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Heterocyclic chalcones are a recently explored subgroup of chalcones that have sparked interest due to their significant antibacterial and antifungal capabilities. Herein, the structure and solubility of two such compounds, (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one and (E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one, are assessed. Single crystals of (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one were grown, allowing structural comparisons between the heterocyclic chalcones and (2E)-1,3-diphenylprop-2-en-1-one, trivially known as trans-chalcone. The two heterocyclic chalcones were found to be less soluble in all solvents tested and to have higher melting points than trans-chalcone, probably due to their stronger intermolecular interactions arising from the functionalized rings. Interestingly, however, it was found that the addition of the thiophene ring in (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one increased both the melting point and solubility of the sample compared with (E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one. This observation may be key for the future crystal engineering of heterocyclic chalcones for pharmaceutical applications.
Supporting information
CCDC reference: 1952662
Data collection: SAINT V8.38A (?, 2016); cell refinement: SAINT V8.38A (?, 2016); data reduction: SAINT V8.38A (?, 2016); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
(E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one
top
Crystal data top
C11H9NOS | Dx = 1.402 Mg m−3 |
Mr = 203.25 | Melting point: 423.42 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.0288 (5) Å | Cell parameters from 5280 reflections |
b = 5.3086 (2) Å | θ = 2.3–27.5° |
c = 24.4440 (8) Å | µ = 0.30 mm−1 |
β = 99.133 (2)° | T = 100 K |
V = 1925.46 (12) Å3 | Block, pale yellow |
Z = 8 | 0.53 × 0.28 × 0.26 mm |
F(000) = 848 | |
Data collection top
Bruker Apex II kappa CCD area detector diffractometer | 6848 independent reflections |
Radiation source: fine-focus sealed tube | 5578 reflections with I > 2σ(I) |
Graphite monochromator | θmax = 27.6°, θmin = 1.4° |
φ and ω scans | h = −19→19 |
Absorption correction: multi-scan TWINABS-2012/1 (Bruker,2012) was used for absorption correction. Final HKLF 4 output contains 30296 reflections, Rint = 0.0380
(11517 with I > 3sig(I), Rint = 0.0251) | k = 0→6 |
Tmin = 0.606, Tmax = 0.746 | l = 0→31 |
6848 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: mixed |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0418P)2 + 0.8248P] where P = (Fo2 + 2Fc2)/3 |
6848 reflections | (Δ/σ)max = 0.001 |
354 parameters | Δρmax = 0.30 e Å−3 |
312 restraints | Δρmin = −0.27 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. Hydrogen atoms on nitrogen atoms were found by difference map after all other
atoms had been refined. All other hydrogen atoms were placed geometrically and
refined using a riding model. There are two molecules in the asymmetric unit, both contain a disordered
thiophene group which has been modelled in two positions. The refined occupancy
ratio is 0.922:0.078 (2) for molecule 1 and 0.884:0.116 (2) for molecule 2.
