(4aR*,10bR*)-8,10-Dimeth­oxy-5-[(4-nitro­phen­yl)sulfon­yl]-3,4,4a,5,6,10b-hexa­hydro­phenanthridine

DiGrandi, M.; Neary, M.C.; Corfield, P.W.R.

doi:10.1107/S2414314625011150

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 12| December 2025| x251115

https://doi.org/10.1107/S2414314625011150

Open

access

(4aR,10bR)-8,10-Dimethoxy-5-[(4-nitrophenyl)sulfonyl]-3,4,4a,5,6,10b-hexahydrophenanthridine

Martin DiGrandi,^a Michelle C. Neary ^b and Peter W. R. Corfield ^c ^*

^aDepartment of Natural Sciences, Fordham University, 113 West 60th Street, New York, NY 10023, USA, ^bDepartment of Chemistry, Hunter College, The City University of New York, New York, 10065 NY, USA, and ^cDepartment of Chemistry and Biochemistry, Fordham University, 441 East Fordham Road, Bronx, NY 10458, USA
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 3 December 2025; accepted 10 December 2025; online 16 December 2025)

The title compound, C₂₁H₂₂N₂O₆S, which was obtained during a study directed to the synthesis of the anti-cancer natural product, pancratistatin, crystallizes with two independent molecules in the asymmetric unit, related by an approximate inversion center near (1/4, 1/2, 1/4) in space group P2₁/c. They have similar but not identical shapes. The crystal structure confirms the expected molecular structure of the compound. In the extended structure, C—H⋯O interactions connect the molecules into a two-dimensional network lying perpendicular to the b axis.

Keywords: crystal structure; pancratistatin; C—H⋯O interactions; Z′ = 2.

CCDC reference: 2514900

Structure description

The title compound, C₂₁H₂₂N₂O₆S, was prepared from a substituted aziridine as a model compound in a project directed toward the synthesis of the anti-cancer natural product, pancratistatin (McClachlan et al., 2005 ). The full details of this chemistry will be published in due course. The title compound crystallizes with two independent molecules in the asymmetric unit, A and B, as seen in Fig. 1. (The atom numbering in molecule B follows that in molecule A, with the addition of 20 to each atom's number. The a,b numbering follows IUPAC practice.) The crystal structure confirms the expected molecular structure of the title compound, with identical chirality at C4a and C10b (both R) in molecule A and C24a and C30b (both S) in molecule B in the arbitrarily chosen asymmetric unit. As the compound crystallizes in the centrosymmetric space group P2₁/c, the unit cell contains equal numbers of chiral molecules and their enantiomers, i.e., the compound is racemic. In addition, the two independent molecules are related by an approximate inversion center near (1/4, 1/2, 1/4), as can be seen in Fig. 1. Inverting molecule B again with the crystallographic inversion center at (1/2, 1/2, 1/2) relates this molecule to molecule A by an approximate translation (1/2, 0, 1/2) along the ac diagonal, as can be seen in projection in Fig. 2. Carolyn Brock has pointed out that approximate symmetry relations often exist between independent molecules in structures with Z′ > 1 (Brock, 2022 , 2024 ), although most of her analyses have focused on non-centrosymmetric space groups.

Figure 1
The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level.

Figure 2
Packing diagram for the title compound. Molecule A is coloured black, and molecule B green. Blue dashed lines indicate C—H⋯O interactions between molecules A and B, while red dashed lines show interactions with the pair of molecules at (1 − x, 1 − y, 1 − z).

The two independent molecules have similar, but not identical shapes, as can be seen from the superposition of an inverted molecule B onto molecule A in Fig. 3. The r.m.s. deviation between non-hydrogen atoms in the superposed structures is 0.43 Å, with a maximum deviation of 1.29 Å for atoms O20B and O40B. Of the fused three-ring phenanthridine system, the six-membered inner ring containing nitrogen atom N5/N25 is held in a boat shape, with ends C6/C10b (A) and C26/C30b (B). The bridge hydrogen atoms H4a and H10b are on the same side of the molecule, which pushes ring C1–C4/C4a/C11b to lie approximately at right angles to the general plane of the other two fused rings. A search of the CSD Database (August 2025 version; Groom et al., 2016 ) using the atoms of the fused three-ring system with the double bond between C1 and C2 but without hydrogen atoms, gave 30 hits. Of these, four hits and three structures have only H atoms at C4a and C10b: refcodes CAVRAT (von Wangelin et al., 2025 ), IHUVOY01 (Liu et al., 2014 ) and REKBEP (Crich & Krishnamurthy, 2006 ). In all three cases, the H atoms at the equivalent positions to our atoms C4a and C10b have the same chirality, leading to a general shape of the three-ringed system similar to the present case.

Figure 3
Overlay plot of molecules A and B, with A in red and B in blue. The two atom pairs furthest apart are shown.

A list of potential C—H ⋯ O hydrogen bonds is given in Table 1. The interactions C12—H12B⋯O40A and C33—H33B⋯O20A link the two molecules in the asymmetric unit together. Three of the contacts link pairs of molecules related by an inversion center at (1/2, 1/2, 1/2), as can be seen in Fig. 2. The remaining C—H⋯O contacts link these groups of four molecules into a two-dimensional network lying perpendicular to the b axis. The closest intermolecular H⋯H contacts are H7⋯H24C(1–x, 1 − y, 1 − z) = 2.13 Å and H22⋯H31B(x, $[{3\over 2}]$ − y, $[{1\over 2}]$ − z) = 2.30 Å. All other intermolecular H⋯H contacts are 2.36 Å or greater.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O31ⁱ	0.95	2.62	3.5424 (17)	164
C12—H12B⋯O32ⁱⁱ	0.98	2.55	3.2682 (18)	130
C12—H12B⋯O40A	0.98	2.49	3.2696 (19)	137
C15—H15⋯O28ⁱⁱⁱ	0.95	2.45	3.2953 (18)	148
C24A—H24C⋯O8ⁱ	1.00	2.62	3.5134 (17)	149
C32—H32A⋯O40Bⁱⁱⁱ	0.98	2.59	3.443 (2)	145
C33—H33B⋯O20A	0.98	2.52	3.4825 (19)	168
C39—H39⋯O20B^iv	0.95	2.65	3.603 (2)	178
C35—H35⋯O8ⁱ	0.95	2.56	3.1495 (18)	120
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Synthesis and crystallization

