The title compound, C
24H
22ClNO
3, contains two independent molecules in the asymmetric unit. In one of the molecules, the furan ring is in a twist conformation, whereas in the other it adopts an envelope conformation. In both molecules, the cyclohexenone rings adopt envelope conformations. The crystal structure is stabilized by intermolecular C—H
O interactions.
Supporting information
CCDC reference: 636213
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.047
- wR factor = 0.138
- Data-to-parameter ratio = 18.7
checkCIF/PLATON results
No syntax errors found
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
3-(4-Methoxyphenyl)-1',6,6-trimethyl-4,5,6,7-tetrahydrospiro[1-benzofuran-
2,3'(3
H,2'
H)-1
H-indole]-2',4-dione
top
Crystal data top
C24H22ClNO3 | F(000) = 1712 |
Mr = 407.88 | Dx = 1.286 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4725 reflections |
a = 13.9638 (8) Å | θ = 1.7–25.0° |
b = 13.8490 (8) Å | µ = 0.21 mm−1 |
c = 22.1754 (13) Å | T = 293 K |
β = 100.851 (1)° | Block, colourless |
V = 4211.7 (4) Å3 | 0.26 × 0.25 × 0.23 mm |
Z = 8 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 7812 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 28.0°, θmin = 1.7° |
ω scans | h = −18→17 |
47537 measured reflections | k = −18→18 |
9908 independent reflections | l = −29→28 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0754P)2 + 0.8149P] where P = (Fo2 + 2Fc2)/3 |
9908 reflections | (Δ/σ)max = 0.001 |
529 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.27 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 | |
C25 | 0.85421 (11) | 0.74807 (10) | 0.33346 (7) | 0.0466 (3) | |
C26 | 0.83254 (11) | 0.85459 (10) | 0.35116 (6) | 0.0428 (3) | |
H26 | 0.8140 | 0.8932 | 0.3138 | 0.051* | |
C27 | 0.93382 (11) | 0.88269 (10) | 0.38339 (6) | 0.0425 (3) | |
C28 | 0.98912 (11) | 0.80384 (10) | 0.39545 (7) | 0.0446 (3) | |
C29 | 0.87985 (13) | 0.74531 (12) | 0.26846 (8) | 0.0564 (4) | |
C30 | 0.75309 (13) | 0.64245 (11) | 0.26806 (8) | 0.0513 (4) | |
C31 | 0.67754 (15) | 0.57869 (14) | 0.24793 (10) | 0.0698 (5) | |
H31 | 0.6625 | 0.5592 | 0.2071 | 0.084* | |
C32 | 0.62545 (16) | 0.54512 (15) | 0.29065 (11) | 0.0790 (6) | |
H32 | 0.5743 | 0.5023 | 0.2782 | 0.095* | |
C33 | 0.64715 (15) | 0.57329 (14) | 0.35088 (11) | 0.0726 (5) | |
H33 | 0.6116 | 0.5485 | 0.3788 | 0.087* | |
C34 | 0.72192 (14) | 0.63871 (11) | 0.37047 (9) | 0.0590 (4) | |
H34 | 0.7364 | 0.6582 | 0.4113 | 0.071* | |
C35 | 0.77425 (12) | 0.67426 (10) | 0.32855 (7) | 0.0475 (3) | |
C36 | 0.82307 (18) | 0.65876 (15) | 0.17097 (9) | 0.0761 (6) | |
H36A | 0.8488 | 0.7122 | 0.1515 | 0.114* | |
H36B | 0.7595 | 0.6425 | 0.1484 | 0.114* | |
H36C | 0.8656 | 0.6041 | 0.1718 | 0.114* | |
C37 | 0.75498 (11) | 0.86356 (9) | 0.39000 (6) | 0.0415 (3) | |
C38 | 0.65993 (12) | 0.88733 (11) | 0.36305 (7) | 0.0509 (4) | |
H38 | 0.6454 | 0.9018 | 0.3214 | 0.061* | |
C39 | 0.58665 (12) | 0.88982 (12) | 0.39706 (8) | 0.0549 (4) | |
H39 | 0.5235 | 0.9068 | 0.3786 | 0.066* | |
C40 | 0.60802 (11) | 0.86698 (11) | 0.45844 (8) | 0.0491 (3) | |
