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There are two independent molecules in the structure of the title compound, C
24H
16N
2O
6, one in a general position, the other on a twofold axis of space group
Pbcn. There are thus one and a half molecules in the asymmetric unit. C—H
O, C—H
N and C—H
π interactions exert some influence on the molecular conformation and packing in the crystal structure.
Supporting information
CCDC reference: 238764
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.118
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C25 - C26 .. 7.73 su
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc.
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C3 .. 5.18 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C22 - C23 .. 6.45 su
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C3 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C4 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C25 - C26 ... 1.45 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1
N1 -C1 -C3 -C8 43.00 17.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2
N1 -C1 -C3 -C4 -135.00 17.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 7
N2 -C2 -C4 -C5 69.00 14.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8
N2 -C2 -C4 -C3 -111.00 14.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 63
N3 -C25 -C26 -C27 138.00 7.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 64
N3 -C25 -C26 -C26 -41.00 7.00 1.555 1.555 1.555 4.656
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
13 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
1 ALERT type 3 Indicator that the structure quality may be low
6 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).
Dimethyl 2,2'-(4,5-dimercapto-
o-phenylenedioxy)dibenzoate
top
Crystal data top
C24H16N2O6 | F(000) = 2664 |
Mr = 428.39 | Dx = 1.382 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 24564 reflections |
a = 22.1158 (16) Å | θ = 1.8–24.3° |
b = 12.8114 (9) Å | µ = 0.10 mm−1 |
c = 21.802 (2) Å | T = 293 K |
V = 6177.2 (9) Å3 | Prism, yellow |
Z = 12 | 0.33 × 0.27 × 0.20 mm |
Data collection top
STOE IPDS-II diffractometer | 2621 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.093 |
Graphite monochromator | θmax = 26.0°, θmin = 1.8° |
Detector resolution: 6.67 pixels mm-1 | h = −27→27 |
