Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001766/ya2032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001766/ya2032Isup2.hkl |
CCDC reference: 636843
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C22H26N2O2·C6H6 | F(000) = 920 |
Mr = 428.56 | Dx = 1.093 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 850 reflections |
a = 8.2760 (18) Å | θ = 2.5–19.1° |
b = 26.636 (6) Å | µ = 0.07 mm−1 |
c = 12.250 (3) Å | T = 291 K |
β = 105.250 (3)° | Block, yellow |
V = 2605.4 (10) Å3 | 0.32 × 0.26 × 0.24 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 5788 independent reflections |
Radiation source: sealed tube | 4361 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 27.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→9 |
Tmin = 0.978, Tmax = 0.984 | k = −34→33 |
15086 measured reflections | l = −15→15 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0844P)2 + 0.1157P] where P = (Fo2 + 2Fc2)/3 |
5788 reflections | (Δ/σ)max = 0.001 |
597 parameters | Δρmax = 0.26 e Å−3 |
1 restraint | Δρmin = −0.22 e Å−3 |
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 | 0.0245 (6) | 0.58090 (17) | 0.6989 (3) | 0.0575 (10) | |
H1 | −0.0882 | 0.5784 | 0.7101 | 0.069* | |
C2 | 0.0097 (5) | 0.58883 (16) | 0.5716 (3) | 0.0531 (9) | |
H2A | −0.0566 | 0.6188 | 0.5479 | 0.064* | |
H2B | 0.1212 | 0.5956 | 0.5635 | 0.064* | |
C3 | −0.0626 (5) | 0.54864 (17) | 0.4923 (4) | 0.0560 (10) | |
H3A | −0.0474 | 0.5562 | 0.4182 | 0.067* | |
H3B | −0.1818 | 0.5460 | 0.4854 | 0.067* | |
C4 | 0.0268 (6) | 0.49716 (18) | 0.5372 (4) | 0.0591 (10) | |
H4A | −0.0333 | 0.4702 | 0.4905 | 0.071* | |
H4B | 0.1392 | 0.4979 | 0.5272 | 0.071* | |
C5 | 0.0390 (5) | 0.48464 (16) | 0.6630 (3) | 0.0543 (9) | |
H5A | −0.0718 | 0.4787 | 0.6732 | 0.065* | |
H5B | 0.1060 | 0.4547 | 0.6859 | 0.065* | |
C6 | 0.1196 (5) | 0.52901 (15) | 0.7335 (3) | 0.0515 (9) | |
H6 | 0.2364 | 0.5322 | 0.7305 | 0.062* | |
C7 | 0.0506 (5) | 0.64376 (15) | 0.8439 (3) | 0.0513 (9) | |
H7 | −0.0543 | 0.6349 | 0.8521 | 0.062* | |
C8 | 0.1409 (5) | 0.68183 (16) | 0.9110 (3) | 0.0526 (9) | |
C9 | 0.0734 (5) | 0.70576 (16) | 0.9899 (4) | 0.0541 (9) | |
H9 | −0.0348 | 0.6982 | 0.9936 | 0.065* | |
C10 | 0.1689 (6) | 0.74112 (17) | 1.0633 (4) | 0.0569 (10) | |
H10 | 0.1245 | 0.7575 | 1.1159 | 0.068* | |
C11 | 0.3317 (6) | 0.75183 (18) | 1.0572 (4) | 0.0617 (11) | |
H11 | 0.3956 | 0.7752 | 1.1066 | 0.074* | |
C12 | 0.3994 (5) | 0.72793 (19) | 0.9783 (3) | 0.0611 (11) | |
C13 | 0.3027 (5) | 0.69261 (17) | 0.9058 (4) | 0.0567 (10) | |
C14 | 0.5710 (5) | 0.74251 (17) | 0.9642 (3) | 0.0548 (9) | |
H14A | 0.5707 | 0.7774 | 0.9448 | 0.082* | |
H14B | 0.5954 | 0.7227 | 0.9050 | 0.082* | |
H14C | 0.6547 | 0.7365 | 1.0337 | 0.082* | |