C41 | 0.70187 (12) | 0.84372 (11) | 0.48694 (7) | 0.0491 (3) | |
H41 | 0.7157 | 0.8288 | 0.5286 | 0.059* | |
C42 | 0.77476 (11) | 0.84305 (10) | 0.45267 (7) | 0.0454 (3) | |
H42 | 0.8383 | 0.8286 | 0.4717 | 0.054* | |
C43 | 0.97171 (11) | 0.97697 (10) | 0.40337 (7) | 0.0448 (3) | |
C44 | 1.07818 (12) | 0.98001 (12) | 0.43389 (8) | 0.0544 (4) | |
H44A | 1.0819 | 0.9801 | 0.4780 | 0.065* | |
H44B | 1.1055 | 1.0406 | 0.4231 | 0.065* | |
C45 | 1.14223 (12) | 0.89742 (12) | 0.41774 (8) | 0.0541 (4) | |
C46 | 1.09265 (12) | 0.80015 (12) | 0.42637 (8) | 0.0551 (4) | |
H46A | 1.1257 | 0.7484 | 0.4091 | 0.066* | |
H46B | 1.0969 | 0.7873 | 0.4698 | 0.066* | |
C47 | 1.24184 (14) | 0.89974 (16) | 0.46090 (11) | 0.0793 (6) | |
H47A | 1.2329 | 0.8946 | 0.5027 | 0.119* | |
H47B | 1.2742 | 0.9594 | 0.4555 | 0.119* | |
H47C | 1.2808 | 0.8467 | 0.4515 | 0.119* | |
C48 | 1.15629 (16) | 0.90634 (17) | 0.35116 (10) | 0.0763 (6) | |
H48A | 1.2028 | 0.8592 | 0.3433 | 0.115* | |
H48B | 1.1797 | 0.9699 | 0.3444 | 0.115* | |
H48C | 1.0951 | 0.8956 | 0.3240 | 0.115* | |
N2 | 0.81607 (11) | 0.68523 (10) | 0.23351 (6) | 0.0563 (3) | |
O4 | 0.94277 (8) | 0.72017 (7) | 0.37616 (5) | 0.0507 (3) | |
O5 | 0.94596 (12) | 0.78906 (12) | 0.25246 (6) | 0.0860 (5) | |
O6 | 0.92099 (9) | 1.04962 (8) | 0.39826 (6) | 0.0610 (3) | |
Cl2 | 0.51525 (3) | 0.86704 (4) | 0.50098 (2) | 0.07172 (15) | |
C1 | 0.83651 (10) | 0.47111 (10) | 0.68278 (6) | 0.0409 (3) | |
C2 | 0.80965 (10) | 0.57961 (10) | 0.66512 (6) | 0.0390 (3) | |
H2 | 0.8203 | 0.6182 | 0.7028 | 0.047* | |
C3 | 0.88923 (10) | 0.60288 (10) | 0.63009 (6) | 0.0402 (3) | |
C4 | 0.94123 (10) | 0.52422 (10) | 0.62403 (7) | 0.0431 (3) | |
C5 | 0.88622 (12) | 0.46632 (11) | 0.75097 (7) | 0.0506 (4) | |
C6 | 0.75117 (12) | 0.37106 (10) | 0.73884 (7) | 0.0472 (3) | |
C7 | 0.67805 (16) | 0.31145 (14) | 0.75099 (10) | 0.0684 (5) | |
H7 | 0.6742 | 0.2941 | 0.7910 | 0.082* | |
C8 | 0.61056 (15) | 0.27839 (15) | 0.70149 (12) | 0.0802 (6) | |
H8 | 0.5608 | 0.2377 | 0.7085 | 0.096* | |
C9 | 0.61515 (15) | 0.30405 (14) | 0.64244 (11) | 0.0751 (6) | |
H9 | 0.5694 | 0.2800 | 0.6100 | 0.090* | |
C10 | 0.68787 (14) | 0.36592 (12) | 0.63087 (8) | 0.0596 (4) | |
H10 | 0.6909 | 0.3840 | 0.5909 | 0.071* | |
C11 | 0.75529 (11) | 0.40001 (10) | 0.67943 (7) | 0.0428 (3) | |
C12 | 0.85416 (19) | 0.38881 (15) | 0.84558 (8) | 0.0766 (6) | |
H12A | 0.8866 | 0.3274 | 0.8507 | 0.115* | |
H12B | 0.7958 | 0.3860 | 0.8625 | 0.115* | |
H12C | 0.8966 | 0.4377 | 0.8664 | 0.115* | |
C13 | 0.70643 (10) | 0.59641 (10) | 0.63134 (6) | 0.0393 (3) | |
C14 | 0.63359 (11) | 0.61422 (12) | 0.66475 (7) | 0.0486 (3) | |
H14 | 0.6496 | 0.6167 | 0.7074 | 0.058* | |
C15 | 0.53778 (12) | 0.62833 (12) | 0.63610 (8) | 0.0536 (4) | |
H15 | 0.4896 | 0.6397 | 0.6591 | 0.064* | |
C16 | 0.51515 (11) | 0.62531 (12) | 0.57331 (8) | 0.0512 (4) | |
C17 | 0.58501 (12) | 0.60819 (13) | 0.53835 (7) | 0.0559 (4) | |
H17 | 0.5684 | 0.6061 | 0.4957 | 0.067* | |
C18 | 0.68084 (11) | 0.59410 (12) | 0.56804 (7) | 0.0500 (3) | |
H18 | 0.7287 | 0.5829 | 0.5449 | 0.060* | |