To a cool (0 °C) solution of 1 (0.1087 g; 0.39 mmol) in dry CH₂Cl₂ (2 ml) was added solid 4-nitrobenzenesulfonyl chloride (2; 0.1049 g; 0.47 mmol; 1.2 eq) followed by the addition of neat triethylamine (0.13 ml; 0.098 g; 0.96 mmol; 2.5 eq) (see reaction scheme in Fig. 4). The reaction was stirred at this temperature for 30 minutes, whereupon it was poured into ether and washed with water. The organic layer was then washed successively with 1M HCl, saturated NaHCO₃, water and brine. The ether layer was dried over MgSO₄, filtered and concentrated in vacuo to give the crude sulfonamide as a yellow glass that crystallized on standing. This was chromatographed on SiO₂, eluting with EtOAc:hex/2:5 from which a purified sample of the title compound, 3, crystallized upon standing.

Figure 4
Reaction scheme.

¹H NMR (400 MHz, CDCl₃): d 8.05–8.07 (d, J = 8.7 Hz, 2H), d 7.76–7.78 (d, J = 8.7 Hz, 2H), d 6.20 (s, 1H), 6.02 (s, 1H), d 5.81–5.83 (m, 1H), d 5.47–5.49 (m, 1H), d 4.54–4.58 (d, J = 16.3 Hz, 1H), d 4.35–4.39 (d, J = 16.3 Hz, 1H), d 4.05–4.08 (m, 1H), 3.83–3.85 (m, 1H), d 3.70 (s, 3H), d 3.69 (s, 3H), d 2.23–2.33 (m, 2H), d 2.12–2.16 (m, 1H), d 1.48–1.86 (m, 1H).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₂₂N₂O₆S
M_r	430.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	130
a, b, c (Å)	14.0490 (4), 30.0167 (9), 10.0866 (3)
β (°)	109.468 (1)
V (Å³)	4010.4 (2)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	1.80
Crystal size (mm)	0.31 × 0.22 × 0.17

Data collection
Diffractometer	Bruker D8 with PHOTON III detector
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.659, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	97099, 8165, 8126
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.084, 1.13
No. of reflections	8165
No. of parameters	545
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.41
Computer programs: APEX4 and SAINT (Bruker, 2022 ), SHELXT2019 (Sheldrick 2015a ), SHELXL2019 (Sheldrick 2015b ), ORTEP III (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2514900

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625011150/hb4549sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625011150/hb4549Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625011150/hb4549Isup3.cml

checkCIF report

Computing details top

(4aR*,10bR*)-8,10-Dimethoxy-5-[(4-nitrophenyl)sulfonyl]-3,4,4a,5,6,10b-hexahydrophenanthridine top

Crystal data top

C₂₁H₂₂N₂O₆S	F(000) = 1808
M_r = 430.46	D_x = 1.426 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 14.0490 (4) Å	Cell parameters from 9717 reflections
b = 30.0167 (9) Å	θ = 4.5–74.4°
c = 10.0866 (3) Å	µ = 1.80 mm⁻¹
β = 109.468 (1)°	T = 130 K
V = 4010.4 (2) Å³	Block, yellow
Z = 8	0.31 × 0.22 × 0.17 mm

