4-Methyl-N-[2-(2-phenyl­ethyn­yl)phen­yl]-N-(prop-2-yn-1-yl)benzene-1-sulfonamide

Dassonneville, B.; Detert, H.; Schollmeyer, D.

doi:10.1107/S2414314625009435

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 10| October 2025| x250943

https://doi.org/10.1107/S2414314625009435

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4-Methyl-N-[2-(2-phenylethynyl)phenyl]-N-(prop-2-yn-1-yl)benzene-1-sulfonamide

Benjamin Dassonneville,^a Heiner Detert ^b ^* and Dieter Schollmeyer ^b

^aUniversity of Mainz, Department of Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany, and ^bUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: [email protected]

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 14 October 2025; accepted 27 October 2025; online 31 October 2025)

The title compound, C₂₄H₁₉NO₂S, was prepared by propargylation of the sulfonamide. The tolyl group points to the planar tolane unit. In the extended structure, two intermolecular hydrogen bridges connect the molecules to form chains.

Keywords: crystal structure; hydrogen bridge; alkyne; sulfonamide.

CCDC reference: 2498200

Structure description

The title compound, C₂₄H₁₉NO₂S (Fig. 1), was prepared as part of a larger project on the synthesis of condensed heterocycles via transition metal catalysis (Dassonneville et al., 2011 ; Letessier et al., 2012 , 2013 ). Whereas O,N-dialkynyl sulfonylanilines were successfully converted to carbolines or indolothiopyranes (Dassonneville et al., 2023a ,b ), attempts to cyclize homologous N-propargyl derivatives failed. The title compound forms monoclinic crystals with four molecules per unit cell. The C1–C14 tolane unit is close to planar [dihedral angle between the phenyl rings: 5.48 (7)°] with very similar propargylic bonds C6—C7 [1.4303 (19) Å] and C8—C9 [1.4328 (19) Å]. The tolyl group points in the direction of the tolane with dihedral angle between the tolyl unit and the terminal phenyl (C9—C14) ring of 38.37 (7)°. The alkyne points towards the benzene (C1–C6) ring of the tolane, as reflected in the torsion angle of 124.65 (12)° for the C17—C16—N15—S1 grouping. In the crystal, two C—H⋯O hydrogen bonds (Table 1) connect the molecules to form chains. Neighbouring chains are connected via overlapping tolane units to form layers parallel to ( $[\overline{1}]$ 101). The C20—H20⋯O2 bridge is characterized by a C⋯O distance of 3.3110 (18) Å (O2⋯H20: 2.44 Å) and a C—H⋯O angle of 152°. The other bridge along C18—H18⋯O2 has a length of C18⋯O2 = 3.231 (2) Å (H18⋯O2: 2.45 Å) with a C—H⋯O angle of 139°. Within the chain, every second molecule is related via a twofold screw axis whereas the molecules in between are symmetrically related via a glide plane (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2ⁱ	0.95	2.44	3.3110 (18)	152
C18—H18⋯O2ⁱⁱ	0.95	2.45	3.231 (2)	139
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
View (Spek, 2009

) of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Part of the packing diagram. View along b-axis direction (Spek, 2009

Synthesis and crystallization

The synthesis of the title compound was performed by deprotonation of N-tosyl-2-phenylethynylaniline (Amjad et al. 2004 ; Martínez-Esperón et al., 2008 ) with potassium hexamethyldisilazanide (KHMDS) at low (ca 200 K) temperature and reaction with progargylic bromide. Purification by column chromatography on silica with toluene as eluent gave the title compound (R_f = 0.23) and a by-product. The title compound crystallized from toluene as off-white cubes with m.p. = 381.5 K. The assignment of NMR signals is based on two-dimensional spectra and follows IUPAC nomenclature. ¹H-NMR (CDCl₃, 600 MHz): 7.71 (d, J = 7.9 Hz, 2 H, 3-H, 5-H, tol), 7.56 (m, 1 H), 7.46 (m, 1 H), 7.37 (m, 4 H), 7.33 (m, 3 H), 7.16 (d, 2 H, J = 7.9 Hz, 2-H, 6-H, tol), 4.65 (bs, 2 H, 1-H prop), 2.28 (s, 3 H, CH₃), 2.24 (t, 1 H, J = 2.5 Hz, 3-H prop); ¹³C-NMR (CDCl₃ 600 MHz): 143.6 (C1, tol), 139.5, 137.1, 133.4 (¹J_CH = 47 Hz), 132.1, 131.6 (2 C), 129.6 (2 C), 129.0, 128.7, 128.7, 128.3 (2 C), 127.7 (2 C), 123.8, 122.7, 94.5, 85.8, 78.3, 73.5 (¹J_CH = 210 Hz, C-3 prop), 40.2 (C-1, prop), 21.5 (CH₃).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₁₉NO₂S
M_r	385.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	12.4866 (5), 11.7479 (3), 14.4481 (6)
β (°)	113.728 (3)
V (Å³)	1940.25 (13)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.19
Crystal size (mm)	0.45 × 0.37 × 0.27

