In the title molecule, C
31H
28N
2O
2, the piperidinone ring adopts the usual twist-boat conformation. The aryl rings at positions 2 and 3 are axial and those at positions 5 and 6 are equatorial. In the crystal structure, there are no hydrogen bonds nor are there any significant π
π stacking interactions and, apart from two weak C—H
π(arene) interactions, molecules are separated by normal van der Waals distances.
Supporting information
CCDC reference: 618260
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.152
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 221.00 A 3
| Author Response: see _publ_section_exptl_refinement (Experimental)
|
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for C31 - C36 .. 5.51 su
PLAT432_ALERT_2_C Short Inter X...Y Contact C53 .. C53 .. 3.19 Ang.
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius,1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
2,6-bis(4-methylphenyl)-1-nitroso-3,5-diphenyltetrahydro-4(1
H)-pyridinone
top
Crystal data top
C31H28N2O2 | Z = 2 |
Mr = 460.55 | F(000) = 488 |
Triclinic, P1 | Dx = 1.100 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 10.4373 (13) Å | Cell parameters from 4893 reflections |
b = 12.0428 (13) Å | θ = 11.3–13.5° |
c = 12.6808 (14) Å | µ = 0.07 mm−1 |
α = 67.947 (12)° | T = 293 K |
β = 71.053 (9)° | Block, colourless |
γ = 78.081 (12)° | 0.26 × 0.18 × 0.12 mm |
V = 1390.7 (3) Å3 | |
Data collection top
Nonius MACH3 4 circle diffractometer | 2525 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω scans | h = −1→12 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→14 |
Tmin = 0.985, Tmax = 0.992 | l = −14→15 |
5778 measured reflections | 3 standard reflections every 60 min |
4893 independent reflections | intensity decay: none |
Refinement top
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)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0769P)2 + 0.0251P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
4893 reflections | Δρmax = 0.16 e Å−3 |
319 parameters | Δρmin = −0.18 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: 0.024 (3) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C2 | 0.3321 (2) | 0.8353 (2) | 0.8445 (2) | 0.0470 (6) | |
H2 | 0.2493 | 0.8220 | 0.9105 | 0.056* | |
C61 | 0.6908 (2) | 0.8032 (2) | 0.8249 (2) | 0.0454 (6) | |
C6 | 0.5694 (2) | 0.8960 (2) | 0.8135 (2) | 0.0458 (6) | |
H6 | 0.5817 | 0.9602 | 0.8382 | 0.055* | |
C3 | 0.3019 (2) | 0.9557 (2) | 0.7498 (2) | 0.0445 (6) | |
H3 | 0.2576 | 0.9358 | 0.7027 | 0.053* | |