Equivalent atom distances in the major and minor components (e.g. C1-C2 and
C1A-C2A) have been restrained to be the same. The ADPs of atoms in close
proximity have also been restrained to be the same. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.95761 (9) | 0.9004 (2) | 0.56582 (5) | 0.0207 (3) | |
N1 | 0.91661 (11) | 0.7276 (3) | 0.45592 (7) | 0.0161 (3) | |
H1 | 0.9515 (15) | 0.849 (4) | 0.4573 (9) | 0.019 (6)* | |
C1 | 0.91434 (12) | 0.7025 (3) | 0.55598 (8) | 0.0155 (4) | |
C2 | 0.88697 (13) | 0.5508 (4) | 0.60112 (8) | 0.0172 (4) | |
H2 | 0.854958 | 0.397849 | 0.592616 | 0.021* | |
C3 | 0.90667 (12) | 0.6262 (3) | 0.65373 (8) | 0.0146 (4) | |
H3A | 0.936942 | 0.783293 | 0.659707 | 0.018* | 0.922 (2) |
H3B | 0.933503 | 0.786732 | 0.661827 | 0.018* | 0.078 (2) |
C4 | 0.88892 (12) | 0.6088 (3) | 0.50027 (8) | 0.0145 (4) | |
C5 | 0.88373 (13) | 0.6041 (4) | 0.40891 (8) | 0.0183 (4) | |
H5 | 0.894015 | 0.648101 | 0.372767 | 0.022* | |
C6 | 0.83261 (13) | 0.4029 (4) | 0.42187 (8) | 0.0188 (4) | |
H6 | 0.800918 | 0.285969 | 0.396519 | 0.023* | |
C7 | 0.83641 (13) | 0.4041 (3) | 0.47953 (8) | 0.0166 (4) | |
H7 | 0.808251 | 0.286627 | 0.500593 | 0.020* | |
S1 | 0.82556 (7) | 0.22169 (12) | 0.69949 (3) | 0.01463 (18) | 0.922 (2) |
C8 | 0.8876 (5) | 0.4982 (7) | 0.70271 (10) | 0.0123 (6) | 0.922 (2) |
C9 | 0.83662 (19) | 0.2044 (5) | 0.77058 (9) | 0.0138 (5) | 0.922 (2) |
H9 | 0.811478 | 0.074504 | 0.790078 | 0.017* | 0.922 (2) |
C10 | 0.8861 (3) | 0.4011 (5) | 0.79548 (13) | 0.0150 (5) | 0.922 (2) |
H10 | 0.899575 | 0.424488 | 0.834454 | 0.018* | 0.922 (2) |
C11 | 0.9146 (4) | 0.5639 (11) | 0.7567 (2) | 0.0203 (12) | 0.922 (2) |
H11 | 0.950029 | 0.709297 | 0.767180 | 0.024* | 0.922 (2) |
S1A | 0.9259 (13) | 0.603 (3) | 0.7625 (7) | 0.013 (2) | 0.078 (2) |
C8A | 0.888 (6) | 0.468 (10) | 0.6986 (7) | 0.015 (3) | 0.078 (2) |
C9A | 0.883 (4) | 0.350 (7) | 0.7938 (15) | 0.015 (3) | 0.078 (2) |
H9A | 0.892863 | 0.311585 | 0.832294 | 0.018* | 0.078 (2) |
C10A | 0.833 (3) | 0.214 (7) | 0.7528 (12) | 0.014 (3) | 0.078 (2) |
H10A | 0.799492 | 0.073619 | 0.762607 | 0.017* | 0.078 (2) |
C11A | 0.828 (3) | 0.275 (8) | 0.6968 (14) | 0.015 (3) | 0.078 (2) |
H11A | 0.791814 | 0.201365 | 0.665486 | 0.018* | 0.078 (2) |
