The structure of the title compound [systematic name: dibenzyl 3,3′-diethyl-4,4′-dimethyl-2,2′-(3-chloropropane-1,1-diyl)dipyrrole-5,5′-dicarboxylate], C
33H
37ClN
2O
4, was determined by single-crystal X-ray diffraction at 130 K. In the crystal structure, the compound forms hydrogen-bonded dimers. The two pyrrole H atoms are bonded to one carbonyl O atom of a symmetry-related molecule. Additional, weaker, C—H
O interactions further stabilize the dimers. The two pyrrole rings are inclined to one another by 63.57 (7)°.
Supporting information
CCDC reference: 264102
Key indicators
- Single-crystal X-ray study
- T = 130 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.117
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 31.00 A 3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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: P3 (Siemens, 1995); cell refinement: P3; data reduction: XDISK (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1995); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
dibenzyl 3,3'-diethyl-4,4'-dimethyl-2,2'-(3-chloropropane-1,1-diyl)dipyrrole-
5,5'-dicarboxylate
top
Crystal data top
C33H37ClN2O4 | Z = 2 |
Mr = 561.10 | F(000) = 596 |
Triclinic, P1 | Dx = 1.248 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.514 (4) Å | Cell parameters from 40 reflections |
b = 13.361 (6) Å | θ = 19–23° |
c = 14.020 (5) Å | µ = 0.17 mm−1 |
α = 92.84 (3)° | T = 130 K |
β = 101.53 (3)° | Block, colorless |
γ = 105.96 (3)° | 0.50 × 0.45 × 0.39 mm |
V = 1493.2 (11) Å3 | |
Data collection top
Siemens R3m/V diffractometer | 5327 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 27.5°, θmin = 1.5° |
ω scans | h = −11→10 |
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995) | k = −17→17 |
Tmin = 0.909, Tmax = 0.939 | l = 0→18 |
7317 measured reflections | 2 standard reflections every 198 reflections |
6854 independent reflections | intensity decay: 1% |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.6397P] where P = (Fo2 + 2Fc2)/3 |
6854 reflections | (Δ/σ)max < 0.001 |
365 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.35 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. The "void" listed as an alert C from CIFCHECK, is located in the
