The asymmetric unit of the title compound, C
20H
21NO
3, contains two crystallographically independent molecules, approximately related by a local twofold axis. These two molecules differ from each other in the orientation of the ethyl group. In both molecules, the piperidone ring adopts a slightly distorted chair conformation, with the phenyl rings and carbethoxy group attached equatorially. The crystal packing is characterized by C—H
π and C—H
O interactions.
Supporting information
CCDC reference: 226963
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.068
- wR factor = 0.183
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.86 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.76 Ratio
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.774
Test value = 0.600
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.77 e/A 3
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.58 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor N1A - H1A ... ?
PLAT420_ALERT_2_C D-H Without Acceptor N1B - H1B ... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 14
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
Ethyl 4-oxo-2,6-diphenyl-4-piperidine-3-carboxylate
top
Crystal data top
C20H21NO3 | F(000) = 1376 |
Mr = 323.39 | Dx = 1.237 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 20.261 (4) Å | θ = 2.5–23° |
b = 7.5561 (15) Å | µ = 0.08 mm−1 |
c = 23.034 (5) Å | T = 150 K |
β = 100.11 (3)° | Needles, colourless |
V = 3471.6 (12) Å3 | 0.44 × 0.30 × 0.24 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD diffractometer | 8517 independent reflections |
Radiation source: fine-focus sealed tube | 6735 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 8 pixels mm-1 | θmax = 28.3°, θmin = 2.0° |
ω scans | h = −26→26 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −10→9 |
Tmin = 0.97, Tmax = 0.98 | l = −29→30 |
31988 measured reflections | |
Refinement top
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.183 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0659P)2 + 3.4759P] where P = (Fo2 + 2Fc2)/3 |
8517 reflections | (Δ/σ)max = 0.001 |
463 parameters | Δρmax = 0.77 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−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 | |
O1A | 0.21725 (7) | 0.2643 (2) | 0.50455 (7) | 0.0379 (4) | |
O2A | 0.18143 (7) | 0.0720 (2) | 0.38108 (7) | 0.0369 (4) | |
O3A | 0.16967 (7) | 0.3632 (2) | 0.36209 (7) | 0.0379 (4) | |
N1A | 0.39021 (8) | 0.1854 (2) | 0.44272 (7) | 0.0221 (3) | |
H1A | 0.4221 (13) | 0.120 (3) | 0.4308 (11) | 0.033 (6)* | |
C2A | 0.32651 (9) | 0.1455 (2) | 0.40369 (8) | 0.0216 (3) | |
H2A | 0.3141 | 0.0221 | 0.4092 | 0.026* | |
C3A | 0.27153 (9) | 0.2702 (2) | 0.41998 (8) | 0.0223 (4) | |
