trans-Di­aqua­bis­(pyridin-2-yl thio­phen-2-yl ketone-κ2N,O)cobalt(II) bis­(tetra­fluorido­borate)

Westcott, B.L.

doi:10.1107/S2414314626007492

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 7| July 2026| x260749

https://doi.org/10.1107/S2414314626007492

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trans-Diaquabis(pyridin-2-yl thiophen-2-yl ketone-κ²N,O)cobalt(II) bis(tetrafluoridoborate)

Barry L. Westcott ^a ^*

^aDepartment of Chemistry and Biochemistry, Central Connecticut State University, 1615 Stanley St., New Britain, CT 06050, USA
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 16 June 2026; accepted 21 July 2026; online 23 July 2026)

The title salt, [Co(C₁₀H₇NOS)₂(H₂O)₂](BF₄)₂, crystallizes in the monoclinic system (space group P2₁/n). In the complex cation, the central Co^II atom (site symmetry 1) has a pseudo-octahedral coordination environment with bonding to pyridyl N [2.0189 (13) Å] and carbonyl O [2.0869 (11) Å] atoms from the 2-thienyl 2-pyridyl ketone ligands. The remaining bonds are to water molecules [2.0903 (13) Å], which form a hydrogen-bonded extended structure with BF₄⁻ counter-ions. The thienyl ring shows disorder through an approximate twofold rotation with an occupancy ratio of 0.951 (3):0.049 (3).

Keywords: crystal structure; cobalt; pyridyl ketone; thiophene; twin structure; disorder.

CCDC reference: 2574968

Structure description

The complex title salt (Fig. 1) is structurally similar to the previously reported Cu^II (Sommerer et al., 1998 ) and Ni^II (Westcott & Nichol, 2026 ) analogs. The Co^II site is located at an inversion center with pseudo-octahedral coordination. The 2-thienyl-2-pyridyl (tpk) ligands coordinate through pyridyl N [2.0189 (13) Å] and carbonyl O [2.0869 (11) Å] atoms in the equatorial plane, and oxygen atoms from water molecules coordinate in the axial positions, leading to an [O₄N₂] coordination set. The Co—O distances with the aqua ligands are significantly shorter than in the Cu^II complex [2.0903 (13) Å versus 2.409 (3) Å], likely due to the Jahn–Teller distortion seen for octahedral Cu^II complexes (Procter et al., 1968 ).

Figure 1
The molecular entities in the crystal structure of the title salt shown with displacement ellipsoids at the 50% probability level. Atoms of the asymmetric unit are labeled and the disordered thienyl ring is shown only for the major component.

All other bond lengths and angles are consistent with the previously reported Cu^II (Sommerer et al., 1998) and Ni^II (Westcott & Nichol, 2026) complexes, and with other Co^II complexes with similar ligands, such as di-2-pyridyl ketone (Crundwell et al., 2003 ) or di-2-pyridyl ketone oxime (Stamou et al., 2025 ).

The thienyl ring in the title complex is 21.22 (8)° out of the plane defined by the central metal cation and the pyridyl ring, while this value is 19.01 (7)° for the Ni^II complex (Westcott & Nichol 2026); however, the rotations are in opposite directions, leading to a difference of ∼40° (Fig. 2).

Figure 2
Overlay of the complex cation of the title compound (blue) with the previously reported Ni^II complex (red) showing the different orientations of the thienyl moiety.

The BF₄⁻ anion acts as a hydrogen-bonding acceptor with the coordinating water molecules as donors (Table 1), leading to a hydrogen-bonded layer extending parallel to (10 $[\overline{1}]$ ), Fig. 3. Additional weak C—H⋯F interactions between the thiophene moiety and the anion (Table 1) consolidate the packing.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯F4ⁱ	0.81 (1)	1.89 (1)	2.683 (2)	164 (3)
O2—H2B⋯F2	0.81 (1)	1.86 (1)	2.669 (2)	178 (4)
C2—H2⋯F1ⁱⁱ	0.95	2.52	3.352 (3)	147
C2—H2⋯F2ⁱⁱ	0.95	2.55	3.460 (3)	161
C4—H4⋯F1ⁱⁱⁱ	0.95	2.57	3.207 (3)	124
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) ; (iii) .