middle of the unit cell and is enclosed by the dimeric aggregates. No evidence
for residual electron density in this area was found. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.86880 (16) | 0.84248 (9) | 0.40702 (9) | 0.0231 (3) | |
H1 | 0.8927 | 0.9112 | 0.4134 | 0.028* | |
C1 | 0.89271 (19) | 0.78220 (11) | 0.48263 (11) | 0.0239 (3) | |
C2 | 0.8381 (2) | 0.67800 (12) | 0.44331 (12) | 0.0258 (3) | |
C3 | 0.7799 (2) | 0.67607 (12) | 0.34109 (12) | 0.0255 (3) | |
C4 | 0.80244 (19) | 0.77918 (11) | 0.32094 (11) | 0.0232 (3) | |
C5 | 0.77050 (19) | 0.82137 (12) | 0.22341 (11) | 0.0244 (3) | |
H5 | 0.7078 | 0.7595 | 0.1741 | 0.029* | |
N2 | 1.04314 (16) | 0.96134 (10) | 0.24056 (9) | 0.0246 (3) | |
H2 | 1.0352 | 0.9944 | 0.2945 | 0.029* | |
C6 | 0.92924 (19) | 0.87283 (11) | 0.19119 (11) | 0.0235 (3) | |
C7 | 0.9857 (2) | 0.84452 (12) | 0.11030 (11) | 0.0263 (3) | |
C8 | 1.1388 (2) | 0.92067 (13) | 0.11068 (12) | 0.0281 (3) | |
C9 | 1.1735 (2) | 0.99173 (12) | 0.19342 (12) | 0.0264 (3) | |
C11 | 0.9804 (2) | 0.83264 (12) | 0.57901 (11) | 0.0249 (3) | |
C12 | 1.0997 (2) | 0.80268 (13) | 0.74047 (12) | 0.0334 (4) | |
H12A | 1.0493 | 0.8492 | 0.7733 | 0.040* | |
H12B | 1.2146 | 0.8431 | 0.7375 | 0.040* | |
C13 | 1.1037 (2) | 0.70967 (12) | 0.79569 (11) | 0.0288 (3) | |
C14 | 1.2523 (2) | 0.70584 (14) | 0.85481 (13) | 0.0343 (4) | |
H14 | 1.3523 | 0.7606 | 0.8580 | 0.041* | |
C15 | 1.2562 (3) | 0.62250 (15) | 0.90952 (14) | 0.0408 (4) | |
H15 | 1.3586 | 0.6207 | 0.9505 | 0.049* | |
C16 | 1.1118 (3) | 0.54227 (15) | 0.90464 (14) | 0.0425 (5) | |
H16 | 1.1148 | 0.4854 | 0.9424 | 0.051* | |
C17 | 0.9632 (3) | 0.54440 (15) | 0.84514 (14) | 0.0435 (5) | |
H17 | 0.8641 | 0.4886 | 0.8412 | 0.052* | |
C18 | 0.9583 (2) | 0.62788 (14) | 0.79112 (13) | 0.0378 (4) | |
H18 | 0.8554 | 0.6295 | 0.7507 | 0.045* | |
O1 | 1.03538 (15) | 0.92778 (8) | 0.60131 (8) | 0.0282 (2) | |
O2 | 0.99939 (15) | 0.76292 (8) | 0.64259 (8) | 0.0312 (3) | |
C21 | 0.8462 (3) | 0.58430 (13) | 0.49646 (13) | 0.0374 (4) | |
H21A | 0.9591 | 0.5967 | 0.5371 | 0.056* | |
H21B | 0.8202 | 0.5226 | 0.4488 | 0.056* | |
H21C | 0.7647 | 0.5723 | 0.5382 | 0.056* | |
C31 | 0.7088 (2) | 0.57901 (12) | 0.26918 (13) | 0.0349 (4) | |
H31A | 0.7847 | 0.5343 | 0.2806 | 0.042* | |