C19 | 0.91233 (10) | 0.69511 (10) | 0.60569 (7) | 0.0423 (3) | |
C20 | 0.99947 (11) | 0.69474 (11) | 0.57407 (8) | 0.0519 (4) | |
H20A | 1.0294 | 0.7582 | 0.5785 | 0.062* | |
H20B | 0.9766 | 0.6835 | 0.5306 | 0.062* | |
C21 | 1.07780 (11) | 0.61893 (12) | 0.59838 (9) | 0.0567 (4) | |
C22 | 1.02982 (12) | 0.51887 (12) | 0.59659 (9) | 0.0575 (4) | |
H22A | 1.0126 | 0.4968 | 0.5544 | 0.069* | |
H22B | 1.0754 | 0.4730 | 0.6193 | 0.069* | |
C23 | 1.15505 (15) | 0.61759 (17) | 0.55767 (12) | 0.0843 (7) | |
H23A | 1.1245 | 0.6038 | 0.5161 | 0.126* | |
H23B | 1.2026 | 0.5687 | 0.5720 | 0.126* | |
H23C | 1.1865 | 0.6794 | 0.5594 | 0.126* | |
C24 | 1.12571 (16) | 0.64284 (19) | 0.66426 (11) | 0.0890 (7) | |
H24A | 1.1506 | 0.7076 | 0.6661 | 0.134* | |
H24B | 1.1783 | 0.5986 | 0.6778 | 0.134* | |
H24C | 1.0784 | 0.6373 | 0.6904 | 0.134* | |
N1 | 0.82902 (11) | 0.41202 (10) | 0.78055 (6) | 0.0528 (3) | |
O1 | 0.90900 (8) | 0.44239 (7) | 0.64694 (5) | 0.0507 (3) | |
O2 | 0.96186 (10) | 0.50615 (11) | 0.77353 (6) | 0.0787 (4) | |
O3 | 0.86410 (8) | 0.76785 (8) | 0.60833 (6) | 0.0565 (3) | |
Cl1 | 0.39468 (3) | 0.64437 (4) | 0.53721 (3) | 0.07825 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C25 | 0.0556 (8) | 0.0390 (7) | 0.0448 (7) | −0.0084 (6) | 0.0082 (6) | −0.0014 (6) |
C26 | 0.0511 (8) | 0.0344 (7) | 0.0396 (7) | −0.0047 (6) | 0.0006 (6) | 0.0041 (5) |
C27 | 0.0461 (7) | 0.0382 (7) | 0.0417 (7) | −0.0056 (6) | 0.0043 (6) | 0.0023 (5) |
C28 | 0.0497 (8) | 0.0375 (7) | 0.0470 (8) | −0.0046 (6) | 0.0098 (6) | 0.0033 (6) |
C29 | 0.0707 (11) | 0.0483 (8) | 0.0525 (9) | −0.0081 (8) | 0.0172 (8) | −0.0025 (7) |
C30 | 0.0605 (10) | 0.0361 (7) | 0.0548 (9) | −0.0003 (6) | 0.0042 (7) | −0.0038 (6) |
C31 | 0.0778 (12) | 0.0533 (10) | 0.0706 (11) | −0.0109 (9) | −0.0058 (10) | −0.0139 (9) |
C32 | 0.0728 (13) | 0.0581 (11) | 0.1010 (16) | −0.0258 (10) | 0.0035 (11) | −0.0089 (11) |
C33 | 0.0720 (12) | 0.0552 (10) | 0.0937 (15) | −0.0203 (9) | 0.0231 (11) | −0.0002 (10) |
C34 | 0.0707 (11) | 0.0445 (8) | 0.0634 (10) | −0.0130 (8) | 0.0162 (8) | −0.0023 (7) |
C35 | 0.0547 (9) | 0.0344 (7) | 0.0524 (8) | −0.0054 (6) | 0.0073 (7) | −0.0032 (6) |
C36 | 0.1083 (17) | 0.0683 (12) | 0.0529 (10) | 0.0033 (11) | 0.0180 (11) | −0.0156 (9) |
C37 | 0.0463 (7) | 0.0332 (6) | 0.0410 (7) | −0.0039 (5) | −0.0023 (6) | 0.0003 (5) |
C38 | 0.0520 (9) | 0.0492 (8) | 0.0453 (8) | −0.0020 (7) | −0.0065 (6) | 0.0081 (6) |
C39 | 0.0434 (8) | 0.0552 (9) | 0.0599 (9) | 0.0021 (7) | −0.0057 (7) | 0.0052 (7) |
C40 | 0.0441 (8) | 0.0441 (8) | 0.0573 (9) | −0.0024 (6) | 0.0053 (7) | −0.0036 (6) |
C41 | 0.0525 (8) | 0.0504 (8) | 0.0408 (7) | 0.0012 (7) | −0.0004 (6) | −0.0002 (6) |
C42 | 0.0431 (7) | 0.0456 (7) | 0.0424 (7) | 0.0021 (6) | −0.0050 (6) | 0.0007 (6) |
C43 | 0.0533 (8) | 0.0389 (7) | 0.0409 (7) | −0.0060 (6) | 0.0053 (6) | 0.0016 (6) |
C44 | 0.0549 (9) | 0.0482 (8) | 0.0567 (9) | −0.0102 (7) | 0.0018 (7) | −0.0063 (7) |
C45 | 0.0456 (8) | 0.0542 (9) | 0.0611 (9) | −0.0080 (7) | 0.0067 (7) | −0.0010 (7) |