H3A | 0.2817 | 0.3914 | 0.4093 | 0.027* | |
C4A | 0.26969 (9) | 0.2655 (3) | 0.48597 (8) | 0.0251 (4) | |
C5A | 0.33729 (9) | 0.2730 (3) | 0.52525 (8) | 0.0252 (4) | |
H5A1 | 0.3324 | 0.2422 | 0.5652 | 0.030* | |
H5A2 | 0.3542 | 0.3932 | 0.5259 | 0.030* | |
C6A | 0.38857 (9) | 0.1471 (2) | 0.50492 (7) | 0.0205 (3) | |
H6A | 0.3744 | 0.0244 | 0.5088 | 0.025* | |
C7A | 0.20290 (9) | 0.2210 (3) | 0.38592 (8) | 0.0266 (4) | |
C8A | 0.10266 (12) | 0.3325 (4) | 0.32770 (13) | 0.0522 (7) | |
H8A1 | 0.0997 | 0.2128 | 0.3122 | 0.063* | |
H8A2 | 0.0945 | 0.4139 | 0.2947 | 0.063* | |
C9A | 0.05198 (14) | 0.3584 (5) | 0.36525 (19) | 0.0790 (12) | |
H9A1 | 0.0634 | 0.2885 | 0.4004 | 0.119* | |
H9A2 | 0.0089 | 0.3226 | 0.3442 | 0.119* | |
H9A3 | 0.0505 | 0.4811 | 0.3757 | 0.119* | |
C61A | 0.45676 (9) | 0.1756 (2) | 0.54343 (8) | 0.0212 (3) | |
C62A | 0.46760 (10) | 0.1118 (3) | 0.60133 (8) | 0.0277 (4) | |
H62A | 0.4341 | 0.0494 | 0.6150 | 0.033* | |
C63A | 0.52865 (11) | 0.1419 (3) | 0.63864 (9) | 0.0332 (5) | |
H63A | 0.5362 | 0.0943 | 0.6805 | 0.040* | |
C64A | 0.57893 (10) | 0.2361 (3) | 0.61894 (10) | 0.0338 (5) | |
H64A | 0.6220 | 0.2583 | 0.6457 | 0.041* | |
C65A | 0.56878 (10) | 0.2992 (3) | 0.56157 (10) | 0.0338 (5) | |
H65A | 0.6028 | 0.3612 | 0.5480 | 0.041* | |
C66A | 0.50745 (10) | 0.2699 (3) | 0.52389 (9) | 0.0279 (4) | |
H66A | 0.5004 | 0.3161 | 0.4837 | 0.034* | |
O1B | 0.27828 (7) | 0.7924 (2) | −0.02208 (7) | 0.0389 (4) | |
O2B | 0.32295 (7) | 0.5959 (2) | 0.10127 (7) | 0.0356 (4) | |
O3B | 0.33800 (7) | 0.8913 (2) | 0.11058 (7) | 0.0375 (4) | |
N1B | 0.11295 (7) | 0.6945 (2) | 0.04870 (7) | 0.0216 (3) | |
H1B | 0.0810 (12) | 0.621 (3) | 0.0621 (10) | 0.027 (6)* | |
C2B | 0.17907 (9) | 0.6589 (2) | 0.08456 (8) | 0.0215 (3) | |
H2B | 0.1927 | 0.5375 | 0.0773 | 0.026* | |
C21B | 0.17636 (9) | 0.6812 (3) | 0.14961 (8) | 0.0241 (4) | |
C22B | 0.21395 (11) | 0.5709 (3) | 0.19125 (9) | 0.0334 (5) | |
H22B | 0.2413 | 0.477 | 0.1784 | 0.040* | |
C23B | 0.21295 (13) | 0.5927 (4) | 0.25108 (10) | 0.0439 (6) | |
H23B | 0.2385 | 0.518 | 0.2786 | 0.053* | |
C25B | 0.13694 (13) | 0.8343 (4) | 0.22887 (10) | 0.0408 (5) | |
H25B | 0.1113 | 0.921 | 0.2413 | 0.049* | |
C24B | 0.17442 (13) | 0.7240 (4) | 0.26981 (10) | 0.0449 (6) | |
H24B | 0.17360 | 0.7390 | 0.3120 | 0.054* | |
C26B | 0.13783 (10) | 0.8143 (3) | 0.16881 (9) | 0.0302 (4) | |
H26B | 0.1114 | 0.894 | 0.1402 | 0.036* | |
C3B | 0.23051 (9) | 0.7907 (2) | 0.06618 (8) | 0.0222 (4) | |
H3B | 0.2200 | 0.9100 | 0.0785 | 0.027* | |
C4B | 0.22792 (9) | 0.7910 (3) | −0.00057 (8) | 0.0253 (4) | |
C5B | 0.15838 (9) | 0.7953 (3) | −0.03677 (8) | 0.0260 (4) | |
H5B1 | 0.1608 | 0.7691 | −0.0776 | 0.031* | |