H31B | 0.7045 | 0.5994 | 0.2020 | 0.042* | |
C32 | 0.5335 (3) | 0.51539 (15) | 0.27634 (17) | 0.0510 (5) | |
H32A | 0.5367 | 0.4946 | 0.3426 | 0.077* | |
H32B | 0.4950 | 0.4526 | 0.2288 | 0.077* | |
H32C | 0.4564 | 0.5581 | 0.2622 | 0.077* | |
C51 | 0.6570 (2) | 0.89354 (13) | 0.22014 (12) | 0.0288 (3) | |
H51A | 0.7158 | 0.9568 | 0.2671 | 0.035* | |
H51B | 0.6365 | 0.9163 | 0.1538 | 0.035* | |
C52 | 0.4912 (2) | 0.84169 (14) | 0.24445 (14) | 0.0357 (4) | |
H52A | 0.4265 | 0.8930 | 0.2447 | 0.043* | |
H52B | 0.5110 | 0.8191 | 0.3109 | 0.043* | |
Cl1 | 0.37083 (6) | 0.73010 (4) | 0.15797 (4) | 0.04837 (14) | |
C71 | 0.8987 (2) | 0.75102 (13) | 0.03589 (12) | 0.0337 (4) | |
H71A | 0.8387 | 0.6932 | 0.0686 | 0.040* | |
H71B | 0.9838 | 0.7276 | 0.0095 | 0.040* | |
C72 | 0.7747 (3) | 0.77275 (18) | −0.04841 (15) | 0.0544 (6) | |
H72A | 0.6886 | 0.7945 | −0.0231 | 0.082* | |
H72B | 0.7219 | 0.7091 | −0.0943 | 0.082* | |
H72C | 0.8336 | 0.8287 | −0.0823 | 0.082* | |
C81 | 1.2387 (3) | 0.92726 (15) | 0.03310 (14) | 0.0396 (4) | |
H81A | 1.1895 | 0.9599 | −0.0216 | 0.059* | |
H81B | 1.2374 | 0.8566 | 0.0096 | 0.059* | |
H81C | 1.3546 | 0.9695 | 0.0606 | 0.059* | |
C91 | 1.3165 (2) | 1.08103 (13) | 0.23212 (12) | 0.0298 (3) | |
C92 | 1.4189 (2) | 1.23391 (13) | 0.34861 (14) | 0.0377 (4) | |
H92A | 1.3644 | 1.2875 | 0.3637 | 0.045* | |
H92B | 1.4835 | 1.2587 | 0.2986 | 0.045* | |
C93 | 1.5378 (2) | 1.22359 (13) | 0.43993 (13) | 0.0337 (4) | |
C94 | 1.6072 (2) | 1.30919 (14) | 0.51102 (15) | 0.0405 (4) | |
H94 | 1.5726 | 1.3706 | 0.5030 | 0.049* | |
C95 | 1.7260 (3) | 1.30640 (17) | 0.59338 (15) | 0.0467 (5) | |
H95 | 1.7748 | 1.3663 | 0.6404 | 0.056* | |
C96 | 1.7733 (2) | 1.21642 (18) | 0.60708 (15) | 0.0457 (5) | |
H96 | 1.8542 | 1.2140 | 0.6637 | 0.055* | |
C97 | 1.7028 (2) | 1.13028 (17) | 0.53835 (15) | 0.0447 (5) | |
H97 | 1.7337 | 1.0679 | 0.5484 | 0.054* | |
C98 | 1.5867 (2) | 1.13377 (15) | 0.45437 (15) | 0.0395 (4) | |
H98 | 1.5407 | 1.0744 | 0.4067 | 0.047* | |
O3 | 1.44559 (15) | 1.10451 (10) | 0.20324 (10) | 0.0412 (3) | |
O4 | 1.29119 (15) | 1.13724 (9) | 0.30841 (9) | 0.0338 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0293 (7) | 0.0212 (6) | 0.0215 (6) | 0.0097 (5) | 0.0080 (5) | 0.0028 (5) |