C46 | 0.0485 (8) | 0.0486 (8) | 0.0663 (10) | 0.0013 (7) | 0.0060 (7) | 0.0058 (7) |
C47 | 0.0499 (10) | 0.0802 (13) | 0.1005 (16) | −0.0063 (9) | −0.0049 (10) | −0.0058 (12) |
C48 | 0.0723 (13) | 0.0882 (14) | 0.0752 (13) | −0.0183 (11) | 0.0310 (10) | −0.0019 (11) |
N2 | 0.0742 (9) | 0.0466 (7) | 0.0478 (7) | −0.0024 (6) | 0.0105 (7) | −0.0089 (6) |
O4 | 0.0526 (6) | 0.0351 (5) | 0.0626 (6) | −0.0033 (4) | 0.0064 (5) | 0.0018 (4) |
O5 | 0.1063 (11) | 0.0944 (11) | 0.0661 (8) | −0.0414 (9) | 0.0386 (8) | −0.0112 (7) |
O6 | 0.0651 (7) | 0.0387 (6) | 0.0728 (8) | 0.0003 (5) | −0.0037 (6) | −0.0016 (5) |
Cl2 | 0.0550 (3) | 0.0863 (3) | 0.0760 (3) | 0.0014 (2) | 0.0178 (2) | −0.0026 (2) |
C1 | 0.0434 (7) | 0.0404 (7) | 0.0392 (7) | −0.0043 (6) | 0.0087 (5) | 0.0016 (5) |
C2 | 0.0418 (7) | 0.0371 (7) | 0.0387 (7) | −0.0038 (5) | 0.0090 (5) | −0.0007 (5) |
C3 | 0.0365 (7) | 0.0390 (7) | 0.0455 (7) | −0.0029 (5) | 0.0085 (5) | 0.0022 (5) |
C4 | 0.0431 (7) | 0.0392 (7) | 0.0477 (8) | −0.0027 (6) | 0.0106 (6) | 0.0033 (6) |
C5 | 0.0541 (9) | 0.0458 (8) | 0.0477 (8) | −0.0012 (7) | −0.0014 (7) | 0.0033 (6) |
C6 | 0.0549 (9) | 0.0406 (7) | 0.0470 (8) | −0.0005 (6) | 0.0119 (7) | 0.0065 (6) |
C7 | 0.0821 (13) | 0.0571 (10) | 0.0725 (12) | −0.0094 (9) | 0.0308 (10) | 0.0165 (9) |
C8 | 0.0662 (12) | 0.0659 (12) | 0.1088 (17) | −0.0266 (10) | 0.0169 (11) | 0.0144 (11) |
C9 | 0.0676 (12) | 0.0599 (11) | 0.0890 (14) | −0.0245 (9) | −0.0076 (10) | 0.0037 (10) |
C10 | 0.0694 (11) | 0.0510 (9) | 0.0529 (9) | −0.0150 (8) | −0.0023 (8) | 0.0031 (7) |
C11 | 0.0465 (8) | 0.0372 (7) | 0.0446 (7) | −0.0057 (6) | 0.0078 (6) | 0.0034 (5) |
C12 | 0.1162 (18) | 0.0688 (12) | 0.0404 (9) | 0.0092 (11) | 0.0033 (10) | 0.0120 (8) |
C13 | 0.0409 (7) | 0.0374 (7) | 0.0415 (7) | −0.0018 (5) | 0.0125 (5) | 0.0012 (5) |
C14 | 0.0484 (8) | 0.0592 (9) | 0.0411 (7) | −0.0008 (7) | 0.0162 (6) | −0.0009 (6) |
C15 | 0.0443 (8) | 0.0629 (10) | 0.0591 (9) | −0.0002 (7) | 0.0237 (7) | 0.0000 (7) |
C16 | 0.0380 (7) | 0.0569 (9) | 0.0586 (9) | −0.0030 (6) | 0.0091 (6) | 0.0037 (7) |
C17 | 0.0473 (8) | 0.0775 (11) | 0.0426 (8) | 0.0012 (8) | 0.0078 (6) | 0.0014 (7) |
C18 | 0.0435 (8) | 0.0667 (10) | 0.0428 (8) | 0.0037 (7) | 0.0155 (6) | 0.0005 (7) |
C19 | 0.0404 (7) | 0.0398 (7) | 0.0458 (7) | −0.0021 (6) | 0.0060 (6) | 0.0049 (6) |
C20 | 0.0468 (8) | 0.0464 (8) | 0.0654 (10) | −0.0024 (6) | 0.0179 (7) | 0.0130 (7) |
C21 | 0.0380 (8) | 0.0578 (9) | 0.0762 (11) | 0.0003 (7) | 0.0155 (7) | 0.0167 (8) |
C22 | 0.0535 (9) | 0.0487 (9) | 0.0768 (11) | 0.0070 (7) | 0.0289 (8) | 0.0115 (8) |
C23 | 0.0525 (11) | 0.0855 (14) | 0.1253 (19) | 0.0107 (9) | 0.0429 (12) | 0.0369 (13) |
C24 | 0.0545 (11) | 0.1098 (18) | 0.0937 (16) | −0.0157 (11) | −0.0094 (11) | 0.0139 (13) |
N1 | 0.0698 (9) | 0.0495 (7) | 0.0373 (6) | −0.0015 (6) | 0.0051 (6) | 0.0075 (5) |
O1 | 0.0576 (6) | 0.0361 (5) | 0.0642 (6) | 0.0002 (4) | 0.0264 (5) | 0.0045 (5) |
O2 | 0.0701 (8) | 0.0835 (9) | 0.0698 (8) | −0.0241 (7) | −0.0196 (7) | 0.0060 (7) |
O3 | 0.0600 (7) | 0.0412 (6) | 0.0715 (7) | 0.0068 (5) | 0.0207 (6) | 0.0082 (5) |