O2 | 0.53652 (9) | 1.3919 (3) | 0.57317 (6) | 0.0213 (3) | |
N2 | 0.58523 (11) | 1.2276 (3) | 0.47241 (7) | 0.0164 (3) | |
H2A | 0.5513 (16) | 1.355 (5) | 0.4677 (10) | 0.029 (7)* | |
C12 | 0.58131 (12) | 1.1960 (4) | 0.57221 (8) | 0.0161 (4) | |
C13 | 0.60668 (13) | 1.0418 (4) | 0.62247 (8) | 0.0171 (4) | |
H13 | 0.637894 | 0.887642 | 0.620031 | 0.021* | |
C14 | 0.58661 (12) | 1.1150 (3) | 0.67132 (8) | 0.0151 (4) | |
H14 | 0.553809 | 1.267843 | 0.671537 | 0.018* | 0.884 (2) |
H14A | 0.555578 | 1.269139 | 0.674166 | 0.018* | 0.116 (2) |
C15 | 0.61125 (12) | 1.1086 (3) | 0.52230 (8) | 0.0153 (4) | |
C16 | 0.62154 (13) | 1.1074 (4) | 0.43253 (8) | 0.0183 (4) | |
H16 | 0.613102 | 1.152523 | 0.394443 | 0.022* | |
C17 | 0.67293 (13) | 0.9083 (4) | 0.45617 (8) | 0.0191 (4) | |
H17 | 0.706558 | 0.793715 | 0.437665 | 0.023* | |
C18 | 0.66604 (13) | 0.9073 (3) | 0.51264 (8) | 0.0180 (4) | |
H18 | 0.693740 | 0.790439 | 0.539494 | 0.022* | |
S2 | 0.67147 (9) | 0.7104 (2) | 0.73047 (4) | 0.01612 (19) | 0.884 (2) |
C19 | 0.6092 (7) | 0.9873 (10) | 0.72389 (12) | 0.0127 (6) | 0.884 (2) |
C20 | 0.6686 (2) | 0.6955 (6) | 0.80047 (10) | 0.0151 (6) | 0.884 (2) |
H20 | 0.696313 | 0.566220 | 0.824101 | 0.018* | 0.884 (2) |
C21 | 0.6215 (3) | 0.8922 (7) | 0.81804 (16) | 0.0168 (6) | 0.884 (2) |
H21 | 0.612535 | 0.916192 | 0.855283 | 0.020* | 0.884 (2) |
C22 | 0.5881 (6) | 1.0544 (14) | 0.7741 (3) | 0.0206 (14) | 0.884 (2) |
H22 | 0.553436 | 1.199809 | 0.779004 | 0.025* | 0.884 (2) |
S2A | 0.5804 (12) | 1.093 (3) | 0.7785 (6) | 0.0158 (17) | 0.116 (2) |
C19A | 0.612 (5) | 0.960 (9) | 0.7198 (9) | 0.014 (3) | 0.116 (2) |
C20A | 0.631 (3) | 0.844 (6) | 0.8166 (12) | 0.017 (3) | 0.116 (2) |
H20A | 0.632461 | 0.821659 | 0.855278 | 0.020* | 0.116 (2) |
C21A | 0.669 (2) | 0.684 (6) | 0.7830 (9) | 0.017 (3) | 0.116 (2) |
H21A | 0.698437 | 0.534473 | 0.797347 | 0.020* | 0.116 (2) |
C22A | 0.662 (3) | 0.747 (6) | 0.7266 (12) | 0.016 (3) | 0.116 (2) |
H22A | 0.686946 | 0.657847 | 0.699005 | 0.019* | 0.116 (2) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0239 (8) | 0.0203 (7) | 0.0178 (7) | −0.0079 (6) | 0.0030 (6) | 0.0010 (6) |
N1 | 0.0178 (8) | 0.0156 (8) | 0.0152 (8) | −0.0031 (7) | 0.0037 (6) | 0.0013 (6) |
C1 | 0.0128 (9) | 0.0162 (9) | 0.0173 (9) | 0.0004 (7) | 0.0020 (7) | 0.0020 (8) |