C15 | 0.2463 (6) | 0.51743 (17) | 0.9325 (4) | 0.0584 (10) | |
H15 | 0.3473 | 0.5235 | 0.9151 | 0.070* | |
C16 | 0.2514 (5) | 0.50663 (16) | 1.0449 (3) | 0.0535 (10) | |
C17 | 0.4042 (5) | 0.50588 (15) | 1.1284 (4) | 0.0589 (11) | |
H17 | 0.5030 | 0.5134 | 1.1092 | 0.071* | |
C18 | 0.4089 (5) | 0.49416 (16) | 1.2384 (4) | 0.0584 (10) | |
H18 | 0.5102 | 0.4947 | 1.2938 | 0.070* | |
C19 | 0.2626 (5) | 0.48155 (15) | 1.2669 (3) | 0.0521 (9) | |
H19 | 0.2670 | 0.4728 | 1.3411 | 0.063* | |
C20 | 0.1106 (5) | 0.48181 (15) | 1.1863 (3) | 0.0508 (9) | |
C21 | 0.1051 (5) | 0.49472 (16) | 1.0758 (3) | 0.0554 (10) | |
C22 | −0.0497 (5) | 0.46954 (16) | 1.2181 (3) | 0.0527 (9) | |
H22A | −0.1166 | 0.4993 | 1.2129 | 0.079* | |
H22B | −0.0232 | 0.4570 | 1.2942 | 0.079* | |
H22C | −0.1111 | 0.4445 | 1.1674 | 0.079* | |
C23 | 0.1568 (5) | 0.31680 (16) | 0.4865 (3) | 0.0517 (9) | |
H23 | 0.0354 | 0.3145 | 0.4757 | 0.062* | |
C24 | 0.1912 (6) | 0.35604 (17) | 0.4028 (3) | 0.0562 (10) | |
H24A | 0.3108 | 0.3614 | 0.4170 | 0.067* | |
H24B | 0.1396 | 0.3878 | 0.4133 | 0.067* | |
C25 | 0.1185 (5) | 0.33725 (16) | 0.2798 (3) | 0.0526 (9) | |
H25A | −0.0021 | 0.3337 | 0.2642 | 0.063* | |
H25B | 0.1422 | 0.3615 | 0.2270 | 0.063* | |
C26 | 0.1982 (5) | 0.28600 (16) | 0.2644 (4) | 0.0543 (10) | |
H26A | 0.1604 | 0.2756 | 0.1859 | 0.065* | |
H26B | 0.3191 | 0.2893 | 0.2837 | 0.065* | |
C27 | 0.1494 (5) | 0.24634 (16) | 0.3398 (3) | 0.0532 (9) | |
H27A | 0.1956 | 0.2140 | 0.3276 | 0.064* | |
H27B | 0.0285 | 0.2433 | 0.3222 | 0.064* | |
C28 | 0.2233 (5) | 0.26381 (15) | 0.4693 (3) | 0.0517 (9) | |
H28 | 0.3460 | 0.2644 | 0.4880 | 0.062* | |
C29 | 0.1368 (6) | 0.33765 (17) | 0.6693 (4) | 0.0579 (10) | |
H29 | 0.0229 | 0.3311 | 0.6416 | 0.069* | |
C30 | 0.1993 (6) | 0.35245 (18) | 0.7864 (4) | 0.0584 (10) | |
C31 | 0.0911 (5) | 0.35568 (16) | 0.8537 (3) | 0.0521 (9) | |
H31 | −0.0215 | 0.3481 | 0.8236 | 0.063* | |
C32 | 0.1473 (5) | 0.37015 (15) | 0.9661 (3) | 0.0494 (9) | |
H32 | 0.0730 | 0.3719 | 1.0113 | 0.059* | |
C33 | 0.3156 (5) | 0.38208 (17) | 1.0108 (4) | 0.0586 (10) | |
H33 | 0.3539 | 0.3919 | 1.0861 | 0.070* | |
C34 | 0.4280 (5) | 0.37932 (15) | 0.9423 (3) | 0.0504 (9) | |
C35 | 0.3688 (5) | 0.36432 (15) | 0.8298 (3) | 0.0520 (9) | |
C36 | 0.6094 (5) | 0.39302 (16) | 0.9899 (3) | 0.0547 (10) | |
H36A | 0.6727 | 0.3633 | 1.0178 | 0.082* | |
H36B | 0.6195 | 0.4165 | 1.0507 | 0.082* | |
H36C | 0.6517 | 0.4079 | 0.9316 | 0.082* | |
C37 | 0.2862 (6) | 0.20715 (16) | 0.6262 (3) | 0.0557 (10) | |
H37 | 0.3990 | 0.2138 | 0.6339 | 0.067* | |
C38 | 0.2376 (5) | 0.17351 (16) | 0.7025 (4) | 0.0551 (9) | |
C39 | 0.3639 (6) | 0.15020 (16) | 0.7864 (3) | 0.0549 (10) | |