Data collection top

Bruker D8 with PHOTON III detector diffractometer	8126 reflections with I > 2σ(I)
Radiation source: microfocus	R_int = 0.039
φ and ω shutterless scans	θ_max = 74.5°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −17→17
T_min = 0.659, T_max = 0.754	k = −37→37
97099 measured reflections	l = −12→12
8165 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.026P)² + 2.560P] where P = (F_o² + 2F_c²)/3
8165 reflections	(Δ/σ)_max = 0.003
545 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.41 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.94870 (11)	0.25816 (5)	0.67438 (16)	0.0243 (3)
H1	0.897712	0.241645	0.695120	0.029*
C2	1.00916 (12)	0.23624 (5)	0.62052 (16)	0.0266 (3)
H2	0.997449	0.205367	0.601121	0.032*
C3	1.09543 (11)	0.25806 (5)	0.58880 (16)	0.0257 (3)
H3A	1.076224	0.263381	0.486357	0.031*
H3B	1.154739	0.237997	0.617181	0.031*
C4	1.12317 (10)	0.30226 (5)	0.66715 (15)	0.0210 (3)
H4A	1.171831	0.318403	0.632801	0.025*
H4B	1.156292	0.296356	0.768738	0.025*
C4A	1.02997 (10)	0.33137 (4)	0.64615 (14)	0.0173 (3)
H4A1	1.052052	0.359811	0.699126	0.017*
N5	0.98193 (8)	0.34236 (4)	0.49316 (12)	0.0171 (2)
C6	0.87796 (10)	0.32601 (5)	0.42045 (14)	0.0190 (3)
H6A	0.879456	0.293432	0.406054	0.023*
H6B	0.850527	0.340349	0.326998	0.023*
C6A	0.81067 (10)	0.33626 (4)	0.50524 (14)	0.0180 (3)
C7	0.71397 (10)	0.35287 (5)	0.44442 (14)	0.0196 (3)
H7	0.688478	0.359075	0.346507	0.024*
C8	0.65462 (10)	0.36037 (5)	0.52819 (14)	0.0196 (3)
C9	0.69327 (10)	0.35412 (5)	0.67320 (14)	0.0206 (3)
H9	0.653384	0.360452	0.730664	0.025*
C10	0.79211 (11)	0.33830 (5)	0.73238 (14)	0.0203 (3)
C11	0.85123 (10)	0.32831 (4)	0.64914 (14)	0.0183 (3)
C10B	0.95513 (10)	0.30779 (5)	0.70530 (14)	0.0191 (3)
H10B	0.980329	0.311662	0.809736	0.019*
O8	0.55768 (7)	0.37374 (4)	0.45705 (11)	0.0260 (2)
C12	0.49169 (11)	0.38288 (5)	0.53539 (16)	0.0254 (3)
H12A	0.424665	0.390797	0.470561	0.038*
H12B	0.518809	0.407713	0.600019	0.038*
H12C	0.486406	0.356372	0.589244	0.038*
O10	0.83736 (8)	0.33101 (4)	0.87362 (10)	0.0290 (2)
C13	0.78436 (13)	0.34577 (7)	0.96395 (16)	0.0362 (4)
H13A	0.827498	0.342182	1.062181	0.054*
H13B	0.722835	0.328024	0.946464	0.054*
H13C	0.766327	0.377243	0.945277	0.054*
S1	1.01283 (2)	0.38887 (2)	0.43588 (3)	0.01768 (8)
O11	1.11285 (7)	0.39955 (3)	0.52662 (11)	0.0229 (2)
O12	0.99192 (8)	0.38435 (3)	0.28724 (10)	0.0245 (2)
C14	0.93163 (10)	0.43182 (4)	0.45622 (14)	0.0185 (3)
C15	0.95430 (11)	0.45349 (5)	0.58486 (15)	0.0231 (3)
H15	1.012007	0.445080	0.661661	0.028*
C16	0.89186 (11)	0.48751 (5)	0.60004 (15)	0.0241 (3)
H16	0.905763	0.502634	0.687191	0.029*
C17	0.80891 (10)	0.49892 (4)	0.48542 (15)	0.0208 (3)
C18	0.78519 (11)	0.47749 (5)	0.35725 (16)	0.0251 (3)
H18	0.727413	0.486006	0.280708	0.030*
C19	0.84732 (11)	0.44333 (5)	0.34248 (15)	0.0243 (3)
H19	0.832448	0.427964	0.255593	0.029*
N20	0.74292 (9)	0.53544 (4)	0.50023 (14)	0.0251 (3)
O20A	0.75675 (9)	0.55033 (3)	0.61827 (12)	0.0300 (2)
O20B	0.67753 (9)	0.54883 (4)	0.39379 (13)	0.0374 (3)
C21	0.60556 (12)	0.73759 (5)	0.93903 (17)	0.0269 (3)
H21	0.668102	0.751315	0.946693	0.032*
C22	0.54434 (13)	0.75894 (5)	0.99282 (17)	0.0299 (3)
H22	0.566007	0.786538	1.039182	0.036*
C23	0.44237 (12)	0.74146 (5)	0.98373 (17)	0.0293 (3)
H23A	0.393530	0.766398	0.964646	0.035*
H23B	0.446074	0.727901	1.074789	0.035*
C24	0.40587 (11)	0.70674 (5)	0.86733 (16)	0.0231 (3)
H24A	0.388528	0.721626	0.774700	0.028*
H24B	0.344091	0.692226	0.873083	0.028*
C24A	0.48673 (10)	0.67140 (4)	0.87960 (14)	0.0174 (3)
H24C	0.459678	0.649885	0.800205	0.017*
N25	0.50776 (8)	0.64619 (4)	1.01483 (12)	0.0173 (2)
C26	0.61178 (10)	0.64899 (5)	1.11877 (14)	0.0209 (3)
H26A	0.619707	0.626634	1.193858	0.025*
H26B	0.622562	0.678886	1.162734	0.025*
C26A	0.68946 (10)	0.64069 (5)	1.04828 (14)	0.0192 (3)
C27	0.77174 (10)	0.61279 (5)	1.10455 (14)	0.0221 (3)
H27	0.782848	0.598560	1.192553	0.026*
C28	0.83793 (10)	0.60600 (5)	1.02962 (15)	0.0222 (3)
C29	0.82250 (10)	0.62638 (5)	0.89996 (15)	0.0208 (3)
H29	0.867858	0.621453	0.849551	0.025*
C30	0.73888 (10)	0.65418 (4)	0.84593 (14)	0.0184 (3)
C31	0.67214 (10)	0.66196 (4)	0.91935 (14)	0.0183 (3)
C30B	0.58264 (10)	0.69282 (4)	0.86619 (14)	0.0186 (3)
H30B	0.570271	0.697974	0.763855	0.019*
O28	0.91723 (8)	0.57787 (4)	1.09176 (11)	0.0317 (3)
C32	0.98958 (14)	0.57149 (8)	1.0218 (2)	0.0452 (5)
H32A	1.043726	0.551930	1.078436	0.068*
H32B	1.018101	0.600350	1.009288	0.068*
H32C	0.956463	0.557827	0.929609	0.068*
O30	0.71697 (7)	0.67612 (3)	0.72038 (10)	0.0224 (2)
C33	0.77642 (11)	0.66600 (5)	0.63390 (16)	0.0252 (3)
H33A	0.748508	0.681441	0.543576	0.038*
H33B	0.775494	0.633786	0.617792	0.038*
H33C	0.846073	0.675835	0.680948	0.038*
S2	0.45126 (2)	0.59815 (2)	1.00168 (3)	0.01761 (8)
O31	0.35200 (7)	0.60336 (3)	0.90064 (11)	0.0226 (2)
O32	0.46291 (8)	0.58351 (3)	1.14117 (11)	0.0254 (2)
C34	0.51642 (10)	0.56000 (4)	0.92854 (15)	0.0190 (3)
C35	0.48500 (11)	0.55444 (5)	0.78342 (15)	0.0227 (3)