C21 | 0.3661 (2) | 0.7246 (2) | 0.8070 (2) | 0.0473 (6) | |
C66 | 0.7027 (3) | 0.6971 (2) | 0.8025 (3) | 0.0602 (8) | |
H66 | 0.6311 | 0.6787 | 0.7853 | 0.072* | |
C51 | 0.6787 (3) | 1.0353 (2) | 0.6125 (2) | 0.0498 (7) | |
C5 | 0.5671 (2) | 0.9530 (2) | 0.6827 (2) | 0.0448 (6) | |
H5 | 0.5895 | 0.8865 | 0.6511 | 0.054* | |
C24 | 0.4355 (3) | 0.5128 (2) | 0.7483 (3) | 0.0620 (8) | |
C31 | 0.2018 (3) | 1.0448 (2) | 0.8011 (2) | 0.0472 (6) | |
C32 | 0.0662 (3) | 1.0545 (3) | 0.8072 (3) | 0.0666 (8) | |
H32 | 0.0360 | 1.0044 | 0.7813 | 0.080* | |
C23 | 0.4024 (3) | 0.5088 (2) | 0.8649 (3) | 0.0644 (8) | |
H23 | 0.4032 | 0.4346 | 0.9246 | 0.077* | |
C65 | 0.8191 (3) | 0.6177 (3) | 0.8052 (3) | 0.0639 (8) | |
H65 | 0.8230 | 0.5461 | 0.7919 | 0.077* | |
C64 | 0.9296 (3) | 0.6423 (3) | 0.8271 (2) | 0.0572 (7) | |
C25 | 0.4312 (3) | 0.6247 (2) | 0.6631 (3) | 0.0603 (7) | |
H25 | 0.4521 | 0.6300 | 0.5844 | 0.072* | |
C22 | 0.3686 (3) | 0.6122 (2) | 0.8934 (2) | 0.0568 (7) | |
H22 | 0.3469 | 0.6068 | 0.9722 | 0.068* | |
C56 | 0.6816 (3) | 1.1356 (3) | 0.6395 (3) | 0.0723 (9) | |
H56 | 0.6144 | 1.1517 | 0.7026 | 0.087* | |
C36 | 0.2422 (3) | 1.1207 (3) | 0.8407 (2) | 0.0644 (8) | |
H36 | 0.3331 | 1.1151 | 0.8387 | 0.077* | |
C4 | 0.4287 (3) | 1.0130 (2) | 0.6639 (2) | 0.0486 (6) | |
C63 | 0.9179 (3) | 0.7476 (3) | 0.8488 (3) | 0.0668 (8) | |
H63 | 0.9906 | 0.7664 | 0.8643 | 0.080* | |
C26 | 0.3969 (3) | 0.7287 (2) | 0.6912 (2) | 0.0500 (7) | |
H26 | 0.3944 | 0.8027 | 0.6315 | 0.060* | |
C52 | 0.7803 (3) | 1.0131 (3) | 0.5189 (2) | 0.0569 (7) | |
H52 | 0.7816 | 0.9454 | 0.4998 | 0.068* | |
C33 | −0.0264 (3) | 1.1380 (3) | 0.8515 (3) | 0.0837 (10) | |
H33 | −0.1180 | 1.1426 | 0.8564 | 0.100* | |
C62 | 0.8015 (3) | 0.8267 (3) | 0.8485 (2) | 0.0601 (7) | |
H62 | 0.7971 | 0.8970 | 0.8643 | 0.072* | |
C27 | 0.4732 (4) | 0.3993 (3) | 0.7156 (3) | 0.0979 (12) | |
H27A | 0.3920 | 0.3685 | 0.7225 | 0.147* | |
H27B | 0.5220 | 0.3402 | 0.7680 | 0.147* | |
H27C | 0.5296 | 0.4174 | 0.6357 | 0.147* | |
C67 | 1.0581 (3) | 0.5573 (3) | 0.8253 (3) | 0.0866 (10) | |
H67A | 1.1344 | 0.6017 | 0.8046 | 0.130* | |
H67B | 1.0713 | 0.5189 | 0.7681 | 0.130* | |
H67C | 1.0505 | 0.4974 | 0.9021 | 0.130* | |
C35 | 0.1509 (4) | 1.2042 (3) | 0.8827 (3) | 0.0787 (9) | |
H35 | 0.1807 | 1.2551 | 0.9079 | 0.094* | |
C54 | 0.8809 (3) | 1.1902 (3) | 0.4807 (3) | 0.0815 (10) | |
H54 | 0.9480 | 1.2425 | 0.4357 | 0.098* | |
C53 | 0.8802 (3) | 1.0910 (3) | 0.4533 (3) | 0.0744 (9) | |
H53 | 0.9475 | 1.0756 | 0.3899 | 0.089* | |