H5B2 | 0.1399 | 0.9133 | −0.0353 | 0.031* | |
C6B | 0.11151 (9) | 0.6608 (2) | −0.01433 (8) | 0.0217 (3) | |
H6B | 0.1278 | 0.5407 | −0.0194 | 0.026* | |
C61B | 0.04106 (9) | 0.6804 (2) | −0.04962 (8) | 0.0230 (4) | |
C62B | 0.02757 (11) | 0.6142 (3) | −0.10716 (9) | 0.0326 (4) | |
H62B | 0.0615 | 0.5550 | −0.1230 | 0.039* | |
C63B | −0.03609 (12) | 0.6355 (3) | −0.14137 (10) | 0.0393 (5) | |
H63B | −0.0461 | 0.5845 | −0.1840 | 0.047* | |
C64B | −0.08570 (10) | 0.7235 (3) | −0.11903 (11) | 0.0364 (5) | |
H64B | −0.1314 | 0.7406 | −0.1443 | 0.044* | |
C65B | −0.07295 (11) | 0.7884 (3) | −0.06216 (11) | 0.0361 (5) | |
H65B | −0.1081 | 0.8487 | −0.0462 | 0.043* | |
C66B | −0.00948 (10) | 0.7674 (3) | −0.02751 (9) | 0.0297 (4) | |
H66B | −0.0007 | 0.8142 | 0.0123 | 0.036* | |
C7B | 0.30141 (9) | 0.7448 (3) | 0.09533 (8) | 0.0261 (4) | |
C8B | 0.41108 (12) | 0.8637 (4) | 0.12857 (12) | 0.0482 (6) | |
H8B1 | 0.4346 | 0.9732 | 0.1240 | 0.058* | |
H8B2 | 0.4262 | 0.7749 | 0.1034 | 0.058* | |
C9B | 0.42662 (15) | 0.8052 (5) | 0.19077 (13) | 0.0619 (8) | |
H9B1 | 0.4135 | 0.8956 | 0.2157 | 0.093* | |
H9B2 | 0.4739 | 0.7838 | 0.2015 | 0.093* | |
H9B3 | 0.4025 | 0.6982 | 0.1954 | 0.093* | |
C21A | 0.33308 (9) | 0.1748 (3) | 0.33992 (8) | 0.0246 (4) | |
C22A | 0.29630 (11) | 0.0710 (3) | 0.29572 (9) | 0.0357 (5) | |
H22A | 0.2674 | −0.025 | 0.3063 | 0.043* | |
C23A | 0.29985 (13) | 0.1014 (4) | 0.23661 (10) | 0.0473 (6) | |
H23A | 0.2729 | 0.028 | 0.2056 | 0.057* | |
C24A | 0.34078 (14) | 0.2328 (4) | 0.22134 (10) | 0.0488 (7) | |
H24A | 0.34367 | 0.2542 | 0.1775 | 0.059* | |
C25A | 0.37794 (13) | 0.3358 (4) | 0.26481 (10) | 0.0445 (6) | |
H25A | 0.4066 | 0.428 | 0.2542 | 0.053* | |
C26A | 0.37407 (11) | 0.3075 (3) | 0.32414 (9) | 0.0324 (4) | |
H26A | 0.3988 | 0.377 | 0.3529 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0252 (7) | 0.0568 (10) | 0.0343 (8) | 0.0056 (7) | 0.0120 (6) | 0.0044 (7) |
O2A | 0.0267 (7) | 0.0337 (8) | 0.0492 (9) | −0.0057 (6) | 0.0035 (6) | 0.0016 (7) |
O3A | 0.0269 (7) | 0.0375 (9) | 0.0437 (9) | −0.0016 (6) | −0.0089 (6) | 0.0081 (7) |
N1A | 0.0194 (7) | 0.0277 (8) | 0.0197 (7) | 0.0003 (6) | 0.0048 (6) | 0.0002 (6) |
C2A | 0.0200 (8) | 0.0228 (9) | 0.0217 (8) | −0.0009 (6) | 0.0031 (6) | 0.0000 (6) |
C3A | 0.0192 (8) | 0.0238 (9) | 0.0238 (8) | −0.0004 (7) | 0.0034 (6) | 0.0018 (7) |
C4A | 0.0238 (8) | 0.0256 (9) | 0.0270 (9) | 0.0036 (7) | 0.0074 (7) | 0.0010 (7) |
C5A | 0.0242 (9) | 0.0305 (10) | 0.0214 (8) | 0.0030 (7) | 0.0057 (7) | −0.0015 (7) |
C6A | 0.0203 (8) | 0.0222 (8) | 0.0193 (8) | −0.0003 (6) | 0.0041 (6) | 0.0000 (6) |
C7A | 0.0216 (8) | 0.0312 (10) | 0.0275 (9) | −0.0008 (7) | 0.0058 (7) | 0.0027 (7) |
