |
C12 | 0.0374 (15) | 0.0359 (14) | 0.0425 (16) | −0.0074 (12) | −0.0073 (12) | −0.0191 (12) |
C13 | 0.0476 (17) | 0.0404 (15) | 0.0435 (16) | 0.0067 (13) | −0.0192 (13) | −0.0209 (13) |
C14 | 0.0197 (13) | 0.0203 (12) | 0.0331 (15) | −0.0048 (10) | −0.0043 (11) | −0.0063 (11) |
C15 | 0.0315 (15) | 0.0217 (13) | 0.0296 (15) | −0.0014 (11) | −0.0043 (12) | −0.0082 (11) |
C16 | 0.0384 (16) | 0.0349 (14) | 0.0373 (16) | −0.0091 (12) | −0.0060 (13) | −0.0163 (12) |
C17 | 0.0304 (15) | 0.0436 (16) | 0.0504 (18) | −0.0145 (12) | 0.0026 (14) | −0.0170 (14) |
C18 | 0.0282 (15) | 0.0390 (15) | 0.0375 (16) | −0.0121 (12) | 0.0058 (12) | −0.0084 (12) |
C19 | 0.0329 (14) | 0.0252 (13) | 0.0257 (15) | −0.0027 (11) | −0.0020 (12) | −0.0052 (11) |
C20 | 0.0262 (14) | 0.0277 (14) | 0.0149 (12) | −0.0015 (12) | 0.0056 (10) | −0.0085 (10) |
C21 | 0.0247 (13) | 0.0233 (13) | 0.0202 (13) | −0.0025 (10) | 0.0024 (10) | −0.0067 (10) |
C22 | 0.0471 (16) | 0.0323 (14) | 0.0326 (15) | −0.0068 (12) | −0.0051 (12) | −0.0101 (12) |
C23 | 0.0414 (16) | 0.0390 (15) | 0.0267 (14) | −0.0062 (12) | 0.0037 (12) | −0.0096 (11) |
C24 | 0.0286 (14) | 0.0353 (14) | 0.0340 (15) | −0.0123 (11) | −0.0043 (11) | −0.0088 (11) |
C25 | 0.0346 (15) | 0.0358 (15) | 0.0482 (16) | −0.0059 (12) | 0.0105 (12) | −0.0120 (13) |
C26 | 0.0323 (14) | 0.0317 (14) | 0.0286 (14) | −0.0072 (11) | 0.0039 (11) | −0.0098 (11) |
C27 | 0.0182 (13) | 0.0242 (13) | 0.0261 (14) | 0.0011 (10) | −0.0037 (10) | −0.0106 (11) |
C28 | 0.0263 (14) | 0.0236 (13) | 0.0311 (15) | −0.0007 (11) | 0.0013 (11) | −0.0098 (11) |
C29 | 0.0419 (16) | 0.0327 (14) | 0.0258 (15) | −0.0003 (12) | 0.0025 (12) | −0.0044 (11) |
C30 | 0.0465 (17) | 0.0403 (16) | 0.0299 (15) | 0.0052 (13) | −0.0080 (13) | −0.0127 (13) |
C31 | 0.0271 (14) | 0.0373 (15) | 0.0421 (17) | 0.0040 (12) | −0.0093 (12) | −0.0217 (13) |
C32 | 0.0238 (13) | 0.0267 (13) | 0.0278 (15) | 0.0019 (11) | −0.0004 (11) | −0.0094 (11) |
C33 | 0.0257 (14) | 0.0201 (13) | 0.0282 (14) | −0.0123 (11) | −0.0004 (12) | −0.0054 (11) |
C34 | 0.0176 (12) | 0.0236 (12) | 0.0256 (13) | −0.0068 (10) | 0.0009 (10) | −0.0081 (10) |
C35 | 0.0363 (15) | 0.0369 (14) | 0.0399 (15) | −0.0122 (12) | 0.0093 (12) | −0.0128 (12) |
C36 | 0.0339 (15) | 0.0419 (15) | 0.0473 (16) | −0.0090 (12) | 0.0046 (12) | −0.0216 (13) |