C2 | 0.0182 (10) | 0.0166 (9) | 0.0168 (9) | −0.0025 (7) | 0.0024 (8) | 0.0016 (8) |
C3 | 0.0125 (9) | 0.0134 (8) | 0.0181 (10) | 0.0007 (7) | 0.0026 (7) | 0.0017 (7) |
C4 | 0.0148 (9) | 0.0145 (9) | 0.0144 (9) | 0.0025 (7) | 0.0031 (7) | 0.0029 (7) |
C5 | 0.0220 (10) | 0.0196 (10) | 0.0135 (9) | 0.0016 (8) | 0.0033 (8) | 0.0008 (8) |
C6 | 0.0198 (10) | 0.0189 (10) | 0.0177 (10) | −0.0012 (8) | 0.0031 (8) | −0.0039 (8) |
C7 | 0.0180 (10) | 0.0152 (9) | 0.0173 (10) | −0.0001 (7) | 0.0046 (8) | 0.0013 (7) |
S1 | 0.0168 (3) | 0.0127 (4) | 0.0142 (3) | −0.0031 (3) | 0.0020 (2) | 0.0003 (2) |
C8 | 0.0109 (9) | 0.0095 (14) | 0.0163 (10) | 0.0013 (13) | 0.0019 (10) | −0.0008 (9) |
C9 | 0.0162 (10) | 0.0165 (10) | 0.0091 (11) | 0.0002 (8) | 0.0036 (11) | 0.0038 (11) |
C10 | 0.0165 (11) | 0.0155 (15) | 0.0132 (10) | 0.0022 (12) | 0.0026 (8) | −0.0009 (10) |
C11 | 0.018 (2) | 0.016 (2) | 0.027 (2) | −0.0024 (13) | 0.0021 (14) | −0.0023 (13) |
S1A | 0.018 (4) | 0.013 (4) | 0.010 (3) | 0.003 (3) | 0.007 (3) | 0.007 (3) |
C8A | 0.016 (5) | 0.015 (5) | 0.013 (5) | 0.003 (5) | 0.003 (5) | −0.002 (5) |
C9A | 0.018 (5) | 0.016 (5) | 0.012 (5) | 0.000 (5) | 0.008 (4) | 0.006 (5) |
C10A | 0.016 (5) | 0.015 (5) | 0.011 (5) | −0.003 (4) | 0.004 (5) | 0.002 (5) |
C11A | 0.018 (5) | 0.016 (5) | 0.012 (5) | 0.002 (5) | 0.007 (5) | 0.001 (5) |
O2 | 0.0239 (8) | 0.0210 (7) | 0.0189 (7) | 0.0086 (6) | 0.0035 (6) | 0.0030 (6) |
N2 | 0.0174 (8) | 0.0157 (8) | 0.0161 (8) | 0.0025 (7) | 0.0023 (7) | 0.0016 (6) |
C12 | 0.0141 (9) | 0.0176 (9) | 0.0159 (9) | −0.0011 (7) | 0.0000 (7) | 0.0014 (7) |
C13 | 0.0171 (9) | 0.0161 (9) | 0.0176 (10) | 0.0026 (7) | 0.0013 (8) | 0.0024 (8) |
C14 | 0.0110 (9) | 0.0151 (9) | 0.0186 (9) | −0.0016 (7) | 0.0005 (7) | 0.0003 (7) |
C15 | 0.0144 (9) | 0.0160 (9) | 0.0153 (9) | −0.0011 (7) | 0.0016 (7) | 0.0018 (7) |
C16 | 0.0198 (10) | 0.0205 (10) | 0.0146 (9) | −0.0028 (8) | 0.0024 (8) | 0.0002 (8) |
C17 | 0.0183 (10) | 0.0198 (10) | 0.0192 (10) | 0.0007 (8) | 0.0034 (8) | −0.0026 (8) |
C18 | 0.0167 (9) | 0.0161 (9) | 0.0204 (10) | 0.0011 (7) | 0.0006 (8) | 0.0020 (8) |
S2 | 0.0178 (4) | 0.0134 (4) | 0.0173 (3) | 0.0031 (3) | 0.0033 (3) | 0.0013 (2) |
C19 | 0.0110 (12) | 0.0107 (16) | 0.0159 (12) | −0.0007 (13) | 0.0009 (12) | −0.0007 (11) |
