Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805037360/at6052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805037360/at6052Isup2.hkl |
CCDC reference: 293816
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.
C37H33N | Z = 2 |
Mr = 491.64 | F(000) = 524 |
Triclinic, P1 | Dx = 1.172 Mg m−3 |
Hall symbol: -P 1 | Melting point: 420 K |
a = 6.1629 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.935 (4) Å | Cell parameters from 1753 reflections |
c = 16.323 (4) Å | θ = 2.5–26.3° |
α = 117.824 (4)° | µ = 0.07 mm−1 |
β = 90.749 (5)° | T = 294 K |
γ = 99.054 (5)° | Plate, yellow |
V = 1393.2 (6) Å3 | 0.40 × 0.16 × 0.08 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 4873 independent reflections |
Radiation source: fine-focus sealed tube | 2678 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −7→5 |
Tmin = 0.974, Tmax = 0.995 | k = −18→18 |
7091 measured reflections | l = −15→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.0464P)2 + 0.1576P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.131 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.14 e Å−3 |
4873 reflections | Δρmin = −0.18 e Å−3 |
344 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 | ||
N1 | 0.5128 (3) | 0.19725 (14) | 0.18886 (15) | 0.0524 (6) | |
C1 | 0.0375 (4) | 0.73899 (17) | 0.27318 (17) | 0.0439 (6) | |
C2 | −0.1596 (4) | 0.72156 (18) | 0.30632 (18) | 0.0537 (7) | |
H2 | −0.2209 | 0.6586 | 0.2924 | 0.064* | |
C3 | −0.2686 (5) | 0.7962 (2) | 0.3601 (2) | 0.0628 (8) | |
H3 | −0.4018 | 0.7828 | 0.3817 | 0.075* | |
C4 | −0.1809 (5) | 0.8891 (2) | 0.3816 (2) | 0.0626 (8) | |
H4 | −0.2534 | 0.9392 | 0.4179 | 0.075* | |
C5 | 0.0144 (5) | 0.90800 (19) | 0.3491 (2) | 0.0615 (8) | |
H5 | 0.0744 | 0.9712 | 0.3636 | 0.074* | |
C6 | 0.1233 (4) | 0.83421 (18) | 0.29494 (18) | 0.0532 (7) | |
H6 | 0.2550 | 0.8481 | 0.2728 | 0.064* | |
C7 | 0.1752 (4) | 0.64209 (16) | 0.11697 (18) | 0.0441 (6) | |
C8 | 0.0105 (4) | 0.65621 (19) | 0.0679 (2) | 0.0570 (7) | |
H8 | −0.1136 | 0.6779 | 0.0966 | 0.068* | |
C9 | 0.0289 (5) | 0.6385 (2) | −0.0226 (2) | 0.0696 (9) | |
H9 | −0.0841 | 0.6473 | −0.0544 | 0.083* | |
C10 | 0.2104 (5) | 0.6083 (2) | −0.0660 (2) | 0.0720 (9) | |
H10 | 0.2213 | 0.5969 | −0.1270 | 0.086* | |
C11 | 0.3773 (5) | 0.5947 (2) | −0.0192 (2) | 0.0693 (8) | |
H11 | 0.5016 | 0.5740 | −0.0483 | 0.083* | |
C12 | 0.3587 (5) | 0.61209 (18) | 0.0715 (2) | 0.0585 (7) | |
H12 | 0.4728 | 0.6034 | 0.1029 | 0.070* | |
