Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032344/ya6264sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032344/ya6264Isup2.hkl |
CCDC reference: 289947
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C31H29N | Dx = 1.147 Mg m−3 |
Mr = 415.55 | Melting point: 378 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4818 (17) Å | Cell parameters from 2899 reflections |
b = 17.071 (3) Å | θ = 2.4–23.1° |
c = 13.460 (2) Å | µ = 0.07 mm−1 |
β = 92.780 (3)° | T = 294 K |
V = 2405.8 (7) Å3 | Block, yellow |
Z = 4 | 0.40 × 0.30 × 0.22 mm |
F(000) = 888 |
Bruker SMART-1000 CCD area-detector diffractometer | 4894 independent reflections |
Radiation source: fine-focus sealed tube | 2709 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −13→10 |
Tmin = 0.947, Tmax = 0.986 | k = −15→21 |
13469 measured reflections | l = −16→16 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.2552P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.045 | (Δ/σ)max < 0.001 |
wR(F2) = 0.128 | Δρmax = 0.17 e Å−3 |
S = 1.01 | Δρmin = −0.15 e Å−3 |
4894 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997) |
291 parameters | Extinction coefficient: 0.0136 (13) |
0 restraints |
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 | ||
N1 | 0.21977 (16) | 0.14371 (9) | −0.14336 (11) | 0.0605 (4) | |
C1 | 0.46795 (16) | 0.14783 (10) | 0.50835 (12) | 0.0465 (4) | |
C2 | 0.56105 (17) | 0.13857 (10) | 0.59347 (12) | 0.0477 (4) | |
C3 | 0.68090 (19) | 0.10444 (11) | 0.58330 (15) | 0.0637 (6) | |
H3 | 0.7023 | 0.0859 | 0.5213 | 0.076* | |
C4 | 0.7681 (2) | 0.09747 (13) | 0.66269 (18) | 0.0790 (7) | |
H4 | 0.8465 | 0.0736 | 0.6539 | 0.095* | |
C5 | 0.7400 (2) | 0.12545 (13) | 0.75455 (17) | 0.0787 (7) | |
H5 | 0.7992 | 0.1211 | 0.8080 | 0.094* | |
C6 | 0.6244 (2) | 0.15975 (13) | 0.76666 (15) | 0.0741 (6) | |
H6 | 0.6046 | 0.1789 | 0.8288 | 0.089* | |
C7 | 0.53623 (19) | 0.16633 (11) | 0.68732 (14) | 0.0599 (5) | |
H7 | 0.4580 | 0.1901 | 0.6972 | 0.072* | |
C8 | 0.36282 (17) | 0.20631 (10) | 0.51745 (11) | 0.0460 (4) | |
C9 | 0.23606 (18) | 0.18248 (12) | 0.50986 (13) | 0.0585 (5) | |
H9 | 0.2168 | 0.1301 | 0.4975 | 0.070* | |
C10 | 0.1377 (2) | 0.23574 (15) | 0.52055 (15) | 0.0701 (6) | |
H10 | 0.0534 | 0.2187 | 0.5163 | 0.084* | |
C11 | 0.1642 (2) | 0.31336 (15) | 0.53727 (15) | 0.0731 (6) | |
H11 | 0.0982 | 0.3491 | 0.5440 | 0.088* | |
C12 | 0.2883 (2) | 0.33777 (13) | 0.54395 (15) | 0.0709 (6) | |
H12 | 0.3066 | 0.3905 | 0.5544 | 0.085* | |
C13 | 0.38694 (19) | 0.28493 (11) | 0.53537 (13) | 0.0577 (5) | |
H13 | 0.4710 | 0.3024 | 0.5417 | 0.069* | |
