The coplanar arrangement of rings in the title molecule, C
25H
18Cl
3N
3O
4, is accompanied by the formation of short intramolecular O
H (2.20 and 2.26 Å) contacts. A strong N—H
N hydrogen bond [N
N = 2.698 (4) Å and N—H
N = 142°] is present and, as a result, the exocyclic bond angles at the C atoms in the 2- and 3-positions of the pyranone ring are slightly distorted. The coplanar rings form a layered structure in which a short intermolecular Cl
Cl(−
x, 1 −
y, 1 −
z) contact of 3.280 (2) Å is observed.
Supporting information
CCDC reference: 234861
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.071
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for Cl1 - C12 = 13.55 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C2 = 11.35 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C23 = 9.08 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for O4 - C24 = 7.83 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for N7 - C6 = 7.77 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 - C16 = 16.38 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 - C6 = 11.54 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C13 - C14 = 10.62 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C17 - C18 = 8.68 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C17 - C22 = 10.68 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C18 - C19 = 10.32 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C19 - C20 = 11.88 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C20 - C21 = 9.83 su
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C16 = 5.32 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 = 6.76 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C24 - C25 = 6.67 su
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C24
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.30
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C3 - C16 = 1.54 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. Cl1 = 3.28 Ang.
0 ALERT level A = In general: serious problem
13 ALERT level B = Potentially serious problem
8 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
20 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK, XPREP (Siemens, 1991); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C25H18Cl3N3O4 | Z = 2 |
Mr = 530.77 | F(000) = 544 |
Triclinic, P1 | Dx = 1.501 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.020 (2) Å | Cell parameters from 24 reflections |
b = 11.390 (3) Å | θ = 20–22° |