ω scan | k = −15→15 |
82028 measured reflections | l = −26→26 |
6080 independent reflections | |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0599P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.80 | (Δ/σ)max < 0.001 |
6080 reflections | Δρmax = 0.23 e Å−3 |
434 parameters | Δρmin = −0.15 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: 0.00106 (16) |
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 | |
O1 | 0.60147 (7) | 0.13723 (12) | 0.61300 (8) | 0.0643 (5) | |
O2 | 0.66107 (8) | 0.31129 (13) | 0.60201 (9) | 0.0696 (5) | |
O3 | 0.60440 (9) | 0.12408 (15) | 0.48690 (9) | 0.0806 (5) | |
O4 | 0.59721 (9) | −0.03981 (15) | 0.45189 (9) | 0.0832 (6) | |
O5 | 0.79331 (9) | 0.48266 (15) | 0.68436 (10) | 0.0872 (6) | |
O6 | 0.69766 (10) | 0.43463 (16) | 0.70231 (10) | 0.0889 (6) | |
O7 | 0.55798 (8) | 0.68426 (12) | 0.75617 (9) | 0.0756 (6) | |
O8 | 0.67944 (9) | 0.73909 (17) | 0.61661 (10) | 0.0910 (6) | |
O9 | 0.60015 (10) | 0.63766 (15) | 0.63743 (10) | 0.0926 (7) | |
N1 | 0.35738 (13) | 0.3175 (2) | 0.59228 (13) | 0.0969 (9) | |
N2 | 0.45192 (12) | 0.5866 (2) | 0.56902 (12) | 0.0914 (8) | |
N3 | 0.58765 (12) | 0.22472 (19) | 0.76046 (11) | 0.0862 (7) | |
C1 | 0.40895 (14) | 0.3189 (2) | 0.59233 (12) | 0.0705 (7) | |
C2 | 0.47584 (12) | 0.5094 (2) | 0.57796 (12) | 0.0673 (7) | |
C3 | 0.47419 (11) | 0.31905 (19) | 0.59355 (10) | 0.0571 (6) | |
C4 | 0.50667 (12) | 0.41178 (18) | 0.58779 (11) | 0.0579 (6) | |
C5 | 0.56884 (12) | 0.41047 (18) | 0.59085 (11) | 0.0607 (7) | |
H5 | 0.5903 | 0.4726 | 0.5875 | 0.073* | |
C6 | 0.59935 (11) | 0.31799 (18) | 0.59878 (11) | 0.0560 (6) | |
C7 | 0.56702 (11) | 0.22498 (18) | 0.60438 (11) | 0.0557 (6) | |
C8 | 0.50526 (12) | 0.22570 (18) | 0.60215 (11) | 0.0590 (6) | |
H8 | 0.4839 | 0.1636 | 0.6064 | 0.071* | |
C9 | 0.57211 (11) | 0.04068 (18) | 0.60894 (13) | 0.0595 (6) | |
C10 | 0.55264 (13) | −0.0034 (2) | 0.66272 (13) | 0.0731 (8) | |
H10 | 0.5568 | 0.0324 | 0.6996 | 0.088* | |
C11 | 0.52665 (13) | −0.1017 (2) | 0.66146 (15) | 0.0823 (8) | |
H11 | 0.5133 | −0.1324 | 0.6977 | 0.099* | |
C12 | 0.52062 (13) | −0.1538 (2) | 0.60730 (16) | 0.0794 (8) | |
H12 | 0.5026 | −0.2194 | 0.6065 | 0.095* | |
C13 | 0.54103 (12) | −0.1095 (2) | 0.55400 (14) | 0.0700 (7) | |
H13 | 0.5369 | −0.1460 | 0.5173 | 0.084* | |