Figure 3
O—H⋯F hydrogen-bonding interactions (dashed lines) in the title compound showing a layered arrangement parallel to (10 $[\overline{1}]$ ).

Synthesis and crystallization

Co(BF₄)₂·6H₂O and acetonitrile were used as received from Thermo-Fisher; 2-thienyl 2-pyridyl ketone (tpk) was used as received from Rieke Metals. The title compound was synthesized following a literature procedure (Sommerer et al., 1998): excess Co(BF₄)₂·6H₂O (0.2108 g, 0.620 mmol) was combined with tpk (0.1825 g, 1.00 mmol) in 35 ml of acetonitrile at room temperature affording a dark-red solution, which was allowed to slowly evaporate until production and isolation of dark-orange crystals suitable for X-ray diffraction (30 d).

Refinement

Crystal data, data collection, and structure refinement details are summarized in Table 2. The unit cell metrically fits an orthorhombic C-centered cell, and the crystal under investigation was twinned by a 180° rotation around the reciprocal c axis. Refinement as a two-component twin with application of the TWIN transformation matrix [ $[\overline{1}]$ 0 0/ 0 $[\overline{1}]$ 0/ 1 0 1] gave a BASF value of 0.2138 (8).

Table 2
Experimental details

Crystal data
Chemical formula	[Co(C₁₀H₇NOS)₃(H₂O)₂](BF₄)₂
M_r	647.03
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	7.2133 (4), 11.9888 (8), 15.2093 (10)
β (°)	103.623 (2)
V (Å³)	1278.28 (14)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.93
Crystal size (mm)	0.24 × 0.21 × 0.15

Data collection
Diffractometer	Bruker D8 Quest
Absorption correction	Multi-scan (TWINABS; Bruker, 2025 )
T_min, T_max	0.618, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	115558, 4990, 4783
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.770

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.099, 1.05
No. of reflections	4990
No. of parameters	231
No. of restraints	168
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.58
Computer programs: APEX6 (Bruker, 2026 ), SAINT (Bruker, 2025), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b), ShelXle (Hübschle et al., 2011 ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

The thiophene substituent is disordered by an approximate twofold rotation. The two disordered moieties were restrained to have similar geometries using the SAME restraint of SHELXL (Sheldrick, 2015b ). The minor moiety was restrained to be close to planar, and U^ij components for disordered atoms closer to each other than 2.0 Å were restrained to be similar (SIMU 0.01 restraint). Subject to these conditions, the occupancy ratio refined to 0.951 (3):0.049 (3). Water H-atom positions were refined and O—H and H⋯H distances were restrained to 0.84 (2) and 1.37 (2) Å, respectively.

Structural data

CCDC reference: 2574968

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626007492/wm4252sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626007492/wm4252Isup2.hkl

checkCIF report

Computing details top

trans-Diaquabis(pyridin-2-yl thiophen-2-yl ketone-κ²N,O)cobalt(II) bis(tetrafluoridoborate) top

Crystal data top

[Co(C₁₀H₇NOS)₃(H₂O)₂](BF₄)₂	F(000) = 650
M_r = 647.03	D_x = 1.681 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.2133 (4) Å	Cell parameters from 9155 reflections
b = 11.9888 (8) Å	θ = 2.2–33.1°
c = 15.2093 (10) Å	µ = 0.93 mm⁻¹
β = 103.623 (2)°	T = 150 K
V = 1278.28 (14) Å³	Block, orange
Z = 2	0.24 × 0.21 × 0.15 mm

