The solubility and stability of heterocyclic chalcones compared with trans-chalcone

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.

Computing details

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

Crystal data

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) Å^3	Block, pale yellow
Z = 8	0.53 × 0.28 × 0.26 mm
F(000) = 848

Data collection

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

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: mixed
wR(F^2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0418P)^2 + 0.8248P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.83 (2)	2.05 (2)	2.841 (2)	160 (2)
N2—H2A···O2^ii	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.