C14 | 0.47490 (18) | 0.10599 (10) | 0.42352 (13) | 0.0537 (5) | |
H14 | 0.5293 | 0.0629 | 0.4259 | 0.064* | |
C15 | 0.40746 (17) | 0.12099 (11) | 0.33060 (13) | 0.0526 (5) | |
H15 | 0.3506 | 0.1629 | 0.3275 | 0.063* | |
C16 | 0.42036 (17) | 0.07897 (11) | 0.24756 (13) | 0.0532 (5) | |
H16 | 0.4683 | 0.0333 | 0.2544 | 0.064* | |
C17 | 0.36818 (16) | 0.09660 (10) | 0.14828 (12) | 0.0466 (4) | |
C18 | 0.37168 (16) | 0.04132 (10) | 0.07216 (13) | 0.0489 (5) | |
H18 | 0.4078 | −0.0074 | 0.0863 | 0.059* | |
C19 | 0.32379 (17) | 0.05607 (10) | −0.02300 (13) | 0.0497 (5) | |
H19 | 0.3277 | 0.0171 | −0.0710 | 0.060* | |
C20 | 0.26938 (17) | 0.12853 (10) | −0.04898 (13) | 0.0486 (4) | |
C21 | 0.26646 (17) | 0.18462 (10) | 0.02727 (13) | 0.0535 (5) | |
H21 | 0.2311 | 0.2336 | 0.0134 | 0.064* | |
C22 | 0.31446 (17) | 0.16878 (10) | 0.12145 (13) | 0.0528 (5) | |
H22 | 0.3111 | 0.2077 | 0.1696 | 0.063* | |
C23 | 0.23721 (19) | 0.09033 (11) | −0.22513 (13) | 0.0594 (5) | |
H23A | 0.3187 | 0.0641 | −0.2140 | 0.071* | |
H23B | 0.2415 | 0.1207 | −0.2858 | 0.071* | |
C24 | 0.13449 (18) | 0.02878 (11) | −0.24072 (14) | 0.0553 (5) | |
C25 | 0.04772 (19) | 0.01214 (13) | −0.16991 (16) | 0.0690 (6) | |
H25 | 0.0500 | 0.0404 | −0.1108 | 0.083* | |
C26 | −0.0423 (2) | −0.04579 (16) | −0.1858 (2) | 0.0918 (8) | |
H26 | −0.0996 | −0.0568 | −0.1370 | 0.110* | |
C27 | −0.0479 (3) | −0.08700 (15) | −0.2722 (3) | 0.1095 (11) | |
H27 | −0.1078 | −0.1267 | −0.2821 | 0.131* | |
C28 | 0.0351 (3) | −0.06989 (17) | −0.3447 (3) | 0.1150 (11) | |
H28 | 0.0299 | −0.0969 | −0.4047 | 0.138* | |
C29 | 0.1267 (2) | −0.01232 (13) | −0.32851 (18) | 0.0865 (7) | |
H29 | 0.1836 | −0.0013 | −0.3776 | 0.104* | |
C30 | 0.1486 (2) | 0.21590 (12) | −0.16801 (15) | 0.0706 (6) | |
H30A | 0.0988 | 0.2303 | −0.1119 | 0.085* | |
H30B | 0.0894 | 0.2057 | −0.2242 | 0.085* | |
C31 | 0.2323 (2) | 0.28325 (13) | −0.19296 (18) | 0.0919 (8) | |
H31A | 0.2920 | 0.2933 | −0.1381 | 0.138* | |
H31B | 0.1807 | 0.3289 | −0.2058 | 0.138* | |
H31C | 0.2780 | 0.2707 | −0.2510 | 0.138* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0808 (12) | 0.0519 (10) | 0.0483 (9) | −0.0008 (8) | −0.0026 (8) | 0.0014 (7) |
C1 | 0.0516 (11) | 0.0432 (10) | 0.0445 (10) | −0.0002 (8) | 0.0019 (8) | 0.0018 (8) |
C2 | 0.0559 (12) | 0.0401 (10) | 0.0468 (11) | −0.0015 (8) | 0.0009 (9) | 0.0050 (8) |
C3 | 0.0688 (14) | 0.0623 (13) | 0.0595 (12) | 0.0162 (10) | −0.0030 (10) | 0.0000 (10) |
C4 | 0.0709 (15) | 0.0771 (16) | 0.0871 (17) | 0.0206 (12) | −0.0146 (13) | 0.0067 (13) |
C5 | 0.0891 (18) | 0.0743 (16) | 0.0695 (15) | 0.0040 (13) | −0.0280 (13) | 0.0107 (12) |