C37 | 0.0373 (15) | 0.0407 (15) | 0.0313 (14) | −0.0097 (12) | 0.0005 (11) | −0.0157 (12) |
C38 | 0.0350 (15) | 0.0401 (15) | 0.0283 (14) | −0.0085 (12) | 0.0015 (11) | −0.0078 (12) |
C39 | 0.0270 (14) | 0.0388 (14) | 0.0255 (13) | −0.0096 (11) | −0.0016 (11) | −0.0059 (11) |
C40 | 0.0340 (15) | 0.0224 (13) | 0.0356 (15) | −0.0063 (11) | −0.0086 (12) | −0.0103 (11) |
C41 | 0.0387 (15) | 0.0230 (13) | 0.0311 (15) | −0.0025 (11) | −0.0069 (12) | −0.0124 (11) |
C42 | 0.0468 (17) | 0.0347 (15) | 0.0417 (17) | −0.0097 (13) | −0.0146 (13) | −0.0126 (13) |
C43 | 0.0547 (19) | 0.0370 (16) | 0.060 (2) | −0.0247 (14) | −0.0106 (16) | −0.0077 (15) |
C44 | 0.0533 (18) | 0.0355 (15) | 0.0426 (17) | −0.0220 (14) | 0.0007 (14) | −0.0052 (13) |
C45 | 0.0524 (18) | 0.0242 (13) | 0.0283 (15) | −0.0074 (12) | −0.0103 (13) | −0.0043 (11) |
C46 | 0.0392 (16) | 0.0222 (13) | 0.0219 (14) | 0.0010 (12) | −0.0115 (12) | −0.0058 (11) |
C47 | 0.0327 (14) | 0.0291 (14) | 0.0305 (14) | 0.0013 (11) | −0.0011 (11) | −0.0192 (11) |
C48 | 0.0391 (16) | 0.0378 (15) | 0.0303 (15) | 0.0062 (12) | −0.0107 (12) | −0.0145 (12) |
C49 | 0.0671 (19) | 0.0420 (16) | 0.0297 (15) | −0.0181 (14) | −0.0052 (14) | −0.0047 (12) |
C50 | 0.0391 (16) | 0.0617 (18) | 0.0450 (17) | −0.0166 (13) | −0.0035 (13) | −0.0236 (14) |
C51 | 0.0468 (18) | 0.0698 (19) | 0.071 (2) | −0.0114 (15) | 0.0131 (15) | −0.0492 (16) |
C52 | 0.0481 (17) | 0.0353 (15) | 0.0566 (17) | −0.0143 (13) | 0.0114 (13) | −0.0150 (13) |
N1 | 0.0423 (13) | 0.0185 (10) | 0.0262 (12) | 0.0040 (9) | −0.0077 (10) | −0.0090 (9) |
N2 | 0.0234 (12) | 0.0206 (11) | 0.0264 (11) | 0.0008 (9) | −0.0025 (9) | −0.0033 (9) |
N3 | 0.0206 (12) | 0.0320 (11) | 0.0245 (12) | −0.0006 (9) | 0.0012 (9) | −0.0115 (9) |
N4 | 0.0345 (13) | 0.0258 (12) | 0.0321 (12) | −0.0047 (10) | −0.0021 (10) | −0.0153 (9) |
O1 | 0.0420 (10) | 0.0205 (9) | 0.0370 (10) | 0.0055 (8) | −0.0149 (8) | −0.0103 (7) |
O2 | 0.0247 (9) | 0.0235 (9) | 0.0324 (9) | 0.0020 (7) | −0.0028 (7) | −0.0066 (7) |
O3 | 0.0275 (10) | 0.0328 (9) | 0.0323 (9) | 0.0011 (7) | 0.0019 (7) | −0.0163 (8) |
O4 | 0.0534 (11) | 0.0255 (9) | 0.0407 (10) | 0.0008 (8) | −0.0124 (8) | −0.0165 (8) |
C1—C6 | 1.389 (3) | C27—N3 | 1.436 (2) |
C1—C2 | 1.393 (3) | C28—C29 | 1.395 (3) |