Data collection top

Bruker D8 Quest diffractometer	4990 independent reflections
Radiation source: fine focus sealed tube X-ray source	4783 reflections with I > 2σ(I)
Triumph curved graphite crystal monochromator	R_int = 0.064
Detector resolution: 7.4074 pixels mm^-1	θ_max = 33.2°, θ_min = 2.8°
ω and phi scans	h = −11→11
Absorption correction: multi-scan (TWINABS; Bruker, 2025)	k = −18→18
T_min = 0.618, T_max = 0.747	l = −23→23
115558 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: mixed
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.059P)² + 0.4235P] where P = (F_o² + 2F_c²)/3
4990 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.92 e Å⁻³
168 restraints	Δρ_min = −0.58 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. The unit cell does metrically fit an orthorhombic C-centered cell and is twinned by this symmetry (180 degree rotation around reciprocal c (0 0 1). Application of the TWIN transformation matrix -1 0 0 0 -1 0 1 0 1 gave a BASF value of 0.2138 (8).

Refined as a 2-component twin.

The thiophene substituent is disordered by an approximate two-fold rotation. The two disordered moieties were restrained to have similar geometries (SAME restraint of ShelXL). The minor moiety was restrained to be close to planar. Uij components of ADPs for disordered atoms closer to each other than 2.0 Angstrom were restrained to be similar (SIMU 0.01 restraint). Subject to these conditions the occupancy ratio refined to 0.951 (3) to 0.049 (3).