Data collection
Diffractometer	Stoe IPDS 2T
Absorption correction	Integration (Stoe & Cie, 2020 )
T_min, T_max	0.919, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	9492, 4603, 4075
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 1.06
No. of reflections	4603
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.36
Computer programs: X-AREA WinXpose, Recipe and Integrate (Stoe & Cie, 2020), SHELXT2014 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 2498200

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314625009435/vm4074sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625009435/vm4074Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625009435/vm4074Isup3.cml

checkCIF report

Computing details top

4-Methyl-N-[2-(2-phenylethynyl)phenyl]-N-(prop-2-yn-1-yl)benzene-\ 1-sulfonamide top

Crystal data top

C₂₄H₁₉NO₂S	D_x = 1.320 Mg m⁻³
M_r = 385.46	Melting point: 381.5 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.4866 (5) Å	Cell parameters from 13782 reflections
b = 11.7479 (3) Å	θ = 2.5–28.4°
c = 14.4481 (6) Å	µ = 0.19 mm⁻¹
β = 113.728 (3)°	T = 120 K
V = 1940.25 (13) Å³	Block, colorless
Z = 4	0.45 × 0.37 × 0.27 mm
F(000) = 808

Data collection top

Stoe IPDS 2T diffractometer	4603 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	4075 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.022
rotation method, ω scans	θ_max = 27.9°, θ_min = 2.5°
Absorption correction: integration software?; reference?	h = −16→16
T_min = 0.919, T_max = 0.962	k = −15→13
9492 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0466P)² + 0.9953P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
4603 reflections	Δρ_max = 0.35 e Å⁻³
254 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints

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. Hydrogen atoms attached to carbons were placed at calculated positions and were refined in the riding-model approximation with C–H = 0.99 Å, and with U_iso(H) = 1.2 U_eq(C).