H35	0.426771	0.569550	0.724723	0.027*
C36	0.53954 (11)	0.52659 (5)	0.72492 (16)	0.0248 (3)
H36	0.519075	0.521986	0.626198	0.030*
C37	0.62415 (11)	0.50589 (4)	0.81450 (16)	0.0229 (3)
C38	0.65638 (11)	0.51090 (5)	0.95883 (16)	0.0254 (3)
H38	0.715213	0.496044	1.016930	0.031*
C39	0.60097 (11)	0.53809 (5)	1.01700 (15)	0.0233 (3)
H39	0.620510	0.541720	1.116052	0.028*
N40	0.68215 (10)	0.47617 (4)	0.75286 (15)	0.0290 (3)
O40A	0.64651 (9)	0.46745 (4)	0.62715 (13)	0.0337 (3)
O40B	0.76304 (9)	0.46191 (4)	0.83064 (15)	0.0428 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0233 (7)	0.0205 (7)	0.0290 (7)	0.0005 (5)	0.0088 (6)	0.0078 (6)
C2	0.0283 (7)	0.0170 (7)	0.0323 (8)	0.0015 (6)	0.0071 (6)	0.0013 (6)
C3	0.0263 (7)	0.0218 (7)	0.0311 (8)	0.0069 (6)	0.0123 (6)	−0.0003 (6)
C4	0.0174 (6)	0.0216 (7)	0.0235 (7)	0.0028 (5)	0.0061 (5)	0.0032 (5)
C4A	0.0177 (6)	0.0171 (6)	0.0160 (6)	0.0016 (5)	0.0042 (5)	0.0007 (5)
N5	0.0160 (5)	0.0176 (5)	0.0179 (5)	0.0006 (4)	0.0059 (4)	0.0014 (4)
C6	0.0179 (6)	0.0222 (7)	0.0169 (6)	−0.0010 (5)	0.0058 (5)	−0.0021 (5)
C6A	0.0190 (6)	0.0177 (6)	0.0179 (6)	−0.0017 (5)	0.0069 (5)	−0.0016 (5)
C7	0.0184 (6)	0.0230 (7)	0.0160 (6)	−0.0007 (5)	0.0039 (5)	−0.0008 (5)
C8	0.0164 (6)	0.0191 (6)	0.0218 (7)	−0.0004 (5)	0.0044 (5)	−0.0004 (5)
C9	0.0203 (6)	0.0235 (7)	0.0204 (7)	0.0019 (5)	0.0102 (5)	0.0003 (5)
C10	0.0220 (7)	0.0226 (7)	0.0171 (6)	0.0023 (5)	0.0075 (5)	0.0029 (5)
C11	0.0184 (6)	0.0187 (6)	0.0184 (6)	0.0012 (5)	0.0067 (5)	0.0017 (5)
C10B	0.0194 (6)	0.0216 (7)	0.0173 (6)	0.0037 (5)	0.0073 (5)	0.0034 (5)
O8	0.0165 (5)	0.0394 (6)	0.0214 (5)	0.0058 (4)	0.0055 (4)	−0.0007 (4)
C12	0.0186 (7)	0.0313 (8)	0.0279 (7)	0.0013 (6)	0.0097 (6)	−0.0033 (6)
O10	0.0264 (5)	0.0467 (7)	0.0166 (5)	0.0136 (5)	0.0110 (4)	0.0073 (4)
C13	0.0307 (8)	0.0630 (12)	0.0194 (7)	0.0129 (8)	0.0143 (6)	0.0048 (7)
S1	0.01737 (15)	0.01847 (16)	0.01969 (16)	0.00300 (12)	0.00948 (12)	0.00345 (12)
O11	0.0169 (5)	0.0228 (5)	0.0302 (5)	0.0004 (4)	0.0097 (4)	0.0040 (4)
O12	0.0286 (5)	0.0286 (5)	0.0207 (5)	0.0063 (4)	0.0140 (4)	0.0048 (4)
C14	0.0185 (6)	0.0165 (6)	0.0220 (6)	0.0011 (5)	0.0088 (5)	0.0033 (5)
C15	0.0233 (7)	0.0223 (7)	0.0220 (7)	0.0029 (5)	0.0055 (6)	0.0032 (5)
C16	0.0287 (7)	0.0224 (7)	0.0227 (7)	0.0009 (6)	0.0104 (6)	−0.0015 (5)
C17	0.0204 (6)	0.0164 (6)	0.0291 (7)	0.0014 (5)	0.0128 (6)	0.0022 (5)
C18	0.0207 (7)	0.0243 (7)	0.0271 (7)	0.0049 (6)	0.0036 (6)	0.0014 (6)
C19	0.0244 (7)	0.0239 (7)	0.0225 (7)	0.0036 (6)	0.0051 (6)	−0.0012 (6)
N20	0.0241 (6)	0.0187 (6)	0.0364 (7)	0.0005 (5)	0.0153 (5)	−0.0001 (5)
O20A	0.0377 (6)	0.0215 (5)	0.0384 (6)	0.0003 (4)	0.0231 (5)	−0.0030 (4)
O20B	0.0280 (6)	0.0360 (6)	0.0432 (7)	0.0148 (5)	0.0051 (5)	−0.0010 (5)
C21	0.0292 (8)	0.0174 (7)	0.0353 (8)	−0.0056 (6)	0.0125 (6)	−0.0020 (6)
C22	0.0403 (9)	0.0184 (7)	0.0326 (8)	−0.0034 (6)	0.0145 (7)	−0.0057 (6)
C23	0.0371 (8)	0.0224 (7)	0.0349 (8)	0.0049 (6)	0.0207 (7)	−0.0026 (6)
C24	0.0222 (7)	0.0218 (7)	0.0276 (7)	0.0041 (5)	0.0114 (6)	0.0024 (6)
C24A	0.0187 (6)	0.0171 (6)	0.0172 (6)	0.0002 (5)	0.0070 (5)	−0.0002 (5)
N25	0.0175 (5)	0.0177 (5)	0.0174 (5)	−0.0017 (4)	0.0067 (4)	−0.0007 (4)
C26	0.0204 (7)	0.0247 (7)	0.0166 (6)	−0.0036 (5)	0.0048 (5)	−0.0027 (5)
C26A	0.0177 (6)	0.0210 (6)	0.0178 (6)	−0.0058 (5)	0.0047 (5)	−0.0040 (5)
C27	0.0198 (6)	0.0266 (7)	0.0171 (6)	−0.0031 (5)	0.0024 (5)	0.0008 (5)
C28	0.0158 (6)	0.0249 (7)	0.0225 (7)	0.0001 (5)	0.0018 (5)	0.0004 (5)
C29	0.0170 (6)	0.0226 (7)	0.0229 (7)	−0.0005 (5)	0.0068 (5)	−0.0014 (5)
C30	0.0192 (6)	0.0171 (6)	0.0192 (6)	−0.0024 (5)	0.0069 (5)	−0.0003 (5)
C31	0.0171 (6)	0.0169 (6)	0.0203 (6)	−0.0030 (5)	0.0057 (5)	−0.0021 (5)
C30B	0.0210 (6)	0.0171 (6)	0.0201 (6)	0.0001 (5)	0.0101 (5)	−0.0002 (5)
O28	0.0222 (5)	0.0424 (7)	0.0285 (6)	0.0114 (5)	0.0060 (4)	0.0094 (5)
C32	0.0332 (9)	0.0629 (13)	0.0429 (10)	0.0258 (9)	0.0172 (8)	0.0180 (9)
O30	0.0238 (5)	0.0248 (5)	0.0230 (5)	0.0064 (4)	0.0135 (4)	0.0061 (4)
C33	0.0266 (7)	0.0287 (7)	0.0255 (7)	0.0066 (6)	0.0156 (6)	0.0047 (6)
S2	0.01831 (16)	0.01753 (15)	0.01911 (16)	−0.00212 (11)	0.00907 (12)	−0.00057 (11)
O31	0.0167 (5)	0.0251 (5)	0.0266 (5)	−0.0023 (4)	0.0079 (4)	−0.0032 (4)
O32	0.0316 (5)	0.0266 (5)	0.0220 (5)	−0.0050 (4)	0.0142 (4)	0.0021 (4)
C34	0.0210 (6)	0.0142 (6)	0.0240 (7)	−0.0025 (5)	0.0102 (5)	−0.0002 (5)
C35	0.0247 (7)	0.0195 (7)	0.0237 (7)	0.0011 (5)	0.0078 (6)	0.0008 (5)
C36	0.0300 (7)	0.0207 (7)	0.0251 (7)	−0.0006 (6)	0.0111 (6)	−0.0016 (6)
C37	0.0249 (7)	0.0139 (6)	0.0340 (8)	−0.0019 (5)	0.0153 (6)	−0.0013 (5)
C38	0.0231 (7)	0.0191 (7)	0.0323 (8)	0.0015 (5)	0.0069 (6)	0.0029 (6)
C39	0.0254 (7)	0.0195 (7)	0.0236 (7)	−0.0014 (5)	0.0060 (6)	0.0014 (5)
N40	0.0299 (7)	0.0187 (6)	0.0445 (8)	−0.0010 (5)	0.0205 (6)	−0.0008 (5)
O40A	0.0411 (6)	0.0250 (5)	0.0432 (7)	−0.0047 (5)	0.0249 (5)	−0.0094 (5)
O40B	0.0332 (6)	0.0399 (7)	0.0579 (8)	0.0137 (5)	0.0190 (6)	0.0017 (6)