C1—N1 | 1.430 (3) | C28—C35 | 1.494 (3) |
C2—C3 | 1.393 (3) | C29—C30 | 1.379 (3) |
C2—C9 | 1.504 (3) | C29—H29 | 0.9500 |
C3—C4 | 1.381 (3) | C30—C31 | 1.377 (3) |
C3—H3 | 0.9500 | C30—H30 | 0.9500 |
C4—C5 | 1.375 (3) | C31—C32 | 1.389 (3) |
C4—H4 | 0.9500 | C31—H31 | 0.9500 |
C5—C6 | 1.385 (3) | C32—C36 | 1.507 (3) |
C5—H5 | 0.9500 | C33—O3 | 1.234 (2) |
C6—C10 | 1.496 (3) | C33—N3 | 1.356 (2) |
C7—O1 | 1.241 (2) | C33—C34 | 1.529 (3) |
C7—N1 | 1.337 (2) | C34—C39 | 1.521 (2) |
C7—C8 | 1.523 (3) | C34—C37 | 1.528 (3) |
C8—C12 | 1.524 (3) | C34—C38 | 1.533 (3) |
C8—C13 | 1.528 (3) | C35—H35A | 0.9800 |
C8—C11 | 1.528 (3) | C35—H35B | 0.9800 |
C9—H9A | 0.9800 | C35—H35C | 0.9800 |
C9—H9B | 0.9800 | C36—H36A | 0.9800 |
C9—H9C | 0.9800 | C36—H36B | 0.9800 |
C10—H10A | 0.9800 | C36—H36C | 0.9800 |
C10—H10B | 0.9800 | C37—H37A | 0.9800 |
C10—H10C | 0.9800 | C37—H37B | 0.9800 |
C11—H11A | 0.9800 | C37—H37C | 0.9800 |
C11—H11B | 0.9800 | C38—H38A | 0.9800 |
C11—H11C | 0.9800 | C38—H38B | 0.9800 |
C12—H12A | 0.9800 | C38—H38C | 0.9800 |
C12—H12B | 0.9800 | C39—H39A | 0.9800 |
C12—H12C | 0.9800 | C39—H39B | 0.9800 |
C13—H13A | 0.9800 | C39—H39C | 0.9800 |
C13—H13B | 0.9800 | C40—C45 | 1.398 (3) |
C13—H13C | 0.9800 | C40—C41 | 1.400 (3) |
C14—C15 | 1.392 (3) | C40—N4 | 1.425 (3) |
C14—C19 | 1.396 (3) | C41—C42 | 1.387 (3) |
C14—N2 | 1.434 (2) | C41—C48 | 1.496 (3) |
C15—C16 | 1.392 (3) | C42—C43 | 1.381 (3) |
C15—C22 | 1.501 (3) | C42—H42 | 0.9500 |
C16—C17 | 1.379 (3) | C43—C44 | 1.383 (3) |
C16—H16 | 0.9500 | C43—H43 | 0.9500 |
C17—C18 | 1.381 (3) | C44—C45 | 1.382 (3) |
C17—H17 | 0.9500 | C44—H44 | 0.9500 |
C18—C19 | 1.388 (3) | C45—C49 | 1.506 (3) |
C18—H18 | 0.9500 | C46—O4 | 1.236 (2) |
C19—C23 | 1.508 (3) | C46—N4 | 1.352 (3) |
C20—O2 | 1.234 (2) | C46—C47 | 1.524 (3) |
C20—N2 | 1.343 (2) | C47—C51 | 1.512 (3) |
C20—C21 | 1.532 (3) | C47—C52 | 1.529 (3) |
C21—C26 | 1.521 (3) | C47—C50 | 1.530 (3) |
C21—C24 | 1.529 (3) | C48—H48A | 0.9800 |
C21—C25 | 1.538 (3) | C48—H48B | 0.9800 |
C22—H22A | 0.9800 | C48—H48C | 0.9800 |
C22—H22B | 0.9800 | C49—H49A | 0.9800 |
C22—H22C | 0.9800 | C49—H49B | 0.9800 |
C23—H23A | 0.9800 | C49—H49C | 0.9800 |
C23—H23B | 0.9800 | C50—H50A | 0.9800 |
C23—H23C | 0.9800 | C50—H50B | 0.9800 |