C1 | 0.0282 (8) | 0.0259 (7) | 0.0221 (7) | 0.0118 (6) | 0.0092 (6) | 0.0054 (6) |
C2 | 0.0282 (8) | 0.0244 (7) | 0.0280 (8) | 0.0104 (6) | 0.0099 (6) | 0.0040 (6) |
C3 | 0.0272 (8) | 0.0255 (7) | 0.0259 (8) | 0.0091 (6) | 0.0096 (6) | 0.0008 (6) |
C4 | 0.0237 (7) | 0.0263 (7) | 0.0216 (7) | 0.0093 (6) | 0.0074 (6) | 0.0013 (6) |
C5 | 0.0266 (8) | 0.0258 (7) | 0.0217 (7) | 0.0089 (6) | 0.0060 (6) | 0.0013 (6) |
N2 | 0.0271 (7) | 0.0284 (6) | 0.0206 (6) | 0.0099 (5) | 0.0087 (5) | 0.0013 (5) |
C6 | 0.0257 (7) | 0.0260 (7) | 0.0203 (7) | 0.0103 (6) | 0.0045 (6) | 0.0027 (6) |
C7 | 0.0335 (8) | 0.0285 (7) | 0.0212 (7) | 0.0145 (6) | 0.0080 (6) | 0.0033 (6) |
C8 | 0.0319 (8) | 0.0354 (8) | 0.0237 (8) | 0.0164 (7) | 0.0115 (6) | 0.0073 (6) |
C9 | 0.0263 (8) | 0.0311 (8) | 0.0262 (8) | 0.0116 (6) | 0.0108 (6) | 0.0050 (6) |
C11 | 0.0305 (8) | 0.0256 (7) | 0.0241 (8) | 0.0123 (6) | 0.0125 (6) | 0.0060 (6) |
C12 | 0.0444 (10) | 0.0293 (8) | 0.0240 (8) | 0.0099 (7) | 0.0029 (7) | 0.0037 (6) |
C13 | 0.0388 (9) | 0.0291 (8) | 0.0214 (8) | 0.0118 (7) | 0.0102 (7) | 0.0039 (6) |
C14 | 0.0386 (9) | 0.0382 (9) | 0.0286 (9) | 0.0133 (7) | 0.0100 (7) | 0.0051 (7) |
C15 | 0.0505 (11) | 0.0480 (11) | 0.0332 (10) | 0.0276 (9) | 0.0105 (8) | 0.0110 (8) |
C16 | 0.0697 (14) | 0.0363 (9) | 0.0332 (10) | 0.0244 (9) | 0.0231 (9) | 0.0147 (8) |
C17 | 0.0535 (12) | 0.0353 (9) | 0.0395 (11) | 0.0049 (8) | 0.0150 (9) | 0.0102 (8) |
C18 | 0.0387 (10) | 0.0404 (9) | 0.0324 (9) | 0.0079 (8) | 0.0074 (8) | 0.0097 (7) |
O1 | 0.0387 (6) | 0.0244 (5) | 0.0233 (6) | 0.0101 (5) | 0.0101 (5) | 0.0016 (4) |
O2 | 0.0446 (7) | 0.0265 (5) | 0.0215 (6) | 0.0106 (5) | 0.0043 (5) | 0.0052 (4) |
C21 | 0.0535 (11) | 0.0258 (8) | 0.0344 (10) | 0.0143 (8) | 0.0087 (8) | 0.0060 (7) |
C31 | 0.0491 (11) | 0.0261 (8) | 0.0288 (9) | 0.0108 (7) | 0.0084 (8) | 0.0000 (6) |
C32 | 0.0512 (12) | 0.0333 (10) | 0.0549 (13) | −0.0011 (8) | 0.0005 (10) | 0.0004 (9) |
C51 | 0.0268 (8) | 0.0312 (8) | 0.0302 (8) | 0.0115 (6) | 0.0055 (6) | 0.0059 (6) |
C52 | 0.0298 (9) | 0.0421 (9) | 0.0390 (10) | 0.0157 (7) | 0.0081 (7) | 0.0061 (8) |
Cl1 | 0.0332 (2) | 0.0439 (3) | 0.0601 (3) | 0.00566 (19) | 0.0007 (2) | 0.0031 (2) |