H39 | 0.4762 | 0.1557 | 0.7901 | 0.066* | |
C40 | 0.3187 (6) | 0.11887 (16) | 0.8637 (4) | 0.0555 (10) | |
H40 | 0.4021 | 0.1041 | 0.9206 | 0.067* | |
C41 | 0.1518 (6) | 0.10897 (16) | 0.8586 (4) | 0.0579 (10) | |
H41 | 0.1233 | 0.0874 | 0.9102 | 0.069* | |
C42 | 0.0281 (5) | 0.13231 (17) | 0.7737 (3) | 0.0546 (9) | |
C43 | 0.0702 (5) | 0.16457 (15) | 0.6960 (3) | 0.0508 (9) | |
C44 | −0.1635 (5) | 0.12319 (15) | 0.7656 (3) | 0.0493 (9) | |
H44A | −0.1738 | 0.0980 | 0.8195 | 0.074* | |
H44B | −0.2197 | 0.1121 | 0.6907 | 0.074* | |
H44C | −0.2132 | 0.1539 | 0.7817 | 0.074* | |
C45 | 0.5927 (6) | 0.54655 (17) | 0.7888 (4) | 0.0605 (11) | |
H45 | 0.6325 | 0.5570 | 0.8636 | 0.073* | |
C46 | 0.5541 (5) | 0.58216 (16) | 0.7012 (4) | 0.0551 (10) | |
H46 | 0.5718 | 0.6161 | 0.7176 | 0.066* | |
C47 | 0.4898 (6) | 0.56670 (16) | 0.5908 (4) | 0.0567 (10) | |
H47 | 0.4619 | 0.5902 | 0.5327 | 0.068* | |
C48 | 0.4671 (6) | 0.51568 (19) | 0.5672 (4) | 0.0678 (13) | |
H48 | 0.4245 | 0.5052 | 0.4927 | 0.081* | |
C49 | 0.5066 (5) | 0.48052 (16) | 0.6520 (4) | 0.0574 (10) | |
H49 | 0.4901 | 0.4466 | 0.6351 | 0.069* | |
C50 | 0.5717 (5) | 0.49615 (16) | 0.7640 (4) | 0.0544 (10) | |
H50 | 0.6009 | 0.4725 | 0.8217 | 0.065* | |
C51 | 0.6987 (5) | 0.32238 (16) | 0.5483 (4) | 0.0562 (10) | |
H51 | 0.7057 | 0.3325 | 0.6221 | 0.067* | |
C52 | 0.6847 (5) | 0.35812 (18) | 0.4627 (4) | 0.0616 (11) | |
H52 | 0.6810 | 0.3921 | 0.4793 | 0.074* | |
C53 | 0.6763 (5) | 0.34285 (16) | 0.3521 (4) | 0.0542 (10) | |
H53 | 0.6683 | 0.3666 | 0.2953 | 0.065* | |
C54 | 0.6798 (5) | 0.29232 (16) | 0.3278 (4) | 0.0602 (11) | |
H54 | 0.6728 | 0.2821 | 0.2541 | 0.072* | |
C55 | 0.6938 (5) | 0.25641 (17) | 0.4126 (3) | 0.0533 (9) | |
H55 | 0.6976 | 0.2225 | 0.3957 | 0.064* | |
C56 | 0.7022 (5) | 0.27147 (16) | 0.5222 (4) | 0.0582 (10) | |
H56 | 0.7101 | 0.2475 | 0.5786 | 0.070* | |
N1 | 0.1126 (4) | 0.61985 (13) | 0.7680 (3) | 0.0537 (8) | |
N2 | 0.1134 (4) | 0.51953 (13) | 0.8526 (3) | 0.0494 (7) | |
N3 | 0.2318 (4) | 0.33302 (13) | 0.6009 (3) | 0.0539 (8) | |
N4 | 0.1688 (4) | 0.22902 (13) | 0.5435 (3) | 0.0519 (8) | |
O1 | 0.3890 (4) | 0.67036 (12) | 0.8424 (3) | 0.0583 (7) | |
H1E | 0.339 (6) | 0.643 (2) | 0.818 (4) | 0.058 (13)* | |
O2 | −0.0432 (3) | 0.49383 (11) | 0.9999 (3) | 0.0551 (7) | |
H2E | −0.029 (7) | 0.498 (2) | 0.933 (5) | 0.083 (18)* | |
O3 | 0.4748 (4) | 0.36165 (11) | 0.7640 (3) | 0.0533 (7) | |
H3E | 0.418 (7) | 0.363 (2) | 0.696 (4) | 0.066 (15)* | |
O4 | −0.0438 (4) | 0.18528 (11) | 0.6124 (3) | 0.0583 (7) | |
H4E | −0.005 (6) | 0.1946 (17) | 0.556 (4) | 0.049 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.062 (3) | 0.059 (2) | 0.050 (2) | 0.007 (2) | 0.0130 (19) | 0.0018 (19) |