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

	x	y	z	U_iso*/U_eq
S1	0.70257 (3)	0.61385 (3)	0.24207 (2)	0.02229 (10)
O1	0.81074 (9)	0.56893 (10)	0.24567 (9)	0.0329 (3)
O2	0.66567 (9)	0.72594 (9)	0.20338 (7)	0.0276 (2)
C1	0.63253 (11)	0.68233 (11)	0.38380 (9)	0.0210 (3)
C2	0.65685 (12)	0.79737 (12)	0.40293 (10)	0.0245 (3)
H2	0.726052	0.828453	0.400793	0.029*
C3	0.58094 (13)	0.86706 (12)	0.42508 (11)	0.0275 (3)
H3	0.597557	0.945912	0.437140	0.033*
C4	0.48040 (13)	0.82170 (13)	0.42969 (11)	0.0281 (3)
H4	0.427802	0.869627	0.444157	0.034*
C5	0.45715 (12)	0.70698 (13)	0.41321 (10)	0.0260 (3)
H5	0.389315	0.676214	0.418217	0.031*
C6	0.53175 (11)	0.63495 (12)	0.38922 (10)	0.0220 (3)
C7	0.50115 (12)	0.51736 (12)	0.37016 (10)	0.0239 (3)
C8	0.46657 (12)	0.42115 (12)	0.35438 (10)	0.0236 (3)
C9	0.41978 (11)	0.30811 (12)	0.33417 (10)	0.0218 (3)
C10	0.48218 (13)	0.21974 (13)	0.31371 (10)	0.0265 (3)
H10	0.557670	0.233824	0.314953	0.032*
C11	0.43428 (16)	0.11233 (13)	0.29175 (11)	0.0340 (3)
H11	0.476185	0.052954	0.276443	0.041*
C12	0.32517 (16)	0.09043 (14)	0.29188 (12)	0.0377 (4)
H12	0.292628	0.016165	0.276887	0.045*
C13	0.26402 (14)	0.17648 (14)	0.31377 (12)	0.0337 (3)
H13	0.189803	0.160897	0.314707	0.040*
C14	0.30993 (12)	0.28574 (13)	0.33447 (10)	0.0261 (3)
H14	0.266990	0.344925	0.348750	0.031*
N15	0.71296 (10)	0.61439 (10)	0.35906 (9)	0.0230 (2)
C16	0.77863 (12)	0.52334 (12)	0.42943 (11)	0.0267 (3)
H16A	0.724042	0.477366	0.448299	0.032*
H16B	0.814650	0.472514	0.395324	0.032*
C17	0.87018 (12)	0.57058 (13)	0.52094 (11)	0.0276 (3)
C18	0.94493 (14)	0.60672 (14)	0.59514 (13)	0.0355 (4)
H18	1.005039	0.635792	0.654812	0.043*
C19	0.59043 (11)	0.51880 (11)	0.17274 (9)	0.0203 (3)
C20	0.61574 (12)	0.40336 (12)	0.17825 (10)	0.0231 (3)
H20	0.692954	0.377034	0.216646	0.028*
C21	0.52737 (13)	0.32719 (12)	0.12728 (10)	0.0251 (3)
H21	0.544846	0.248336	0.128784	0.030*
C22	0.41271 (12)	0.36439 (12)	0.07357 (10)	0.0242 (3)
C23	0.39009 (12)	0.48050 (13)	0.06791 (10)	0.0252 (3)
H23	0.312802	0.506968	0.030008	0.030*
C24	0.47833 (11)	0.55862 (12)	0.11664 (10)	0.0227 (3)
H24	0.462188	0.637945	0.111623	0.027*
C25	0.31639 (14)	0.27906 (15)	0.02433 (12)	0.0350 (3)
H25A	0.243835	0.319163	−0.016472	0.052*
H25B	0.304597	0.234149	0.076625	0.052*
H25C	0.338064	0.228357	−0.019186	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01870 (16)	0.02383 (18)	0.02494 (17)	−0.00220 (12)	0.00939 (12)	−0.00065 (12)
O1	0.0205 (5)	0.0407 (6)	0.0402 (6)	−0.0017 (4)	0.0148 (4)	−0.0037 (5)
O2	0.0314 (5)	0.0234 (5)	0.0276 (5)	−0.0050 (4)	0.0115 (4)	0.0023 (4)
C1	0.0215 (6)	0.0200 (6)	0.0183 (6)	0.0010 (5)	0.0048 (5)	0.0007 (5)
C2	0.0245 (6)	0.0225 (7)	0.0237 (6)	−0.0034 (5)	0.0068 (5)	0.0000 (5)
C3	0.0314 (7)	0.0201 (7)	0.0270 (7)	0.0000 (5)	0.0075 (6)	−0.0020 (5)
C4	0.0278 (7)	0.0288 (7)	0.0251 (7)	0.0057 (6)	0.0081 (5)	−0.0013 (5)
C5	0.0237 (6)	0.0300 (7)	0.0229 (6)	−0.0005 (5)	0.0080 (5)	−0.0003 (5)
C6	0.0232 (6)	0.0221 (6)	0.0180 (6)	−0.0015 (5)	0.0054 (5)	0.0010 (5)
C7	0.0233 (6)	0.0254 (7)	0.0228 (6)	−0.0017 (5)	0.0090 (5)	0.0014 (5)
C8	0.0236 (6)	0.0251 (7)	0.0220 (6)	−0.0010 (5)	0.0091 (5)	0.0020 (5)
C9	0.0233 (6)	0.0219 (6)	0.0182 (6)	−0.0014 (5)	0.0061 (5)	0.0028 (5)
C10	0.0295 (7)	0.0280 (7)	0.0214 (6)	0.0031 (6)	0.0098 (5)	0.0029 (5)
C11	0.0489 (9)	0.0230 (7)	0.0254 (7)	0.0052 (6)	0.0103 (6)	0.0004 (5)
C12	0.0508 (10)	0.0233 (7)	0.0283 (8)	−0.0109 (7)	0.0045 (7)	0.0011 (6)
C13	0.0286 (7)	0.0370 (9)	0.0290 (7)	−0.0113 (6)	0.0049 (6)	0.0081 (6)
C14	0.0242 (7)	0.0274 (7)	0.0254 (7)	−0.0003 (5)	0.0087 (5)	0.0053 (5)
N15	0.0223 (5)	0.0217 (6)	0.0222 (5)	0.0025 (4)	0.0061 (4)	0.0009 (4)
C16	0.0243 (7)	0.0221 (7)	0.0284 (7)	0.0024 (5)	0.0051 (5)	0.0026 (5)
C17	0.0245 (7)	0.0270 (7)	0.0291 (7)	0.0041 (6)	0.0085 (6)	0.0043 (6)
C18	0.0280 (7)	0.0355 (9)	0.0341 (8)	0.0029 (6)	0.0033 (6)	−0.0002 (6)
C19	0.0198 (6)	0.0226 (6)	0.0202 (6)	−0.0004 (5)	0.0099 (5)	−0.0010 (5)
C20	0.0227 (6)	0.0247 (7)	0.0226 (6)	0.0045 (5)	0.0100 (5)	0.0004 (5)
C21	0.0316 (7)	0.0206 (6)	0.0248 (6)	0.0019 (5)	0.0131 (6)	−0.0013 (5)
C22	0.0266 (7)	0.0275 (7)	0.0193 (6)	−0.0043 (5)	0.0100 (5)	−0.0016 (5)
C23	0.0195 (6)	0.0296 (7)	0.0249 (6)	0.0017 (5)	0.0073 (5)	0.0007 (5)
C24	0.0222 (6)	0.0211 (6)	0.0252 (6)	0.0024 (5)	0.0098 (5)	0.0012 (5)
C25	0.0345 (8)	0.0357 (9)	0.0324 (8)	−0.0112 (7)	0.0110 (6)	−0.0062 (6)