C13 | 0.1544 (4) | 0.65992 (16) | 0.21373 (17) | 0.0422 (6) | |
C14 | 0.2390 (4) | 0.60759 (16) | 0.24752 (18) | 0.0477 (7) | |
H14 | 0.2917 | 0.5534 | 0.2052 | 0.057* | |
C15 | 0.2540 (4) | 0.62885 (17) | 0.34325 (18) | 0.0505 (7) | |
H15 | 0.2022 | 0.6837 | 0.3848 | 0.061* | |
C16 | 0.3344 (4) | 0.57849 (17) | 0.37991 (18) | 0.0495 (7) | |
H16 | 0.3571 | 0.6080 | 0.4445 | 0.059* | |
C17 | 0.3901 (4) | 0.48203 (16) | 0.32873 (17) | 0.0424 (6) | |
C18 | 0.2505 (4) | 0.40865 (16) | 0.25323 (17) | 0.0460 (6) | |
H18 | 0.1252 | 0.4229 | 0.2339 | 0.055* | |
C19 | 0.2900 (4) | 0.31596 (16) | 0.20607 (17) | 0.0439 (6) | |
H19 | 0.1927 | 0.2694 | 0.1556 | 0.053* | |
C20 | 0.4755 (4) | 0.29123 (17) | 0.23358 (17) | 0.0424 (6) | |
C21 | 0.6171 (4) | 0.36473 (17) | 0.30876 (17) | 0.0466 (7) | |
H21 | 0.7428 | 0.3502 | 0.3276 | 0.056* | |
C22 | 0.5788 (4) | 0.45827 (17) | 0.35649 (17) | 0.0435 (6) | |
C23 | 0.7395 (4) | 0.53356 (18) | 0.43739 (19) | 0.0610 (8) | |
H23A | 0.6664 | 0.5561 | 0.4933 | 0.091* | |
H23B | 0.7931 | 0.5867 | 0.4261 | 0.091* | |
H23C | 0.8613 | 0.5057 | 0.4443 | 0.091* | |
C24 | 0.7210 (4) | 0.1748 (2) | 0.20850 (19) | 0.0587 (8) | |
H24A | 0.8401 | 0.2244 | 0.2120 | 0.070* | |
H24B | 0.7403 | 0.1141 | 0.1566 | 0.070* | |
C25 | 0.7428 (4) | 0.16712 (17) | 0.29677 (18) | 0.0486 (7) | |
C26 | 0.5675 (5) | 0.1316 (2) | 0.3292 (2) | 0.0642 (8) | |
H26 | 0.4272 | 0.1150 | 0.2982 | 0.077* | |
C27 | 0.5952 (6) | 0.1199 (2) | 0.4075 (2) | 0.0761 (9) | |
H27 | 0.4746 | 0.0954 | 0.4286 | 0.091* | |
C28 | 0.8019 (7) | 0.1447 (2) | 0.4535 (2) | 0.0733 (10) | |
H28 | 0.8221 | 0.1365 | 0.5058 | 0.088* | |
C29 | 0.9765 (6) | 0.1810 (2) | 0.4228 (2) | 0.0786 (10) | |
H29 | 1.1162 | 0.1982 | 0.4544 | 0.094* | |
C30 | 0.9489 (5) | 0.1928 (2) | 0.3453 (2) | 0.0667 (8) | |
H30 | 1.0701 | 0.2183 | 0.3253 | 0.080* | |
C31 | 0.3526 (4) | 0.12062 (17) | 0.11640 (18) | 0.0538 (7) | |
H31A | 0.2069 | 0.1263 | 0.1378 | 0.065* | |
H31B | 0.3827 | 0.0592 | 0.1076 | 0.065* | |
C32 | 0.3481 (4) | 0.11918 (16) | 0.02341 (18) | 0.0451 (6) | |
C33 | 0.5377 (5) | 0.14524 (19) | −0.0090 (2) | 0.0596 (7) | |
H33 | 0.6711 | 0.1659 | 0.0279 | 0.072* | |
C34 | 0.5347 (5) | 0.1415 (2) | −0.0952 (2) | 0.0725 (9) | |
H34 | 0.6649 | 0.1597 | −0.1157 | 0.087* | |
C35 | 0.3391 (6) | 0.1108 (2) | −0.1507 (2) | 0.0771 (9) | |
H35 | 0.3366 | 0.1076 | −0.2090 | 0.093* | |
C36 | 0.1491 (6) | 0.0851 (2) | −0.1199 (2) | 0.0788 (10) | |
H36 | 0.0163 | 0.0642 | −0.1573 | 0.095* | |