C14 | 0.56785 (11) | −0.01108 (18) | 0.55345 (12) | 0.0592 (6) | |
C15 | 0.59137 (12) | 0.0343 (2) | 0.49523 (13) | 0.0674 (7) | |
C16 | 0.62095 (16) | −0.0073 (3) | 0.39308 (14) | 0.1005 (10) | |
H16A | 0.6229 | −0.0663 | 0.3661 | 0.151* | |
H16B | 0.6607 | 0.0212 | 0.3985 | 0.151* | |
H16C | 0.5949 | 0.0449 | 0.3757 | 0.151* | |
C17 | 0.69304 (12) | 0.3877 (2) | 0.56942 (14) | 0.0671 (7) | |
C18 | 0.68602 (13) | 0.3904 (2) | 0.50672 (15) | 0.0815 (8) | |
H18 | 0.6599 | 0.3439 | 0.4874 | 0.098* | |
C19 | 0.71782 (15) | 0.4621 (3) | 0.47289 (15) | 0.0889 (9) | |
H19 | 0.7125 | 0.4657 | 0.4306 | 0.107* | |
C20 | 0.75733 (14) | 0.5285 (2) | 0.50146 (16) | 0.0863 (9) | |
H20 | 0.7788 | 0.5773 | 0.4786 | 0.104* | |
C21 | 0.76552 (12) | 0.5231 (2) | 0.56459 (16) | 0.0768 (8) | |
H21 | 0.7933 | 0.5671 | 0.5835 | 0.092* | |
C22 | 0.73255 (11) | 0.4528 (2) | 0.59964 (13) | 0.0633 (7) | |
C23 | 0.73789 (13) | 0.4544 (2) | 0.66689 (15) | 0.0677 (7) | |
C24 | 0.80549 (16) | 0.4909 (3) | 0.74952 (15) | 0.1018 (11) | |
H24A | 0.8468 | 0.5116 | 0.7557 | 0.153* | |
H24B | 0.7987 | 0.4244 | 0.7687 | 0.153* | |
H24C | 0.7791 | 0.5420 | 0.7674 | 0.153* | |
C25 | 0.56397 (12) | 0.3028 (2) | 0.75635 (11) | 0.0613 (7) | |
C26 | 0.53156 (10) | 0.40089 (17) | 0.75287 (10) | 0.0531 (6) | |
C27 | 0.56297 (11) | 0.49449 (18) | 0.75626 (11) | 0.0587 (6) | |
H27 | 0.6048 | 0.4946 | 0.7604 | 0.070* | |
C28 | 0.53156 (10) | 0.58706 (17) | 0.75336 (11) | 0.0579 (6) | |
C29 | 0.61995 (12) | 0.69344 (19) | 0.76755 (14) | 0.0661 (7) | |
C30 | 0.63799 (15) | 0.7077 (2) | 0.82688 (16) | 0.0828 (9) | |
H30 | 0.6098 | 0.7041 | 0.8585 | 0.099* | |
C31 | 0.69803 (17) | 0.7276 (2) | 0.84004 (16) | 0.0888 (9) | |
H31 | 0.7102 | 0.7370 | 0.8805 | 0.107* | |
C32 | 0.73926 (15) | 0.7335 (2) | 0.79398 (17) | 0.0848 (9) | |
H32 | 0.7797 | 0.7458 | 0.8030 | 0.102* | |
C33 | 0.72134 (12) | 0.72117 (19) | 0.73398 (15) | 0.0719 (7) | |
H33 | 0.7498 | 0.7261 | 0.7027 | 0.086* | |
C34 | 0.66103 (12) | 0.70144 (18) | 0.71954 (13) | 0.0628 (7) | |
C35 | 0.64255 (14) | 0.6882 (2) | 0.65442 (15) | 0.0714 (8) | |
C36 | 0.66687 (15) | 0.7318 (3) | 0.55180 (15) | 0.1029 (11) | |
H36A | 0.6960 | 0.7721 | 0.5294 | 0.154* | |
H36B | 0.6270 | 0.7582 | 0.5437 | 0.154* | |