C34 | 0.0168 (4) | 1.2130 (3) | 0.8879 (3) | 0.0824 (10) | |
H34 | −0.0447 | 1.2701 | 0.9161 | 0.099* | |
C55 | 0.7824 (4) | 1.2126 (3) | 0.5746 (3) | 0.0879 (10) | |
H55 | 0.7834 | 1.2793 | 0.5945 | 0.106* | |
N2 | 0.4019 (3) | 0.8323 (2) | 1.00562 (19) | 0.0616 (6) | |
N1 | 0.4387 (2) | 0.84879 (17) | 0.89004 (16) | 0.0450 (5) | |
O1 | 0.41972 (19) | 1.10153 (17) | 0.57916 (16) | 0.0691 (6) | |
O2 | 0.4901 (2) | 0.85139 (19) | 1.04107 (17) | 0.0755 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0387 (14) | 0.0510 (15) | 0.0411 (13) | −0.0047 (12) | −0.0056 (12) | −0.0083 (12) |
C61 | 0.0424 (15) | 0.0484 (15) | 0.0371 (13) | −0.0020 (12) | −0.0100 (11) | −0.0072 (11) |
C6 | 0.0449 (15) | 0.0452 (14) | 0.0415 (14) | −0.0028 (12) | −0.0103 (12) | −0.0103 (11) |
C3 | 0.0399 (14) | 0.0465 (14) | 0.0435 (14) | −0.0011 (11) | −0.0127 (12) | −0.0114 (11) |
C21 | 0.0387 (14) | 0.0486 (15) | 0.0455 (15) | −0.0015 (12) | −0.0105 (12) | −0.0080 (12) |
C66 | 0.0457 (17) | 0.0588 (18) | 0.0752 (19) | 0.0012 (14) | −0.0188 (15) | −0.0224 (15) |
C51 | 0.0453 (16) | 0.0479 (15) | 0.0440 (14) | −0.0013 (12) | −0.0092 (12) | −0.0061 (12) |
C5 | 0.0431 (15) | 0.0431 (14) | 0.0399 (13) | 0.0008 (11) | −0.0056 (11) | −0.0120 (11) |
C24 | 0.0610 (19) | 0.0468 (16) | 0.075 (2) | −0.0015 (13) | −0.0198 (16) | −0.0177 (15) |
C31 | 0.0440 (16) | 0.0454 (14) | 0.0446 (14) | −0.0039 (12) | −0.0080 (12) | −0.0105 (12) |
C32 | 0.0501 (19) | 0.0681 (19) | 0.077 (2) | −0.0020 (15) | −0.0108 (15) | −0.0268 (16) |
C23 | 0.068 (2) | 0.0425 (16) | 0.071 (2) | −0.0107 (14) | −0.0210 (16) | −0.0006 (14) |
C65 | 0.0582 (19) | 0.0508 (16) | 0.077 (2) | 0.0027 (14) | −0.0202 (16) | −0.0177 (15) |
C64 | 0.0435 (16) | 0.0621 (18) | 0.0502 (16) | 0.0035 (14) | −0.0142 (13) | −0.0048 (13) |
C25 | 0.0578 (18) | 0.0618 (18) | 0.0600 (17) | 0.0024 (14) | −0.0154 (14) | −0.0237 (15) |
C22 | 0.0551 (17) | 0.0528 (17) | 0.0516 (16) | −0.0049 (13) | −0.0150 (13) | −0.0053 (13) |
C56 | 0.068 (2) | 0.0542 (18) | 0.079 (2) | −0.0130 (16) | 0.0000 (17) | −0.0185 (16) |
C36 | 0.0562 (18) | 0.0692 (19) | 0.0662 (18) | −0.0017 (15) | −0.0119 (15) | −0.0272 (16) |
C4 | 0.0496 (16) | 0.0454 (15) | 0.0394 (14) | −0.0009 (12) | −0.0088 (12) | −0.0066 (12) |
C63 | 0.0495 (18) | 0.079 (2) | 0.075 (2) | −0.0025 (16) | −0.0281 (15) | −0.0212 (17) |
C26 | 0.0491 (16) | 0.0425 (15) | 0.0509 (16) | −0.0034 (12) | −0.0140 (13) | −0.0077 (12) |
C52 | 0.0440 (16) | 0.0737 (19) | 0.0452 (15) | −0.0024 (14) | −0.0127 (13) | −0.0125 (14) |