C20 | 0.0175 (11) | 0.0175 (11) | 0.0101 (13) | −0.0004 (9) | 0.0013 (12) | 0.0036 (13) |
C21 | 0.0168 (16) | 0.0185 (17) | 0.0151 (11) | −0.0010 (12) | 0.0028 (9) | −0.0021 (11) |
C22 | 0.019 (2) | 0.016 (2) | 0.027 (2) | 0.0016 (16) | 0.0028 (15) | −0.0017 (16) |
S2A | 0.021 (3) | 0.016 (3) | 0.010 (3) | −0.001 (3) | 0.001 (2) | 0.003 (2) |
C19A | 0.015 (5) | 0.018 (5) | 0.011 (4) | −0.004 (4) | 0.005 (4) | −0.002 (4) |
C20A | 0.019 (5) | 0.018 (5) | 0.013 (4) | 0.001 (4) | 0.000 (4) | 0.004 (4) |
C21A | 0.018 (4) | 0.017 (4) | 0.015 (5) | 0.002 (4) | 0.002 (5) | 0.004 (5) |
C22A | 0.016 (5) | 0.019 (5) | 0.012 (5) | −0.005 (4) | 0.003 (4) | 0.001 (4) |
Geometric parameters (Å, º) top
N1—H1 | 0.83 (2) | N2—H2A | 0.84 (2) |
C1—O1 | 1.239 (2) | C12—O2 | 1.241 (2) |
C1—C4 | 1.443 (3) | C12—C15 | 1.442 (3) |
C2—C1 | 1.476 (3) | C13—C12 | 1.475 (3) |
C2—H2 | 0.9500 | C13—H13 | 0.9500 |
C3—C2 | 1.335 (3) | C14—C13 | 1.335 (3) |
C3—H3A | 0.9500 | C14—H14 | 0.9500 |
C3—H3B | 0.9500 | C14—H14A | 0.9500 |
C4—N1 | 1.374 (2) | C15—N2 | 1.374 (2) |
C4—C7 | 1.390 (3) | C15—C18 | 1.392 (3) |
C5—N1 | 1.347 (2) | C16—N2 | 1.351 (2) |
C5—H5 | 0.9500 | C16—H16 | 0.9500 |
C6—C5 | 1.381 (3) | C17—C16 | 1.381 (3) |
C6—H6 | 0.9500 | C17—H17 | 0.9500 |
C7—C6 | 1.402 (3) | C18—C17 | 1.400 (3) |
C7—H7 | 0.9500 | C18—H18 | 0.9500 |
C8—C3 | 1.444 (3) | C19—C14 | 1.445 (3) |
C8—S1 | 1.734 (3) | C19—S2 | 1.736 (3) |
C9—S1 | 1.722 (2) | C20—S2 | 1.720 (3) |
C9—H9 | 0.9500 | C20—H20 | 0.9500 |
C9—C10 | 1.368 (3) | C20—C21 | 1.367 (3) |
C10—H10 | 0.9500 | C21—H21 | 0.9500 |
C10—C11 | 1.399 (6) | C21—C22 | 1.406 (7) |
C11—C8 | 1.363 (6) | C22—C19 | 1.362 (7) |
C11—H11 | 0.9500 | C22—H22 | 0.9500 |
C8A—C3 | 1.445 (12) | C19A—C14 | 1.443 (12) |
C8A—S1A | 1.731 (13) | C19A—S2A | 1.731 (14) |
C9A—S1A | 1.723 (13) | C20A—S2A | 1.722 (13) |
C9A—H9A | 0.9500 | C20A—H20A | 0.9500 |
C9A—C10A | 1.362 (13) | C20A—C21A | 1.365 (12) |
C10A—H10A | 0.9500 | C21A—H21A | 0.9500 |
C10A—C11A | 1.397 (14) | C21A—C22A | 1.407 (14) |
C11A—C8A | 1.359 (14) | C22A—C19A | 1.353 (14) |
C11A—H11A | 0.9500 | C22A—H22A | 0.9500 |
| | | |
C4—N1—H1 | 126.5 (15) | C15—N2—H2A | 124.8 (16) |
C5—N1—H1 | 123.9 (15) | C16—N2—H2A | 125.8 (16) |
C5—N1—C4 | 109.47 (16) | C16—N2—C15 | 109.44 (16) |