H36C | 0.6692 | 0.6601 | 0.5391 | 0.154* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0605 (10) | 0.0478 (10) | 0.0846 (12) | 0.0019 (8) | −0.0094 (9) | −0.0053 (8) |
O2 | 0.0577 (11) | 0.0584 (10) | 0.0925 (14) | −0.0066 (9) | −0.0099 (10) | 0.0064 (10) |
O3 | 0.0917 (14) | 0.0620 (12) | 0.0881 (14) | −0.0046 (10) | 0.0039 (11) | 0.0107 (10) |
O4 | 0.0924 (14) | 0.0836 (13) | 0.0737 (13) | −0.0116 (11) | 0.0127 (11) | −0.0128 (11) |
O5 | 0.0747 (14) | 0.0933 (14) | 0.0937 (16) | −0.0188 (11) | −0.0165 (11) | −0.0068 (11) |
O6 | 0.0752 (14) | 0.1013 (15) | 0.0902 (16) | 0.0032 (12) | 0.0018 (12) | −0.0036 (12) |
O7 | 0.0550 (11) | 0.0469 (10) | 0.1249 (17) | −0.0045 (8) | 0.0052 (10) | 0.0011 (10) |
O8 | 0.0928 (15) | 0.1026 (16) | 0.0776 (15) | −0.0157 (12) | 0.0081 (12) | −0.0089 (12) |
O9 | 0.1014 (16) | 0.0692 (13) | 0.1073 (16) | −0.0196 (12) | −0.0267 (13) | 0.0002 (11) |
N1 | 0.0645 (17) | 0.121 (2) | 0.105 (2) | 0.0065 (15) | −0.0003 (15) | 0.0154 (16) |
N2 | 0.1027 (19) | 0.0706 (17) | 0.101 (2) | 0.0220 (15) | −0.0071 (16) | −0.0028 (14) |
N3 | 0.111 (2) | 0.0620 (15) | 0.0855 (18) | 0.0250 (14) | −0.0079 (15) | −0.0054 (13) |
C1 | 0.069 (2) | 0.0784 (19) | 0.0643 (18) | 0.0053 (16) | 0.0019 (15) | 0.0038 (14) |
C2 | 0.0744 (18) | 0.0628 (18) | 0.0648 (17) | 0.0083 (15) | 0.0000 (14) | −0.0052 (14) |
C3 | 0.0561 (16) | 0.0636 (16) | 0.0517 (15) | 0.0018 (13) | 0.0006 (12) | −0.0042 (12) |
C4 | 0.0681 (18) | 0.0532 (15) | 0.0525 (15) | 0.0058 (13) | −0.0004 (12) | −0.0044 (12) |
C5 | 0.0701 (18) | 0.0489 (15) | 0.0630 (17) | −0.0045 (13) | −0.0026 (13) | −0.0034 (12) |
C6 | 0.0559 (16) | 0.0544 (15) | 0.0576 (16) | −0.0024 (13) | −0.0041 (12) | −0.0059 (12) |
C7 | 0.0625 (17) | 0.0478 (14) | 0.0568 (16) | 0.0022 (13) | −0.0049 (12) | −0.0056 (12) |
C8 | 0.0638 (17) | 0.0505 (14) | 0.0627 (17) | −0.0035 (13) | −0.0030 (13) | −0.0041 (12) |
C9 | 0.0587 (15) | 0.0460 (14) | 0.0737 (19) | −0.0007 (12) | −0.0054 (14) | 0.0006 (14) |
C10 | 0.084 (2) | 0.0641 (17) | 0.071 (2) | 0.0051 (15) | 0.0006 (15) | −0.0013 (15) |
C11 | 0.094 (2) | 0.0677 (19) | 0.085 (2) | −0.0033 (17) | 0.0102 (18) | 0.0157 (17) |
C12 | 0.085 (2) | 0.0512 (16) | 0.101 (2) | −0.0033 (14) | 0.0080 (19) | 0.0078 (17) |
C13 | 0.0719 (18) | 0.0540 (16) | 0.084 (2) | −0.0006 (14) | 0.0009 (16) | −0.0081 (15) |
C14 | 0.0589 (15) | 0.0488 (15) | 0.0699 (18) | 0.0001 (12) | −0.0022 (13) | −0.0004 (13) |