C8A | 0.0349 (12) | 0.0525 (16) | 0.0605 (17) | −0.0033 (11) | −0.0153 (11) | 0.0103 (13) |
C9A | 0.0321 (13) | 0.078 (2) | 0.123 (3) | −0.0002 (14) | 0.0011 (16) | −0.039 (2) |
C61A | 0.0200 (8) | 0.0194 (8) | 0.0240 (8) | 0.0007 (6) | 0.0031 (6) | −0.0028 (6) |
C62A | 0.0266 (9) | 0.0315 (10) | 0.0244 (9) | −0.0038 (8) | 0.0026 (7) | 0.0014 (7) |
C63A | 0.0352 (11) | 0.0344 (11) | 0.0265 (10) | 0.0009 (9) | −0.0039 (8) | −0.0004 (8) |
C64A | 0.0270 (9) | 0.0300 (11) | 0.0405 (11) | 0.0004 (8) | −0.0049 (8) | −0.0061 (9) |
C65A | 0.0235 (9) | 0.0333 (11) | 0.0438 (12) | −0.0068 (8) | 0.0039 (8) | −0.0007 (9) |
C66A | 0.0249 (9) | 0.0296 (10) | 0.0292 (9) | −0.0020 (7) | 0.0045 (7) | 0.0014 (8) |
O1B | 0.0263 (7) | 0.0597 (11) | 0.0332 (8) | −0.0070 (7) | 0.0120 (6) | −0.0046 (7) |
O2B | 0.0231 (7) | 0.0312 (8) | 0.0514 (9) | 0.0038 (6) | 0.0033 (6) | −0.0046 (7) |
O3B | 0.0285 (7) | 0.0298 (8) | 0.0485 (9) | −0.0013 (6) | −0.0091 (6) | −0.0011 (7) |
N1B | 0.0183 (7) | 0.0268 (8) | 0.0200 (7) | −0.0006 (6) | 0.0038 (5) | 0.0012 (6) |
C2B | 0.0197 (8) | 0.0213 (8) | 0.0229 (8) | 0.0014 (6) | 0.0027 (6) | 0.0011 (6) |
C21B | 0.0236 (8) | 0.0254 (9) | 0.0230 (8) | −0.0036 (7) | 0.0028 (7) | 0.0008 (7) |
C22B | 0.0292 (10) | 0.0386 (12) | 0.0306 (10) | −0.0014 (9) | 0.0006 (8) | 0.0082 (9) |
C23B | 0.0437 (12) | 0.0587 (16) | 0.0267 (10) | −0.0088 (11) | −0.0013 (9) | 0.0137 (10) |
C25B | 0.0454 (13) | 0.0475 (14) | 0.0322 (11) | −0.0079 (11) | 0.0141 (10) | −0.0109 (10) |
C24B | 0.0526 (14) | 0.0594 (16) | 0.0229 (10) | −0.0187 (12) | 0.0074 (9) | −0.0002 (10) |
C26B | 0.0322 (10) | 0.0309 (10) | 0.0278 (10) | −0.0001 (8) | 0.0066 (8) | −0.0005 (8) |
C3B | 0.0199 (8) | 0.0226 (9) | 0.0239 (8) | −0.0003 (7) | 0.0032 (6) | −0.0005 (7) |
C4B | 0.0225 (8) | 0.0268 (9) | 0.0273 (9) | −0.0029 (7) | 0.0059 (7) | −0.0004 (7) |
C5B | 0.0243 (9) | 0.0326 (10) | 0.0218 (8) | −0.0021 (8) | 0.0058 (7) | 0.0019 (7) |
C6B | 0.0202 (8) | 0.0234 (9) | 0.0217 (8) | 0.0016 (7) | 0.0039 (6) | −0.0008 (6) |
C61B | 0.0225 (8) | 0.0213 (9) | 0.0246 (9) | −0.0005 (7) | 0.0026 (7) | 0.0009 (7) |
C62B | 0.0315 (10) | 0.0356 (11) | 0.0291 (10) | 0.0036 (9) | 0.0005 (8) | −0.0064 (8) |
C63B | 0.0391 (12) | 0.0386 (12) | 0.0351 (11) | 0.0002 (10) | −0.0076 (9) | −0.0053 (9) |
C64B | 0.0254 (9) | 0.0323 (11) | 0.0462 (12) | −0.0011 (8) | −0.0082 (9) | 0.0050 (9) |
C65B | 0.0248 (9) | 0.0374 (12) | 0.0455 (12) | 0.0041 (9) | 0.0047 (9) | 0.0018 (9) |
C66B | 0.0243 (9) | 0.0335 (11) | 0.0316 (10) | 0.0025 (8) | 0.0056 (8) | −0.0003 (8) |
C7B | 0.0205 (8) | 0.0305 (10) | 0.0272 (9) | −0.0001 (7) | 0.0036 (7) | −0.0024 (7) |
C8B | 0.0337 (12) | 0.0439 (14) | 0.0615 (16) | −0.0062 (10) | −0.0068 (11) | 0.0055 (12) |