C33 | 0.0494 (19) | 0.088 (2) | 0.096 (3) | 0.0138 (18) | −0.0053 (18) | −0.034 (2) |
C62 | 0.0556 (19) | 0.0634 (18) | 0.0646 (18) | −0.0008 (15) | −0.0221 (15) | −0.0225 (15) |
C27 | 0.121 (3) | 0.058 (2) | 0.116 (3) | −0.004 (2) | −0.030 (3) | −0.034 (2) |
C67 | 0.054 (2) | 0.087 (2) | 0.101 (2) | 0.0120 (17) | −0.0250 (18) | −0.018 (2) |
C35 | 0.088 (3) | 0.075 (2) | 0.072 (2) | 0.0036 (19) | −0.0092 (19) | −0.0392 (18) |
C54 | 0.062 (2) | 0.086 (3) | 0.074 (2) | −0.0299 (19) | −0.0129 (18) | 0.0056 (19) |
C53 | 0.0451 (18) | 0.105 (3) | 0.0545 (18) | −0.0148 (18) | −0.0066 (15) | −0.0082 (18) |
C34 | 0.079 (3) | 0.066 (2) | 0.076 (2) | 0.0119 (19) | 0.0081 (19) | −0.0302 (18) |
C55 | 0.087 (3) | 0.062 (2) | 0.103 (3) | −0.0272 (19) | −0.015 (2) | −0.0135 (19) |
N2 | 0.0650 (16) | 0.0742 (16) | 0.0396 (13) | 0.0009 (12) | −0.0139 (12) | −0.0168 (11) |
N1 | 0.0431 (13) | 0.0513 (12) | 0.0335 (11) | −0.0010 (10) | −0.0079 (9) | −0.0102 (9) |
O1 | 0.0572 (13) | 0.0674 (13) | 0.0526 (11) | 0.0023 (10) | −0.0130 (9) | 0.0071 (10) |
O2 | 0.0842 (16) | 0.0939 (16) | 0.0492 (11) | −0.0079 (12) | −0.0223 (11) | −0.0216 (11) |
Geometric parameters (Å, º) top
C2—N1 | 1.469 (3) | C64—C67 | 1.509 (4) |
C2—C21 | 1.516 (3) | C25—C26 | 1.375 (4) |
C2—C3 | 1.546 (3) | C25—H25 | 0.9300 |
C2—H2 | 0.9800 | C22—H22 | 0.9300 |
C61—C66 | 1.384 (3) | C56—C55 | 1.383 (4) |
C61—C62 | 1.387 (4) | C56—H56 | 0.9300 |
C61—C6 | 1.513 (3) | C36—C35 | 1.372 (4) |
C6—N1 | 1.474 (3) | C36—H36 | 0.9300 |
C6—C5 | 1.545 (3) | C4—O1 | 1.210 (3) |
C6—H6 | 0.9800 | C63—C62 | 1.380 (4) |
C3—C31 | 1.512 (3) | C63—H63 | 0.9300 |
C3—C4 | 1.514 (3) | C26—H26 | 0.9300 |
C3—H3 | 0.9800 | C52—C53 | 1.382 (4) |
C21—C26 | 1.381 (3) | C52—H52 | 0.9300 |
C21—C22 | 1.387 (3) | C33—C34 | 1.360 (5) |
C66—C65 | 1.383 (4) | C33—H33 | 0.9300 |
C66—H66 | 0.9300 | C62—H62 | 0.9300 |
C51—C52 | 1.382 (4) | C27—H27A | 0.9600 |
C51—C56 | 1.383 (4) | C27—H27B | 0.9600 |
C51—C5 | 1.507 (3) | C27—H27C | 0.9600 |
C5—C4 | 1.526 (3) | C67—H67A | 0.9600 |
C5—H5 | 0.9800 | C67—H67B | 0.9600 |
C24—C25 | 1.377 (4) | C67—H67C | 0.9600 |
C24—C23 | 1.389 (4) | C35—C34 | 1.363 (5) |
C24—C27 | 1.514 (4) | C35—H35 | 0.9300 |
C31—C32 | 1.375 (4) | C54—C53 | 1.366 (4) |
C31—C36 | 1.380 (4) | C54—C55 | 1.371 (5) |
C32—C33 | 1.390 (4) | C54—H54 | 0.9300 |
C32—H32 | 0.9300 | C53—H53 | 0.9300 |
C23—C22 | 1.371 (4) | C34—H34 | 0.9300 |
C23—H23 | 0.9300 | C55—H55 | 0.9300 |
C65—C64 | 1.380 (4) | N2—O2 | 1.239 (3) |
C65—H65 | 0.9300 | N2—N1 | 1.335 (3) |
C64—C63 | 1.371 (4) | | |
| | | |