Water H atom positions were refined and O-H and H···H distances were restrained to 0.84 (2) and 1.37 (2) Angstrom, respectively. Some water H atom positions were further restrained based on hydrogen bonding considerations.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Co1	0.500000	0.500000	0.500000	0.02485 (7)
F1	0.2496 (3)	0.09814 (16)	0.40896 (11)	0.0684 (5)
F2	0.2007 (3)	0.25203 (12)	0.32495 (14)	0.0682 (5)
F3	0.4698 (2)	0.1494 (2)	0.33606 (13)	0.0761 (6)
F4	0.1826 (3)	0.08622 (19)	0.25758 (13)	0.0830 (6)
N1	0.35744 (18)	0.65047 (11)	0.50282 (9)	0.0272 (2)
C1	0.2108 (3)	0.66595 (17)	0.54098 (12)	0.0357 (3)
H1	0.172569	0.606240	0.573802	0.043*
O1	0.63194 (17)	0.60567 (9)	0.42424 (8)	0.0278 (2)
O2	0.2908 (2)	0.45919 (11)	0.38414 (9)	0.0413 (3)
H2A	0.279 (5)	0.503 (2)	0.3424 (15)	0.062*
H2B	0.266 (5)	0.3962 (13)	0.3655 (19)	0.062*
C2	0.1118 (3)	0.76632 (19)	0.53445 (13)	0.0422 (4)
H2	0.010753	0.775885	0.564101	0.051*
C3	0.1625 (3)	0.85102 (18)	0.48457 (14)	0.0434 (4)
H3	0.096248	0.920120	0.478913	0.052*
C4	0.3128 (3)	0.83522 (14)	0.44185 (12)	0.0354 (3)
H4	0.347505	0.892141	0.405316	0.043*
C5	0.4095 (2)	0.73449 (12)	0.45430 (9)	0.0252 (2)
C6	0.5748 (2)	0.70440 (11)	0.41513 (9)	0.0238 (2)
S1	0.81191 (9)	0.72350 (5)	0.30243 (3)	0.03521 (14)	0.951 (3)
C7	0.6698 (3)	0.78152 (15)	0.36741 (12)	0.0267 (3)	0.951 (3)
C8	0.6793 (5)	0.8966 (3)	0.3668 (2)	0.0385 (6)	0.951 (3)
H8	0.613994	0.943791	0.399664	0.046*	0.951 (3)
C9	0.7978 (4)	0.9359 (2)	0.31144 (17)	0.0475 (5)	0.951 (3)
H9	0.819995	1.012702	0.302468	0.057*	0.951 (3)
C10	0.8764 (4)	0.8518 (2)	0.27245 (15)	0.0457 (5)	0.951 (3)
H10	0.958393	0.863475	0.232761	0.055*	0.951 (3)
S1B	0.641 (3)	0.9146 (15)	0.3538 (13)	0.040 (2)	0.049 (3)
C7B	0.662 (5)	0.772 (2)	0.365 (2)	0.036 (3)	0.049 (3)
C8B	0.788 (6)	0.731 (3)	0.316 (3)	0.037 (3)	0.049 (3)
H8B	0.816978	0.653858	0.312593	0.044*	0.049 (3)
C9B	0.867 (6)	0.816 (3)	0.273 (3)	0.041 (3)	0.049 (3)
H9B	0.958416	0.803783	0.238039	0.050*	0.049 (3)
C10B	0.797 (5)	0.918 (3)	0.286 (2)	0.041 (3)	0.049 (3)
H10B	0.831310	0.983895	0.259243	0.049*	0.049 (3)
B1	0.2782 (3)	0.14565 (15)	0.33038 (12)	0.0294 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.03299 (13)	0.02138 (11)	0.02170 (11)	−0.00081 (9)	0.00948 (10)	0.00206 (9)
F1	0.0812 (12)	0.0736 (11)	0.0577 (9)	0.0076 (9)	0.0306 (8)	0.0260 (8)
F2	0.0762 (11)	0.0261 (5)	0.0926 (12)	0.0049 (6)	0.0007 (10)	0.0003 (7)
F3	0.0369 (7)	0.1274 (17)	0.0669 (10)	0.0009 (9)	0.0183 (7)	0.0025 (11)
F4	0.0865 (13)	0.0901 (14)	0.0624 (9)	−0.0011 (11)	−0.0025 (9)	−0.0491 (10)
N1	0.0301 (5)	0.0292 (5)	0.0239 (5)	0.0016 (4)	0.0095 (4)	−0.0016 (4)
C1	0.0336 (7)	0.0469 (9)	0.0293 (6)	0.0015 (6)	0.0127 (6)	−0.0051 (6)
O1	0.0345 (5)	0.0221 (4)	0.0295 (5)	0.0034 (4)	0.0131 (4)	0.0039 (3)
O2	0.0612 (8)	0.0278 (5)	0.0286 (5)	−0.0070 (6)	−0.0018 (5)	0.0033 (4)
C2	0.0302 (7)	0.0576 (12)	0.0388 (8)	0.0089 (7)	0.0082 (6)	−0.0153 (8)
C3	0.0336 (7)	0.0439 (9)	0.0490 (10)	0.0135 (7)	0.0022 (7)	−0.0126 (8)
C4	0.0358 (7)	0.0284 (7)	0.0395 (8)	0.0078 (6)	0.0037 (6)	−0.0016 (6)
C5	0.0278 (6)	0.0232 (5)	0.0239 (5)	0.0018 (5)	0.0046 (4)	−0.0017 (4)
C6	0.0284 (6)	0.0221 (5)	0.0207 (5)	−0.0007 (4)	0.0050 (4)	0.0008 (4)
S1	0.0430 (3)	0.0378 (2)	0.0284 (2)	−0.01227 (17)	0.01575 (17)	−0.00512 (16)
C7	0.0345 (7)	0.0227 (6)	0.0224 (6)	−0.0030 (5)	0.0059 (5)	0.0016 (5)
C8	0.0442 (14)	0.0280 (11)	0.0403 (13)	−0.0046 (9)	0.0037 (10)	0.0059 (8)
C9	0.0605 (12)	0.0359 (9)	0.0427 (11)	−0.0152 (9)	0.0054 (10)	0.0131 (8)
C10	0.0578 (12)	0.0489 (12)	0.0317 (8)	−0.0223 (10)	0.0132 (8)	0.0083 (8)
S1B	0.048 (4)	0.032 (4)	0.038 (4)	−0.009 (4)	0.005 (4)	0.002 (4)
C7B	0.043 (5)	0.030 (5)	0.033 (5)	−0.006 (5)	0.006 (5)	−0.002 (5)
C8B	0.046 (5)	0.036 (5)	0.029 (5)	−0.014 (5)	0.010 (5)	0.000 (5)
C9B	0.051 (5)	0.039 (5)	0.033 (5)	−0.014 (5)	0.008 (5)	0.003 (5)
C10B	0.050 (5)	0.036 (5)	0.035 (5)	−0.014 (5)	0.009 (5)	0.008 (5)
B1	0.0329 (7)	0.0273 (7)	0.0283 (7)	−0.0003 (6)	0.0080 (6)	−0.0047 (5)