C9B | 0.0525 (16) | 0.075 (2) | 0.0520 (16) | 0.0129 (15) | −0.0085 (13) | −0.0038 (15) |
C21A | 0.0228 (8) | 0.0282 (9) | 0.0224 (8) | 0.0054 (7) | 0.0032 (7) | −0.0004 (7) |
C22A | 0.0308 (10) | 0.0448 (13) | 0.0304 (10) | 0.0010 (9) | 0.0026 (8) | −0.0100 (9) |
C23A | 0.0428 (13) | 0.0715 (18) | 0.0252 (10) | 0.0105 (13) | −0.0005 (9) | −0.0131 (11) |
C24A | 0.0526 (14) | 0.0718 (19) | 0.0226 (10) | 0.0230 (13) | 0.0081 (10) | 0.0053 (11) |
C25A | 0.0502 (14) | 0.0503 (15) | 0.0358 (12) | 0.0093 (12) | 0.0159 (10) | 0.0165 (11) |
C26A | 0.0386 (11) | 0.0320 (11) | 0.0270 (10) | 0.0010 (9) | 0.0069 (8) | 0.0047 (8) |
Geometric parameters (Å, º) top
O1A—C4A | 1.213 (2) | C21B—C26B | 1.392 (3) |
O2A—C7A | 1.205 (3) | C22B—C23B | 1.391 (3) |
O3A—C7A | 1.334 (2) | C22B—H22B | 0.98 |
O3A—C8A | 1.465 (3) | C23B—C24B | 1.378 (4) |
N1A—C6A | 1.468 (2) | C23B—H23B | 0.94 |
N1A—C2A | 1.469 (2) | C25B—C24B | 1.382 (4) |
N1A—H1A | 0.90 (3) | C25B—C26B | 1.395 (3) |
C2A—C21A | 1.514 (2) | C25B—H25B | 0.91 |
C2A—C3A | 1.554 (2) | C24B—H24B | 0.98 |
C2A—H2A | 0.98 | C26B—H26B | 0.98 |
C3A—C7A | 1.518 (2) | C3B—C7B | 1.515 (2) |
C3A—C4A | 1.527 (3) | C3B—C4B | 1.529 (3) |
C3A—H3A | 0.98 | C3B—H3B | 0.98 |
C4A—C5A | 1.504 (3) | C4B—C5B | 1.506 (3) |
C5A—C6A | 1.541 (2) | C5B—C6B | 1.541 (3) |
C5A—H5A1 | 0.97 | C5B—H5B1 | 0.97 |
C5A—H5A2 | 0.97 | C5B—H5B2 | 0.97 |
C6A—C61A | 1.520 (2) | C6B—C61B | 1.521 (2) |
C6A—H6A | 0.98 | C6B—H6B | 0.98 |
C8A—C9A | 1.467 (5) | C61B—C66B | 1.387 (3) |
C8A—H8A1 | 0.97 | C61B—C62B | 1.398 (3) |
C8A—H8A2 | 0.97 | C62B—C63B | 1.398 (3) |
C9A—H9A1 | 0.96 | C62B—H62B | 0.95 |
C9A—H9A2 | 0.96 | C63B—C64B | 1.378 (3) |
C9A—H9A3 | 0.96 | C63B—H63B | 1.04 |
C61A—C66A | 1.388 (3) | C64B—C65B | 1.380 (3) |
C61A—C62A | 1.399 (3) | C64B—H64B | 1.01 |
C62A—C63A | 1.395 (3) | C65B—C66B | 1.398 (3) |
C62A—H62A | 0.93 | C65B—H65B | 0.97 |
C63A—C64A | 1.383 (3) | C66B—H66B | 0.97 |
C63A—H63A | 1.02 | C8B—C9B | 1.479 (4) |
C64A—C65A | 1.386 (3) | C8B—H8B1 | 0.97 |
C64A—H64A | 0.99 | C8B—H8B2 | 0.97 |
C65A—C66A | 1.403 (3) | C9B—H9B1 | 0.96 |
C65A—H65A | 0.93 | C9B—H9B2 | 0.96 |
C66A—H66A | 0.98 | C9B—H9B3 | 0.96 |
O1B—C4B | 1.210 (2) | C21A—C26A | 1.390 (3) |
O2B—C7B | 1.206 (3) | C21A—C22A | 1.393 (3) |
O3B—C7B | 1.344 (2) | C22A—C23A | 1.395 (3) |
O3B—C8B | 1.481 (3) | C22A—H22A | 0.99 |
N1B—C6B | 1.469 (2) | C23A—C24A | 1.378 (4) |
N1B—C2B | 1.470 (2) | C23A—H23A | 0.99 |
N1B—H1B | 0.95 (2) | C24A—C25A | 1.383 (4) |
C2B—C21B | 1.518 (3) | C24A—H24A | 1.03 |
C2B—C3B | 1.553 (2) | C25A—C26A | 1.399 (3) |
C2B—H2B | 0.98 | C25A—H25A | 0.96 |
C21B—C22B | 1.392 (3) | C26A—H26A | 0.92 |
| | | |
C7A—O3A—C8A | 116.57 (18) | C22B—C23B—H23B | 119.9 |