Geometric parameters (Å, º) top

C1—C2	1.326 (2)	C21—C22	1.325 (2)
C1—C10B	1.518 (2)	C21—C30B	1.5138 (19)
C1—H1	0.9500	C21—H21	0.9500
C2—C3	1.503 (2)	C22—C23	1.499 (2)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.527 (2)	C23—C24	1.525 (2)
C3—H3A	0.9900	C23—H23A	0.9900
C3—H3B	0.9900	C23—H23B	0.9900
C4—C4A	1.5291 (18)	C24—C24A	1.5289 (18)
C4—H4A	0.9900	C24—H24A	0.9900
C4—H4B	0.9900	C24—H24B	0.9900
C4A—N5	1.5004 (16)	C24A—N25	1.5005 (17)
C4A—C10B	1.5430 (18)	C24A—C30B	1.5392 (18)
C4A—H4A1	1.0000	C24A—H24C	1.0000
N5—C6	1.4826 (16)	N25—C26	1.4901 (17)
N5—S1	1.6244 (11)	N25—S2	1.6300 (11)
C6—C6A	1.5028 (18)	C26—C26A	1.5086 (19)
C6—H6A	0.9900	C26—H26A	0.9900
C6—H6B	0.9900	C26—H26B	0.9900
C6A—C7	1.3838 (19)	C26A—C27	1.387 (2)
C6A—C11	1.3918 (19)	C26A—C31	1.3953 (19)
C7—C8	1.3891 (19)	C27—C28	1.395 (2)
C7—H7	0.9500	C27—H27	0.9500
C8—O8	1.3710 (16)	C28—O28	1.3719 (17)
C8—C9	1.3929 (19)	C28—C29	1.394 (2)
C9—C10	1.3992 (19)	C29—C30	1.3953 (19)
C9—H9	0.9500	C29—H29	0.9500
C10—O10	1.3704 (16)	C30—O30	1.3684 (16)
C10—C11	1.3962 (19)	C30—C31	1.3946 (19)
C11—C10B	1.5098 (18)	C31—C30B	1.5090 (19)
C10B—H10B	1.0000	C30B—H30B	1.0000
O8—C12	1.4308 (17)	O28—C32	1.431 (2)
C12—H12A	0.9800	C32—H32A	0.9800
C12—H12B	0.9800	C32—H32B	0.9800
C12—H12C	0.9800	C32—H32C	0.9800
O10—C13	1.4258 (18)	O30—C33	1.4269 (16)
C13—H13A	0.9800	C33—H33A	0.9800
C13—H13B	0.9800	C33—H33B	0.9800
C13—H13C	0.9800	C33—H33C	0.9800
S1—O11	1.4345 (10)	S2—O32	1.4305 (10)
S1—O12	1.4349 (10)	S2—O31	1.4353 (10)
S1—C14	1.7782 (14)	S2—C34	1.7732 (14)
C14—C19	1.3903 (19)	C34—C39	1.390 (2)
C14—C15	1.390 (2)	C34—C35	1.391 (2)
C15—C16	1.388 (2)	C35—C36	1.391 (2)
C15—H15	0.9500	C35—H35	0.9500
C16—C17	1.383 (2)	C36—C37	1.378 (2)
C16—H16	0.9500	C36—H36	0.9500
C17—C18	1.382 (2)	C37—C38	1.381 (2)
C17—N20	1.4752 (18)	C37—N40	1.4778 (19)
C18—C19	1.386 (2)	C38—C39	1.386 (2)
C18—H18	0.9500	C38—H38	0.9500
C19—H19	0.9500	C39—H39	0.9500
N20—O20A	1.2251 (17)	N40—O40A	1.2263 (18)
N20—O20B	1.2250 (17)	N40—O40B	1.2230 (19)