C15 | 0.0613 (17) | 0.0653 (17) | 0.076 (2) | 0.0006 (14) | −0.0029 (15) | −0.0032 (17) |
C16 | 0.102 (2) | 0.129 (3) | 0.071 (2) | −0.015 (2) | 0.0146 (18) | −0.006 (2) |
C17 | 0.0578 (16) | 0.0631 (16) | 0.080 (2) | 0.0017 (14) | −0.0028 (15) | 0.0008 (15) |
C18 | 0.074 (2) | 0.087 (2) | 0.083 (2) | −0.0086 (17) | −0.0054 (17) | −0.0039 (18) |
C19 | 0.082 (2) | 0.107 (2) | 0.079 (2) | 0.0011 (19) | 0.0010 (18) | −0.003 (2) |
C20 | 0.072 (2) | 0.093 (2) | 0.093 (3) | −0.0013 (17) | 0.0130 (18) | 0.013 (2) |
C21 | 0.0558 (17) | 0.0711 (18) | 0.104 (3) | −0.0042 (14) | 0.0012 (16) | 0.0033 (17) |
C22 | 0.0517 (15) | 0.0607 (15) | 0.077 (2) | 0.0018 (13) | −0.0024 (14) | −0.0022 (15) |
C23 | 0.0544 (18) | 0.0560 (16) | 0.093 (2) | 0.0036 (13) | −0.0008 (17) | −0.0042 (15) |
C24 | 0.121 (3) | 0.091 (2) | 0.093 (3) | −0.006 (2) | −0.034 (2) | −0.0121 (18) |
C25 | 0.0742 (18) | 0.0571 (16) | 0.0526 (16) | 0.0004 (14) | 0.0012 (13) | −0.0020 (13) |
C26 | 0.0631 (14) | 0.0466 (13) | 0.0495 (14) | 0.0077 (11) | 0.0040 (13) | 0.0009 (11) |
C27 | 0.0538 (14) | 0.0532 (14) | 0.0690 (17) | 0.0020 (12) | 0.0040 (13) | 0.0019 (12) |
C28 | 0.0575 (14) | 0.0477 (14) | 0.0685 (16) | −0.0023 (11) | 0.0074 (13) | 0.0011 (12) |
C29 | 0.0586 (18) | 0.0520 (15) | 0.088 (2) | −0.0066 (12) | 0.0003 (16) | −0.0008 (14) |
C30 | 0.087 (2) | 0.075 (2) | 0.086 (2) | −0.0077 (17) | 0.0123 (18) | 0.0096 (17) |
C31 | 0.099 (3) | 0.084 (2) | 0.083 (2) | −0.0171 (19) | −0.011 (2) | 0.0066 (17) |
C32 | 0.075 (2) | 0.080 (2) | 0.100 (3) | −0.0148 (16) | −0.016 (2) | 0.0050 (19) |
C33 | 0.0614 (18) | 0.0610 (16) | 0.093 (2) | −0.0098 (13) | 0.0008 (16) | 0.0024 (15) |
C34 | 0.0598 (17) | 0.0458 (14) | 0.083 (2) | −0.0041 (12) | −0.0027 (15) | −0.0044 (13) |
C35 | 0.0717 (19) | 0.0476 (15) | 0.095 (2) | 0.0008 (15) | −0.0049 (18) | −0.0050 (16) |
C36 | 0.116 (3) | 0.114 (3) | 0.079 (2) | 0.019 (2) | 0.002 (2) | −0.009 (2) |
Geometric parameters (Å, º) top
O1—C7 | 1.371 (3) | C14—C15 | 1.490 (4) |
O1—C9 | 1.400 (3) | C16—H16A | 0.9600 |
O2—C6 | 1.370 (3) | C16—H16B | 0.9600 |
O2—C17 | 1.401 (3) | C16—H16C | 0.9600 |
O3—C15 | 1.200 (3) | C17—C22 | 1.376 (3) |
O4—C15 | 1.345 (3) | C17—C18 | 1.376 (4) |
O4—C16 | 1.447 (3) | C18—C19 | 1.373 (4) |
O5—C23 | 1.334 (3) | C18—H18 | 0.9300 |