C24—H24A | 0.9800 | C50—H50C | 0.9800 |
C24—H24B | 0.9800 | C51—H51A | 0.9800 |
C24—H24C | 0.9800 | C51—H51B | 0.9800 |
C25—H25A | 0.9800 | C51—H51C | 0.9800 |
C25—H25B | 0.9800 | C52—H52A | 0.9800 |
C25—H25C | 0.9800 | C52—H52B | 0.9800 |
C26—H26A | 0.9800 | C52—H52C | 0.9800 |
C26—H26B | 0.9800 | N1—H1A | 0.849 (18) |
C26—H26C | 0.9800 | N2—H2A | 0.874 (18) |
C27—C32 | 1.391 (3) | N3—H3A | 0.850 (18) |
C27—C28 | 1.396 (3) | N4—H4A | 0.874 (19) |
C6—C1—C2 | 122.6 (2) | C30—C29—C28 | 120.9 (2) |
C6—C1—N1 | 119.8 (2) | C30—C29—H29 | 119.6 |
C2—C1—N1 | 117.6 (2) | C28—C29—H29 | 119.6 |
C3—C2—C1 | 117.4 (2) | C31—C30—C29 | 120.4 (2) |
C3—C2—C9 | 121.7 (2) | C31—C30—H30 | 119.8 |
C1—C2—C9 | 120.9 (2) | C29—C30—H30 | 119.8 |
C4—C3—C2 | 121.0 (2) | C30—C31—C32 | 120.7 (2) |
C4—C3—H3 | 119.5 | C30—C31—H31 | 119.7 |
C2—C3—H3 | 119.5 | C32—C31—H31 | 119.7 |
C5—C4—C3 | 120.0 (2) | C31—C32—C27 | 118.25 (19) |
C5—C4—H4 | 120.0 | C31—C32—C36 | 120.9 (2) |
C3—C4—H4 | 120.0 | C27—C32—C36 | 120.89 (19) |
C4—C5—C6 | 121.3 (3) | O3—C33—N3 | 121.8 (2) |
C4—C5—H5 | 119.3 | O3—C33—C34 | 122.56 (19) |
C6—C5—H5 | 119.3 | N3—C33—C34 | 115.67 (19) |
C5—C6—C1 | 117.7 (2) | C39—C34—C37 | 109.27 (16) |
C5—C6—C10 | 121.6 (2) | C39—C34—C33 | 109.26 (17) |
C1—C6—C10 | 120.7 (2) | C37—C34—C33 | 110.52 (16) |
O1—C7—N1 | 121.44 (19) | C39—C34—C38 | 109.61 (16) |
O1—C7—C8 | 120.05 (19) | C37—C34—C38 | 109.46 (17) |
N1—C7—C8 | 118.41 (18) | C33—C34—C38 | 108.72 (16) |
C7—C8—C12 | 108.39 (16) | C28—C35—H35A | 109.5 |
C7—C8—C13 | 113.36 (17) | C28—C35—H35B | 109.5 |
C12—C8—C13 | 109.50 (17) | H35A—C35—H35B | 109.5 |
C7—C8—C11 | 105.99 (16) | C28—C35—H35C | 109.5 |
C12—C8—C11 | 109.93 (17) | H35A—C35—H35C | 109.5 |
C13—C8—C11 | 109.58 (17) | H35B—C35—H35C | 109.5 |
C2—C9—H9A | 109.5 | C32—C36—H36A | 109.5 |
C2—C9—H9B | 109.5 | C32—C36—H36B | 109.5 |
H9A—C9—H9B | 109.5 | H36A—C36—H36B | 109.5 |
C2—C9—H9C | 109.5 | C32—C36—H36C | 109.5 |
H9A—C9—H9C | 109.5 | H36A—C36—H36C | 109.5 |
H9B—C9—H9C | 109.5 | H36B—C36—H36C | 109.5 |
C6—C10—H10A | 109.5 | C34—C37—H37A | 109.5 |
C6—C10—H10B | 109.5 | C34—C37—H37B | 109.5 |
H10A—C10—H10B | 109.5 | H37A—C37—H37B | 109.5 |
C6—C10—H10C | 109.5 | C34—C37—H37C | 109.5 |
H10A—C10—H10C | 109.5 | H37A—C37—H37C | 109.5 |
H10B—C10—H10C | 109.5 | H37B—C37—H37C | 109.5 |