Cl1 | 0.0392 (2) | 0.1093 (4) | 0.0836 (3) | 0.0020 (2) | 0.0047 (2) | 0.0099 (3) |
Geometric parameters (Å, º) top
C25—O4 | 1.461 (2) | C1—O1 | 1.455 (2) |
C25—C35 | 1.503 (2) | C1—C11 | 1.493 (2) |
C25—C29 | 1.550 (2) | C1—C5 | 1.542 (2) |
C25—C26 | 1.571 (2) | C1—C2 | 1.580 (2) |
C26—C37 | 1.510 (2) | C2—C3 | 1.506 (2) |
C26—C27 | 1.511 (2) | C2—C13 | 1.512 (2) |
C26—H26 | 0.98 | C2—H2 | 0.98 |
C27—C28 | 1.335 (2) | C3—C4 | 1.330 (2) |
C27—C43 | 1.4466 (19) | C3—C19 | 1.4471 (19) |
C28—O4 | 1.357 (2) | C4—O1 | 1.353 (2) |
C28—C46 | 1.480 (2) | C4—C22 | 1.480 (2) |
C29—O5 | 1.212 (2) | C5—O2 | 1.213 (2) |
C29—N2 | 1.351 (2) | C5—N1 | 1.353 (2) |
C30—C31 | 1.384 (2) | C6—C7 | 1.379 (2) |
C30—C35 | 1.390 (2) | C6—C11 | 1.389 (2) |
C30—N2 | 1.402 (2) | C6—N1 | 1.407 (2) |
C31—C32 | 1.379 (3) | C7—C8 | 1.383 (3) |
C31—H31 | 0.93 | C7—H7 | 0.93 |
C32—C33 | 1.370 (3) | C8—C9 | 1.370 (3) |
C32—H32 | 0.93 | C8—H8 | 0.93 |
C33—C34 | 1.389 (2) | C9—C10 | 1.389 (3) |
C33—H33 | 0.93 | C9—H9 | 0.93 |
C34—C35 | 1.377 (2) | C10—C11 | 1.374 (2) |
C34—H34 | 0.93 | C10—H10 | 0.93 |
C36—N2 | 1.455 (2) | C12—N1 | 1.455 (2) |
C36—H36A | 0.96 | C12—H12A | 0.96 |
C36—H36B | 0.96 | C12—H12B | 0.96 |
C36—H36C | 0.96 | C12—H12C | 0.96 |
C37—C38 | 1.389 (2) | C13—C18 | 1.382 (2) |
C37—C42 | 1.394 (2) | C13—C14 | 1.3884 (19) |
C38—C39 | 1.381 (3) | C14—C15 | 1.383 (2) |
C38—H38 | 0.93 | C14—H14 | 0.93 |
C39—C40 | 1.374 (2) | C15—C16 | 1.369 (2) |
C39—H39 | 0.93 | C15—H15 | 0.93 |
C40—C41 | 1.382 (2) | C16—C17 | 1.376 (2) |
C40—Cl2 | 1.740 (2) | C16—Cl1 | 1.7416 (16) |
C41—C42 | 1.380 (2) | C17—C18 | 1.389 (2) |
C41—H41 | 0.93 | C17—H17 | 0.93 |
C42—H42 | 0.93 | C18—H18 | 0.93 |
C43—O6 | 1.223 (2) | C19—O3 | 1.2193 (17) |
C43—C44 | 1.514 (2) | C19—C20 | 1.514 (2) |
C44—C45 | 1.535 (2) | C20—C21 | 1.539 (2) |
C44—H44A | 0.97 | C20—H20A | 0.97 |
C44—H44B | 0.97 | C20—H20B | 0.97 |
C45—C48 | 1.530 (3) | C21—C24 | 1.524 (3) |
C45—C47 | 1.533 (2) | C21—C23 | 1.532 (3) |
C45—C46 | 1.543 (2) | C21—C22 | 1.536 (2) |
C46—H46A | 0.97 | C22—H22A | 0.97 |
C46—H46B | 0.97 | C22—H22B | 0.97 |
C47—H47A | 0.96 | C23—H23A | 0.96 |
C47—H47B | 0.96 | C23—H23B | 0.96 |
C47—H47C | 0.96 | C23—H23C | 0.96 |
C48—H48A | 0.96 | C24—H24A | 0.96 |
C48—H48B | 0.96 | C24—H24B | 0.96 |
C48—H48C | 0.96 | C24—H24C | 0.96 |
| | | |
O4—C25—C35 | 113.19 (12) | O1—C1—C11 | 113.11 (11) |
O4—C25—C29 | 106.31 (13) | O1—C1—C5 | 107.03 (12) |
C35—C25—C29 | 102.39 (12) | C11—C1—C5 | 102.59 (11) |
O4—C25—C26 | 105.42 (11) | O1—C1—C2 | 106.36 (10) |
C35—C25—C26 | 118.79 (13) | C11—C1—C2 | 118.18 (12) |
C29—C25—C26 | 110.17 (12) | C5—C1—C2 | 109.03 (11) |
C37—C26—C27 | 114.65 (12) | C3—C2—C13 | 116.03 (11) |
C37—C26—C25 | 114.35 (11) | C3—C2—C1 | 99.65 (11) |
C27—C26—C25 | 98.80 (11) | C13—C2—C1 | 115.39 (11) |
C37—C26—H26 | 109.5 | C3—C2—H2 | 108.4 |
C27—C26—H26 | 109.5 | C13—C2—H2 | 108.4 |
C25—C26—H26 | 109.5 | C1—C2—H2 | 108.4 |
C28—C27—C43 | 120.83 (13) | C4—C3—C19 | 121.39 (13) |
C28—C27—C26 | 109.79 (12) | C4—C3—C2 | 110.30 (12) |