C37 | 0.1524 (5) | 0.08980 (19) | −0.0332 (2) | 0.0624 (8) | |
H37 | 0.0211 | 0.0729 | −0.0125 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0677 (15) | 0.0485 (13) | 0.0450 (15) | 0.0217 (12) | −0.0033 (11) | 0.0224 (11) |
C1 | 0.0528 (16) | 0.0445 (15) | 0.0393 (16) | 0.0091 (13) | −0.0023 (12) | 0.0241 (12) |
C2 | 0.0551 (17) | 0.0488 (16) | 0.0564 (19) | 0.0083 (14) | 0.0018 (14) | 0.0248 (14) |
C3 | 0.0539 (17) | 0.070 (2) | 0.064 (2) | 0.0195 (16) | 0.0072 (14) | 0.0291 (16) |
C4 | 0.080 (2) | 0.0566 (19) | 0.052 (2) | 0.0294 (17) | 0.0027 (16) | 0.0213 (15) |
C5 | 0.088 (2) | 0.0419 (15) | 0.056 (2) | 0.0143 (16) | 0.0002 (16) | 0.0237 (14) |
C6 | 0.0666 (18) | 0.0480 (16) | 0.0522 (19) | 0.0102 (14) | 0.0067 (14) | 0.0300 (14) |
C7 | 0.0497 (16) | 0.0396 (14) | 0.0430 (17) | 0.0053 (12) | 0.0013 (12) | 0.0207 (12) |
C8 | 0.0541 (17) | 0.0698 (18) | 0.052 (2) | 0.0128 (14) | 0.0038 (14) | 0.0322 (16) |
C9 | 0.068 (2) | 0.087 (2) | 0.056 (2) | 0.0038 (17) | −0.0072 (16) | 0.0387 (18) |
C10 | 0.088 (2) | 0.077 (2) | 0.048 (2) | 0.0058 (19) | 0.0050 (18) | 0.0299 (17) |
C11 | 0.078 (2) | 0.074 (2) | 0.062 (2) | 0.0241 (17) | 0.0230 (17) | 0.0339 (17) |
C12 | 0.0666 (19) | 0.0628 (17) | 0.056 (2) | 0.0223 (15) | 0.0112 (15) | 0.0335 (15) |
C13 | 0.0465 (15) | 0.0370 (13) | 0.0429 (16) | 0.0050 (12) | −0.0011 (12) | 0.0197 (12) |
C14 | 0.0604 (17) | 0.0375 (14) | 0.0427 (17) | 0.0121 (12) | 0.0040 (12) | 0.0162 (12) |
C15 | 0.0638 (18) | 0.0432 (14) | 0.0424 (17) | 0.0148 (13) | 0.0044 (13) | 0.0172 (13) |
C16 | 0.0626 (17) | 0.0459 (15) | 0.0422 (17) | 0.0098 (13) | 0.0011 (13) | 0.0229 (13) |
C17 | 0.0502 (15) | 0.0431 (14) | 0.0386 (16) | 0.0083 (12) | 0.0025 (12) | 0.0236 (13) |
C18 | 0.0490 (15) | 0.0475 (15) | 0.0491 (17) | 0.0131 (13) | −0.0005 (12) | 0.0279 (14) |
C19 | 0.0465 (15) | 0.0435 (14) | 0.0428 (16) | 0.0055 (12) | −0.0046 (12) | 0.0225 (12) |
C20 | 0.0487 (15) | 0.0466 (15) | 0.0406 (16) | 0.0128 (12) | 0.0047 (12) | 0.0267 (13) |
C21 | 0.0447 (15) | 0.0557 (16) | 0.0499 (18) | 0.0124 (13) | 0.0008 (12) | 0.0329 (14) |
C22 | 0.0440 (15) | 0.0480 (15) | 0.0395 (16) | 0.0016 (12) | −0.0039 (12) | 0.0238 (13) |
C23 | 0.0601 (18) | 0.0607 (17) | 0.060 (2) | 0.0028 (14) | −0.0101 (14) | 0.0296 (15) |
C24 | 0.0744 (19) | 0.0685 (18) | 0.0487 (19) | 0.0375 (15) | 0.0140 (14) | 0.0331 (15) |
C25 | 0.0614 (18) | 0.0474 (15) | 0.0448 (17) | 0.0263 (14) | 0.0075 (14) | 0.0233 (13) |