N1—C2—C21 | 111.43 (19) | C23—C22—H22 | 119.3 |
N1—C2—C3 | 108.96 (19) | C21—C22—H22 | 119.3 |
C21—C2—C3 | 116.0 (2) | C55—C56—C51 | 121.3 (3) |
N1—C2—H2 | 106.6 | C55—C56—H56 | 119.3 |
C21—C2—H2 | 106.6 | C51—C56—H56 | 119.3 |
C3—C2—H2 | 106.6 | C35—C36—C31 | 121.3 (3) |
C66—C61—C62 | 116.9 (2) | C35—C36—H36 | 119.4 |
C66—C61—C6 | 122.4 (2) | C31—C36—H36 | 119.4 |
C62—C61—C6 | 120.5 (2) | O1—C4—C3 | 120.0 (2) |
N1—C6—C61 | 113.52 (19) | O1—C4—C5 | 121.1 (2) |
N1—C6—C5 | 111.25 (19) | C3—C4—C5 | 118.7 (2) |
C61—C6—C5 | 110.10 (19) | C64—C63—C62 | 121.9 (3) |
N1—C6—H6 | 107.2 | C64—C63—H63 | 119.1 |
C61—C6—H6 | 107.2 | C62—C63—H63 | 119.1 |
C5—C6—H6 | 107.2 | C25—C26—C21 | 120.8 (2) |
C31—C3—C4 | 111.2 (2) | C25—C26—H26 | 119.6 |
C31—C3—C2 | 113.5 (2) | C21—C26—H26 | 119.6 |
C4—C3—C2 | 113.51 (19) | C51—C52—C53 | 120.5 (3) |
C31—C3—H3 | 106.0 | C51—C52—H52 | 119.8 |
C4—C3—H3 | 106.0 | C53—C52—H52 | 119.8 |
C2—C3—H3 | 106.0 | C34—C33—C32 | 120.1 (3) |
C26—C21—C22 | 117.6 (2) | C34—C33—H33 | 119.9 |
C26—C21—C2 | 123.9 (2) | C32—C33—H33 | 119.9 |
C22—C21—C2 | 118.5 (2) | C63—C62—C61 | 121.2 (3) |
C65—C66—C61 | 121.2 (3) | C63—C62—H62 | 119.4 |
C65—C66—H66 | 119.4 | C61—C62—H62 | 119.4 |
C61—C66—H66 | 119.4 | C24—C27—H27A | 109.5 |
C52—C51—C56 | 118.1 (3) | C24—C27—H27B | 109.5 |
C52—C51—C5 | 121.0 (2) | H27A—C27—H27B | 109.5 |
C56—C51—C5 | 120.8 (2) | C24—C27—H27C | 109.5 |
C51—C5—C4 | 112.48 (19) | H27A—C27—H27C | 109.5 |
C51—C5—C6 | 110.7 (2) | H27B—C27—H27C | 109.5 |
C4—C5—C6 | 114.74 (19) | C64—C67—H67A | 109.5 |
C51—C5—H5 | 106.1 | C64—C67—H67B | 109.5 |
C4—C5—H5 | 106.1 | H67A—C67—H67B | 109.5 |
C6—C5—H5 | 106.1 | C64—C67—H67C | 109.5 |
C25—C24—C23 | 117.2 (3) | H67A—C67—H67C | 109.5 |
C25—C24—C27 | 121.1 (3) | H67B—C67—H67C | 109.5 |
C23—C24—C27 | 121.7 (3) | C34—C35—C36 | 120.5 (3) |
C32—C31—C36 | 117.6 (3) | C34—C35—H35 | 119.8 |
C32—C31—C3 | 120.3 (2) | C36—C35—H35 | 119.8 |
C36—C31—C3 | 122.1 (2) | C53—C54—C55 | 119.8 (3) |
C31—C32—C33 | 120.9 (3) | C53—C54—H54 | 120.1 |
C31—C32—H32 | 119.5 | C55—C54—H54 | 120.1 |
C33—C32—H32 | 119.5 | C54—C53—C52 | 120.6 (3) |
C22—C23—C24 | 121.2 (3) | C54—C53—H53 | 119.7 |
C22—C23—H23 | 119.4 | C52—C53—H53 | 119.7 |
C24—C23—H23 | 119.4 | C33—C34—C35 | 119.6 (3) |
C64—C65—C66 | 121.6 (3) | C33—C34—H34 | 120.2 |
C64—C65—H65 | 119.2 | C35—C34—H34 | 120.2 |
C66—C65—H65 | 119.2 | C54—C55—C56 | 119.6 (3) |
C63—C64—C65 | 117.1 (3) | C54—C55—H55 | 120.2 |
C63—C64—C67 | 121.6 (3) | C56—C55—H55 | 120.2 |
C65—C64—C67 | 121.2 (3) | O2—N2—N1 | 114.2 (2) |