C71 | 0.0442 (10) | 0.0332 (8) | 0.0265 (8) | 0.0141 (7) | 0.0109 (7) | 0.0003 (7) |
C72 | 0.0606 (14) | 0.0564 (13) | 0.0376 (11) | 0.0180 (11) | −0.0076 (10) | −0.0052 (9) |
C81 | 0.0466 (11) | 0.0478 (10) | 0.0334 (10) | 0.0187 (9) | 0.0218 (8) | 0.0077 (8) |
C91 | 0.0302 (8) | 0.0333 (8) | 0.0288 (8) | 0.0116 (7) | 0.0088 (7) | 0.0076 (6) |
C92 | 0.0359 (9) | 0.0285 (8) | 0.0438 (11) | 0.0048 (7) | 0.0042 (8) | 0.0028 (7) |
C93 | 0.0278 (8) | 0.0354 (9) | 0.0380 (10) | 0.0059 (7) | 0.0118 (7) | 0.0049 (7) |
C94 | 0.0390 (10) | 0.0346 (9) | 0.0446 (11) | 0.0059 (8) | 0.0093 (8) | 0.0009 (8) |
C95 | 0.0391 (11) | 0.0512 (11) | 0.0414 (11) | 0.0017 (9) | 0.0071 (9) | −0.0011 (9) |
C96 | 0.0279 (9) | 0.0688 (13) | 0.0409 (11) | 0.0134 (9) | 0.0088 (8) | 0.0102 (10) |
C97 | 0.0382 (10) | 0.0562 (12) | 0.0486 (12) | 0.0229 (9) | 0.0154 (9) | 0.0121 (9) |
C98 | 0.0377 (10) | 0.0411 (10) | 0.0424 (11) | 0.0154 (8) | 0.0101 (8) | 0.0021 (8) |
O3 | 0.0302 (7) | 0.0485 (7) | 0.0452 (8) | 0.0055 (6) | 0.0163 (6) | 0.0082 (6) |
O4 | 0.0306 (6) | 0.0319 (6) | 0.0360 (7) | 0.0048 (5) | 0.0081 (5) | −0.0019 (5) |
Geometric parameters (Å, º) top
N1—C4 | 1.362 (2) | C21—H21B | 0.9800 |
N1—C1 | 1.3793 (19) | C21—H21C | 0.9800 |
N1—H1 | 0.8800 | C31—C32 | 1.526 (3) |
C1—C2 | 1.387 (2) | C31—H31A | 0.9900 |
C1—C11 | 1.438 (2) | C31—H31B | 0.9900 |
C2—C3 | 1.416 (2) | C32—H32A | 0.9800 |
C2—C21 | 1.499 (2) | C32—H32B | 0.9800 |
C3—C4 | 1.389 (2) | C32—H32C | 0.9800 |
C3—C31 | 1.503 (2) | C51—C52 | 1.506 (2) |
C4—C5 | 1.508 (2) | C51—H51A | 0.9900 |
C5—C6 | 1.506 (2) | C51—H51B | 0.9900 |
C5—C51 | 1.538 (2) | C52—Cl1 | 1.796 (2) |
C5—H5 | 1.0000 | C52—H52A | 0.9900 |
N2—C6 | 1.356 (2) | C52—H52B | 0.9900 |
N2—C9 | 1.380 (2) | C71—C72 | 1.516 (3) |
N2—H2 | 0.8800 | C71—H71A | 0.9900 |
C6—C7 | 1.391 (2) | C71—H71B | 0.9900 |
C7—C8 | 1.415 (2) | C72—H72A | 0.9800 |
C7—C71 | 1.500 (2) | C72—H72B | 0.9800 |
C8—C9 | 1.391 (2) | C72—H72C | 0.9800 |
C8—C81 | 1.501 (2) | C81—H81A | 0.9800 |
C9—C91 | 1.440 (2) | C81—H81B | 0.9800 |
C11—O1 | 1.2278 (19) | C81—H81C | 0.9800 |
C11—O2 | 1.3401 (18) | C91—O3 | 1.213 (2) |
C12—O2 | 1.451 (2) | C91—O4 | 1.362 (2) |
C12—C13 | 1.501 (2) | C92—O4 | 1.442 (2) |
C12—H12A | 0.9900 | C92—C93 | 1.503 (3) |