C26 | 0.069 (2) | 0.078 (2) | 0.056 (2) | 0.0186 (16) | 0.0022 (15) | 0.0390 (17) |
C27 | 0.100 (3) | 0.080 (2) | 0.062 (2) | 0.019 (2) | 0.0135 (19) | 0.0445 (19) |
C28 | 0.127 (3) | 0.0548 (18) | 0.042 (2) | 0.035 (2) | −0.004 (2) | 0.0210 (16) |
C29 | 0.095 (3) | 0.077 (2) | 0.064 (2) | 0.028 (2) | −0.0167 (19) | 0.0311 (19) |
C30 | 0.069 (2) | 0.075 (2) | 0.064 (2) | 0.0215 (16) | 0.0008 (16) | 0.0364 (17) |
C31 | 0.0753 (19) | 0.0401 (14) | 0.0515 (19) | 0.0132 (14) | 0.0068 (15) | 0.0255 (14) |
C32 | 0.0610 (18) | 0.0348 (13) | 0.0395 (17) | 0.0090 (13) | 0.0035 (13) | 0.0177 (12) |
C33 | 0.0672 (19) | 0.0643 (18) | 0.051 (2) | 0.0069 (15) | −0.0011 (15) | 0.0323 (16) |
C34 | 0.084 (2) | 0.084 (2) | 0.061 (2) | 0.0103 (18) | 0.0144 (18) | 0.0456 (19) |
C35 | 0.107 (3) | 0.080 (2) | 0.050 (2) | 0.016 (2) | −0.002 (2) | 0.0353 (18) |
C36 | 0.087 (3) | 0.087 (2) | 0.062 (2) | 0.011 (2) | −0.0166 (19) | 0.036 (2) |
C37 | 0.0605 (19) | 0.0654 (18) | 0.062 (2) | 0.0084 (15) | −0.0002 (15) | 0.0313 (16) |
N1—C20 | 1.386 (3) | C19—C20 | 1.400 (3) |
N1—C31 | 1.452 (3) | C19—H19 | 0.9300 |
N1—C24 | 1.455 (3) | C20—C21 | 1.396 (3) |
C1—C2 | 1.377 (3) | C21—C22 | 1.384 (3) |
C1—C6 | 1.396 (3) | C21—H21 | 0.9300 |
C1—C13 | 1.487 (3) | C22—C23 | 1.509 (3) |
C2—C3 | 1.389 (3) | C23—H23A | 0.9600 |
C2—H2 | 0.9300 | C23—H23B | 0.9600 |
C3—C4 | 1.367 (4) | C23—H23C | 0.9600 |
C3—H3 | 0.9300 | C24—C25 | 1.508 (3) |
C4—C5 | 1.368 (4) | C24—H24A | 0.9700 |
C4—H4 | 0.9300 | C24—H24B | 0.9700 |
C5—C6 | 1.381 (3) | C25—C26 | 1.367 (4) |
C5—H5 | 0.9300 | C25—C30 | 1.384 (3) |
C6—H6 | 0.9300 | C26—C27 | 1.387 (4) |
C7—C12 | 1.385 (3) | C26—H26 | 0.9300 |
C7—C8 | 1.393 (3) | C27—C28 | 1.372 (4) |
C7—C13 | 1.480 (3) | C27—H27 | 0.9300 |
C8—C9 | 1.378 (4) | C28—C29 | 1.354 (4) |
C8—H8 | 0.9300 | C28—H28 | 0.9300 |
C9—C10 | 1.363 (4) | C29—C30 | 1.374 (4) |
C9—H9 | 0.9300 | C29—H29 | 0.9300 |
C10—C11 | 1.375 (4) | C30—H30 | 0.9300 |
C10—H10 | 0.9300 | C31—C32 | 1.507 (3) |
C11—C12 | 1.384 (4) | C31—H31A | 0.9700 |
C11—H11 | 0.9300 | C31—H31B | 0.9700 |
C12—H12 | 0.9300 | C32—C33 | 1.374 (3) |
C13—C14 | 1.353 (3) | C32—C37 | 1.384 (3) |
C14—C15 | 1.434 (3) | C33—C34 | 1.380 (4) |
C14—H14 | 0.9300 | C33—H33 | 0.9300 |
C15—C16 | 1.347 (3) | C34—C35 | 1.372 (4) |
C15—H15 | 0.9300 | C34—H34 | 0.9300 |
C16—C17 | 1.467 (3) | C35—C36 | 1.360 (4) |
C16—H16 | 0.9300 | C35—H35 | 0.9300 |
C17—C18 | 1.392 (3) | C36—C37 | 1.381 (4) |
C17—C22 | 1.409 (3) | C36—H36 | 0.9300 |