C6 | 0.0930 (18) | 0.0790 (16) | 0.0491 (12) | 0.0032 (13) | −0.0108 (12) | 0.0018 (11) |
C7 | 0.0638 (13) | 0.0640 (13) | 0.0516 (12) | 0.0009 (10) | 0.0003 (10) | 0.0011 (9) |
C8 | 0.0520 (11) | 0.0518 (12) | 0.0342 (9) | 0.0042 (9) | 0.0014 (8) | 0.0012 (8) |
C9 | 0.0578 (13) | 0.0674 (13) | 0.0500 (11) | −0.0028 (10) | −0.0014 (9) | −0.0003 (9) |
C10 | 0.0485 (13) | 0.1020 (19) | 0.0595 (13) | 0.0070 (12) | 0.0002 (10) | −0.0045 (12) |
C11 | 0.0707 (16) | 0.0907 (18) | 0.0575 (13) | 0.0287 (13) | −0.0008 (11) | −0.0086 (12) |
C12 | 0.0798 (17) | 0.0616 (14) | 0.0712 (14) | 0.0180 (12) | 0.0034 (12) | −0.0063 (10) |
C13 | 0.0584 (12) | 0.0550 (13) | 0.0599 (12) | 0.0047 (10) | 0.0059 (9) | −0.0049 (9) |
C14 | 0.0601 (12) | 0.0472 (11) | 0.0533 (11) | 0.0051 (9) | −0.0022 (9) | −0.0031 (9) |
C15 | 0.0524 (12) | 0.0548 (12) | 0.0506 (11) | 0.0008 (9) | 0.0013 (9) | −0.0066 (9) |
C16 | 0.0527 (11) | 0.0512 (11) | 0.0554 (11) | 0.0008 (9) | 0.0010 (9) | −0.0077 (9) |
C17 | 0.0447 (10) | 0.0485 (11) | 0.0468 (10) | −0.0043 (8) | 0.0043 (8) | −0.0079 (8) |
C18 | 0.0472 (11) | 0.0444 (11) | 0.0551 (11) | 0.0026 (8) | 0.0036 (9) | −0.0059 (8) |
C19 | 0.0546 (11) | 0.0463 (11) | 0.0485 (11) | −0.0039 (9) | 0.0045 (9) | −0.0107 (8) |
C20 | 0.0498 (11) | 0.0462 (11) | 0.0502 (11) | −0.0062 (8) | 0.0062 (8) | −0.0019 (8) |
C21 | 0.0623 (12) | 0.0427 (11) | 0.0561 (12) | 0.0023 (9) | 0.0099 (9) | −0.0020 (9) |
C22 | 0.0636 (12) | 0.0460 (11) | 0.0494 (11) | −0.0025 (9) | 0.0101 (9) | −0.0098 (8) |
C23 | 0.0702 (13) | 0.0619 (13) | 0.0466 (11) | −0.0084 (10) | 0.0072 (9) | 0.0013 (9) |
C24 | 0.0546 (12) | 0.0491 (12) | 0.0615 (12) | 0.0020 (9) | −0.0035 (10) | 0.0016 (9) |
C25 | 0.0552 (13) | 0.0788 (15) | 0.0721 (14) | −0.0052 (11) | −0.0043 (11) | 0.0166 (11) |
C26 | 0.0558 (15) | 0.093 (2) | 0.125 (2) | −0.0150 (14) | −0.0125 (15) | 0.0335 (17) |
C27 | 0.0689 (19) | 0.0649 (18) | 0.191 (4) | −0.0111 (13) | −0.027 (2) | −0.001 (2) |
C28 | 0.088 (2) | 0.091 (2) | 0.163 (3) | −0.0017 (17) | −0.016 (2) | −0.062 (2) |
C29 | 0.0808 (16) | 0.0797 (16) | 0.0992 (18) | −0.0032 (13) | 0.0067 (13) | −0.0339 (14) |
C30 | 0.0837 (16) | 0.0679 (14) | 0.0605 (13) | 0.0102 (12) | 0.0067 (11) | 0.0083 (10) |
C31 | 0.118 (2) | 0.0713 (16) | 0.0886 (17) | 0.0087 (14) | 0.0335 (15) | 0.0205 (13) |
N1—C20 | 1.374 (2) | C16—C17 | 1.451 (2) |
N1—C23 | 1.447 (2) | C16—H16 | 0.9300 |
N1—C30 | 1.470 (2) | C17—C18 | 1.395 (2) |
C1—C14 | 1.352 (2) | C17—C22 | 1.395 (2) |
C1—C2 | 1.477 (2) | C18—C19 | 1.376 (2) |
C1—C8 | 1.496 (2) | C18—H18 | 0.9300 |