C2 | 0.056 (2) | 0.050 (2) | 0.054 (2) | 0.0131 (18) | 0.0175 (18) | 0.0163 (18) |
C3 | 0.051 (2) | 0.061 (2) | 0.057 (2) | 0.0036 (19) | 0.0146 (19) | 0.003 (2) |
C4 | 0.054 (2) | 0.060 (2) | 0.067 (3) | 0.0058 (19) | 0.023 (2) | −0.004 (2) |
C5 | 0.052 (2) | 0.056 (2) | 0.056 (2) | −0.0057 (18) | 0.0144 (18) | −0.0125 (18) |
C6 | 0.056 (2) | 0.053 (2) | 0.047 (2) | −0.0042 (18) | 0.0172 (18) | 0.0069 (17) |
C7 | 0.043 (2) | 0.052 (2) | 0.056 (2) | 0.0092 (17) | 0.0087 (17) | 0.0039 (18) |
C8 | 0.050 (2) | 0.052 (2) | 0.054 (2) | −0.0020 (17) | 0.0108 (18) | −0.0012 (17) |
C9 | 0.053 (2) | 0.051 (2) | 0.056 (2) | 0.0116 (17) | 0.0112 (18) | −0.0007 (18) |
C10 | 0.057 (2) | 0.057 (2) | 0.053 (2) | 0.0058 (19) | 0.0085 (18) | −0.0095 (19) |
C11 | 0.055 (2) | 0.063 (3) | 0.057 (2) | 0.005 (2) | −0.0041 (19) | 0.001 (2) |
C12 | 0.052 (2) | 0.073 (3) | 0.047 (2) | −0.015 (2) | −0.0069 (17) | −0.004 (2) |
C13 | 0.050 (2) | 0.059 (2) | 0.059 (2) | −0.0119 (18) | 0.0106 (18) | −0.0092 (19) |
C14 | 0.054 (2) | 0.060 (2) | 0.047 (2) | −0.0108 (19) | 0.0061 (17) | −0.0167 (18) |
C15 | 0.062 (3) | 0.058 (2) | 0.053 (2) | −0.009 (2) | 0.0111 (19) | −0.0119 (19) |
C16 | 0.051 (2) | 0.061 (2) | 0.0447 (19) | −0.0040 (18) | 0.0057 (17) | −0.0117 (17) |
C17 | 0.053 (2) | 0.053 (2) | 0.054 (2) | −0.0148 (17) | −0.0156 (18) | −0.0109 (18) |
C18 | 0.054 (2) | 0.048 (2) | 0.059 (2) | −0.0106 (18) | −0.0102 (19) | −0.0129 (18) |
C19 | 0.053 (2) | 0.049 (2) | 0.045 (2) | −0.0113 (17) | −0.0045 (16) | −0.0134 (16) |
C20 | 0.048 (2) | 0.051 (2) | 0.051 (2) | −0.0046 (17) | 0.0092 (16) | −0.0046 (17) |
C21 | 0.054 (2) | 0.054 (2) | 0.051 (2) | −0.0069 (18) | 0.0007 (18) | −0.0098 (18) |
C22 | 0.055 (2) | 0.057 (2) | 0.047 (2) | −0.0167 (18) | 0.0136 (17) | 0.0032 (17) |
C23 | 0.048 (2) | 0.054 (2) | 0.052 (2) | −0.0082 (17) | 0.0115 (17) | −0.0086 (17) |
C24 | 0.060 (2) | 0.057 (2) | 0.052 (2) | −0.0200 (19) | 0.0159 (18) | −0.0053 (18) |
C25 | 0.053 (2) | 0.057 (2) | 0.048 (2) | −0.0098 (18) | 0.0132 (17) | 0.0034 (17) |
C26 | 0.054 (2) | 0.057 (2) | 0.053 (2) | −0.0109 (18) | 0.0143 (18) | −0.0148 (18) |
C27 | 0.057 (2) | 0.057 (2) | 0.0459 (19) | −0.0096 (18) | 0.0139 (17) | −0.0170 (18) |
C28 | 0.053 (2) | 0.049 (2) | 0.052 (2) | −0.0120 (17) | 0.0119 (18) | −0.0035 (17) |
C29 | 0.054 (2) | 0.061 (2) | 0.054 (2) | 0.0145 (19) | 0.0069 (18) | −0.0018 (19) |
C30 | 0.052 (2) | 0.065 (3) | 0.054 (2) | −0.0017 (19) | 0.0062 (18) | −0.0042 (19) |
C31 | 0.057 (2) | 0.051 (2) | 0.050 (2) | −0.0020 (18) | 0.0157 (18) | −0.0014 (17) |
C32 | 0.055 (2) | 0.050 (2) | 0.0469 (19) | 0.0141 (17) | 0.0207 (17) | −0.0147 (16) |
C33 | 0.053 (2) | 0.063 (3) | 0.056 (2) | 0.0077 (19) | 0.0086 (19) | 0.009 (2) |