C8—C11—H11A | 109.5 | C34—C38—H38A | 109.5 |
C8—C11—H11B | 109.5 | C34—C38—H38B | 109.5 |
H11A—C11—H11B | 109.5 | H38A—C38—H38B | 109.5 |
C8—C11—H11C | 109.5 | C34—C38—H38C | 109.5 |
H11A—C11—H11C | 109.5 | H38A—C38—H38C | 109.5 |
H11B—C11—H11C | 109.5 | H38B—C38—H38C | 109.5 |
C8—C12—H12A | 109.5 | C34—C39—H39A | 109.5 |
C8—C12—H12B | 109.5 | C34—C39—H39B | 109.5 |
H12A—C12—H12B | 109.5 | H39A—C39—H39B | 109.5 |
C8—C12—H12C | 109.5 | C34—C39—H39C | 109.5 |
H12A—C12—H12C | 109.5 | H39A—C39—H39C | 109.5 |
H12B—C12—H12C | 109.5 | H39B—C39—H39C | 109.5 |
C8—C13—H13A | 109.5 | C45—C40—C41 | 121.8 (2) |
C8—C13—H13B | 109.5 | C45—C40—N4 | 118.55 (19) |
H13A—C13—H13B | 109.5 | C41—C40—N4 | 119.6 (2) |
C8—C13—H13C | 109.5 | C42—C41—C40 | 117.6 (2) |
H13A—C13—H13C | 109.5 | C42—C41—C48 | 121.2 (2) |
H13B—C13—H13C | 109.5 | C40—C41—C48 | 121.1 (2) |
C15—C14—C19 | 122.19 (19) | C43—C42—C41 | 121.5 (2) |
C15—C14—N2 | 119.67 (19) | C43—C42—H42 | 119.3 |
C19—C14—N2 | 118.10 (18) | C41—C42—H42 | 119.3 |
C14—C15—C16 | 117.5 (2) | C42—C43—C44 | 119.8 (2) |
C14—C15—C22 | 121.12 (19) | C42—C43—H43 | 120.1 |
C16—C15—C22 | 121.32 (19) | C44—C43—H43 | 120.1 |
C17—C16—C15 | 121.4 (2) | C45—C44—C43 | 121.0 (2) |
C17—C16—H16 | 119.3 | C45—C44—H44 | 119.5 |
C15—C16—H16 | 119.3 | C43—C44—H44 | 119.5 |
C16—C17—C18 | 119.9 (2) | C44—C45—C40 | 118.3 (2) |
C16—C17—H17 | 120.0 | C44—C45—C49 | 121.2 (2) |
C18—C17—H17 | 120.0 | C40—C45—C49 | 120.5 (2) |
C17—C18—C19 | 120.8 (2) | O4—C46—N4 | 121.2 (2) |
C17—C18—H18 | 119.6 | O4—C46—C47 | 121.9 (2) |
C19—C18—H18 | 119.6 | N4—C46—C47 | 116.89 (19) |
C18—C19—C14 | 118.12 (19) | C51—C47—C46 | 109.46 (18) |
C18—C19—C23 | 121.3 (2) | C51—C47—C52 | 109.10 (19) |
C14—C19—C23 | 120.57 (19) | C46—C47—C52 | 110.20 (17) |
O2—C20—N2 | 121.52 (19) | C51—C47—C50 | 109.40 (18) |
O2—C20—C21 | 121.90 (19) | C46—C47—C50 | 108.64 (18) |
N2—C20—C21 | 116.51 (18) | C52—C47—C50 | 110.02 (18) |
C26—C21—C24 | 109.68 (16) | C41—C48—H48A | 109.5 |
C26—C21—C20 | 110.05 (16) | C41—C48—H48B | 109.5 |
C24—C21—C20 | 108.00 (16) | H48A—C48—H48B | 109.5 |
C26—C21—C25 | 108.80 (17) | C41—C48—H48C | 109.5 |
C24—C21—C25 | 110.08 (17) | H48A—C48—H48C | 109.5 |
C20—C21—C25 | 110.21 (17) | H48B—C48—H48C | 109.5 |
C15—C22—H22A | 109.5 | C45—C49—H49A | 109.5 |