O5—C24 | 1.450 (3) | C19—C20 | 1.369 (4) |
O6—C23 | 1.205 (3) | C19—H19 | 0.9300 |
O7—C28 | 1.377 (3) | C20—C21 | 1.390 (4) |
O7—C29 | 1.398 (3) | C20—H20 | 0.9300 |
O8—C35 | 1.331 (3) | C21—C22 | 1.389 (4) |
O8—C36 | 1.443 (4) | C21—H21 | 0.9300 |
O9—C35 | 1.198 (3) | C22—C23 | 1.471 (4) |
N1—C1 | 1.141 (3) | C24—H24A | 0.9600 |
N2—C2 | 1.139 (3) | C24—H24B | 0.9600 |
N3—C25 | 1.133 (3) | C24—H24C | 0.9600 |
C1—C3 | 1.443 (4) | C25—C26 | 1.449 (3) |
C2—C4 | 1.440 (4) | C26—C27 | 1.388 (3) |
C3—C8 | 1.392 (3) | C26—C26i | 1.401 (4) |
C3—C4 | 1.394 (3) | C27—C28 | 1.376 (3) |
C4—C5 | 1.376 (3) | C27—H27 | 0.9300 |
C5—C6 | 1.374 (3) | C28—C28i | 1.404 (5) |
C5—H5 | 0.9300 | C29—C30 | 1.366 (4) |
C6—C7 | 1.395 (3) | C29—C34 | 1.390 (4) |
C7—C8 | 1.367 (3) | C30—C31 | 1.382 (4) |
C8—H8 | 0.9300 | C30—H30 | 0.9300 |
C9—C10 | 1.371 (3) | C31—C32 | 1.359 (4) |
C9—C14 | 1.383 (3) | C31—H31 | 0.9300 |
C10—C11 | 1.385 (4) | C32—C33 | 1.376 (4) |
C10—H10 | 0.9300 | C32—H32 | 0.9300 |
C11—C12 | 1.363 (4) | C33—C34 | 1.393 (4) |
C11—H11 | 0.9300 | C33—H33 | 0.9300 |
C12—C13 | 1.370 (4) | C34—C35 | 1.487 (4) |
C12—H12 | 0.9300 | C36—H36A | 0.9600 |
C13—C14 | 1.394 (3) | C36—H36B | 0.9600 |
C13—H13 | 0.9300 | C36—H36C | 0.9600 |
| | | |
C7—O1—C9 | 117.26 (17) | C20—C19—C18 | 119.9 (3) |
C6—O2—C17 | 115.67 (19) | C20—C19—H19 | 120.0 |
C15—O4—C16 | 117.0 (2) | C18—C19—H19 | 120.0 |
C23—O5—C24 | 118.1 (3) | C19—C20—C21 | 120.2 (3) |
C28—O7—C29 | 120.00 (19) | C19—C20—H20 | 119.9 |
C35—O8—C36 | 117.2 (2) | C21—C20—H20 | 119.9 |
N1—C1—C3 | 178.7 (3) | C22—C21—C20 | 120.6 (3) |
N2—C2—C4 | 178.6 (3) | C22—C21—H21 | 119.7 |
C8—C3—C4 | 119.3 (2) | C20—C21—H21 | 119.7 |
C8—C3—C1 | 119.6 (2) | C17—C22—C21 | 117.6 (3) |
C4—C3—C1 | 121.0 (2) | C17—C22—C23 | 122.5 (3) |
C5—C4—C3 | 120.0 (2) | C21—C22—C23 | 119.8 (3) |
C5—C4—C2 | 119.4 (2) | O6—C23—O5 | 123.6 (3) |
C3—C4—C2 | 120.6 (2) | O6—C23—C22 | 125.2 (3) |
C6—C5—C4 | 120.5 (2) | O5—C23—C22 | 111.2 (3) |
C6—C5—H5 | 119.8 | O5—C24—H24A | 109.5 |
C4—C5—H5 | 119.8 | O5—C24—H24B | 109.5 |
O2—C6—C5 | 123.4 (2) | H24A—C24—H24B | 109.5 |
O2—C6—C7 | 116.9 (2) | O5—C24—H24C | 109.5 |
C5—C6—C7 | 119.7 (2) | H24A—C24—H24C | 109.5 |
C8—C7—O1 | 124.5 (2) | H24B—C24—H24C | 109.5 |
C8—C7—C6 | 120.2 (2) | N3—C25—C26 | 177.4 (3) |
O1—C7—C6 | 115.3 (2) | C27—C26—C26i | 120.22 (13) |