C34 | 0.049 (2) | 0.046 (2) | 0.0445 (19) | −0.0121 (16) | −0.0079 (16) | −0.0057 (16) |
C35 | 0.049 (2) | 0.047 (2) | 0.053 (2) | −0.0024 (17) | 0.0024 (17) | −0.0069 (17) |
C36 | 0.050 (2) | 0.051 (2) | 0.048 (2) | −0.0105 (17) | −0.0142 (17) | −0.0171 (17) |
C37 | 0.055 (2) | 0.057 (2) | 0.053 (2) | 0.0087 (18) | 0.0124 (18) | −0.0133 (18) |
C38 | 0.052 (2) | 0.051 (2) | 0.057 (2) | 0.0102 (18) | 0.0050 (18) | −0.0036 (18) |
C39 | 0.052 (2) | 0.051 (2) | 0.056 (2) | 0.0115 (18) | 0.0048 (18) | 0.0054 (18) |
C40 | 0.062 (2) | 0.049 (2) | 0.053 (2) | 0.0146 (19) | 0.0108 (18) | 0.0104 (17) |
C41 | 0.061 (3) | 0.053 (2) | 0.052 (2) | −0.0081 (18) | 0.0015 (18) | 0.0156 (18) |
C42 | 0.052 (2) | 0.058 (2) | 0.053 (2) | −0.0068 (18) | 0.0124 (18) | 0.0066 (18) |
C43 | 0.052 (2) | 0.051 (2) | 0.052 (2) | −0.0015 (17) | 0.0183 (18) | −0.0029 (17) |
C44 | 0.051 (2) | 0.047 (2) | 0.0496 (19) | −0.0185 (17) | 0.0123 (17) | 0.0106 (16) |
C45 | 0.059 (2) | 0.055 (2) | 0.058 (2) | −0.0037 (19) | −0.0018 (19) | 0.0138 (19) |
C46 | 0.057 (2) | 0.048 (2) | 0.062 (2) | −0.0163 (18) | 0.020 (2) | −0.0182 (18) |
C47 | 0.058 (2) | 0.052 (2) | 0.063 (2) | 0.0203 (18) | 0.022 (2) | 0.0219 (19) |
C48 | 0.053 (2) | 0.065 (3) | 0.068 (3) | −0.019 (2) | −0.014 (2) | 0.014 (2) |
C49 | 0.058 (2) | 0.049 (2) | 0.064 (2) | 0.0216 (18) | 0.0135 (19) | −0.0167 (19) |
C50 | 0.059 (2) | 0.051 (2) | 0.056 (2) | 0.0194 (19) | 0.0196 (19) | 0.0084 (18) |
C51 | 0.051 (2) | 0.057 (2) | 0.058 (2) | −0.0099 (18) | 0.0090 (18) | 0.0249 (19) |
C52 | 0.057 (2) | 0.056 (2) | 0.055 (2) | −0.0145 (19) | −0.0144 (18) | 0.0137 (19) |
C53 | 0.041 (2) | 0.061 (2) | 0.056 (2) | −0.0147 (17) | 0.0045 (17) | −0.0143 (19) |
C54 | 0.052 (2) | 0.053 (2) | 0.061 (2) | −0.0151 (18) | −0.0113 (19) | 0.0097 (19) |
C55 | 0.048 (2) | 0.059 (2) | 0.052 (2) | −0.0055 (17) | 0.0114 (17) | 0.0164 (18) |
C56 | 0.056 (2) | 0.053 (2) | 0.064 (3) | −0.0116 (19) | 0.015 (2) | 0.010 (2) |
N1 | 0.0556 (19) | 0.0545 (19) | 0.0509 (17) | −0.0163 (15) | 0.0139 (15) | 0.0042 (15) |
N2 | 0.0518 (18) | 0.0519 (17) | 0.0431 (16) | 0.0002 (14) | 0.0101 (14) | −0.0005 (14) |
N3 | 0.0536 (19) | 0.0480 (18) | 0.0559 (19) | −0.0148 (15) | 0.0071 (16) | 0.0001 (15) |
N4 | 0.0574 (19) | 0.0508 (18) | 0.0484 (17) | −0.0052 (15) | 0.0154 (15) | −0.0147 (15) |
O1 | 0.0573 (17) | 0.0581 (18) | 0.0623 (17) | −0.0200 (14) | 0.0207 (14) | −0.0164 (14) |
O2 | 0.0501 (16) | 0.0561 (16) | 0.0553 (17) | −0.0135 (13) | 0.0073 (14) | −0.0070 (13) |
O3 | 0.0514 (16) | 0.0511 (16) | 0.0567 (17) | −0.0142 (12) | 0.0128 (14) | −0.0052 (13) |
O4 | 0.0563 (17) | 0.0515 (16) | 0.0564 (17) | −0.0017 (13) | −0.0039 (14) | −0.0075 (13) |
C1—N1 | 1.414 (6) | C27—H27A | 0.9700 |