C43—C27—C26 | 129.29 (13) | C19—C3—C2 | 128.31 (12) |
C27—C28—O4 | 114.33 (13) | C3—C4—O1 | 114.93 (12) |
C27—C28—C46 | 126.78 (14) | C3—C4—C22 | 126.67 (13) |
O4—C28—C46 | 118.89 (13) | O1—C4—C22 | 118.39 (12) |
O5—C29—N2 | 126.59 (16) | O2—C5—N1 | 126.90 (15) |
O5—C29—C25 | 125.60 (15) | O2—C5—C1 | 125.54 (15) |
N2—C29—C25 | 107.81 (14) | N1—C5—C1 | 107.55 (12) |
C31—C30—C35 | 121.62 (17) | C7—C6—C11 | 121.53 (16) |
C31—C30—N2 | 127.74 (16) | C7—C6—N1 | 128.45 (15) |
C35—C30—N2 | 110.63 (14) | C11—C6—N1 | 110.02 (13) |
C32—C31—C30 | 117.53 (18) | C6—C7—C8 | 117.53 (17) |
C32—C31—H31 | 121.2 | C6—C7—H7 | 121.2 |
C30—C31—H31 | 121.2 | C8—C7—H7 | 121.2 |
C33—C32—C31 | 121.69 (17) | C9—C8—C7 | 121.68 (17) |
C33—C32—H32 | 119.2 | C9—C8—H8 | 119.2 |
C31—C32—H32 | 119.2 | C7—C8—H8 | 119.2 |
C32—C33—C34 | 120.42 (19) | C8—C9—C10 | 120.26 (18) |
C32—C33—H33 | 119.8 | C8—C9—H9 | 119.9 |
C34—C33—H33 | 119.8 | C10—C9—H9 | 119.9 |
C35—C34—C33 | 119.02 (17) | C11—C10—C9 | 118.96 (17) |
C35—C34—H34 | 120.5 | C11—C10—H10 | 120.5 |
C33—C34—H34 | 120.5 | C9—C10—H10 | 120.5 |
C34—C35—C30 | 119.66 (15) | C10—C11—C6 | 119.98 (14) |
C34—C35—C25 | 132.52 (14) | C10—C11—C1 | 131.89 (14) |
C30—C35—C25 | 107.79 (13) | C6—C11—C1 | 108.06 (13) |
N2—C36—H36A | 109.5 | N1—C12—H12A | 109.5 |
N2—C36—H36B | 109.5 | N1—C12—H12B | 109.5 |
H36A—C36—H36B | 109.5 | H12A—C12—H12B | 109.5 |
N2—C36—H36C | 109.5 | N1—C12—H12C | 109.5 |
H36A—C36—H36C | 109.5 | H12A—C12—H12C | 109.5 |
H36B—C36—H36C | 109.5 | H12B—C12—H12C | 109.5 |
C38—C37—C42 | 118.11 (14) | C18—C13—C14 | 118.08 (13) |
C38—C37—C26 | 120.26 (13) | C18—C13—C2 | 122.65 (12) |
C42—C37—C26 | 121.53 (13) | C14—C13—C2 | 119.26 (12) |
C39—C38—C37 | 121.15 (14) | C15—C14—C13 | 121.51 (14) |
C39—C38—H38 | 119.4 | C15—C14—H14 | 119.2 |
C37—C38—H38 | 119.4 | C13—C14—H14 | 119.2 |
C40—C39—C38 | 119.34 (14) | C16—C15—C14 | 118.75 (14) |
C40—C39—H39 | 120.3 | C16—C15—H15 | 120.6 |
C38—C39—H39 | 120.3 | C14—C15—H15 | 120.6 |
C39—C40—C41 | 121.14 (15) | C15—C16—C17 | 121.72 (15) |
C39—C40—Cl2 | 119.46 (12) | C15—C16—Cl1 | 118.75 (12) |
C41—C40—Cl2 | 119.40 (13) | C17—C16—Cl1 | 119.54 (13) |
C42—C41—C40 | 118.94 (14) | C16—C17—C18 | 118.62 (14) |
C42—C41—H41 | 120.5 | C16—C17—H17 | 120.7 |
C40—C41—H41 | 120.5 | C18—C17—H17 | 120.7 |
C41—C42—C37 | 121.29 (13) | C13—C18—C17 | 121.32 (14) |
C41—C42—H42 | 119.4 | C13—C18—H18 | 119.3 |
C37—C42—H42 | 119.4 | C17—C18—H18 | 119.3 |
O6—C43—C27 | 122.82 (14) | O3—C19—C3 | 123.18 (13) |
O6—C43—C44 | 121.42 (13) | O3—C19—C20 | 121.61 (13) |
C27—C43—C44 | 115.72 (13) | C3—C19—C20 | 115.17 (12) |
C43—C44—C45 | 116.18 (13) | C19—C20—C21 | 114.85 (12) |
C43—C44—H44A | 108.2 | C19—C20—H20A | 108.6 |
C45—C44—H44A | 108.2 | C21—C20—H20A | 108.6 |
C43—C44—H44B | 108.2 | C19—C20—H20B | 108.6 |
C45—C44—H44B | 108.2 | C21—C20—H20B | 108.6 |
H44A—C44—H44B | 107.4 | H20A—C20—H20B | 107.5 |
C48—C45—C47 | 109.54 (17) | C24—C21—C23 | 109.68 (17) |
C48—C45—C44 | 110.55 (16) | C24—C21—C22 | 109.35 (16) |
C47—C45—C44 | 109.79 (15) | C23—C21—C22 | 109.02 (16) |