C7—C8—C3 | 120.3 (2) | C27—C26—C25 | 119.9 (2) |
C7—C8—H8 | 119.9 | C26i—C26—C25 | 119.83 (14) |
C3—C8—H8 | 119.9 | C28—C27—C26 | 119.3 (2) |
C10—C9—C14 | 122.0 (2) | C28—C27—H27 | 120.3 |
C10—C9—O1 | 117.1 (2) | C26—C27—H27 | 120.3 |
C14—C9—O1 | 120.7 (2) | C27—C28—O7 | 124.3 (2) |
C9—C10—C11 | 119.2 (3) | C27—C28—C28i | 120.46 (14) |
C9—C10—H10 | 120.4 | O7—C28—C28i | 115.26 (12) |
C11—C10—H10 | 120.4 | C30—C29—C34 | 120.8 (3) |
C12—C11—C10 | 120.2 (3) | C30—C29—O7 | 117.8 (3) |
C12—C11—H11 | 119.9 | C34—C29—O7 | 120.9 (3) |
C10—C11—H11 | 119.9 | C29—C30—C31 | 120.1 (3) |
C11—C12—C13 | 120.0 (3) | C29—C30—H30 | 119.9 |
C11—C12—H12 | 120.0 | C31—C30—H30 | 119.9 |
C13—C12—H12 | 120.0 | C32—C31—C30 | 120.1 (3) |
C12—C13—C14 | 121.5 (3) | C32—C31—H31 | 119.9 |
C12—C13—H13 | 119.3 | C30—C31—H31 | 119.9 |
C14—C13—H13 | 119.3 | C31—C32—C33 | 120.2 (3) |
C9—C14—C13 | 117.1 (2) | C31—C32—H32 | 119.9 |
C9—C14—C15 | 122.3 (2) | C33—C32—H32 | 119.9 |
C13—C14—C15 | 120.6 (2) | C32—C33—C34 | 120.8 (3) |
O3—C15—O4 | 123.2 (3) | C32—C33—H33 | 119.6 |
O3—C15—C14 | 125.9 (3) | C34—C33—H33 | 119.6 |
O4—C15—C14 | 110.9 (2) | C29—C34—C33 | 118.0 (3) |
O4—C16—H16A | 109.5 | C29—C34—C35 | 122.1 (3) |
O4—C16—H16B | 109.5 | C33—C34—C35 | 120.0 (3) |
H16A—C16—H16B | 109.5 | O9—C35—O8 | 123.6 (3) |
O4—C16—H16C | 109.5 | O9—C35—C34 | 124.9 (3) |
H16A—C16—H16C | 109.5 | O8—C35—C34 | 111.5 (3) |
H16B—C16—H16C | 109.5 | O8—C36—H36A | 109.5 |
C22—C17—C18 | 122.1 (3) | O8—C36—H36B | 109.5 |
C22—C17—O2 | 120.1 (3) | H36A—C36—H36B | 109.5 |
C18—C17—O2 | 117.7 (3) | O8—C36—H36C | 109.5 |
C19—C18—C17 | 119.5 (3) | H36A—C36—H36C | 109.5 |
C19—C18—H18 | 120.2 | H36B—C36—H36C | 109.5 |
C17—C18—H18 | 120.2 | | |
| | | |
N1—C1—C3—C8 | 43 (17) | C22—C17—C18—C19 | −2.1 (4) |
N1—C1—C3—C4 | −135 (17) | O2—C17—C18—C19 | −178.2 (2) |
C8—C3—C4—C5 | −0.2 (4) | C17—C18—C19—C20 | 1.7 (5) |
C1—C3—C4—C5 | 178.1 (2) | C18—C19—C20—C21 | 0.3 (5) |
C8—C3—C4—C2 | 179.1 (2) | C19—C20—C21—C22 | −1.9 (4) |
C1—C3—C4—C2 | −2.5 (4) | C18—C17—C22—C21 | 0.4 (4) |
N2—C2—C4—C5 | 69 (14) | O2—C17—C22—C21 | 176.5 (2) |
N2—C2—C4—C3 | −111 (14) | C18—C17—C22—C23 | 176.5 (3) |
C3—C4—C5—C6 | 0.9 (4) | O2—C17—C22—C23 | −7.4 (4) |
C2—C4—C5—C6 | −178.5 (2) | C20—C21—C22—C17 | 1.5 (4) |
C17—O2—C6—C5 | −29.3 (3) | C20—C21—C22—C23 | −174.7 (3) |