C18—C19 | 1.375 (3) | C37—H37 | 0.9300 |
C18—H18 | 0.9300 | ||
C20—N1—C31 | 120.73 (19) | C21—C20—C19 | 117.0 (2) |
C20—N1—C24 | 120.6 (2) | C22—C21—C20 | 122.9 (2) |
C31—N1—C24 | 118.5 (2) | C22—C21—H21 | 118.5 |
C2—C1—C6 | 117.7 (2) | C20—C21—H21 | 118.5 |
C2—C1—C13 | 122.1 (2) | C21—C22—C17 | 119.5 (2) |
C6—C1—C13 | 120.2 (2) | C21—C22—C23 | 119.7 (2) |
C1—C2—C3 | 121.2 (3) | C17—C22—C23 | 120.8 (2) |
C1—C2—H2 | 119.4 | C22—C23—H23A | 109.5 |
C3—C2—H2 | 119.4 | C22—C23—H23B | 109.5 |
C4—C3—C2 | 120.2 (3) | H23A—C23—H23B | 109.5 |
C4—C3—H3 | 119.9 | C22—C23—H23C | 109.5 |
C2—C3—H3 | 119.9 | H23A—C23—H23C | 109.5 |
C3—C4—C5 | 119.5 (3) | H23B—C23—H23C | 109.5 |
C3—C4—H4 | 120.3 | N1—C24—C25 | 115.5 (2) |
C5—C4—H4 | 120.3 | N1—C24—H24A | 108.4 |
C4—C5—C6 | 120.7 (3) | C25—C24—H24A | 108.4 |
C4—C5—H5 | 119.6 | N1—C24—H24B | 108.4 |
C6—C5—H5 | 119.6 | C25—C24—H24B | 108.4 |
C5—C6—C1 | 120.6 (3) | H24A—C24—H24B | 107.5 |
C5—C6—H6 | 119.7 | C26—C25—C30 | 118.1 (3) |
C1—C6—H6 | 119.7 | C26—C25—C24 | 122.5 (3) |
C12—C7—C8 | 117.0 (3) | C30—C25—C24 | 119.3 (3) |
C12—C7—C13 | 122.0 (2) | C25—C26—C27 | 121.2 (3) |
C8—C7—C13 | 121.0 (2) | C25—C26—H26 | 119.4 |
C9—C8—C7 | 120.9 (3) | C27—C26—H26 | 119.4 |
C9—C8—H8 | 119.6 | C28—C27—C26 | 119.5 (3) |
C7—C8—H8 | 119.6 | C28—C27—H27 | 120.2 |
C10—C9—C8 | 120.9 (3) | C26—C27—H27 | 120.2 |
C10—C9—H9 | 119.5 | C29—C28—C27 | 119.9 (3) |
C8—C9—H9 | 119.5 | C29—C28—H28 | 120.1 |
C9—C10—C11 | 119.7 (3) | C27—C28—H28 | 120.1 |
C9—C10—H10 | 120.2 | C28—C29—C30 | 120.6 (3) |
C11—C10—H10 | 120.2 | C28—C29—H29 | 119.7 |
C10—C11—C12 | 119.5 (3) | C30—C29—H29 | 119.7 |
C10—C11—H11 | 120.3 | C29—C30—C25 | 120.8 (3) |
C12—C11—H11 | 120.3 | C29—C30—H30 | 119.6 |
C11—C12—C7 | 122.0 (3) | C25—C30—H30 | 119.6 |
C11—C12—H12 | 119.0 | N1—C31—C32 | 115.6 (2) |
C7—C12—H12 | 119.0 | N1—C31—H31A | 108.4 |
C14—C13—C7 | 122.0 (2) | C32—C31—H31A | 108.4 |
C14—C13—C1 | 121.0 (2) | N1—C31—H31B | 108.4 |
C7—C13—C1 | 117.01 (19) | C32—C31—H31B | 108.4 |
C13—C14—C15 | 125.3 (2) | H31A—C31—H31B | 107.5 |
C13—C14—H14 | 117.3 | C33—C32—C37 | 117.6 (3) |
C15—C14—H14 | 117.3 | C33—C32—C31 | 121.4 (2) |
C16—C15—C14 | 127.4 (2) | C37—C32—C31 | 121.0 (3) |
C16—C15—H15 | 116.3 | C32—C33—C34 | 121.5 (3) |
C14—C15—H15 | 116.3 | C32—C33—H33 | 119.3 |
C15—C16—C17 | 126.9 (2) | C34—C33—H33 | 119.3 |
C15—C16—H16 | 116.6 | C35—C34—C33 | 119.9 (3) |
C17—C16—H16 | 116.6 | C35—C34—H34 | 120.0 |
C18—C17—C22 | 117.3 (2) | C33—C34—H34 | 120.0 |