C1—C2 | 1.546 (6) | C27—H27B | 0.9700 |
C1—C6 | 1.592 (6) | C28—N4 | 1.451 (5) |
C1—H1 | 0.9800 | C28—H28 | 0.9800 |
C2—C3 | 1.464 (6) | C29—N3 | 1.297 (6) |
C2—H2A | 0.9700 | C29—C30 | 1.447 (6) |
C2—H2B | 0.9700 | C29—H29 | 0.9300 |
C3—C4 | 1.586 (6) | C30—C31 | 1.370 (6) |
C3—H3A | 0.9700 | C30—C35 | 1.400 (6) |
C3—H3B | 0.9700 | C31—C32 | 1.387 (5) |
C4—C5 | 1.555 (6) | C31—H31 | 0.9300 |
C4—H4A | 0.9700 | C32—C33 | 1.393 (6) |
C4—H4B | 0.9700 | C32—H32 | 0.9300 |
C5—C6 | 1.511 (6) | C33—C34 | 1.410 (6) |
C5—H5A | 0.9700 | C33—H33 | 0.9300 |
C5—H5B | 0.9700 | C34—C35 | 1.394 (5) |
C6—N2 | 1.495 (5) | C34—C36 | 1.505 (5) |
C6—H6 | 0.9800 | C35—O3 | 1.340 (5) |
C7—N1 | 1.336 (5) | C36—H36A | 0.9600 |
C7—C8 | 1.393 (6) | C36—H36B | 0.9600 |
C7—H7 | 0.9300 | C36—H36C | 0.9600 |
C8—C13 | 1.387 (6) | C37—N4 | 1.339 (6) |
C8—C9 | 1.392 (6) | C37—C38 | 1.427 (6) |
C9—C10 | 1.395 (6) | C37—H37 | 0.9300 |
C9—H9 | 0.9300 | C38—C43 | 1.388 (6) |
C10—C11 | 1.398 (7) | C38—C39 | 1.403 (5) |
C10—H10 | 0.9300 | C39—C40 | 1.386 (6) |
C11—C12 | 1.392 (7) | C39—H39 | 0.9300 |
C11—H11 | 0.9300 | C40—C41 | 1.391 (6) |
C12—C13 | 1.393 (6) | C40—H40 | 0.9300 |
C12—C14 | 1.526 (6) | C41—C42 | 1.399 (6) |
C13—O1 | 1.326 (5) | C41—H41 | 0.9300 |
C14—H14A | 0.9600 | C42—C43 | 1.393 (6) |
C14—H14B | 0.9600 | C42—C44 | 1.581 (6) |
C14—H14C | 0.9600 | C43—O4 | 1.317 (5) |
C15—N2 | 1.266 (5) | C44—H44A | 0.9600 |
C15—C16 | 1.396 (6) | C44—H44B | 0.9600 |
C15—H15 | 0.9300 | C44—H44C | 0.9600 |
C16—C21 | 1.397 (6) | C45—C50 | 1.377 (6) |
C16—C17 | 1.402 (5) | C45—C46 | 1.405 (6) |
C17—C18 | 1.374 (6) | C45—H45 | 0.9300 |
C17—H17 | 0.9300 | C46—C47 | 1.379 (6) |
C18—C19 | 1.386 (6) | C46—H46 | 0.9300 |
C18—H18 | 0.9300 | C47—C48 | 1.392 (7) |
C19—C20 | 1.380 (5) | C47—H47 | 0.9300 |
C19—H19 | 0.9300 | C48—C49 | 1.373 (6) |
C20—C21 | 1.385 (6) | C48—H48 | 0.9300 |
C20—C22 | 1.514 (6) | C49—C50 | 1.399 (6) |
C21—O2 | 1.331 (5) | C49—H49 | 0.9300 |
C22—H22A | 0.9600 | C50—H50 | 0.9300 |
C22—H22B | 0.9600 | C51—C56 | 1.395 (7) |
C22—H22C | 0.9600 | C51—C52 | 1.399 (6) |
C23—N3 | 1.441 (5) | C51—H51 | 0.9300 |
C23—C24 | 1.542 (6) | C52—C53 | 1.398 (6) |
C23—C28 | 1.549 (6) | C52—H52 | 0.9300 |
C23—H23 | 0.9800 | C53—C54 | 1.381 (6) |
C24—C25 | 1.552 (5) | C53—H53 | 0.9300 |
C24—H24A | 0.9700 | C54—C55 | 1.395 (6) |
C24—H24B | 0.9700 | C54—H54 | 0.9300 |
C25—C26 | 1.549 (6) | C55—C56 | 1.385 (6) |
C25—H25A | 0.9700 | C55—H55 | 0.9300 |
C25—H25B | 0.9700 | C56—H56 | 0.9300 |
C26—C27 | 1.526 (6) | O1—H1E | 0.86 (5) |
C26—H26A | 0.9700 | O2—H2E | 0.87 (6) |
C26—H26B | 0.9700 | O3—H3E | 0.85 (5) |
C27—C28 | 1.611 (5) | O4—H4E | 0.88 (5) |
N1—C1—C2 | 113.3 (4) | C25—C26—H26B | 109.6 |