C2—C7 | 1.386 (2) | C19—C20 | 1.399 (2) |
C2—C3 | 1.397 (2) | C19—H19 | 0.9300 |
C3—C4 | 1.377 (3) | C20—C21 | 1.405 (2) |
C3—H3 | 0.9300 | C21—C22 | 1.368 (2) |
C4—C5 | 1.371 (3) | C21—H21 | 0.9300 |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—C6 | 1.363 (3) | C23—C24 | 1.512 (3) |
C5—H5 | 0.9300 | C23—H23A | 0.9700 |
C6—C7 | 1.382 (3) | C23—H23B | 0.9700 |
C6—H6 | 0.9300 | C24—C29 | 1.373 (3) |
C7—H7 | 0.9300 | C24—C25 | 1.379 (3) |
C8—C13 | 1.385 (2) | C25—C26 | 1.376 (3) |
C8—C9 | 1.389 (2) | C25—H25 | 0.9300 |
C9—C10 | 1.387 (3) | C26—C27 | 1.358 (4) |
C9—H9 | 0.9300 | C26—H26 | 0.9300 |
C10—C11 | 1.370 (3) | C27—C28 | 1.370 (4) |
C10—H10 | 0.9300 | C27—H27 | 0.9300 |
C11—C12 | 1.365 (3) | C28—C29 | 1.384 (3) |
C11—H11 | 0.9300 | C28—H28 | 0.9300 |
C12—C13 | 1.381 (3) | C29—H29 | 0.9300 |
C12—H12 | 0.9300 | C30—C31 | 1.495 (3) |
C13—H13 | 0.9300 | C30—H30A | 0.9700 |
C14—C15 | 1.430 (2) | C30—H30B | 0.9700 |
C14—H14 | 0.9300 | C31—H31A | 0.9600 |
C15—C16 | 1.340 (2) | C31—H31B | 0.9600 |
C15—H15 | 0.9300 | C31—H31C | 0.9600 |
C20—N1—C23 | 121.90 (16) | C22—C17—C16 | 123.45 (15) |
C20—N1—C30 | 122.13 (15) | C19—C18—C17 | 122.58 (16) |
C23—N1—C30 | 115.95 (15) | C19—C18—H18 | 118.7 |
C14—C1—C2 | 122.55 (16) | C17—C18—H18 | 118.7 |
C14—C1—C8 | 119.45 (16) | C18—C19—C20 | 121.35 (16) |
C2—C1—C8 | 117.99 (15) | C18—C19—H19 | 119.3 |
C7—C2—C3 | 116.19 (17) | C20—C19—H19 | 119.3 |
C7—C2—C1 | 121.63 (17) | N1—C20—C19 | 121.95 (16) |
C3—C2—C1 | 122.13 (16) | N1—C20—C21 | 121.76 (16) |
C4—C3—C2 | 121.73 (19) | C19—C20—C21 | 116.29 (16) |
C4—C3—H3 | 119.1 | C22—C21—C20 | 121.48 (17) |
C2—C3—H3 | 119.1 | C22—C21—H21 | 119.3 |
C5—C4—C3 | 120.4 (2) | C20—C21—H21 | 119.3 |
C5—C4—H4 | 119.8 | C21—C22—C17 | 122.69 (16) |
C3—C4—H4 | 119.8 | C21—C22—H22 | 118.7 |
C6—C5—C4 | 119.3 (2) | C17—C22—H22 | 118.7 |
C6—C5—H5 | 120.4 | N1—C23—C24 | 115.33 (16) |
C4—C5—H5 | 120.4 | N1—C23—H23A | 108.4 |
C5—C6—C7 | 120.5 (2) | C24—C23—H23A | 108.4 |
C5—C6—H6 | 119.8 | N1—C23—H23B | 108.4 |
C7—C6—H6 | 119.8 | C24—C23—H23B | 108.4 |
C6—C7—C2 | 121.9 (2) | H23A—C23—H23B | 107.5 |
C6—C7—H7 | 119.0 | C29—C24—C25 | 118.42 (19) |
C2—C7—H7 | 119.0 | C29—C24—C23 | 119.13 (18) |
C13—C8—C9 | 117.56 (17) | C25—C24—C23 | 122.45 (18) |
C13—C8—C1 | 122.14 (16) | C26—C25—C24 | 120.7 (2) |
C9—C8—C1 | 120.29 (16) | C26—C25—H25 | 119.6 |
C10—C9—C8 | 120.90 (19) | C24—C25—H25 | 119.6 |
C10—C9—H9 | 119.6 | C27—C26—C25 | 120.4 (3) |
C8—C9—H9 | 119.6 | C27—C26—H26 | 119.8 |
C11—C10—C9 | 120.4 (2) | C25—C26—H26 | 119.8 |
C11—C10—H10 | 119.8 | C26—C27—C28 | 119.8 (3) |
C9—C10—H10 | 119.8 | C26—C27—H27 | 120.1 |