C18—C17—C16 | 120.7 (2) | C36—C35—C34 | 119.7 (3) |
C22—C17—C16 | 121.9 (2) | C36—C35—H35 | 120.1 |
C19—C18—C17 | 122.8 (2) | C34—C35—H35 | 120.1 |
C19—C18—H18 | 118.6 | C35—C36—C37 | 120.2 (3) |
C17—C18—H18 | 118.6 | C35—C36—H36 | 119.9 |
C18—C19—C20 | 120.4 (2) | C37—C36—H36 | 119.9 |
C18—C19—H19 | 119.8 | C36—C37—C32 | 121.1 (3) |
C20—C19—H19 | 119.8 | C36—C37—H37 | 119.4 |
N1—C20—C21 | 122.0 (2) | C32—C37—H37 | 119.4 |
N1—C20—C19 | 121.0 (2) | ||
C6—C1—C2—C3 | −0.5 (4) | C24—N1—C20—C19 | 171.0 (2) |
C13—C1—C2—C3 | −178.6 (2) | C18—C19—C20—N1 | 177.6 (2) |
C1—C2—C3—C4 | −0.2 (4) | C18—C19—C20—C21 | −1.1 (4) |
C2—C3—C4—C5 | 0.4 (4) | N1—C20—C21—C22 | −177.7 (2) |
C3—C4—C5—C6 | 0.0 (4) | C19—C20—C21—C22 | 1.0 (4) |
C4—C5—C6—C1 | −0.7 (4) | C20—C21—C22—C17 | −0.4 (4) |
C2—C1—C6—C5 | 0.9 (4) | C20—C21—C22—C23 | 179.7 (2) |
C13—C1—C6—C5 | 179.1 (2) | C18—C17—C22—C21 | −0.2 (4) |
C12—C7—C8—C9 | 1.6 (4) | C16—C17—C22—C21 | 176.5 (2) |
C13—C7—C8—C9 | −179.3 (2) | C18—C17—C22—C23 | 179.7 (2) |
C7—C8—C9—C10 | −1.1 (4) | C16—C17—C22—C23 | −3.6 (4) |
C8—C9—C10—C11 | 0.3 (5) | C20—N1—C24—C25 | 79.5 (3) |
C9—C10—C11—C12 | −0.1 (5) | C31—N1—C24—C25 | −105.2 (3) |
C10—C11—C12—C7 | 0.6 (4) | N1—C24—C25—C26 | 34.3 (3) |
C8—C7—C12—C11 | −1.3 (4) | N1—C24—C25—C30 | −148.7 (2) |
C13—C7—C12—C11 | 179.5 (2) | C30—C25—C26—C27 | −1.1 (4) |
C12—C7—C13—C14 | −33.6 (4) | C24—C25—C26—C27 | 176.0 (2) |
C8—C7—C13—C14 | 147.3 (3) | C25—C26—C27—C28 | 0.2 (4) |
C12—C7—C13—C1 | 145.9 (2) | C26—C27—C28—C29 | 0.6 (4) |
C8—C7—C13—C1 | −33.2 (3) | C27—C28—C29—C30 | −0.4 (5) |
C2—C1—C13—C14 | −65.6 (3) | C28—C29—C30—C25 | −0.5 (4) |
C6—C1—C13—C14 | 116.3 (3) | C26—C25—C30—C29 | 1.2 (4) |
C2—C1—C13—C7 | 114.9 (3) | C24—C25—C30—C29 | −176.0 (2) |
C6—C1—C13—C7 | −63.2 (3) | C20—N1—C31—C32 | 75.9 (3) |
C7—C13—C14—C15 | 170.6 (2) | C24—N1—C31—C32 | −99.4 (3) |
C1—C13—C14—C15 | −8.9 (4) | N1—C31—C32—C33 | 35.1 (3) |
C13—C14—C15—C16 | 179.3 (3) | N1—C31—C32—C37 | −146.0 (2) |
C14—C15—C16—C17 | −11.2 (4) | C37—C32—C33—C34 | −0.6 (4) |
C15—C16—C17—C18 | −43.3 (4) | C31—C32—C33—C34 | 178.2 (2) |
C15—C16—C17—C22 | 140.2 (3) | C32—C33—C34—C35 | −0.3 (4) |
C22—C17—C18—C19 | 0.0 (4) | C33—C34—C35—C36 | 0.6 (5) |
C16—C17—C18—C19 | −176.7 (2) | C34—C35—C36—C37 | 0.0 (5) |
C17—C18—C19—C20 | 0.6 (4) | C35—C36—C37—C32 | −1.0 (4) |
C31—N1—C20—C21 | 174.4 (2) | C33—C32—C37—C36 | 1.3 (4) |
C24—N1—C20—C21 | −10.4 (4) | C31—C32—C37—C36 | −177.6 (2) |
C31—N1—C20—C19 | −4.2 (4) |