c = 12.890 (3) Å | µ = 0.43 mm−1 |
α = 73.95 (2)° | T = 293 K |
β = 86.18 (2)° | Polyhedron, yellow |
γ = 67.49 (2)° | 0.25 × 0.2 × 0.2 mm |
V = 1174.5 (5) Å3 | |
Data collection top
Siemens P3/PC diffractometer | θmax = 25.0°, θmin = 2.5° |
2θ/ω scans | h = −9→10 |
4323 measured reflections | k = 0→13 |
4106 independent reflections | l = −14→15 |
1737 reflections with I > 2σ(I) | 2 standard reflections every 98 reflections |
Rint = 0.077 | intensity decay: 1% |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = exp(2.00(sinθ/λ)2)/σ2(Fo2) |
R[F2 > 2σ(F2)] = 0.043 | (Δ/σ)max = 0.01 |
wR(F2) = 0.071 | Δρmax = 0.19 e Å−3 |
S = 0.92 | Δρmin = −0.15 e Å−3 |
4106 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
317 parameters | Extinction coefficient: 0.0060 (5) |
0 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.11722 (7) | 0.51062 (7) | 0.39792 (5) | 0.0935 (2) | |
Cl2 | 0.25202 (7) | 0.50208 (6) | 0.16860 (5) | 0.07838 (18) | |
Cl3 | 1.18957 (7) | 0.98670 (7) | 0.12625 (5) | 0.0818 (2) | |
O1 | 0.35305 (13) | 0.72038 (12) | 0.58927 (9) | 0.0510 (4) | |
C2 | 0.4710 (2) | 0.75370 (18) | 0.53230 (15) | 0.0427 (5) | |
C3 | 0.5543 (2) | 0.81505 (19) | 0.58056 (15) | 0.0475 (6) | |
C4 | 0.52092 (19) | 0.82912 (19) | 0.68041 (14) | 0.0453 (5) | |
H4 | 0.5769 | 0.8657 | 0.7112 | 0.054* | |
C4A | 0.4016 (2) | 0.78914 (19) | 0.74052 (14) | 0.0444 (6) | |
C5 | 0.3622 (2) | 0.7954 (2) | 0.84744 (15) | 0.0530 (6) | |
C6 | 0.2424 (2) | 0.7503 (2) | 0.89325 (16) | 0.0646 (6) | |
H6 | 0.2133 | 0.7565 | 0.9627 | 0.078* | |
N7 | 0.16775 (18) | 0.69951 (18) | 0.84422 (14) | 0.0658 (6) | |
C8 | 0.1994 (2) | 0.6940 (2) | 0.74420 (16) | 0.0557 (6) | |
C8A | 0.3207 (2) | 0.73430 (19) | 0.69206 (15) | 0.0441 (6) | |
N1 | 0.50580 (16) | 0.73224 (15) | 0.43971 (12) | 0.0507 (5) | |
C10 | 0.4365 (2) | 0.67431 (19) | 0.38233 (15) | 0.0495 (6) | |
C11 | 0.3193 (2) | 0.62361 (19) | 0.41863 (16) | 0.0511 (6) | |
H11 | 0.2793 | 0.6253 | 0.4868 | 0.061* | |
C12 | 0.2611 (2) | 0.5702 (2) | 0.35315 (16) | 0.0542 (6) | |
C13 | 0.3219 (2) | 0.5657 (2) | 0.25138 (16) | 0.0577 (6) | |
C14 | 0.4424 (2) | 0.6138 (2) | 0.21785 (16) | 0.0641 (6) | |
H14 | 0.4855 | 0.6103 | 0.1507 | 0.077* | |
C15 | 0.4989 (2) | 0.6666 (2) | 0.28337 (15) | 0.0559 (6) | |
H15 | 0.5805 | 0.6974 | 0.2601 | 0.067* | |
C16 | 0.6852 (2) | 0.86291 (19) | 0.52368 (14) | 0.0480 (5) | |
O2 | 0.73725 (15) | 0.92131 (14) | 0.56770 (11) | 0.0719 (4) | |
N2 | 0.72985 (17) | 0.83695 (16) | 0.43170 (12) | 0.0542 (5) | |