C48—C45—C46 | 109.40 (15) | C24—C21—C20 | 110.03 (17) |
C47—C45—C46 | 108.45 (15) | C23—C21—C20 | 109.56 (14) |
C44—C45—C46 | 109.08 (14) | C22—C21—C20 | 109.18 (13) |
C28—C46—C45 | 109.54 (13) | C4—C22—C21 | 109.78 (13) |
C28—C46—H46A | 109.8 | C4—C22—H22A | 109.7 |
C45—C46—H46A | 109.8 | C21—C22—H22A | 109.7 |
C28—C46—H46B | 109.8 | C4—C22—H22B | 109.7 |
C45—C46—H46B | 109.8 | C21—C22—H22B | 109.7 |
H46A—C46—H46B | 108.2 | H22A—C22—H22B | 108.2 |
C45—C47—H47A | 109.5 | C21—C23—H23A | 109.5 |
C45—C47—H47B | 109.5 | C21—C23—H23B | 109.5 |
H47A—C47—H47B | 109.5 | H23A—C23—H23B | 109.5 |
C45—C47—H47C | 109.5 | C21—C23—H23C | 109.5 |
H47A—C47—H47C | 109.5 | H23A—C23—H23C | 109.5 |
H47B—C47—H47C | 109.5 | H23B—C23—H23C | 109.5 |
C45—C48—H48A | 109.5 | C21—C24—H24A | 109.5 |
C45—C48—H48B | 109.5 | C21—C24—H24B | 109.5 |
H48A—C48—H48B | 109.5 | H24A—C24—H24B | 109.5 |
C45—C48—H48C | 109.5 | C21—C24—H24C | 109.5 |
H48A—C48—H48C | 109.5 | H24A—C24—H24C | 109.5 |
H48B—C48—H48C | 109.5 | H24B—C24—H24C | 109.5 |
C29—N2—C30 | 111.12 (13) | C5—N1—C6 | 111.03 (12) |
C29—N2—C36 | 123.11 (16) | C5—N1—C12 | 123.30 (16) |
C30—N2—C36 | 125.17 (15) | C6—N1—C12 | 125.10 (15) |
C28—O4—C25 | 105.90 (11) | C4—O1—C1 | 106.91 (10) |
| | | |
O4—C25—C26—C37 | −100.02 (13) | O1—C1—C2—C3 | −11.39 (13) |
C35—C25—C26—C37 | 28.12 (18) | C11—C1—C2—C3 | −139.80 (12) |
C29—C25—C26—C37 | 145.68 (13) | C5—C1—C2—C3 | 103.70 (12) |
O4—C25—C26—C27 | 22.21 (13) | O1—C1—C2—C13 | 113.60 (12) |
C35—C25—C26—C27 | 150.35 (13) | C11—C1—C2—C13 | −14.80 (17) |
C29—C25—C26—C27 | −92.10 (14) | C5—C1—C2—C13 | −131.31 (13) |
C37—C26—C27—C28 | 107.80 (14) | C13—C2—C3—C4 | −119.22 (14) |
C25—C26—C27—C28 | −14.21 (15) | C1—C2—C3—C4 | 5.33 (14) |
C37—C26—C27—C43 | −68.92 (19) | C13—C2—C3—C19 | 61.69 (19) |
C25—C26—C27—C43 | 169.06 (15) | C1—C2—C3—C19 | −173.77 (14) |
C43—C27—C28—O4 | 177.43 (13) | C19—C3—C4—O1 | −177.51 (13) |
C26—C27—C28—O4 | 0.39 (18) | C2—C3—C4—O1 | 3.32 (18) |
C43—C27—C28—C46 | −3.1 (2) | C19—C3—C4—C22 | 4.0 (2) |
C26—C27—C28—C46 | 179.88 (15) | C2—C3—C4—C22 | −175.18 (15) |
O4—C25—C29—O5 | −55.7 (2) | O1—C1—C5—O2 | 53.6 (2) |
C35—C25—C29—O5 | −174.64 (19) | C11—C1—C5—O2 | 172.85 (17) |
C26—C25—C29—O5 | 58.1 (2) | C2—C1—C5—O2 | −61.1 (2) |
O4—C25—C29—N2 | 123.85 (14) | O1—C1—C5—N1 | −127.85 (13) |
C35—C25—C29—N2 | 4.88 (18) | C11—C1—C5—N1 | −8.57 (16) |
C26—C25—C29—N2 | −122.41 (14) | C2—C1—C5—N1 | 117.50 (13) |
C35—C30—C31—C32 | −2.0 (3) | C11—C6—C7—C8 | 2.3 (3) |
N2—C30—C31—C32 | 179.48 (18) | N1—C6—C7—C8 | −178.43 (18) |
C30—C31—C32—C33 | −0.1 (3) | C6—C7—C8—C9 | −0.5 (3) |
C31—C32—C33—C34 | 1.3 (3) | C7—C8—C9—C10 | −1.0 (4) |
C32—C33—C34—C35 | −0.4 (3) | C8—C9—C10—C11 | 0.6 (3) |
C33—C34—C35—C30 | −1.6 (3) | C9—C10—C11—C6 | 1.2 (3) |
C33—C34—C35—C25 | 176.31 (18) | C9—C10—C11—C1 | −175.29 (17) |
C31—C30—C35—C34 | 2.8 (3) | C7—C6—C11—C10 | −2.8 (3) |
N2—C30—C35—C34 | −178.40 (15) | N1—C6—C11—C10 | 177.87 (15) |
C31—C30—C35—C25 | −175.51 (16) | C7—C6—C11—C1 | 174.52 (15) |
N2—C30—C35—C25 | 3.24 (18) | N1—C6—C11—C1 | −4.85 (17) |