Geometric parameters (Å, º) top

Co1—N1	2.0819 (13)	C4—C5	1.385 (2)
Co1—N1ⁱ	2.0819 (13)	C4—H4	0.9500
Co1—O1	2.0869 (11)	C5—C6	1.497 (2)
Co1—O1ⁱ	2.0869 (11)	C6—C7B	1.36 (3)
Co1—O2	2.0902 (13)	C6—C7	1.444 (2)
Co1—O2ⁱ	2.0903 (13)	S1—C10	1.700 (2)
F1—B1	1.383 (2)	S1—C7	1.729 (2)
F2—B1	1.387 (2)	C7—C8	1.382 (4)
F3—B1	1.365 (2)	C8—C9	1.414 (4)
F4—B1	1.360 (2)	C8—H8	0.9500
N1—C1	1.334 (2)	C9—C10	1.359 (4)
N1—C5	1.3531 (19)	C9—H9	0.9500
C1—C2	1.391 (3)	C10—H10	0.9500
C1—H1	0.9500	S1B—C10B	1.698 (19)
O1—C6	1.2502 (17)	S1B—C7B	1.73 (2)
O2—H2A	0.811 (13)	C7B—C8B	1.39 (2)
O2—H2B	0.812 (13)	C8B—C9B	1.413 (19)
C2—C3	1.368 (3)	C8B—H8B	0.9500
C2—H2	0.9500	C9B—C10B	1.345 (19)
C3—C4	1.402 (3)	C9B—H9B	0.9500
C3—H3	0.9500	C10B—H10B	0.9500

N1—Co1—N1ⁱ	180.0	O1—C6—C7B	116.0 (15)
N1—Co1—O1	77.12 (5)	O1—C6—C7	118.63 (14)
N1ⁱ—Co1—O1	102.88 (5)	O1—C6—C5	117.16 (12)
N1—Co1—O1ⁱ	102.88 (5)	C7B—C6—C5	126.7 (15)
N1ⁱ—Co1—O1ⁱ	77.12 (5)	C7—C6—C5	124.21 (14)
O1—Co1—O1ⁱ	180.0	C10—S1—C7	91.47 (11)
N1—Co1—O2	87.60 (6)	C8—C7—C6	132.3 (2)
N1ⁱ—Co1—O2	92.40 (6)	C8—C7—S1	111.14 (19)
O1—Co1—O2	90.53 (5)	C6—C7—S1	116.43 (13)
O1ⁱ—Co1—O2	89.48 (5)	C7—C8—C9	112.0 (3)
N1—Co1—O2ⁱ	92.40 (6)	C7—C8—H8	124.0
N1ⁱ—Co1—O2ⁱ	87.60 (6)	C9—C8—H8	124.0
O1—Co1—O2ⁱ	89.47 (5)	C10—C9—C8	112.7 (2)
O1ⁱ—Co1—O2ⁱ	90.52 (5)	C10—C9—H9	123.7
O2—Co1—O2ⁱ	180.00 (5)	C8—C9—H9	123.7
C1—N1—C5	118.95 (15)	C9—C10—S1	112.68 (17)
C1—N1—Co1	125.15 (12)	C9—C10—H10	123.7
C5—N1—Co1	115.59 (9)	S1—C10—H10	123.7
N1—C1—C2	122.40 (18)	C10B—S1B—C7B	91.6 (13)
N1—C1—H1	118.8	C6—C7B—C8B	122 (3)
C2—C1—H1	118.8	C6—C7B—S1B	127 (3)
C6—O1—Co1	117.04 (9)	C8B—C7B—S1B	110.4 (17)
Co1—O2—H2A	115 (2)	C7B—C8B—C9B	112 (2)
Co1—O2—H2B	125 (2)	C7B—C8B—H8B	123.8
H2A—O2—H2B	111 (2)	C9B—C8B—H8B	123.8
C3—C2—C1	118.82 (17)	C10B—C9B—C8B	112 (2)
C3—C2—H2	120.6	C10B—C9B—H9B	123.8
C1—C2—H2	120.6	C8B—C9B—H9B	123.8
C2—C3—C4	119.58 (17)	C9B—C10B—S1B	113.2 (18)
C2—C3—H3	120.2	C9B—C10B—H10B	123.4
C4—C3—H3	120.2	S1B—C10B—H10B	123.4
C5—C4—C3	118.29 (18)	F4—B1—F3	112.37 (18)
C5—C4—H4	120.9	F4—B1—F1	109.74 (19)
C3—C4—H4	120.9	F3—B1—F1	108.29 (17)
N1—C5—C4	121.89 (15)	F4—B1—F2	108.26 (18)
N1—C5—C6	112.77 (12)	F3—B1—F2	111.16 (19)
C4—C5—C6	125.32 (14)	F1—B1—F2	106.87 (17)