C12—H12B | 0.9900 | C92—H92A | 0.9900 |
C13—C14 | 1.382 (3) | C92—H92B | 0.9900 |
C13—C18 | 1.396 (2) | C93—C98 | 1.386 (3) |
C14—C15 | 1.387 (2) | C93—C94 | 1.389 (3) |
C14—H14 | 0.9500 | C94—C95 | 1.384 (3) |
C15—C16 | 1.378 (3) | C94—H94 | 0.9500 |
C15—H15 | 0.9500 | C95—C96 | 1.380 (3) |
C16—C17 | 1.377 (3) | C95—H95 | 0.9500 |
C16—H16 | 0.9500 | C96—C97 | 1.376 (3) |
C17—C18 | 1.384 (3) | C96—H96 | 0.9500 |
C17—H17 | 0.9500 | C97—C98 | 1.389 (3) |
C18—H18 | 0.9500 | C97—H97 | 0.9500 |
C21—H21A | 0.9800 | C98—H98 | 0.9500 |
| | | |
C4—N1—C1 | 109.47 (13) | C3—C31—C32 | 113.27 (16) |
C4—N1—H1 | 125.3 | C3—C31—H31A | 108.9 |
C1—N1—H1 | 125.3 | C32—C31—H31A | 108.9 |
N1—C1—C2 | 107.93 (14) | C3—C31—H31B | 108.9 |
N1—C1—C11 | 119.44 (13) | C32—C31—H31B | 108.9 |
C2—C1—C11 | 132.17 (14) | H31A—C31—H31B | 107.7 |
C1—C2—C3 | 107.06 (14) | C31—C32—H32A | 109.5 |
C1—C2—C21 | 127.32 (15) | C31—C32—H32B | 109.5 |
C3—C2—C21 | 125.55 (14) | H32A—C32—H32B | 109.5 |
C4—C3—C2 | 107.39 (14) | C31—C32—H32C | 109.5 |
C4—C3—C31 | 127.29 (15) | H32A—C32—H32C | 109.5 |
C2—C3—C31 | 125.32 (14) | H32B—C32—H32C | 109.5 |
N1—C4—C3 | 108.14 (14) | C52—C51—C5 | 113.04 (14) |
N1—C4—C5 | 122.65 (13) | C52—C51—H51A | 109.0 |
C3—C4—C5 | 129.15 (14) | C5—C51—H51A | 109.0 |
C6—C5—C4 | 112.91 (13) | C52—C51—H51B | 109.0 |
C6—C5—C51 | 111.53 (13) | C5—C51—H51B | 109.0 |
C4—C5—C51 | 112.59 (13) | H51A—C51—H51B | 107.8 |
C6—C5—H5 | 106.4 | C51—C52—Cl1 | 111.78 (13) |
C4—C5—H5 | 106.4 | C51—C52—H52A | 109.3 |
C51—C5—H5 | 106.4 | Cl1—C52—H52A | 109.3 |
C6—N2—C9 | 109.64 (13) | C51—C52—H52B | 109.3 |
C6—N2—H2 | 125.2 | Cl1—C52—H52B | 109.3 |
C9—N2—H2 | 125.2 | H52A—C52—H52B | 107.9 |
N2—C6—C7 | 108.20 (14) | C7—C71—C72 | 113.18 (15) |
N2—C6—C5 | 122.33 (14) | C7—C71—H71A | 108.9 |
C7—C6—C5 | 129.46 (14) | C72—C71—H71A | 108.9 |
C6—C7—C8 | 107.41 (14) | C7—C71—H71B | 108.9 |
C6—C7—C71 | 126.12 (15) | C72—C71—H71B | 108.9 |
C8—C7—C71 | 126.47 (15) | H71A—C71—H71B | 107.8 |
C9—C8—C7 | 106.93 (14) | C71—C72—H72A | 109.5 |
C9—C8—C81 | 126.55 (16) | C71—C72—H72B | 109.5 |
C7—C8—C81 | 126.42 (16) | H72A—C72—H72B | 109.5 |
N2—C9—C8 | 107.79 (14) | C71—C72—H72C | 109.5 |
N2—C9—C91 | 121.75 (14) | H72A—C72—H72C | 109.5 |