H2 | 0.6864 | 0.7937 | 0.4105 | 0.065* | |
C17 | 0.8441 (2) | 0.87390 (19) | 0.36290 (14) | 0.0517 (6) | |
C18 | 0.9441 (2) | 0.9266 (2) | 0.39163 (16) | 0.0534 (6) | |
H18 | 0.94 | 0.9396 | 0.46 | 0.064* | |
C19 | 1.0510 (2) | 0.9603 (2) | 0.31876 (16) | 0.0632 (7) | |
H19 | 1.118 | 0.9964 | 0.3381 | 0.076* | |
C20 | 1.0577 (2) | 0.9406 (2) | 0.21916 (17) | 0.0640 (7) | |
C21 | 0.9621 (2) | 0.8859 (2) | 0.19042 (16) | 0.0630 (7) | |
H21 | 0.9684 | 0.8724 | 0.122 | 0.076* | |
C22 | 0.8584 (2) | 0.8508 (2) | 0.26031 (16) | 0.0515 (6) | |
H22 | 0.7959 | 0.8113 | 0.2404 | 0.062* | |
C23 | 0.4480 (2) | 0.8470 (2) | 0.91081 (16) | 0.0615 (6) | |
H23A | 0.4447 | 0.9332 | 0.8695 | 0.074* | |
H23B | 0.396 | 0.8551 | 0.9783 | 0.074* | |
O3 | 0.60924 (14) | 0.75544 (13) | 0.93177 (11) | 0.0599 (4) | |
C24 | 0.6894 (2) | 0.7581 (2) | 1.01209 (15) | 0.0487 (6) | |
O4 | 0.63530 (16) | 0.83786 (15) | 1.06191 (11) | 0.0751 (5) | |
C25 | 0.8529 (2) | 0.6556 (2) | 1.0276 (2) | 0.0794 (8) | |
H25A | 0.9054 | 0.6563 | 1.0897 | 0.095* | |
H25B | 0.9124 | 0.6735 | 0.9647 | 0.095* | |
H25C | 0.8477 | 0.5704 | 1.0384 | 0.095* | |
C26 | 0.1048 (2) | 0.6442 (2) | 0.68991 (18) | 0.0750 (7) | |
H26A | 0.1766 | 0.5709 | 0.6652 | 0.09* | |
H26B | 0.0431 | 0.7133 | 0.6293 | 0.09* | |
H26C | 0.0337 | 0.6159 | 0.7402 | 0.09* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0945 (3) | 0.1211 (4) | 0.1039 (5) | −0.0728 (3) | 0.0094 (3) | −0.0459 (4) |
Cl2 | 0.0937 (3) | 0.0921 (3) | 0.0705 (3) | −0.0421 (3) | −0.0229 (3) | −0.0388 (3) |
Cl3 | 0.0922 (4) | 0.1021 (4) | 0.0694 (4) | −0.0580 (3) | 0.0342 (3) | −0.0284 (3) |
O1 | 0.0576 (6) | 0.0796 (8) | 0.0392 (7) | −0.0471 (6) | 0.0060 (6) | −0.0228 (6) |
C2 | 0.0429 (9) | 0.0495 (11) | 0.0430 (10) | −0.0179 (9) | −0.0024 (9) | −0.0226 (9) |
C3 | 0.0561 (11) | 0.0442 (11) | 0.0437 (11) | −0.0198 (9) | −0.0171 (9) | −0.0086 (9) |
C4 | 0.0369 (9) | 0.0660 (11) | 0.0467 (11) | −0.0256 (9) | −0.0027 (8) | −0.0265 (9) |
C4A | 0.0408 (10) | 0.0539 (11) | 0.0436 (11) | −0.0149 (9) | 0.0017 (9) | −0.0257 (9) |
C5 | 0.0469 (11) | 0.0686 (13) | 0.0441 (11) | −0.0143 (10) | −0.0072 (9) | −0.0253 (10) |
C6 | 0.0725 (12) | 0.1051 (14) | 0.0424 (11) | −0.0538 (11) | 0.0180 (10) | −0.0350 (10) |
N7 | 0.0617 (10) | 0.0930 (13) | 0.0574 (11) | −0.0435 (9) | 0.0162 (9) | −0.0260 (10) |
C8 | 0.0543 (11) | 0.0676 (14) | 0.0505 (12) | −0.0299 (10) | −0.0003 (10) | −0.0142 (11) |
C8A | 0.0417 (10) | 0.0560 (12) | 0.0372 (10) | −0.0204 (9) | −0.0022 (9) | −0.0129 (9) |