O1—C1—C2 | 121.16 (17) | O2—C12—C13 | 121.24 (17) |
O1—C1—C4 | 121.83 (17) | O2—C12—C15 | 121.89 (17) |
C4—C1—C2 | 117.00 (16) | C15—C12—C13 | 116.87 (16) |
C1—C2—H2 | 119.6 | C12—C13—H13 | 119.4 |
C3—C2—C1 | 120.75 (18) | C14—C13—C12 | 121.22 (17) |
C3—C2—H2 | 119.6 | C14—C13—H13 | 119.4 |
C2—C3—H3A | 116.0 | C13—C14—H14 | 116.4 |
C2—C3—H3B | 119.4 | C13—C14—H14A | 120.0 |
C2—C3—C8 | 127.94 (19) | C13—C14—C19 | 127.2 (2) |
C2—C3—C8A | 121.1 (10) | C13—C14—C19A | 120.1 (8) |
C8—C3—H3A | 116.0 | C19—C14—H14 | 116.4 |
C8A—C3—H3B | 119.4 | C19A—C14—H14A | 120.0 |
N1—C4—C1 | 121.21 (17) | N2—C15—C12 | 121.33 (17) |
N1—C4—C7 | 107.25 (16) | N2—C15—C18 | 107.16 (16) |
C7—C4—C1 | 131.54 (17) | C18—C15—C12 | 131.51 (17) |
N1—C5—H5 | 125.6 | N2—C16—H16 | 125.6 |
N1—C5—C6 | 108.84 (17) | N2—C16—C17 | 108.83 (17) |
C6—C5—H5 | 125.6 | C17—C16—H16 | 125.6 |
C5—C6—H6 | 126.5 | C16—C17—H17 | 126.5 |
C5—C6—C7 | 106.95 (17) | C16—C17—C18 | 106.94 (17) |
C7—C6—H6 | 126.5 | C18—C17—H17 | 126.5 |
C4—C7—C6 | 107.48 (17) | C15—C18—C17 | 107.62 (17) |
C4—C7—H7 | 126.3 | C15—C18—H18 | 126.2 |
C6—C7—H7 | 126.3 | C17—C18—H18 | 126.2 |
C9—S1—C8 | 91.96 (12) | C20—S2—C19 | 91.87 (15) |
C3—C8—S1 | 122.46 (18) | C14—C19—S2 | 121.8 (2) |
C11—C8—C3 | 127.9 (3) | C22—C19—C14 | 128.5 (4) |
C11—C8—S1 | 109.6 (3) | C22—C19—S2 | 109.7 (3) |
S1—C9—H9 | 124.2 | S2—C20—H20 | 124.0 |
C10—C9—S1 | 111.5 (2) | C21—C20—S2 | 111.9 (3) |
C10—C9—H9 | 124.2 | C21—C20—H20 | 124.0 |
C9—C10—H10 | 124.1 | C20—C21—H21 | 124.2 |
C9—C10—C11 | 111.9 (3) | C20—C21—C22 | 111.5 (4) |
C11—C10—H10 | 124.1 | C22—C21—H21 | 124.2 |
C8—C11—C10 | 115.0 (4) | C19—C22—C21 | 115.0 (5) |
C8—C11—H11 | 122.5 | C19—C22—H22 | 122.5 |
C10—C11—H11 | 122.5 | C21—C22—H22 | 122.5 |
C9A—S1A—C8A | 89.1 (16) | C20A—S2A—C19A | 88.9 (13) |
C3—C8A—S1A | 111.5 (14) | C14—C19A—S2A | 112.2 (13) |
C11A—C8A—C3 | 128 (3) | C22A—C19A—C14 | 130.3 (19) |
C11A—C8A—S1A | 118 (2) | C22A—C19A—S2A | 117.2 (15) |
S1A—C9A—H9A | 126.6 | S2A—C20A—H20A | 125.0 |
C10A—C9A—S1A | 107 (3) | C21A—C20A—S2A | 110 (2) |
C10A—C9A—H9A | 126.6 | C21A—C20A—H20A | 125.0 |
C9A—C10A—H10A | 118.8 | C20A—C21A—H21A | 121.0 |
C9A—C10A—C11A | 122 (4) | C20A—C21A—C22A | 118 (3) |
C11A—C10A—H10A | 118.8 | C22A—C21A—H21A | 121.0 |