C15—C22—H22B | 109.5 | C45—C49—H49B | 109.5 |
H22A—C22—H22B | 109.5 | H49A—C49—H49B | 109.5 |
C15—C22—H22C | 109.5 | C45—C49—H49C | 109.5 |
H22A—C22—H22C | 109.5 | H49A—C49—H49C | 109.5 |
H22B—C22—H22C | 109.5 | H49B—C49—H49C | 109.5 |
C19—C23—H23A | 109.5 | C47—C50—H50A | 109.5 |
C19—C23—H23B | 109.5 | C47—C50—H50B | 109.5 |
H23A—C23—H23B | 109.5 | H50A—C50—H50B | 109.5 |
C19—C23—H23C | 109.5 | C47—C50—H50C | 109.5 |
H23A—C23—H23C | 109.5 | H50A—C50—H50C | 109.5 |
H23B—C23—H23C | 109.5 | H50B—C50—H50C | 109.5 |
C21—C24—H24A | 109.5 | C47—C51—H51A | 109.5 |
C21—C24—H24B | 109.5 | C47—C51—H51B | 109.5 |
H24A—C24—H24B | 109.5 | H51A—C51—H51B | 109.5 |
C21—C24—H24C | 109.5 | C47—C51—H51C | 109.5 |
H24A—C24—H24C | 109.5 | H51A—C51—H51C | 109.5 |
H24B—C24—H24C | 109.5 | H51B—C51—H51C | 109.5 |
C21—C25—H25A | 109.5 | C47—C52—H52A | 109.5 |
C21—C25—H25B | 109.5 | C47—C52—H52B | 109.5 |
H25A—C25—H25B | 109.5 | H52A—C52—H52B | 109.5 |
C21—C25—H25C | 109.5 | C47—C52—H52C | 109.5 |
H25A—C25—H25C | 109.5 | H52A—C52—H52C | 109.5 |
H25B—C25—H25C | 109.5 | H52B—C52—H52C | 109.5 |
C21—C26—H26A | 109.5 | C7—N1—C1 | 123.82 (17) |
C21—C26—H26B | 109.5 | C7—N1—H1A | 119.9 (14) |
H26A—C26—H26B | 109.5 | C1—N1—H1A | 115.2 (14) |
C21—C26—H26C | 109.5 | C20—N2—C14 | 124.50 (17) |
H26A—C26—H26C | 109.5 | C20—N2—H2A | 120.0 (13) |
H26B—C26—H26C | 109.5 | C14—N2—H2A | 115.0 (13) |
C32—C27—C28 | 122.12 (19) | C33—N3—C27 | 123.64 (18) |
C32—C27—N3 | 118.72 (18) | C33—N3—H3A | 120.4 (13) |
C28—C27—N3 | 119.11 (18) | C27—N3—H3A | 115.9 (13) |
C29—C28—C27 | 117.66 (19) | C46—N4—C40 | 123.98 (19) |
C29—C28—C35 | 121.04 (19) | C46—N4—H4A | 120.9 (13) |
C27—C28—C35 | 121.30 (19) | C40—N4—H4A | 115.0 (13) |
C6—C1—C2—C3 | 0.8 (3) | C30—C31—C32—C27 | −0.4 (3) |
N1—C1—C2—C3 | −177.10 (18) | C30—C31—C32—C36 | 178.65 (19) |
C6—C1—C2—C9 | −178.5 (2) | C28—C27—C32—C31 | 0.9 (3) |
N1—C1—C2—C9 | 3.6 (3) | N3—C27—C32—C31 | −176.47 (18) |
C1—C2—C3—C4 | 0.3 (3) | C28—C27—C32—C36 | −178.13 (19) |
C9—C2—C3—C4 | 179.6 (2) | N3—C27—C32—C36 | 4.5 (3) |
C2—C3—C4—C5 | −1.2 (3) | O3—C33—C34—C39 | −6.0 (3) |
C3—C4—C5—C6 | 1.0 (3) | N3—C33—C34—C39 | 173.96 (16) |
C4—C5—C6—C1 | 0.1 (3) | O3—C33—C34—C37 | −126.2 (2) |
C4—C5—C6—C10 | −179.0 (2) | N3—C33—C34—C37 | 53.7 (2) |