N1 | 0.0641 (8) | 0.0690 (9) | 0.0436 (9) | −0.0445 (8) | −0.0005 (7) | −0.0249 (8) |
C10 | 0.0505 (10) | 0.0678 (12) | 0.0469 (11) | −0.0312 (9) | −0.0022 (9) | −0.0276 (9) |
C11 | 0.0550 (10) | 0.0658 (12) | 0.0487 (11) | −0.0369 (9) | −0.0031 (9) | −0.0194 (9) |
C12 | 0.0520 (10) | 0.0653 (12) | 0.0574 (13) | −0.0329 (10) | −0.0064 (10) | −0.0182 (10) |
C13 | 0.0722 (12) | 0.0545 (12) | 0.0532 (12) | −0.0247 (10) | −0.0192 (10) | −0.0192 (10) |
C14 | 0.0809 (12) | 0.0899 (14) | 0.0425 (11) | −0.0525 (11) | −0.0010 (10) | −0.0209 (10) |
C15 | 0.0561 (10) | 0.0857 (13) | 0.0515 (12) | −0.0450 (10) | 0.0080 (10) | −0.0335 (10) |
C16 | 0.0635 (10) | 0.0700 (11) | 0.0352 (10) | −0.0495 (9) | −0.0021 (9) | −0.0166 (9) |
O2 | 0.0818 (7) | 0.1204 (9) | 0.0585 (8) | −0.0713 (7) | 0.0108 (7) | −0.0485 (7) |
N2 | 0.0739 (9) | 0.0764 (10) | 0.0357 (9) | −0.0501 (8) | 0.0061 (8) | −0.0214 (8) |
C17 | 0.0726 (11) | 0.0745 (12) | 0.0299 (10) | −0.0485 (10) | −0.0038 (9) | −0.0168 (9) |
C18 | 0.0535 (10) | 0.0767 (13) | 0.0411 (11) | −0.0339 (10) | 0.0032 (9) | −0.0203 (10) |
C19 | 0.0681 (12) | 0.0864 (14) | 0.0543 (13) | −0.0443 (11) | −0.0033 (11) | −0.0256 (11) |
C20 | 0.0616 (10) | 0.0868 (14) | 0.0615 (14) | −0.0534 (10) | −0.0001 (10) | −0.0110 (11) |
C21 | 0.0831 (13) | 0.0941 (14) | 0.0329 (11) | −0.0525 (12) | 0.0130 (10) | −0.0251 (10) |
C22 | 0.0519 (10) | 0.0655 (12) | 0.0534 (12) | −0.0346 (9) | 0.0049 (10) | −0.0243 (10) |
C23 | 0.0578 (12) | 0.0850 (14) | 0.0531 (11) | −0.0201 (11) | −0.0048 (10) | −0.0451 (10) |
O3 | 0.0433 (7) | 0.0804 (9) | 0.0652 (8) | −0.0133 (7) | −0.0033 (6) | −0.0471 (7) |
C24 | 0.0424 (10) | 0.0750 (13) | 0.0399 (10) | −0.0275 (10) | 0.0020 (9) | −0.0257 (10) |
O4 | 0.0856 (9) | 0.1098 (10) | 0.0544 (8) | −0.0469 (8) | 0.0014 (7) | −0.0458 (7) |
C25 | 0.0538 (13) | 0.1005 (17) | 0.0910 (17) | −0.0300 (13) | −0.0003 (12) | −0.0356 (14) |
C26 | 0.0711 (11) | 0.1157 (15) | 0.0732 (15) | −0.0689 (11) | 0.0103 (11) | −0.0331 (12) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.684 (2) | C14—H14 | 0.9299 |
Cl2—C13 | 1.711 (2) | C15—H15 | 0.93 |
Cl3—C20 | 1.751 (2) | C16—O2 | 1.212 (2) |
O1—C2 | 1.366 (2) | C16—N2 | 1.302 (2) |
O1—C8A | 1.376 (2) | N2—C17 | 1.425 (2) |
C2—N1 | 1.279 (2) | N2—H2 | 0.8412 |
C2—C3 | 1.464 (3) | C17—C18 | 1.375 (3) |
C3—C4 | 1.341 (3) | C17—C22 | 1.406 (3) |
C3—C16 | 1.545 (3) | C18—C19 | 1.387 (3) |
C4—C4A | 1.427 (3) | C18—H18 | 0.93 |