C8—C9—C91 | 130.42 (15) | H72B—C72—H72C | 109.5 |
O1—C11—O2 | 123.23 (15) | C8—C81—H81A | 109.5 |
O1—C11—C1 | 124.98 (14) | C8—C81—H81B | 109.5 |
O2—C11—C1 | 111.77 (13) | H81A—C81—H81B | 109.5 |
O2—C12—C13 | 107.12 (13) | C8—C81—H81C | 109.5 |
O2—C12—H12A | 110.3 | H81A—C81—H81C | 109.5 |
C13—C12—H12A | 110.3 | H81B—C81—H81C | 109.5 |
O2—C12—H12B | 110.3 | O3—C91—O4 | 122.88 (16) |
C13—C12—H12B | 110.3 | O3—C91—C9 | 125.82 (16) |
H12A—C12—H12B | 108.5 | O4—C91—C9 | 111.29 (14) |
C14—C13—C18 | 118.97 (16) | O4—C92—C93 | 113.25 (15) |
C14—C13—C12 | 119.88 (16) | O4—C92—H92A | 108.9 |
C18—C13—C12 | 121.12 (16) | C93—C92—H92A | 108.9 |
C13—C14—C15 | 120.42 (17) | O4—C92—H92B | 108.9 |
C13—C14—H14 | 119.8 | C93—C92—H92B | 108.9 |
C15—C14—H14 | 119.8 | H92A—C92—H92B | 107.7 |
C16—C15—C14 | 120.14 (18) | C98—C93—C94 | 118.53 (18) |
C16—C15—H15 | 119.9 | C98—C93—C92 | 122.73 (17) |
C14—C15—H15 | 119.9 | C94—C93—C92 | 118.69 (17) |
C17—C16—C15 | 120.09 (17) | C95—C94—C93 | 121.09 (19) |
C17—C16—H16 | 120.0 | C95—C94—H94 | 119.5 |
C15—C16—H16 | 120.0 | C93—C94—H94 | 119.5 |
C16—C17—C18 | 120.02 (18) | C96—C95—C94 | 119.82 (19) |
C16—C17—H17 | 120.0 | C96—C95—H95 | 120.1 |
C18—C17—H17 | 120.0 | C94—C95—H95 | 120.1 |
C17—C18—C13 | 120.35 (18) | C97—C96—C95 | 119.68 (19) |
C17—C18—H18 | 119.8 | C97—C96—H96 | 120.2 |
C13—C18—H18 | 119.8 | C95—C96—H96 | 120.2 |
C11—O2—C12 | 117.74 (13) | C96—C97—C98 | 120.59 (19) |
C2—C21—H21A | 109.5 | C96—C97—H97 | 119.7 |
C2—C21—H21B | 109.5 | C98—C97—H97 | 119.7 |
H21A—C21—H21B | 109.5 | C93—C98—C97 | 120.25 (19) |
C2—C21—H21C | 109.5 | C93—C98—H98 | 119.9 |
H21A—C21—H21C | 109.5 | C97—C98—H98 | 119.9 |
H21B—C21—H21C | 109.5 | C91—O4—C92 | 117.02 (14) |
| | | |
C4—N1—C1—C2 | −0.73 (17) | C2—C1—C11—O1 | 172.65 (17) |
C4—N1—C1—C11 | 172.48 (14) | N1—C1—C11—O2 | −177.16 (13) |
N1—C1—C2—C3 | 0.06 (17) | C2—C1—C11—O2 | −5.9 (2) |
C11—C1—C2—C3 | −171.95 (16) | O2—C12—C13—C14 | 137.08 (16) |
N1—C1—C2—C21 | 177.02 (16) | O2—C12—C13—C18 | −45.1 (2) |
C11—C1—C2—C21 | 5.0 (3) | C18—C13—C14—C15 | −0.7 (3) |
C1—C2—C3—C4 | 0.61 (18) | C12—C13—C14—C15 | 177.17 (16) |
C21—C2—C3—C4 | −176.42 (16) | C13—C14—C15—C16 | 0.6 (3) |
C1—C2—C3—C31 | −179.86 (15) | C14—C15—C16—C17 | 0.2 (3) |
C21—C2—C3—C31 | 3.1 (3) | C15—C16—C17—C18 | −0.9 (3) |