C5—N1—C1—C2	−1.5 (2)	C5—C6—C7—C8	21.1 (3)
Co1—N1—C1—C2	−174.79 (14)	O1—C6—C7—S1	16.1 (2)
N1—C1—C2—C3	2.2 (3)	C5—C6—C7—S1	−163.28 (11)
C1—C2—C3—C4	−0.4 (3)	C10—S1—C7—C8	−1.8 (2)
C2—C3—C4—C5	−2.1 (3)	C10—S1—C7—C6	−178.32 (15)
C1—N1—C5—C4	−1.1 (2)	C6—C7—C8—C9	177.5 (2)
Co1—N1—C5—C4	172.80 (12)	S1—C7—C8—C9	1.7 (3)
C1—N1—C5—C6	−179.52 (13)	C7—C8—C9—C10	−0.7 (3)
Co1—N1—C5—C6	−5.59 (15)	C8—C9—C10—S1	−0.7 (3)
C3—C4—C5—N1	2.9 (2)	C7—S1—C10—C9	1.4 (2)
C3—C4—C5—C6	−178.94 (15)	O1—C6—C7B—C8B	9.1 (17)
Co1—O1—C6—C7B	−179.8 (12)	C5—C6—C7B—C8B	−166.4 (15)
Co1—O1—C6—C7	176.64 (11)	O1—C6—C7B—S1B	−170.0 (15)
Co1—O1—C6—C5	−3.91 (16)	C5—C6—C7B—S1B	15 (3)
N1—C5—C6—O1	6.33 (18)	C10B—S1B—C7B—C6	179 (2)
C4—C5—C6—O1	−171.99 (15)	C10B—S1B—C7B—C8B	−0.2 (13)
N1—C5—C6—C7B	−178.3 (14)	C6—C7B—C8B—C9B	−178 (3)
C4—C5—C6—C7B	3.4 (14)	S1B—C7B—C8B—C9B	1.4 (18)
N1—C5—C6—C7	−174.25 (14)	C7B—C8B—C9B—C10B	−2 (3)
C4—C5—C6—C7	7.4 (2)	C8B—C9B—C10B—S1B	2 (4)
O1—C6—C7—C8	−159.5 (3)	C7B—S1B—C10B—C9B	−1 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···F4ⁱⁱ	0.81 (1)	1.89 (1)	2.683 (2)	164 (3)
O2—H2B···F2	0.81 (1)	1.86 (1)	2.669 (2)	178 (4)
C2—H2···F1ⁱⁱⁱ	0.95	2.52	3.352 (3)	147
C2—H2···F2ⁱⁱⁱ	0.95	2.55	3.460 (3)	161
C4—H4···F1^iv	0.95	2.57	3.207 (3)	124

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

Acknowledgements

This work was supported by a CSU-AAUP grant. All data were collected at Purdue University by Dr Matthias Zeller as part of the American Crystallographic Association Summer Course (2026). Dr Zeller also assisted with the refinement.

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