C2—C1—C6—C5 | −1.0 (3) | O3—C33—C34—C38 | 113.6 (2) |
N1—C1—C6—C5 | 176.85 (18) | N3—C33—C34—C38 | −66.5 (2) |
C2—C1—C6—C10 | 178.06 (19) | C45—C40—C41—C42 | −0.7 (3) |
N1—C1—C6—C10 | −4.1 (3) | N4—C40—C41—C42 | 177.63 (19) |
O1—C7—C8—C12 | 42.4 (3) | C45—C40—C41—C48 | −179.59 (19) |
N1—C7—C8—C12 | −141.14 (19) | N4—C40—C41—C48 | −1.2 (3) |
O1—C7—C8—C13 | 164.20 (19) | C40—C41—C42—C43 | −0.2 (3) |
N1—C7—C8—C13 | −19.4 (3) | C48—C41—C42—C43 | 178.7 (2) |
O1—C7—C8—C11 | −75.6 (2) | C41—C42—C43—C44 | 0.1 (4) |
N1—C7—C8—C11 | 100.9 (2) | C42—C43—C44—C45 | 0.9 (4) |
C19—C14—C15—C16 | −1.2 (3) | C43—C44—C45—C40 | −1.7 (3) |
N2—C14—C15—C16 | 176.35 (18) | C43—C44—C45—C49 | 177.8 (2) |
C19—C14—C15—C22 | 179.56 (18) | C41—C40—C45—C44 | 1.7 (3) |
N2—C14—C15—C22 | −2.8 (3) | N4—C40—C45—C44 | −176.7 (2) |
C14—C15—C16—C17 | −0.2 (3) | C41—C40—C45—C49 | −177.86 (19) |
C22—C15—C16—C17 | 179.03 (19) | N4—C40—C45—C49 | 3.8 (3) |
C15—C16—C17—C18 | 0.9 (3) | O4—C46—C47—C51 | −5.6 (3) |
C16—C17—C18—C19 | −0.3 (3) | N4—C46—C47—C51 | 175.32 (19) |
C17—C18—C19—C14 | −1.0 (3) | O4—C46—C47—C52 | −125.6 (2) |
C17—C18—C19—C23 | 179.1 (2) | N4—C46—C47—C52 | 55.3 (2) |
C15—C14—C19—C18 | 1.8 (3) | O4—C46—C47—C50 | 113.8 (2) |
N2—C14—C19—C18 | −175.80 (18) | N4—C46—C47—C50 | −65.3 (2) |
C15—C14—C19—C23 | −178.28 (19) | O1—C7—N1—C1 | 2.0 (3) |
N2—C14—C19—C23 | 4.1 (3) | C8—C7—N1—C1 | −174.4 (2) |
O2—C20—C21—C26 | −8.6 (3) | C6—C1—N1—C7 | 78.7 (3) |
N2—C20—C21—C26 | 174.51 (17) | C2—C1—N1—C7 | −103.3 (2) |
O2—C20—C21—C24 | 111.1 (2) | O2—C20—N2—C14 | −5.1 (3) |
N2—C20—C21—C24 | −65.8 (2) | C21—C20—N2—C14 | 171.82 (18) |
O2—C20—C21—C25 | −128.60 (19) | C15—C14—N2—C20 | 77.5 (3) |
N2—C20—C21—C25 | 54.5 (2) | C19—C14—N2—C20 | −104.8 (2) |
C32—C27—C28—C29 | −0.6 (3) | O3—C33—N3—C27 | 2.2 (3) |
N3—C27—C28—C29 | 176.84 (18) | C34—C33—N3—C27 | −177.77 (17) |
C32—C27—C28—C35 | −179.76 (19) | C32—C27—N3—C33 | −109.8 (2) |
N3—C27—C28—C35 | −2.3 (3) | C28—C27—N3—C33 | 72.7 (3) |
C27—C28—C29—C30 | −0.3 (3) | O4—C46—N4—C40 | −1.4 (3) |
C35—C28—C29—C30 | 178.85 (19) | C47—C46—N4—C40 | 177.65 (18) |
C28—C29—C30—C31 | 0.9 (3) | C45—C40—N4—C46 | −112.3 (2) |
C29—C30—C31—C32 | −0.5 (3) | C41—C40—N4—C46 | 69.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4i | 0.849 (18) | 2.009 (19) | 2.802 (2) | 155.1 (19) |