C2—C1—C10B	124.67 (13)	C22—C21—C30B	124.47 (14)
C2—C1—H1	117.7	C22—C21—H21	117.8
C10B—C1—H1	117.7	C30B—C21—H21	117.8
C1—C2—C3	122.90 (13)	C21—C22—C23	122.88 (14)
C1—C2—H2	118.6	C21—C22—H22	118.6
C3—C2—H2	118.6	C23—C22—H22	118.6
C2—C3—C4	110.70 (12)	C22—C23—C24	110.82 (12)
C2—C3—H3A	109.5	C22—C23—H23A	109.5
C4—C3—H3A	109.5	C24—C23—H23A	109.5
C2—C3—H3B	109.5	C22—C23—H23B	109.5
C4—C3—H3B	109.5	C24—C23—H23B	109.5
H3A—C3—H3B	108.1	H23A—C23—H23B	108.1
C3—C4—C4A	111.46 (11)	C23—C24—C24A	111.20 (12)
C3—C4—H4A	109.3	C23—C24—H24A	109.4
C4A—C4—H4A	109.3	C24A—C24—H24A	109.4
C3—C4—H4B	109.3	C23—C24—H24B	109.4
C4A—C4—H4B	109.3	C24A—C24—H24B	109.4
H4A—C4—H4B	108.0	H24A—C24—H24B	108.0
N5—C4A—C4	109.82 (11)	N25—C24A—C24	109.84 (11)
N5—C4A—C10B	111.57 (10)	N25—C24A—C30B	112.19 (11)
C4—C4A—C10B	110.28 (11)	C24—C24A—C30B	110.59 (11)
N5—C4A—H4A1	108.4	N25—C24A—H24C	108.0
C4—C4A—H4A1	108.4	C24—C24A—H24C	108.0
C10B—C4A—H4A1	108.4	C30B—C24A—H24C	108.0
C6—N5—C4A	117.86 (10)	C26—N25—C24A	117.45 (10)
C6—N5—S1	116.39 (9)	C26—N25—S2	116.35 (9)
C4A—N5—S1	118.22 (9)	C24A—N25—S2	115.41 (9)
N5—C6—C6A	110.71 (11)	N25—C26—C26A	110.67 (11)
N5—C6—H6A	109.5	N25—C26—H26A	109.5
C6A—C6—H6A	109.5	C26A—C26—H26A	109.5
N5—C6—H6B	109.5	N25—C26—H26B	109.5
C6A—C6—H6B	109.5	C26A—C26—H26B	109.5
H6A—C6—H6B	108.1	H26A—C26—H26B	108.1
C7—C6A—C11	121.63 (12)	C27—C26A—C31	121.37 (13)
C7—C6A—C6	122.15 (12)	C27—C26A—C26	122.83 (12)
C11—C6A—C6	116.22 (12)	C31—C26A—C26	115.78 (12)
C6A—C7—C8	119.23 (12)	C26A—C27—C28	118.80 (13)
C6A—C7—H7	120.4	C26A—C27—H27	120.6
C8—C7—H7	120.4	C28—C27—H27	120.6
O8—C8—C9	124.10 (12)	O28—C28—C29	123.20 (13)
O8—C8—C7	114.96 (12)	O28—C28—C27	115.40 (13)
C9—C8—C7	120.93 (12)	C29—C28—C27	121.40 (13)
C8—C9—C10	118.54 (12)	C30—C29—C28	118.45 (13)
C8—C9—H9	120.7	C30—C29—H29	120.8
C10—C9—H9	120.7	C28—C29—H29	120.8
O10—C10—C11	115.34 (12)	O30—C30—C31	115.30 (12)
O10—C10—C9	123.24 (12)	O30—C30—C29	123.35 (12)
C11—C10—C9	121.41 (12)	C31—C30—C29	121.35 (12)
C6A—C11—C10	118.12 (12)	C26A—C31—C30	118.62 (12)
C6A—C11—C10B	118.02 (12)	C26A—C31—C30B	118.55 (12)
C10—C11—C10B	123.82 (12)	C30—C31—C30B	122.83 (12)
C11—C10B—C1	109.83 (11)	C31—C30B—C21	110.80 (12)
C11—C10B—C4A	111.47 (11)	C31—C30B—C24A	111.26 (11)
C1—C10B—C4A	111.85 (11)	C21—C30B—C24A	112.27 (11)
C11—C10B—H10B	107.8	C31—C30B—H30B	107.4
C1—C10B—H10B	107.8	C21—C30B—H30B	107.4
C4A—C10B—H10B	107.8	C24A—C30B—H30B	107.4
C8—O8—C12	118.72 (11)	C28—O28—C32	117.34 (12)
O8—C12—H12A	109.5	O28—C32—H32A	109.5
O8—C12—H12B	109.5	O28—C32—H32B	109.5
H12A—C12—H12B	109.5	H32A—C32—H32B	109.5
O8—C12—H12C	109.5	O28—C32—H32C	109.5
H12A—C12—H12C	109.5	H32A—C32—H32C	109.5
H12B—C12—H12C	109.5	H32B—C32—H32C	109.5
C10—O10—C13	117.04 (11)	C30—O30—C33	117.80 (11)
O10—C13—H13A	109.5	O30—C33—H33A	109.5
O10—C13—H13B	109.5	O30—C33—H33B	109.5
H13A—C13—H13B	109.5	H33A—C33—H33B	109.5
O10—C13—H13C	109.5	O30—C33—H33C	109.5
H13A—C13—H13C	109.5	H33A—C33—H33C	109.5
H13B—C13—H13C	109.5	H33B—C33—H33C	109.5
O11—S1—O12	120.24 (6)	O32—S2—O31	119.84 (6)
O11—S1—N5	106.63 (6)	O32—S2—N25	107.39 (6)
O12—S1—N5	107.72 (6)	O31—S2—N25	107.04 (6)
O11—S1—C14	107.10 (6)	O32—S2—C34	107.76 (6)
O12—S1—C14	105.86 (6)	O31—S2—C34	106.79 (6)
N5—S1—C14	108.93 (6)	N25—S2—C34	107.48 (6)
C19—C14—C15	121.41 (13)	C39—C34—C35	121.49 (13)
C19—C14—S1	119.20 (11)	C39—C34—S2	119.18 (11)
C15—C14—S1	119.39 (10)	C35—C34—S2	119.24 (11)
C14—C15—C16	119.39 (13)	C36—C35—C34	119.47 (13)
C14—C15—H15	120.3	C36—C35—H35	120.3
C16—C15—H15	120.3	C34—C35—H35	120.3
C17—C16—C15	118.51 (13)	C37—C36—C35	118.00 (14)
C17—C16—H16	120.7	C37—C36—H36	121.0
C15—C16—H16	120.7	C35—C36—H36	121.0
C18—C17—C16	122.69 (13)	C38—C37—C36	123.37 (13)
C18—C17—N20	118.49 (13)	C38—C37—N40	118.44 (13)
C16—C17—N20	118.82 (13)	C36—C37—N40	118.19 (13)
C17—C18—C19	118.73 (13)	C37—C38—C39	118.51 (13)
C17—C18—H18	120.6	C37—C38—H38	120.7
C19—C18—H18	120.6	C39—C38—H38	120.7
C14—C19—C18	119.27 (13)	C38—C39—C34	119.15 (13)
C14—C19—H19	120.4	C38—C39—H39	120.4
C18—C19—H19	120.4	C34—C39—H39	120.4
O20A—N20—O20B	124.18 (13)	O40A—N40—O40B	124.09 (14)
O20A—N20—C17	117.91 (12)	O40A—N40—C37	118.13 (13)
O20B—N20—C17	117.92 (12)	O40B—N40—C37	117.78 (14)