C8A—C11A—C10A | 102 (3) | C19A—C22A—C21A | 106 (2) |
C8A—C11A—H11A | 128.9 | C19A—C22A—H22A | 127.1 |
C10A—C11A—H11A | 128.9 | C21A—C22A—H22A | 127.1 |
| | | |
O1—C1—C4—N1 | 4.1 (3) | O2—C12—C15—N2 | −5.4 (3) |
O1—C1—C4—C7 | −175.24 (19) | O2—C12—C15—C18 | 175.3 (2) |
N1—C4—C7—C6 | −0.3 (2) | N2—C15—C18—C17 | 0.3 (2) |
C1—C4—N1—C5 | −179.78 (17) | C12—C15—N2—C16 | −179.33 (17) |
C1—C4—C7—C6 | 179.10 (19) | C12—C15—C18—C17 | 179.8 (2) |
C2—C1—C4—N1 | −175.50 (17) | C13—C12—C15—N2 | 174.82 (17) |
C2—C1—C4—C7 | 5.1 (3) | C13—C12—C15—C18 | −4.5 (3) |
C3—C2—C1—O1 | 1.4 (3) | C14—C13—C12—O2 | −3.7 (3) |
C3—C2—C1—C4 | −179.01 (18) | C14—C13—C12—C15 | 176.07 (18) |
C3—C8—S1—C9 | 179.5 (5) | C14—C19—S2—C20 | 179.1 (7) |
C3—C8A—S1A—C9A | 178 (6) | C14—C19A—S2A—C20A | −177 (5) |
C4—C7—C6—C5 | 0.8 (2) | C15—C18—C17—C16 | −0.7 (2) |
C6—C5—N1—C4 | 0.8 (2) | C17—C16—N2—C15 | −0.6 (2) |
C7—C4—N1—C5 | −0.3 (2) | C18—C15—N2—C16 | 0.2 (2) |
C7—C6—C5—N1 | −1.0 (2) | C18—C17—C16—N2 | 0.8 (2) |
S1—C8—C3—C2 | −4.9 (7) | S2—C19—C14—C13 | 1.7 (10) |
S1—C9—C10—C11 | 0.0 (5) | S2—C20—C21—C22 | −0.1 (7) |
C8—C3—C2—C1 | −177.9 (4) | C19—C14—C13—C12 | −178.2 (6) |
C9—C10—C11—C8 | 0.5 (8) | C20—C21—C22—C19 | −0.6 (12) |
C10—C9—S1—C8 | −0.4 (4) | C21—C20—S2—C19 | 0.5 (5) |
C10—C11—C8—C3 | −179.5 (6) | C21—C22—C19—C14 | −178.9 (8) |
C10—C11—C8—S1 | −0.7 (8) | C21—C22—C19—S2 | 0.9 (12) |
C11—C8—C3—C2 | 173.7 (6) | C22—C19—C14—C13 | −178.5 (9) |
C11—C8—S1—C9 | 0.6 (5) | C22—C19—S2—C20 | −0.8 (8) |
S1A—C8A—C3—C2 | 177 (3) | S2A—C19A—C14—C13 | 179 (3) |
S1A—C9A—C10A—C11A | 5 (7) | S2A—C20A—C21A—C22A | 1 (5) |
C8A—C3—C2—C1 | −174 (5) | C19A—C14—C13—C12 | 180 (4) |
C9A—C10A—C11A—C8A | 5 (8) | C20A—C21A—C22A—C19A | −3 (7) |
C10A—C9A—S1A—C8A | −10 (6) | C21A—C20A—S2A—C19A | 1 (5) |
C10A—C11A—C8A—C3 | −174 (8) | C21A—C22A—C19A—C14 | 177 (7) |
C10A—C11A—C8A—S1A | −13 (8) | C21A—C22A—C19A—S2A | 4 (8) |
C11A—C8A—C3—C2 | −22 (11) | C22A—C19A—C14—C13 | 6 (11) |
C11A—C8A—S1A—C9A | 14 (8) | C22A—C19A—S2A—C20A | −3 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.83 (2) | 2.05 (2) | 2.841 (2) | 160 (2) |
N2—H2A···O2ii | 0.84 (2) | 2.03 (2) | 2.832 (2) | 158 (2) |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+3, −z+1. |
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