C17—O2—C6—C7 | 151.1 (2) | C24—O5—C23—O6 | −0.6 (4) |
C4—C5—C6—O2 | 179.8 (2) | C24—O5—C23—C22 | 178.4 (2) |
C4—C5—C6—C7 | −0.7 (4) | C17—C22—C23—O6 | −29.7 (4) |
C9—O1—C7—C8 | 11.2 (3) | C21—C22—C23—O6 | 146.4 (3) |
C9—O1—C7—C6 | −169.9 (2) | C17—C22—C23—O5 | 151.4 (2) |
O2—C6—C7—C8 | 179.4 (2) | C21—C22—C23—O5 | −32.6 (3) |
C5—C6—C7—C8 | −0.2 (4) | N3—C25—C26—C27 | 138 (7) |
O2—C6—C7—O1 | 0.5 (3) | N3—C25—C26—C26i | −41 (7) |
C5—C6—C7—O1 | −179.1 (2) | C26i—C26—C27—C28 | −0.6 (4) |
O1—C7—C8—C3 | 179.6 (2) | C25—C26—C27—C28 | −179.5 (2) |
C6—C7—C8—C3 | 0.8 (4) | C26—C27—C28—O7 | −179.9 (2) |
C4—C3—C8—C7 | −0.6 (4) | C26—C27—C28—C28i | −0.4 (4) |
C1—C3—C8—C7 | −179.0 (2) | C29—O7—C28—C27 | −5.4 (4) |
C7—O1—C9—C10 | −95.2 (3) | C29—O7—C28—C28i | 175.1 (3) |
C7—O1—C9—C14 | 90.1 (3) | C28—O7—C29—C30 | −94.1 (3) |
C14—C9—C10—C11 | −1.5 (4) | C28—O7—C29—C34 | 94.2 (3) |
O1—C9—C10—C11 | −176.1 (2) | C34—C29—C30—C31 | −1.8 (4) |
C9—C10—C11—C12 | 0.0 (4) | O7—C29—C30—C31 | −173.6 (2) |
C10—C11—C12—C13 | 0.9 (4) | C29—C30—C31—C32 | 0.3 (5) |
C11—C12—C13—C14 | −0.4 (4) | C30—C31—C32—C33 | 0.9 (5) |
C10—C9—C14—C13 | 1.9 (4) | C31—C32—C33—C34 | −0.7 (4) |
O1—C9—C14—C13 | 176.4 (2) | C30—C29—C34—C33 | 2.0 (4) |
C10—C9—C14—C15 | −177.2 (2) | O7—C29—C34—C33 | 173.5 (2) |
O1—C9—C14—C15 | −2.8 (4) | C30—C29—C34—C35 | −178.9 (2) |
C12—C13—C14—C9 | −1.0 (4) | O7—C29—C34—C35 | −7.4 (4) |
C12—C13—C14—C15 | 178.2 (2) | C32—C33—C34—C29 | −0.7 (4) |
C16—O4—C15—O3 | 0.5 (4) | C32—C33—C34—C35 | −179.9 (3) |
C16—O4—C15—C14 | −178.7 (2) | C36—O8—C35—O9 | −0.1 (4) |
C9—C14—C15—O3 | −16.1 (4) | C36—O8—C35—C34 | 179.4 (2) |
C13—C14—C15—O3 | 164.8 (3) | C29—C34—C35—O9 | −26.4 (4) |
C9—C14—C15—O4 | 163.1 (2) | C33—C34—C35—O9 | 152.7 (3) |
C13—C14—C15—O4 | −16.0 (3) | C29—C34—C35—O8 | 154.0 (2) |
C6—O2—C17—C22 | 121.1 (2) | C33—C34—C35—O8 | −26.9 (3) |
C6—O2—C17—C18 | −62.7 (3) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O9 | 0.93 | 2.39 | 3.159 (3) | 140 |
C27—H27···O6 | 0.93 | 2.53 | 3.293 (3) | 139 |
C21—H21···O1ii | 0.93 | 2.58 | 3.450 (3) | 157 |
C30—H30···N2i | 0.93 | 2.57 | 3.393 (4) | 147 |
C24—H24B···Cg5iii | 0.96 | 2.75 | 3.624 (4) | 152 |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+3/2, y+1/2, z; (iii) −x+3/2, y−1/2, z. |
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