C10B—C1—C2—C3	2.7 (2)	C30B—C21—C22—C23	−1.9 (3)
C1—C2—C3—C4	17.9 (2)	C21—C22—C23—C24	−19.2 (2)
C2—C3—C4—C4A	−49.57 (16)	C22—C23—C24—C24A	50.05 (17)
C3—C4—C4A—N5	−61.70 (14)	C23—C24—C24A—N25	63.46 (15)
C3—C4—C4A—C10B	61.65 (15)	C23—C24—C24A—C30B	−60.90 (15)
C4—C4A—N5—C6	117.03 (12)	C24—C24A—N25—C26	−117.81 (12)
C10B—C4A—N5—C6	−5.56 (15)	C30B—C24A—N25—C26	5.62 (16)
C4—C4A—N5—S1	−94.30 (12)	C24—C24A—N25—S2	99.01 (11)
C10B—C4A—N5—S1	143.11 (9)	C30B—C24A—N25—S2	−137.56 (9)
C4A—N5—C6—C6A	48.04 (15)	C24A—N25—C26—C26A	−48.18 (15)
S1—N5—C6—C6A	−101.19 (11)	S2—N25—C26—C26A	94.66 (12)
N5—C6—C6A—C7	136.21 (13)	N25—C26—C26A—C27	−134.50 (13)
N5—C6—C6A—C11	−43.49 (16)	N25—C26—C26A—C31	43.72 (16)
C11—C6A—C7—C8	−2.2 (2)	C31—C26A—C27—C28	−0.2 (2)
C6—C6A—C7—C8	178.09 (12)	C26—C26A—C27—C28	177.94 (13)
C6A—C7—C8—O8	−175.47 (12)	C26A—C27—C28—O28	−179.76 (13)
C6A—C7—C8—C9	4.1 (2)	C26A—C27—C28—C29	−0.4 (2)
O8—C8—C9—C10	176.93 (13)	O28—C28—C29—C30	179.55 (13)
C7—C8—C9—C10	−2.6 (2)	C27—C28—C29—C30	0.3 (2)
C8—C9—C10—O10	179.97 (13)	C28—C29—C30—O30	179.45 (13)
C8—C9—C10—C11	−0.8 (2)	C28—C29—C30—C31	0.5 (2)
C7—C6A—C11—C10	−1.1 (2)	C27—C26A—C31—C30	0.9 (2)
C6—C6A—C11—C10	178.61 (12)	C26—C26A—C31—C30	−177.36 (12)
C7—C6A—C11—C10B	176.69 (12)	C27—C26A—C31—C30B	−178.41 (12)
C6—C6A—C11—C10B	−3.61 (18)	C26—C26A—C31—C30B	3.34 (18)
O10—C10—C11—C6A	−178.09 (12)	O30—C30—C31—C26A	179.91 (12)
C9—C10—C11—C6A	2.6 (2)	C29—C30—C31—C26A	−1.0 (2)
O10—C10—C11—C10B	4.3 (2)	O30—C30—C31—C30B	−0.82 (19)
C9—C10—C11—C10B	−175.01 (13)	C29—C30—C31—C30B	178.22 (12)
C6A—C11—C10B—C1	−77.42 (15)	C26A—C31—C30B—C21	78.86 (15)
C10—C11—C10B—C1	100.23 (15)	C30—C31—C30B—C21	−100.41 (15)
C6A—C11—C10B—C4A	47.13 (16)	C26A—C31—C30B—C24A	−46.79 (16)
C10—C11—C10B—C4A	−135.22 (14)	C30—C31—C30B—C24A	133.94 (13)
C2—C1—C10B—C11	132.95 (15)	C22—C21—C30B—C31	−133.25 (16)
C2—C1—C10B—C4A	8.6 (2)	C22—C21—C30B—C24A	−8.2 (2)
N5—C4A—C10B—C11	−40.59 (15)	N25—C24A—C30B—C31	40.34 (15)
C4—C4A—C10B—C11	−162.91 (11)	C24—C24A—C30B—C31	163.35 (11)
N5—C4A—C10B—C1	82.81 (13)	N25—C24A—C30B—C21	−84.49 (14)
C4—C4A—C10B—C1	−39.51 (15)	C24—C24A—C30B—C21	38.52 (16)
C9—C8—O8—C12	1.4 (2)	C29—C28—O28—C32	3.4 (2)
C7—C8—O8—C12	−179.07 (12)	C27—C28—O28—C32	−177.25 (15)
C11—C10—O10—C13	172.66 (14)	C31—C30—O30—C33	−173.75 (12)
C9—C10—O10—C13	−8.1 (2)	C29—C30—O30—C33	7.23 (19)
C6—N5—S1—O11	176.22 (9)	C26—N25—S2—O32	48.08 (11)
C4A—N5—S1—O11	27.10 (11)	C24A—N25—S2—O32	−168.32 (9)
C6—N5—S1—O12	−53.44 (11)	C26—N25—S2—O31	177.97 (9)
C4A—N5—S1—O12	157.44 (9)	C24A—N25—S2—O31	−38.44 (10)
C6—N5—S1—C14	60.96 (11)	C26—N25—S2—C34	−67.62 (11)
C4A—N5—S1—C14	−88.17 (10)	C24A—N25—S2—C34	75.97 (10)
O11—S1—C14—C19	148.52 (11)	O32—S2—C34—C39	−30.21 (13)
O12—S1—C14—C19	19.08 (13)	O31—S2—C34—C39	−160.18 (11)
N5—S1—C14—C19	−96.51 (12)	N25—S2—C34—C39	85.25 (12)
O11—S1—C14—C15	−30.81 (13)	O32—S2—C34—C35	153.16 (11)
O12—S1—C14—C15	−160.25 (11)	O31—S2—C34—C35	23.19 (13)
N5—S1—C14—C15	84.16 (12)	N25—S2—C34—C35	−91.38 (12)
C19—C14—C15—C16	−0.4 (2)	C39—C34—C35—C36	−0.4 (2)
S1—C14—C15—C16	178.94 (11)	S2—C34—C35—C36	176.14 (11)
C14—C15—C16—C17	−0.4 (2)	C34—C35—C36—C37	−0.8 (2)
C15—C16—C17—C18	0.8 (2)	C35—C36—C37—C38	1.0 (2)
C15—C16—C17—N20	−179.22 (13)	C35—C36—C37—N40	179.83 (13)
C16—C17—C18—C19	−0.4 (2)	C36—C37—C38—C39	0.1 (2)
N20—C17—C18—C19	179.58 (13)	N40—C37—C38—C39	−178.79 (13)
C15—C14—C19—C18	0.7 (2)	C37—C38—C39—C34	−1.3 (2)
S1—C14—C19—C18	−178.57 (11)	C35—C34—C39—C38	1.5 (2)
C17—C18—C19—C14	−0.4 (2)	S2—C34—C39—C38	−175.10 (11)
C18—C17—N20—O20A	170.76 (13)	C38—C37—N40—O40A	171.06 (13)
C16—C17—N20—O20A	−9.26 (19)	C36—C37—N40—O40A	−7.84 (19)
C18—C17—N20—O20B	−8.95 (19)	C38—C37—N40—O40B	−9.2 (2)
C16—C17—N20—O20B	171.02 (13)	C36—C37—N40—O40B	171.93 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O31ⁱ	0.95	2.62	3.5424 (17)	164
C12—H12B···O32ⁱⁱ	0.98	2.55	3.2682 (18)	130
C12—H12B···O40A	0.98	2.49	3.2696 (19)	137
C15—H15···O28ⁱⁱⁱ	0.95	2.45	3.2953 (18)	148
C24A—H24C···O8ⁱ	1.00	2.62	3.5134 (17)	149
C32—H32A···O40Bⁱⁱⁱ	0.98	2.59	3.443 (2)	145
C33—H33B···O20A	0.98	2.52	3.4825 (19)	168
C39—H39···O20B^iv	0.95	2.65	3.603 (2)	178
C35—H35···O8ⁱ	0.95	2.56	3.1495 (18)	120