C1—N1—C4—C3 | 1.12 (17) | C16—C17—C18—C13 | 0.7 (3) |
C1—N1—C4—C5 | −176.41 (14) | C14—C13—C18—C17 | 0.1 (3) |
C2—C3—C4—N1 | −1.06 (17) | C12—C13—C18—C17 | −177.79 (17) |
C31—C3—C4—N1 | 179.43 (15) | O1—C11—O2—C12 | −4.3 (2) |
C2—C3—C4—C5 | 176.26 (15) | C1—C11—O2—C12 | 174.27 (14) |
C31—C3—C4—C5 | −3.3 (3) | C13—C12—O2—C11 | −178.93 (14) |
N1—C4—C5—C6 | 71.21 (18) | C4—C3—C31—C32 | −107.8 (2) |
C3—C4—C5—C6 | −105.77 (18) | C2—C3—C31—C32 | 72.7 (2) |
N1—C4—C5—C51 | −56.19 (19) | C6—C5—C51—C52 | 175.59 (14) |
C3—C4—C5—C51 | 126.83 (17) | C4—C5—C51—C52 | −56.29 (19) |
C9—N2—C6—C7 | 0.03 (17) | C5—C51—C52—Cl1 | −62.05 (17) |
C9—N2—C6—C5 | −178.75 (13) | C6—C7—C71—C72 | 88.3 (2) |
C4—C5—C6—N2 | −65.19 (18) | C8—C7—C71—C72 | −90.9 (2) |
C51—C5—C6—N2 | 62.76 (19) | N2—C9—C91—O3 | 169.26 (16) |
C4—C5—C6—C7 | 116.31 (17) | C8—C9—C91—O3 | −8.5 (3) |
C51—C5—C6—C7 | −115.74 (18) | N2—C9—C91—O4 | −9.7 (2) |
N2—C6—C7—C8 | −0.99 (17) | C8—C9—C91—O4 | 172.54 (16) |
C5—C6—C7—C8 | 177.67 (15) | O4—C92—C93—C98 | 34.7 (3) |
N2—C6—C7—C71 | 179.64 (14) | O4—C92—C93—C94 | −148.13 (17) |
C5—C6—C7—C71 | −1.7 (3) | C98—C93—C94—C95 | 1.7 (3) |
C6—C7—C8—C9 | 1.57 (17) | C92—C93—C94—C95 | −175.57 (18) |
C71—C7—C8—C9 | −179.07 (15) | C93—C94—C95—C96 | −1.9 (3) |
C6—C7—C8—C81 | −174.83 (16) | C94—C95—C96—C97 | 0.4 (3) |
C71—C7—C8—C81 | 4.5 (3) | C95—C96—C97—C98 | 1.3 (3) |
C6—N2—C9—C8 | 0.97 (17) | C94—C93—C98—C97 | 0.0 (3) |
C6—N2—C9—C91 | −177.23 (14) | C92—C93—C98—C97 | 177.11 (18) |
C7—C8—C9—N2 | −1.55 (17) | C96—C97—C98—C93 | −1.4 (3) |
C81—C8—C9—N2 | 174.84 (15) | O3—C91—O4—C92 | 6.2 (2) |
C7—C8—C9—C91 | 176.44 (16) | C9—C91—O4—C92 | −174.77 (14) |
C81—C8—C9—C91 | −7.2 (3) | C93—C92—O4—C91 | −98.98 (18) |
N1—C1—C11—O1 | 1.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 | 2.10 | 2.966 (2) | 167 |
N2—H2···O1i | 0.88 | 2.03 | 2.893 (2) | 166 |
C5—H5···Cl1 | 1.00 | 2.75 | 3.204 (2) | 108 |
C14—H14···O3ii | 0.95 | 2.45 | 3.340 (3) | 157 |
C21—H21A···O2 | 0.98 | 2.51 | 2.886 (2) | 103 |
C51—H51A···O1i | 0.99 | 2.57 | 3.489 (3) | 154 |
C81—H81C···O3 | 0.98 | 2.47 | 3.141 (3) | 125 |
C92—H92B···O3 | 0.99 | 2.31 | 2.692 (3) | 102 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+3, −y+2, −z+1. |