C6A—N1A—C2A | 112.88 (14) | C24B—C25B—C26B | 120.7 (2) |
C6A—N1A—H1A | 109.3 (16) | C24B—C25B—H25B | 119.7 |
C2A—N1A—H1A | 107.6 (16) | C26B—C25B—H25B | 119.7 |
N1A—C2A—C21A | 110.25 (15) | C23B—C24B—C25B | 119.6 (2) |
N1A—C2A—C3A | 108.54 (14) | C23B—C24B—H24B | 120.2 |
C21A—C2A—C3A | 109.55 (14) | C25B—C24B—H24B | 120.2 |
N1A—C2A—H2A | 109.5 | C21B—C26B—C25B | 119.9 (2) |
C21A—C2A—H2A | 109.5 | C21B—C26B—H26B | 120.0 |
C3A—C2A—H2A | 109.5 | C25B—C26B—H26B | 120.0 |
C7A—C3A—C4A | 109.17 (15) | C7B—C3B—C4B | 107.96 (15) |
C7A—C3A—C2A | 110.93 (15) | C7B—C3B—C2B | 111.20 (15) |
C4A—C3A—C2A | 111.71 (14) | C4B—C3B—C2B | 111.64 (14) |
C7A—C3A—H3A | 108.3 | C7B—C3B—H3B | 108.7 |
C4A—C3A—H3A | 108.3 | C4B—C3B—H3B | 108.7 |
C2A—C3A—H3A | 108.3 | C2B—C3B—H3B | 108.7 |
O1A—C4A—C5A | 123.33 (18) | O1B—C4B—C5B | 123.17 (18) |
O1A—C4A—C3A | 121.81 (17) | O1B—C4B—C3B | 121.95 (17) |
C5A—C4A—C3A | 114.77 (15) | C5B—C4B—C3B | 114.85 (15) |
C4A—C5A—C6A | 112.65 (15) | C4B—C5B—C6B | 111.81 (15) |
C4A—C5A—H5A1 | 109.1 | C4B—C5B—H5B1 | 109.3 |
C6A—C5A—H5A1 | 109.1 | C6B—C5B—H5B1 | 109.3 |
C4A—C5A—H5A2 | 109.1 | C4B—C5B—H5B2 | 109.3 |
C6A—C5A—H5A2 | 109.1 | C6B—C5B—H5B2 | 109.3 |
H5A1—C5A—H5A2 | 107.8 | H5B1—C5B—H5B2 | 107.9 |
N1A—C6A—C61A | 111.56 (14) | N1B—C6B—C61B | 111.42 (15) |
N1A—C6A—C5A | 107.88 (14) | N1B—C6B—C5B | 108.10 (15) |
C61A—C6A—C5A | 109.11 (14) | C61B—C6B—C5B | 109.42 (15) |
N1A—C6A—H6A | 109.4 | N1B—C6B—H6B | 109.3 |
C61A—C6A—H6A | 109.4 | C61B—C6B—H6B | 109.3 |
C5A—C6A—H6A | 109.4 | C5B—C6B—H6B | 109.3 |
O2A—C7A—O3A | 124.53 (18) | C66B—C61B—C62B | 118.93 (18) |
O2A—C7A—C3A | 124.04 (18) | C66B—C61B—C6B | 122.29 (17) |
O3A—C7A—C3A | 111.43 (17) | C62B—C61B—C6B | 118.74 (17) |
O3A—C8A—C9A | 109.8 (2) | C63B—C62B—C61B | 120.0 (2) |
O3A—C8A—H8A1 | 109.7 | C63B—C62B—H62B | 120.0 |
C9A—C8A—H8A1 | 109.7 | C61B—C62B—H62B | 120.0 |
O3A—C8A—H8A2 | 109.7 | C64B—C63B—C62B | 120.4 (2) |
C9A—C8A—H8A2 | 109.7 | C64B—C63B—H63B | 119.8 |
H8A1—C8A—H8A2 | 108.2 | C62B—C63B—H63B | 119.8 |
C8A—C9A—H9A1 | 109.5 | C63B—C64B—C65B | 119.92 (19) |
C8A—C9A—H9A2 | 109.5 | C63B—C64B—H64B | 120.0 |
H9A1—C9A—H9A2 | 109.5 | C65B—C64B—H64B | 120.0 |
C8A—C9A—H9A3 | 109.5 | C64B—C65B—C66B | 120.1 (2) |
H9A1—C9A—H9A3 | 109.5 | C64B—C65B—H65B | 120.0 |
H9A2—C9A—H9A3 | 109.5 | C66B—C65B—H65B | 120.0 |
C66A—C61A—C62A | 118.99 (17) | C61B—C66B—C65B | 120.6 (2) |
C66A—C61A—C6A | 122.12 (16) | C61B—C66B—H66B | 119.7 |
C62A—C61A—C6A | 118.82 (16) | C65B—C66B—H66B | 119.7 |
C63A—C62A—C61A | 120.33 (19) | O2B—C7B—O3B | 124.52 (17) |
C63A—C62A—H62A | 119.8 | O2B—C7B—C3B | 124.04 (17) |
C61A—C62A—H62A | 119.8 | O3B—C7B—C3B | 111.34 (16) |
C64A—C63A—C62A | 120.41 (19) | O3B—C8B—C9B | 110.2 (2) |
C64A—C63A—H63A | 119.8 | O3B—C8B—H8B1 | 109.6 |