C4—H4 | 0.93 | C19—C20 | 1.356 (3) |
C4A—C8A | 1.392 (3) | C19—H19 | 0.93 |
C4A—C5 | 1.414 (3) | C20—C21 | 1.361 (3) |
C5—C6 | 1.397 (3) | C21—C22 | 1.350 (3) |
C5—C23 | 1.519 (3) | C21—H21 | 0.9299 |
C6—N7 | 1.321 (3) | C22—H22 | 0.9301 |
C6—H6 | 0.93 | C23—O3 | 1.418 (2) |
N7—C8 | 1.315 (3) | C23—H23A | 0.97 |
C8—C8A | 1.406 (3) | C23—H23B | 0.97 |
C8—C26 | 1.487 (3) | O3—C24 | 1.315 (2) |
N1—C10 | 1.421 (2) | C24—O4 | 1.191 (2) |
C10—C15 | 1.371 (3) | C24—C25 | 1.473 (3) |
C10—C11 | 1.386 (3) | C25—H25A | 0.9599 |
C11—C12 | 1.395 (3) | C25—H25B | 0.96 |
C11—H11 | 0.9301 | C25—H25C | 0.96 |
C12—C13 | 1.394 (3) | C26—H26A | 0.9599 |
C13—C14 | 1.390 (3) | C26—H26B | 0.96 |
C14—C15 | 1.381 (3) | C26—H26C | 0.9599 |
| | | |
C2—O1—C8A | 121.61 (15) | O2—C16—C3 | 117.77 (17) |
N1—C2—O1 | 120.56 (17) | N2—C16—C3 | 116.67 (17) |
N1—C2—C3 | 121.67 (18) | C16—N2—C17 | 127.15 (18) |
O1—C2—C3 | 117.78 (16) | C16—N2—H2 | 116.4 |
C4—C3—C2 | 119.94 (18) | C17—N2—H2 | 116.4 |
C4—C3—C16 | 116.52 (18) | C18—C17—C22 | 118.21 (18) |
C2—C3—C16 | 123.52 (17) | C18—C17—N2 | 124.27 (17) |
C3—C4—C4A | 121.48 (19) | C22—C17—N2 | 117.49 (17) |
C3—C4—H4 | 119.2 | C17—C18—C19 | 120.13 (19) |
C4A—C4—H4 | 119.3 | C17—C18—H18 | 120 |
C8A—C4A—C5 | 116.69 (18) | C19—C18—H18 | 119.9 |
C8A—C4A—C4 | 117.66 (17) | C20—C19—C18 | 120.0 (2) |
C5—C4A—C4 | 125.60 (19) | C20—C19—H19 | 120 |
C6—C5—C4A | 117.2 (2) | C18—C19—H19 | 120 |
C6—C5—C23 | 121.17 (18) | C19—C20—C21 | 120.6 (2) |
C4A—C5—C23 | 121.60 (19) | C19—C20—Cl3 | 119.91 (17) |
N7—C6—C5 | 124.2 (2) | C21—C20—Cl3 | 119.52 (17) |
N7—C6—H6 | 117.9 | C22—C21—C20 | 120.6 (2) |
C5—C6—H6 | 117.9 | C22—C21—H21 | 119.7 |
C8—N7—C6 | 120.23 (19) | C20—C21—H21 | 119.7 |
N7—C8—C8A | 119.7 (2) | C21—C22—C17 | 120.5 (2) |
N7—C8—C26 | 118.31 (19) | C21—C22—H22 | 119.7 |
C8A—C8—C26 | 122.01 (19) | C17—C22—H22 | 119.8 |
O1—C8A—C4A | 121.37 (17) | O3—C23—C5 | 107.66 (16) |
O1—C8A—C8 | 116.83 (18) | O3—C23—H23A | 110.3 |
C4A—C8A—C8 | 121.78 (19) | C5—C23—H23A | 110.3 |
C2—N1—C10 | 128.40 (17) | O3—C23—H23B | 110.1 |
C15—C10—C11 | 119.32 (19) | C5—C23—H23B | 110.1 |
C15—C10—N1 | 114.36 (18) | H23A—C23—H23B | 108.5 |
C11—C10—N1 | 126.29 (18) | C24—O3—C23 | 116.97 (15) |
C10—C11—C12 | 120.21 (19) | O4—C24—O3 | 122.77 (16) |
C10—C11—H11 | 119.9 | O4—C24—C25 | 125.64 (19) |
C12—C11—H11 | 119.9 | O3—C24—C25 | 111.54 (18) |
C11—C12—C13 | 120.26 (19) | C24—C25—H25A | 109.4 |
C11—C12—Cl1 | 119.59 (16) | C24—C25—H25B | 109.3 |
C13—C12—Cl1 | 120.15 (17) | H25A—C25—H25B | 109.5 |