O4—C25—C35—C34 | 63.1 (2) | O1—C1—C11—C10 | −60.3 (2) |
C29—C25—C35—C34 | 177.13 (18) | C5—C1—C11—C10 | −175.20 (18) |
C26—C25—C35—C34 | −61.3 (2) | C2—C1—C11—C10 | 64.9 (2) |
O4—C25—C35—C30 | −118.80 (14) | O1—C1—C11—C6 | 122.90 (13) |
C29—C25—C35—C30 | −4.80 (17) | C5—C1—C11—C6 | 7.97 (16) |
C26—C25—C35—C30 | 116.77 (15) | C2—C1—C11—C6 | −111.94 (14) |
C27—C26—C37—C38 | 148.06 (13) | C3—C2—C13—C18 | 25.82 (19) |
C25—C26—C37—C38 | −98.84 (15) | C1—C2—C13—C18 | −90.17 (16) |
C27—C26—C37—C42 | −35.69 (18) | C3—C2—C13—C14 | −154.69 (13) |
C25—C26—C37—C42 | 77.41 (16) | C1—C2—C13—C14 | 89.32 (16) |
C42—C37—C38—C39 | −0.6 (2) | C18—C13—C14—C15 | 0.7 (2) |
C26—C37—C38—C39 | 175.79 (14) | C2—C13—C14—C15 | −178.83 (14) |
C37—C38—C39—C40 | −1.0 (2) | C13—C14—C15—C16 | −0.5 (2) |
C38—C39—C40—C41 | 1.5 (2) | C14—C15—C16—C17 | 0.3 (3) |
C38—C39—C40—Cl2 | −178.37 (12) | C14—C15—C16—Cl1 | −179.32 (13) |
C39—C40—C41—C42 | −0.4 (2) | C15—C16—C17—C18 | −0.3 (3) |
Cl2—C40—C41—C42 | 179.43 (12) | Cl1—C16—C17—C18 | 179.39 (13) |
C40—C41—C42—C37 | −1.2 (2) | C14—C13—C18—C17 | −0.6 (2) |
C38—C37—C42—C41 | 1.7 (2) | C2—C13—C18—C17 | 178.89 (15) |
C26—C37—C42—C41 | −174.66 (13) | C16—C17—C18—C13 | 0.4 (3) |
C28—C27—C43—O6 | −173.11 (15) | C4—C3—C19—O3 | 177.12 (15) |
C26—C27—C43—O6 | 3.3 (2) | C2—C3—C19—O3 | −3.9 (2) |
C28—C27—C43—C44 | 4.3 (2) | C4—C3—C19—C20 | −0.7 (2) |
C26—C27—C43—C44 | −179.24 (14) | C2—C3—C19—C20 | 178.30 (13) |
O6—C43—C44—C45 | −158.72 (15) | O3—C19—C20—C21 | 153.13 (15) |
C27—C43—C44—C45 | 23.8 (2) | C3—C19—C20—C21 | −29.0 (2) |
C43—C44—C45—C48 | 69.79 (19) | C19—C20—C21—C24 | −66.32 (19) |
C43—C44—C45—C47 | −169.24 (16) | C19—C20—C21—C23 | 173.01 (16) |
C43—C44—C45—C46 | −50.54 (19) | C19—C20—C21—C22 | 53.7 (2) |
C27—C28—C46—C45 | −25.1 (2) | C3—C4—C22—C21 | 22.0 (2) |
O4—C28—C46—C45 | 154.32 (14) | O1—C4—C22—C21 | −156.45 (14) |
C48—C45—C46—C28 | −72.37 (19) | C24—C21—C22—C4 | 72.50 (19) |
C47—C45—C46—C28 | 168.21 (16) | C23—C21—C22—C4 | −167.59 (16) |
C44—C45—C46—C28 | 48.67 (18) | C20—C21—C22—C4 | −47.93 (19) |
O5—C29—N2—C30 | 176.27 (19) | O2—C5—N1—C6 | −175.27 (17) |
C25—C29—N2—C30 | −3.25 (19) | C1—C5—N1—C6 | 6.18 (18) |
O5—C29—N2—C36 | 4.8 (3) | O2—C5—N1—C12 | −3.5 (3) |
C25—C29—N2—C36 | −174.75 (16) | C1—C5—N1—C12 | 177.92 (15) |
C31—C30—N2—C29 | 178.73 (18) | C7—C6—N1—C5 | 179.70 (18) |
C35—C30—N2—C29 | 0.1 (2) | C11—C6—N1—C5 | −0.98 (19) |
C31—C30—N2—C36 | −10.0 (3) | C7—C6—N1—C12 | 8.1 (3) |
C35—C30—N2—C36 | 171.36 (17) | C11—C6—N1—C12 | −172.55 (16) |
C27—C28—O4—C25 | 15.12 (17) | C3—C4—O1—C1 | −11.25 (17) |
C46—C28—O4—C25 | −164.41 (13) | C22—C4—O1—C1 | 167.38 (14) |
C35—C25—O4—C28 | −154.81 (13) | C11—C1—O1—C4 | 145.20 (12) |
C29—C25—O4—C28 | 93.57 (13) | C5—C1—O1—C4 | −102.56 (13) |
C26—C25—O4—C28 | −23.39 (14) | C2—C1—O1—C4 | 13.88 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O3i | 0.93 | 2.42 | 3.337 (3) | 169 |
C15—H15···O5ii | 0.93 | 2.47 | 3.295 (2) | 148 |
C31—H31···O6iii | 0.93 | 2.41 | 3.299 (3) | 160 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x+3/2, y−1/2, −z+1/2. |