C12—C11—C10 | 119.4 (2) | C28—C27—H27 | 120.1 |
C12—C11—H11 | 120.3 | C27—C28—C29 | 119.9 (3) |
C10—C11—H11 | 120.3 | C27—C28—H28 | 120.0 |
C11—C12—C13 | 120.7 (2) | C29—C28—H28 | 120.0 |
C11—C12—H12 | 119.7 | C24—C29—C28 | 120.7 (3) |
C13—C12—H12 | 119.7 | C24—C29—H29 | 119.7 |
C12—C13—C8 | 121.09 (19) | C28—C29—H29 | 119.7 |
C12—C13—H13 | 119.5 | N1—C30—C31 | 113.47 (19) |
C8—C13—H13 | 119.5 | N1—C30—H30A | 108.9 |
C1—C14—C15 | 126.85 (17) | C31—C30—H30A | 108.9 |
C1—C14—H14 | 116.6 | N1—C30—H30B | 108.9 |
C15—C14—H14 | 116.6 | C31—C30—H30B | 108.9 |
C16—C15—C14 | 124.61 (18) | H30A—C30—H30B | 107.7 |
C16—C15—H15 | 117.7 | C30—C31—H31A | 109.5 |
C14—C15—H15 | 117.7 | C30—C31—H31B | 109.5 |
C15—C16—C17 | 127.46 (17) | H31A—C31—H31B | 109.5 |
C15—C16—H16 | 116.3 | C30—C31—H31C | 109.5 |
C17—C16—H16 | 116.3 | H31A—C31—H31C | 109.5 |
C18—C17—C22 | 115.60 (16) | H31B—C31—H31C | 109.5 |
C18—C17—C16 | 120.94 (16) | ||
C14—C1—C2—C7 | −163.70 (18) | C15—C16—C17—C22 | 12.0 (3) |
C8—C1—C2—C7 | 16.6 (2) | C22—C17—C18—C19 | −0.9 (3) |
C14—C1—C2—C3 | 19.0 (3) | C16—C17—C18—C19 | −179.64 (16) |
C8—C1—C2—C3 | −160.67 (17) | C17—C18—C19—C20 | 0.6 (3) |
C7—C2—C3—C4 | 1.3 (3) | C23—N1—C20—C19 | −9.2 (3) |
C1—C2—C3—C4 | 178.68 (18) | C30—N1—C20—C19 | 172.32 (17) |
C2—C3—C4—C5 | −1.2 (3) | C23—N1—C20—C21 | 171.79 (17) |
C3—C4—C5—C6 | 0.5 (3) | C30—N1—C20—C21 | −6.7 (3) |
C4—C5—C6—C7 | 0.0 (3) | C18—C19—C20—N1 | −179.17 (16) |
C5—C6—C7—C2 | 0.2 (3) | C18—C19—C20—C21 | −0.1 (3) |
C3—C2—C7—C6 | −0.8 (3) | N1—C20—C21—C22 | 179.10 (17) |
C1—C2—C7—C6 | −178.21 (18) | C19—C20—C21—C22 | 0.0 (3) |
C14—C1—C8—C13 | −121.10 (19) | C20—C21—C22—C17 | −0.5 (3) |
C2—C1—C8—C13 | 58.6 (2) | C18—C17—C22—C21 | 0.9 (3) |
C14—C1—C8—C9 | 60.1 (2) | C16—C17—C22—C21 | 179.54 (17) |
C2—C1—C8—C9 | −120.14 (18) | C20—N1—C23—C24 | 90.5 (2) |
C13—C8—C9—C10 | −0.4 (3) | C30—N1—C23—C24 | −91.0 (2) |
C1—C8—C9—C10 | 178.43 (16) | N1—C23—C24—C29 | 165.20 (18) |
C8—C9—C10—C11 | 1.0 (3) | N1—C23—C24—C25 | −14.8 (3) |
C9—C10—C11—C12 | −0.4 (3) | C29—C24—C25—C26 | 1.8 (3) |
C10—C11—C12—C13 | −0.9 (3) | C23—C24—C25—C26 | −178.24 (19) |
C11—C12—C13—C8 | 1.6 (3) | C24—C25—C26—C27 | −0.7 (4) |
C9—C8—C13—C12 | −0.9 (3) | C25—C26—C27—C28 | −1.1 (4) |
C1—C8—C13—C12 | −179.69 (16) | C26—C27—C28—C29 | 1.9 (4) |
C2—C1—C14—C15 | −166.25 (17) | C25—C24—C29—C28 | −1.0 (3) |
C8—C1—C14—C15 | 13.5 (3) | C23—C24—C29—C28 | 179.0 (2) |
C1—C14—C15—C16 | 178.01 (19) | C27—C28—C29—C24 | −0.8 (4) |
C14—C15—C16—C17 | −171.37 (17) | C20—N1—C30—C31 | 85.6 (2) |
C15—C16—C17—C18 | −169.42 (18) | C23—N1—C30—C31 | −92.9 (2) |