N1—C1—C6 | 109.7 (3) | H26A—C26—H26B | 108.1 |
C2—C1—C6 | 106.8 (3) | C26—C27—C28 | 107.7 (3) |
N1—C1—H1 | 109.0 | C26—C27—H27A | 110.2 |
C2—C1—H1 | 109.0 | C28—C27—H27A | 110.2 |
C6—C1—H1 | 109.0 | C26—C27—H27B | 110.2 |
C3—C2—C1 | 118.6 (4) | C28—C27—H27B | 110.2 |
C3—C2—H2A | 107.7 | H27A—C27—H27B | 108.5 |
C1—C2—H2A | 107.7 | N4—C28—C23 | 108.4 (3) |
C3—C2—H2B | 107.7 | N4—C28—C27 | 109.4 (3) |
C1—C2—H2B | 107.7 | C23—C28—C27 | 109.9 (3) |
H2A—C2—H2B | 107.1 | N4—C28—H28 | 109.7 |
C2—C3—C4 | 109.3 (3) | C23—C28—H28 | 109.7 |
C2—C3—H3A | 109.8 | C27—C28—H28 | 109.7 |
C4—C3—H3A | 109.8 | N3—C29—C30 | 123.2 (4) |
C2—C3—H3B | 109.8 | N3—C29—H29 | 118.4 |
C4—C3—H3B | 109.8 | C30—C29—H29 | 118.4 |
H3A—C3—H3B | 108.3 | C31—C30—C35 | 120.4 (4) |
C5—C4—C3 | 115.6 (4) | C31—C30—C29 | 119.6 (4) |
C5—C4—H4A | 108.4 | C35—C30—C29 | 120.0 (4) |
C3—C4—H4A | 108.4 | C30—C31—C32 | 120.9 (4) |
C5—C4—H4B | 108.4 | C30—C31—H31 | 119.6 |
C3—C4—H4B | 108.4 | C32—C31—H31 | 119.6 |
H4A—C4—H4B | 107.4 | C31—C32—C33 | 119.6 (4) |
C6—C5—C4 | 107.6 (4) | C31—C32—H32 | 120.2 |
C6—C5—H5A | 110.2 | C33—C32—H32 | 120.2 |
C4—C5—H5A | 110.2 | C32—C33—C34 | 120.1 (4) |
C6—C5—H5B | 110.2 | C32—C33—H33 | 119.9 |
C4—C5—H5B | 110.2 | C34—C33—H33 | 119.9 |
H5A—C5—H5B | 108.5 | C35—C34—C33 | 119.2 (4) |
N2—C6—C5 | 107.6 (3) | C35—C34—C36 | 120.5 (4) |
N2—C6—C1 | 105.4 (3) | C33—C34—C36 | 120.3 (4) |
C5—C6—C1 | 114.4 (4) | O3—C35—C34 | 119.6 (4) |
N2—C6—H6 | 109.8 | O3—C35—C30 | 120.6 (4) |
C5—C6—H6 | 109.8 | C34—C35—C30 | 119.8 (4) |
C1—C6—H6 | 109.8 | C34—C36—H36A | 109.5 |
N1—C7—C8 | 120.8 (4) | C34—C36—H36B | 109.5 |
N1—C7—H7 | 119.6 | H36A—C36—H36B | 109.5 |
C8—C7—H7 | 119.6 | C34—C36—H36C | 109.5 |
C13—C8—C9 | 120.4 (4) | H36A—C36—H36C | 109.5 |
C13—C8—C7 | 119.9 (4) | H36B—C36—H36C | 109.5 |
C9—C8—C7 | 119.4 (4) | N4—C37—C38 | 119.7 (4) |
C8—C9—C10 | 119.6 (4) | N4—C37—H37 | 120.2 |
C8—C9—H9 | 120.2 | C38—C37—H37 | 120.2 |
C10—C9—H9 | 120.2 | C43—C38—C39 | 120.4 (4) |
C9—C10—C11 | 119.6 (4) | C43—C38—C37 | 121.3 (4) |
C9—C10—H10 | 120.2 | C39—C38—C37 | 118.3 (4) |
C11—C10—H10 | 120.2 | C40—C39—C38 | 119.0 (4) |
C12—C11—C10 | 120.9 (4) | C40—C39—H39 | 120.5 |
C12—C11—H11 | 119.6 | C38—C39—H39 | 120.5 |
C10—C11—H11 | 119.6 | C39—C40—C41 | 121.8 (4) |
C11—C12—C13 | 118.9 (4) | C39—C40—H40 | 119.1 |
C11—C12—C14 | 121.3 (4) | C41—C40—H40 | 119.1 |
C13—C12—C14 | 119.7 (4) | C40—C41—C42 | 118.3 (4) |
O1—C13—C8 | 127.6 (4) | C40—C41—H41 | 120.9 |
O1—C13—C12 | 111.6 (4) | C42—C41—H41 | 120.9 |
C8—C13—C12 | 120.7 (4) | C43—C42—C41 | 121.1 (4) |
C12—C14—H14A | 109.5 | C43—C42—C44 | 118.6 (4) |
C12—C14—H14B | 109.5 | C41—C42—C44 | 120.3 (4) |
H14A—C14—H14B | 109.5 | O4—C43—C38 | 118.2 (4) |
C12—C14—H14C | 109.5 | O4—C43—C42 | 122.2 (4) |