C62A—C63A—H63A | 119.8 | C9B—C8B—H8B1 | 109.6 |
C63A—C64A—C65A | 119.69 (19) | O3B—C8B—H8B2 | 109.6 |
C63A—C64A—H64A | 120.2 | C9B—C8B—H8B2 | 109.6 |
C65A—C64A—H64A | 120.2 | H8B1—C8B—H8B2 | 108.1 |
C64A—C65A—C66A | 120.2 (2) | C8B—C9B—H9B1 | 109.5 |
C64A—C65A—H65A | 119.9 | C8B—C9B—H9B2 | 109.5 |
C66A—C65A—H65A | 119.9 | H9B1—C9B—H9B2 | 109.5 |
C61A—C66A—C65A | 120.38 (19) | C8B—C9B—H9B3 | 109.5 |
C61A—C66A—H66A | 119.8 | H9B1—C9B—H9B3 | 109.5 |
C65A—C66A—H66A | 119.8 | H9B2—C9B—H9B3 | 109.5 |
C7B—O3B—C8B | 115.84 (17) | C26A—C21A—C22A | 118.83 (19) |
C6B—N1B—C2B | 112.43 (14) | C26A—C21A—C2A | 121.14 (17) |
C6B—N1B—H1B | 109.0 (14) | C22A—C21A—C2A | 120.00 (18) |
C2B—N1B—H1B | 108.4 (14) | C21A—C22A—C23A | 120.6 (2) |
N1B—C2B—C21B | 110.30 (15) | C21A—C22A—H22A | 119.7 |
N1B—C2B—C3B | 108.56 (14) | C23A—C22A—H22A | 119.7 |
C21B—C2B—C3B | 109.87 (14) | C24A—C23A—C22A | 120.3 (2) |
N1B—C2B—H2B | 109.4 | C24A—C23A—H23A | 119.9 |
C21B—C2B—H2B | 109.4 | C22A—C23A—H23A | 119.9 |
C3B—C2B—H2B | 109.4 | C23A—C24A—C25A | 119.8 (2) |
C22B—C21B—C26B | 118.89 (19) | C23A—C24A—H24A | 120.1 |
C22B—C21B—C2B | 120.21 (18) | C25A—C24A—H24A | 120.1 |
C26B—C21B—C2B | 120.88 (17) | C24A—C25A—C26A | 120.3 (2) |
C23B—C22B—C21B | 120.7 (2) | C24A—C25A—H25A | 119.9 |
C23B—C22B—H22B | 119.7 | C26A—C25A—H25A | 119.9 |
C21B—C22B—H22B | 119.7 | C21A—C26A—C25A | 120.3 (2) |
C24B—C23B—C22B | 120.2 (2) | C21A—C26A—H26A | 119.9 |
C24B—C23B—H23B | 119.9 | C25A—C26A—H26A | 119.9 |
| | | |
C6A—N1A—C2A—C21A | −175.78 (15) | C2B—C21B—C26B—C25B | −178.95 (19) |
C6A—N1A—C2A—C3A | 64.23 (19) | C24B—C25B—C26B—C21B | 0.5 (3) |
N1A—C2A—C3A—C7A | −173.45 (14) | N1B—C2B—C3B—C7B | −172.06 (15) |
C21A—C2A—C3A—C7A | 66.11 (19) | C21B—C2B—C3B—C7B | 67.25 (19) |
N1A—C2A—C3A—C4A | −51.40 (19) | N1B—C2B—C3B—C4B | −51.41 (19) |
C21A—C2A—C3A—C4A | −171.83 (15) | C21B—C2B—C3B—C4B | −172.10 (15) |
C7A—C3A—C4A—O1A | −15.9 (3) | C7B—C3B—C4B—O1B | −14.4 (3) |
C2A—C3A—C4A—O1A | −138.9 (2) | C2B—C3B—C4B—O1B | −137.0 (2) |
C7A—C3A—C4A—C5A | 167.49 (16) | C7B—C3B—C4B—C5B | 167.43 (16) |
C2A—C3A—C4A—C5A | 44.4 (2) | C2B—C3B—C4B—C5B | 44.9 (2) |
O1A—C4A—C5A—C6A | 137.7 (2) | O1B—C4B—C5B—C6B | 135.4 (2) |
C3A—C4A—C5A—C6A | −45.7 (2) | C3B—C4B—C5B—C6B | −46.5 (2) |
C2A—N1A—C6A—C61A | 175.38 (15) | C2B—N1B—C6B—C61B | 174.20 (15) |
C2A—N1A—C6A—C5A | −64.79 (19) | C2B—N1B—C6B—C5B | −65.54 (19) |
C4A—C5A—C6A—N1A | 53.4 (2) | C4B—C5B—C6B—N1B | 54.4 (2) |
C4A—C5A—C6A—C61A | 174.78 (15) | C4B—C5B—C6B—C61B | 175.96 (16) |
C8A—O3A—C7A—O2A | −0.2 (3) | N1B—C6B—C61B—C66B | 17.1 (3) |
C8A—O3A—C7A—C3A | 179.67 (19) | C5B—C6B—C61B—C66B | −102.4 (2) |
C4A—C3A—C7A—O2A | −76.3 (2) | N1B—C6B—C61B—C62B | −165.42 (18) |