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+2; (iv) x, y, z+1.

Acknowledgements

We are grateful to Carolyn Brock and Sean Parkin for helpful discussions. Continuing support from the Department of Chemistry and Biochemistry at Fordham University is acknowledged and appreciated. The X-ray Diffractometer purchase was funded by the grant detailed below.

Funding information

Funding for this research was provided by: Air Force Office of Scientific Research (grant No. FA9550-20-1-0158).

References

Brock, C. P. (2022). Acta Cryst. B78, 576–588. Web of Science CrossRef IUCr Journals Google Scholar
Brock, C. P. (2024). Cryst. Growth Des. 24, 6211–6217. CrossRef Google Scholar
Bruker (2022). APEX4 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Crich, D. & Krishnamurthy, V. (2006). Tetrahedron 62, 6830–6840. CSD CrossRef Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Liu, D., Ai, L., Li, F., Zhao, A., Chen, J., Zhang, H. & Liu, J. (2014). Org. Biomol. Chem. 12, 3191–3200. CSD CrossRef PubMed Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
McLachlan, A., Kekre, N., McNulty, J. & Pandey, S. (2005). Apoptosis 10, 619–630. CrossRef PubMed Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wangelin, A. J. von, Neumann, H., Gördes, D., Hübner, S., Wendler, C., Klaus, S., Strübing, D., Spannenberg, A., Jiao, H., El Firdoussi, L., Thurow, K., Stoll, N. & Beller, M. (2005). Synthesis pp. 2029–2038. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.