H14A—C14—H14C | 109.5 | C38—C43—C42 | 119.5 (4) |
H14B—C14—H14C | 109.5 | C42—C44—H44A | 109.5 |
N2—C15—C16 | 124.5 (4) | C42—C44—H44B | 109.5 |
N2—C15—H15 | 117.7 | H44A—C44—H44B | 109.5 |
C16—C15—H15 | 117.7 | C42—C44—H44C | 109.5 |
C15—C16—C21 | 120.7 (4) | H44A—C44—H44C | 109.5 |
C15—C16—C17 | 120.7 (4) | H44B—C44—H44C | 109.5 |
C21—C16—C17 | 118.6 (4) | C50—C45—C46 | 120.0 (4) |
C18—C17—C16 | 120.4 (4) | C50—C45—H45 | 120.0 |
C18—C17—H17 | 119.8 | C46—C45—H45 | 120.0 |
C16—C17—H17 | 119.8 | C47—C46—C45 | 119.9 (4) |
C17—C18—C19 | 120.1 (4) | C47—C46—H46 | 120.0 |
C17—C18—H18 | 120.0 | C45—C46—H46 | 120.0 |
C19—C18—H18 | 120.0 | C46—C47—C48 | 119.5 (4) |
C20—C19—C18 | 120.7 (4) | C46—C47—H47 | 120.3 |
C20—C19—H19 | 119.7 | C48—C47—H47 | 120.3 |
C18—C19—H19 | 119.7 | C49—C48—C47 | 121.1 (4) |
C19—C20—C21 | 119.3 (4) | C49—C48—H48 | 119.5 |
C19—C20—C22 | 120.7 (4) | C47—C48—H48 | 119.5 |
C21—C20—C22 | 120.0 (4) | C48—C49—C50 | 119.5 (4) |
O2—C21—C20 | 117.7 (4) | C48—C49—H49 | 120.2 |
O2—C21—C16 | 121.4 (4) | C50—C49—H49 | 120.2 |
C20—C21—C16 | 120.9 (4) | C45—C50—C49 | 120.0 (4) |
C20—C22—H22A | 109.5 | C45—C50—H50 | 120.0 |
C20—C22—H22B | 109.5 | C49—C50—H50 | 120.0 |
H22A—C22—H22B | 109.5 | C56—C51—C52 | 119.5 (4) |
C20—C22—H22C | 109.5 | C56—C51—H51 | 120.3 |
H22A—C22—H22C | 109.5 | C52—C51—H51 | 120.3 |
H22B—C22—H22C | 109.5 | C53—C52—C51 | 120.1 (5) |
N3—C23—C24 | 109.6 (3) | C53—C52—H52 | 119.9 |
N3—C23—C28 | 109.1 (3) | C51—C52—H52 | 119.9 |
C24—C23—C28 | 113.1 (3) | C54—C53—C52 | 119.6 (4) |
N3—C23—H23 | 108.3 | C54—C53—H53 | 120.2 |
C24—C23—H23 | 108.3 | C52—C53—H53 | 120.2 |
C28—C23—H23 | 108.3 | C53—C54—C55 | 120.6 (4) |
C23—C24—C25 | 109.6 (3) | C53—C54—H54 | 119.7 |
C23—C24—H24A | 109.8 | C55—C54—H54 | 119.7 |
C25—C24—H24A | 109.8 | C56—C55—C54 | 119.8 (4) |
C23—C24—H24B | 109.8 | C56—C55—H55 | 120.1 |
C25—C24—H24B | 109.8 | C54—C55—H55 | 120.1 |
H24A—C24—H24B | 108.2 | C55—C56—C51 | 120.3 (4) |
C26—C25—C24 | 109.5 (3) | C55—C56—H56 | 119.8 |
C26—C25—H25A | 109.8 | C51—C56—H56 | 119.8 |
C24—C25—H25A | 109.8 | C7—N1—C1 | 122.3 (4) |
C26—C25—H25B | 109.8 | C15—N2—C6 | 121.1 (4) |
C24—C25—H25B | 109.8 | C29—N3—C23 | 118.5 (3) |
H25A—C25—H25B | 108.2 | C37—N4—C28 | 117.9 (4) |
C27—C26—C25 | 110.3 (3) | C13—O1—H1E | 108 (3) |
C27—C26—H26A | 109.6 | C21—O2—H2E | 109 (4) |
C25—C26—H26A | 109.6 | C35—O3—H3E | 108 (4) |
C27—C26—H26B | 109.6 | C43—O4—H4E | 113 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4E···N4 | 0.88 (5) | 1.74 (5) | 2.438 (5) | 135 (4) |
O3—H3E···N3 | 0.85 (5) | 1.84 (5) | 2.550 (4) | 140 (5) |
O2—H2E···N2 | 0.87 (6) | 1.81 (6) | 2.577 (5) | 146 (5) |
O1—H1E···N1 | 0.86 (5) | 1.91 (5) | 2.604 (4) | 137 (4) |