C26—C25—C24 | 121.9 (3) | N2—N1—C2 | 115.1 (2) |
C26—C25—H25 | 119.1 | N2—N1—C6 | 120.7 (2) |
C24—C25—H25 | 119.1 | C2—N1—C6 | 123.50 (18) |
C23—C22—C21 | 121.3 (3) | | |
| | | |
C66—C61—C6—N1 | 58.6 (3) | C5—C51—C56—C55 | −179.0 (3) |
C62—C61—C6—N1 | −127.2 (2) | C32—C31—C36—C35 | −1.0 (4) |
C66—C61—C6—C5 | −66.9 (3) | C3—C31—C36—C35 | 177.4 (3) |
C62—C61—C6—C5 | 107.3 (3) | C31—C3—C4—O1 | −57.5 (3) |
N1—C2—C3—C31 | −84.1 (2) | C2—C3—C4—O1 | 173.2 (2) |
C21—C2—C3—C31 | 149.3 (2) | C31—C3—C4—C5 | 126.0 (2) |
N1—C2—C3—C4 | 44.1 (3) | C2—C3—C4—C5 | −3.4 (3) |
C21—C2—C3—C4 | −82.5 (3) | C51—C5—C4—O1 | 18.8 (3) |
N1—C2—C21—C26 | −112.3 (3) | C6—C5—C4—O1 | 146.5 (2) |
C3—C2—C21—C26 | 13.1 (3) | C51—C5—C4—C3 | −164.7 (2) |
N1—C2—C21—C22 | 66.7 (3) | C6—C5—C4—C3 | −37.0 (3) |
C3—C2—C21—C22 | −167.9 (2) | C65—C64—C63—C62 | −0.3 (4) |
C62—C61—C66—C65 | 0.9 (4) | C67—C64—C63—C62 | 178.8 (3) |
C6—C61—C66—C65 | 175.2 (2) | C24—C25—C26—C21 | 0.5 (4) |
C52—C51—C5—C4 | −111.5 (3) | C22—C21—C26—C25 | −1.2 (4) |
C56—C51—C5—C4 | 68.0 (3) | C2—C21—C26—C25 | 177.8 (2) |
C52—C51—C5—C6 | 118.7 (2) | C56—C51—C52—C53 | −1.1 (4) |
C56—C51—C5—C6 | −61.8 (3) | C5—C51—C52—C53 | 178.3 (2) |
N1—C6—C5—C51 | 161.4 (2) | C31—C32—C33—C34 | 1.1 (5) |
C61—C6—C5—C51 | −71.9 (3) | C64—C63—C62—C61 | −0.5 (4) |
N1—C6—C5—C4 | 32.8 (3) | C66—C61—C62—C63 | 0.3 (4) |
C61—C6—C5—C4 | 159.5 (2) | C6—C61—C62—C63 | −174.2 (2) |
C4—C3—C31—C32 | 133.9 (3) | C31—C36—C35—C34 | 0.9 (5) |
C2—C3—C31—C32 | −96.7 (3) | C55—C54—C53—C52 | 0.5 (5) |
C4—C3—C31—C36 | −44.6 (3) | C51—C52—C53—C54 | 0.7 (4) |
C2—C3—C31—C36 | 84.8 (3) | C32—C33—C34—C35 | −1.3 (5) |
C36—C31—C32—C33 | 0.1 (4) | C36—C35—C34—C33 | 0.3 (5) |
C3—C31—C32—C33 | −178.4 (3) | C53—C54—C55—C56 | −1.2 (5) |
C25—C24—C23—C22 | −0.8 (4) | C51—C56—C55—C54 | 0.7 (5) |
C27—C24—C23—C22 | 179.9 (3) | O2—N2—N1—C2 | −175.7 (2) |
C61—C66—C65—C64 | −1.8 (4) | O2—N2—N1—C6 | −5.0 (3) |
C66—C65—C64—C63 | 1.5 (4) | C21—C2—N1—N2 | −111.8 (2) |
C66—C65—C64—C67 | −177.7 (3) | C3—C2—N1—N2 | 119.0 (2) |
C23—C24—C25—C26 | 0.6 (4) | C21—C2—N1—C6 | 77.9 (3) |
C27—C24—C25—C26 | 179.9 (3) | C3—C2—N1—C6 | −51.4 (3) |
C24—C23—C22—C21 | 0.0 (4) | C61—C6—N1—N2 | 77.1 (3) |
C26—C21—C22—C23 | 1.0 (4) | C5—C6—N1—N2 | −158.0 (2) |
C2—C21—C22—C23 | −178.1 (2) | C61—C6—N1—C2 | −113.0 (2) |
C52—C51—C56—C55 | 0.4 (4) | C5—C6—N1—C2 | 11.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C66—H66···Cg | 0.93 | 2.69 | 3.613 (4) | 169 |
C67—H67A···Cgi | 0.96 | 2.72 | 3.608 (4) | 153 |
Symmetry code: (i) x+1, y, z. |