N2—H2A···O1ii | 0.874 (18) | 2.006 (19) | 2.876 (2) | 173.4 (19) |
N3—H3A···O2 | 0.850 (18) | 2.042 (19) | 2.879 (2) | 168.4 (19) |
N4—H4A···O3 | 0.874 (19) | 2.07 (2) | 2.937 (2) | 174.2 (18) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H19NO |
Mr | 205.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 10.799 (1), 15.330 (1), 16.173 (1) |
α, β, γ (°) | 70.004 (8), 89.800 (7), 81.487 (7) |
V (Å3) | 2485.1 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.36 × 0.16 × 0.16 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.976, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26845, 10127, 4638 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.119, 0.97 |
No. of reflections | 10127 |
No. of parameters | 571 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.22 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek 2003) and ORTEP-3 (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4i | 0.849 (18) | 2.009 (19) | 2.802 (2) | 155.1 (19) |
N2—H2A···O1ii | 0.874 (18) | 2.006 (19) | 2.876 (2) | 173.4 (19) |
N3—H3A···O2 | 0.850 (18) | 2.042 (19) | 2.879 (2) | 168.4 (19) |
N4—H4A···O3 | 0.874 (19) | 2.07 (2) | 2.937 (2) | 174.2 (18) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
In the present work, the structure of N-(2,6-dimethylphenyl)-2,2,2- trimethylacetamide has been determined, as part of our study of the effect of ring and side chain substitutions on the solid state structures of chemically and biologically significant compounds such as acetanilides (Gowda, Foro, & Fuess, 2007a; Gowda, Foro, & Fuess, 2007b; Gowda et al., 2007; Gowda, Kožíšek, Tokarčík & Fuess, 2007a, 2007b). The title compound crystallizes with four molecules in the asymmetric unit (Figs. 1 & 2). The structure of resembles those of N-(2,6-dimethylphenyl)-acetamide (Gowda, Foro, & Fuess, 2007a, b), N-(2-methylphenyl)- 2,2,2-trimethylacetamide (Gowda, Kožíšek, Tokarčík & Fuess, 2007b), N-(3,5-dimethylphenyl)-2,2,2-trimethylacetamide (Gowda, Kožíšek, Tokarčík & Fuess, 2007a), N-(2,6-dimethylphenyl)-2,2,2-trichloroacetamide (Gowda, Foro, & Fuess, 2007a) and other closely related acetanilides (Gowda et al., 2007), with somewhat slightly different bond parameters. The molecules are linked into chains through N—H···O hydrogen bonds (Table 1).