C2A—C3A—C7A—O2A | 47.2 (3) | C5B—C6B—C61B—C62B | 75.1 (2) |
C4A—C3A—C7A—O3A | 103.79 (18) | C66B—C61B—C62B—C63B | −0.3 (3) |
C2A—C3A—C7A—O3A | −132.69 (17) | C6B—C61B—C62B—C63B | −177.9 (2) |
C7A—O3A—C8A—C9A | 94.7 (3) | C61B—C62B—C63B—C64B | 0.8 (4) |
N1A—C6A—C61A—C66A | 15.8 (2) | C62B—C63B—C64B—C65B | −1.2 (4) |
C5A—C6A—C61A—C66A | −103.3 (2) | C63B—C64B—C65B—C66B | 1.0 (4) |
N1A—C6A—C61A—C62A | −167.30 (17) | C62B—C61B—C66B—C65B | 0.1 (3) |
C5A—C6A—C61A—C62A | 73.6 (2) | C6B—C61B—C66B—C65B | 177.60 (19) |
C66A—C61A—C62A—C63A | −0.4 (3) | C64B—C65B—C66B—C61B | −0.5 (3) |
C6A—C61A—C62A—C63A | −177.39 (18) | C8B—O3B—C7B—O2B | 8.0 (3) |
C61A—C62A—C63A—C64A | 0.5 (3) | C8B—O3B—C7B—C3B | −168.45 (18) |
C62A—C63A—C64A—C65A | −0.7 (3) | C4B—C3B—C7B—O2B | −82.0 (2) |
C63A—C64A—C65A—C66A | 0.9 (3) | C2B—C3B—C7B—O2B | 40.8 (3) |
C62A—C61A—C66A—C65A | 0.6 (3) | C4B—C3B—C7B—O3B | 94.48 (19) |
C6A—C61A—C66A—C65A | 177.49 (18) | C2B—C3B—C7B—O3B | −142.73 (17) |
C64A—C65A—C66A—C61A | −0.9 (3) | C7B—O3B—C8B—C9B | −81.2 (3) |
C6B—N1B—C2B—C21B | −175.40 (15) | N1A—C2A—C21A—C26A | −33.7 (2) |
C6B—N1B—C2B—C3B | 64.17 (19) | C3A—C2A—C21A—C26A | 85.7 (2) |
N1B—C2B—C21B—C22B | 144.10 (18) | N1A—C2A—C21A—C22A | 148.08 (18) |
C3B—C2B—C21B—C22B | −96.3 (2) | C3A—C2A—C21A—C22A | −92.5 (2) |
N1B—C2B—C21B—C26B | −37.5 (2) | C26A—C21A—C22A—C23A | −0.9 (3) |
C3B—C2B—C21B—C26B | 82.1 (2) | C2A—C21A—C22A—C23A | 177.4 (2) |
C26B—C21B—C22B—C23B | 0.2 (3) | C21A—C22A—C23A—C24A | 1.1 (4) |
C2B—C21B—C22B—C23B | 178.63 (19) | C22A—C23A—C24A—C25A | −0.6 (4) |
C21B—C22B—C23B—C24B | 0.1 (3) | C23A—C24A—C25A—C26A | −0.1 (4) |
C22B—C23B—C24B—C25B | −0.2 (4) | C22A—C21A—C26A—C25A | 0.2 (3) |
C26B—C25B—C24B—C23B | −0.1 (4) | C2A—C21A—C26A—C25A | −178.10 (19) |
C22B—C21B—C26B—C25B | −0.6 (3) | C24A—C25A—C26A—C21A | 0.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6A···O2Bi | 0.98 | 2.69 | 3.332 (2) | 124 |
C6B—H6B···O2Aii | 0.98 | 2.83 | 3.479 (2) | 124 |
C62A—H62A···O2Bi | 0.93 | 2.48 | 3.324 (3) | 153 |
C62B—H62B···O2Aii | 0.95 | 2.60 | 3.474 (3) | 154 |
C65A—H65A···O1Biii | 0.93 | 2.63 | 3.380 (3) | 138 |
C65B—H65B···O1Aiv | 0.97 | 2.64 | 3.421 (3) | 138 |
N1A—H1A···Cg3v | 0.90 (3) | 2.78 (2) | 3.586 (2) | 151 (2) |
N1B—H1B···Cg4vi | 0.95 (2) | 2.80 (2) | 3.677 (2) | 155 (2) |
C9A—H9A3···Cg4vii | 0.96 | 3.04 | 3.911 (4) | 151 |
C8B—H8B1···Cg3viii | 0.97 | 3.21 | 4.159 (2) | 167 |
C23A—H23A···Cg2ix | 0.99 | 3.17 | 3.906 (3) | 133 |
C23B—H23B···Cg1 | 0.94 | 3.10 | 3.848 (3) | 139 |
C63B—H63B···Cg2vi | 1.04 | 3.37 | 3.928 (3) | 115 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x, y+1/2, −z+1/2; (v) −x+1, −y, −z+1; (vi) −x, −y+1, −z; (vii) x, −y+3/2, z+1/2; (viii) x, −y+3/2, z−1/2; (ix) x, y−1, z. |