C14—C13—C12 | 118.55 (19) | C24—C25—H25C | 109.8 |
C14—C13—Cl2 | 120.00 (17) | H25A—C25—H25C | 109.5 |
C12—C13—Cl2 | 121.45 (17) | H25B—C25—H25C | 109.5 |
C15—C14—C13 | 120.6 (2) | C8—C26—H26A | 109.4 |
C15—C14—H14 | 119.7 | C8—C26—H26B | 109.6 |
C13—C14—H14 | 119.7 | H26A—C26—H26B | 109.5 |
C10—C15—C14 | 121.0 (2) | C8—C26—H26C | 109.4 |
C10—C15—H15 | 119.5 | H26A—C26—H26C | 109.5 |
C14—C15—H15 | 119.5 | H26B—C26—H26C | 109.5 |
O2—C16—N2 | 125.55 (19) | | |
| | | |
C8A—O1—C2—N1 | 175.58 (15) | C10—C11—C12—C13 | 0.9 (3) |
C8A—O1—C2—C3 | −4.8 (2) | C10—C11—C12—Cl1 | −179.29 (14) |
N1—C2—C3—C4 | −176.20 (17) | C11—C12—C13—C14 | 0.9 (3) |
O1—C2—C3—C4 | 4.2 (2) | Cl1—C12—C13—C14 | −178.97 (15) |
N1—C2—C3—C16 | 2.1 (3) | C11—C12—C13—Cl2 | −179.44 (14) |
O1—C2—C3—C16 | −177.48 (15) | Cl1—C12—C13—Cl2 | 0.7 (2) |
C2—C3—C4—C4A | −1.9 (3) | C12—C13—C14—C15 | −0.9 (3) |
C16—C3—C4—C4A | 179.63 (15) | Cl2—C13—C14—C15 | 179.34 (15) |
C3—C4—C4A—C8A | 0.2 (3) | C11—C10—C15—C14 | 2.5 (3) |
C3—C4—C4A—C5 | 177.49 (18) | N1—C10—C15—C14 | −179.39 (17) |
C8A—C4A—C5—C6 | −2.1 (3) | C13—C14—C15—C10 | −0.7 (3) |
C4—C4A—C5—C6 | −179.42 (17) | C4—C3—C16—O2 | −7.2 (2) |
C8A—C4A—C5—C23 | 177.00 (17) | C2—C3—C16—O2 | 174.48 (16) |
C4—C4A—C5—C23 | −0.3 (3) | C4—C3—C16—N2 | 173.03 (16) |
C4A—C5—C6—N7 | 1.9 (3) | C2—C3—C16—N2 | −5.3 (2) |
C23—C5—C6—N7 | −177.21 (18) | O2—C16—N2—C17 | −1.8 (3) |
C5—C6—N7—C8 | −3.0 (3) | C3—C16—N2—C17 | 178.01 (15) |
C6—N7—C8—C8A | 4.3 (3) | C16—N2—C17—C18 | 10.5 (3) |
C6—N7—C8—C26 | −176.06 (18) | C16—N2—C17—C22 | −171.66 (17) |
C2—O1—C8A—C4A | 3.2 (2) | C22—C17—C18—C19 | 2.5 (3) |
C2—O1—C8A—C8 | −178.53 (16) | N2—C17—C18—C19 | −179.62 (18) |
C5—C4A—C8A—O1 | −178.29 (16) | C17—C18—C19—C20 | −0.4 (3) |
C4—C4A—C8A—O1 | −0.8 (2) | C18—C19—C20—C21 | −1.1 (3) |
C5—C4A—C8A—C8 | 3.6 (3) | C18—C19—C20—Cl3 | 178.58 (15) |
C4—C4A—C8A—C8 | −178.91 (17) | C19—C20—C21—C22 | 0.4 (3) |
N7—C8—C8A—O1 | 177.06 (16) | Cl3—C20—C21—C22 | −179.32 (16) |
C26—C8—C8A—O1 | −2.6 (3) | C20—C21—C22—C17 | 1.9 (3) |
N7—C8—C8A—C4A | −4.7 (3) | C18—C17—C22—C21 | −3.3 (3) |
C26—C8—C8A—C4A | 175.63 (17) | N2—C17—C22—C21 | 178.72 (17) |
O1—C2—N1—C10 | −0.3 (3) | C6—C5—C23—O3 | 111.5 (2) |
C3—C2—N1—C10 | −179.89 (16) | C4A—C5—C23—O3 | −67.6 (2) |
C2—N1—C10—C15 | 179.09 (17) | C5—C23—O3—C24 | −159.29 (17) |
C2—N1—C10—C11 | −2.9 (3) | C23—O3—C24—O4 | −4.5 (3) |
C15—C10—C11—C12 | −2.5 (3) | C23—O3—C24—C25 | 178.07 (18) |
N1—C10—C11—C12 | 179.57 (17) | | |