Geometric parameters (Å, º) top

S1—O1	1.4314 (11)	C12—H12	0.9500
S1—O2	1.4324 (11)	C13—C14	1.388 (2)
S1—N15	1.6424 (12)	C13—H13	0.9500
S1—C19	1.7556 (13)	C14—H14	0.9500
C1—C2	1.3883 (19)	N15—C16	1.4763 (17)
C1—C6	1.4067 (18)	C16—C17	1.465 (2)
C1—N15	1.4362 (17)	C16—H16A	0.9900
C2—C3	1.384 (2)	C16—H16B	0.9900
C2—H2	0.9500	C17—C18	1.181 (2)
C3—C4	1.390 (2)	C18—H18	0.9500
C3—H3	0.9500	C19—C24	1.3864 (18)
C4—C5	1.379 (2)	C19—C20	1.3875 (19)
C4—H4	0.9500	C20—C21	1.381 (2)
C5—C6	1.4013 (19)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.396 (2)
C6—C7	1.4303 (19)	C21—H21	0.9500
C7—C8	1.199 (2)	C22—C23	1.389 (2)
C8—C9	1.4328 (19)	C22—C25	1.506 (2)
C9—C14	1.3983 (19)	C23—C24	1.3884 (19)
C9—C10	1.399 (2)	C23—H23	0.9500
C10—C11	1.378 (2)	C24—H24	0.9500
C10—H10	0.9500	C25—H25A	0.9800
C11—C12	1.387 (3)	C25—H25B	0.9800
C11—H11	0.9500	C25—H25C	0.9800
C12—C13	1.378 (3)

O1—S1—O2	120.25 (7)	C14—C13—H13	119.7
O1—S1—N15	106.34 (6)	C13—C14—C9	119.58 (14)
O2—S1—N15	106.13 (6)	C13—C14—H14	120.2
O1—S1—C19	108.09 (6)	C9—C14—H14	120.2
O2—S1—C19	107.74 (6)	C1—N15—C16	118.78 (11)
N15—S1—C19	107.71 (6)	C1—N15—S1	119.00 (9)
C2—C1—C6	120.20 (13)	C16—N15—S1	119.87 (10)
C2—C1—N15	118.14 (12)	C17—C16—N15	111.26 (12)
C6—C1—N15	121.66 (12)	C17—C16—H16A	109.4
C3—C2—C1	120.44 (13)	N15—C16—H16A	109.4
C3—C2—H2	119.8	C17—C16—H16B	109.4
C1—C2—H2	119.8	N15—C16—H16B	109.4
C2—C3—C4	120.01 (13)	H16A—C16—H16B	108.0
C2—C3—H3	120.0	C18—C17—C16	178.78 (17)
C4—C3—H3	120.0	C17—C18—H18	180.0
C5—C4—C3	119.86 (13)	C24—C19—C20	121.10 (12)
C5—C4—H4	120.1	C24—C19—S1	120.31 (10)
C3—C4—H4	120.1	C20—C19—S1	118.55 (10)
C4—C5—C6	121.21 (13)	C21—C20—C19	119.21 (13)
C4—C5—H5	119.4	C21—C20—H20	120.4
C6—C5—H5	119.4	C19—C20—H20	120.4
C5—C6—C1	118.26 (13)	C20—C21—C22	120.95 (13)
C5—C6—C7	118.57 (12)	C20—C21—H21	119.5
C1—C6—C7	123.17 (13)	C22—C21—H21	119.5
C8—C7—C6	174.45 (15)	C23—C22—C21	118.62 (13)
C7—C8—C9	177.32 (15)	C23—C22—C25	121.40 (13)
C14—C9—C10	119.44 (13)	C21—C22—C25	119.97 (13)
C14—C9—C8	119.59 (13)	C24—C23—C22	121.22 (13)
C10—C9—C8	120.97 (12)	C24—C23—H23	119.4
C11—C10—C9	120.07 (14)	C22—C23—H23	119.4
C11—C10—H10	120.0	C19—C24—C23	118.81 (13)
C9—C10—H10	120.0	C19—C24—H24	120.6
C10—C11—C12	120.35 (15)	C23—C24—H24	120.6
C10—C11—H11	119.8	C22—C25—H25A	109.5
C12—C11—H11	119.8	C22—C25—H25B	109.5
C13—C12—C11	119.96 (14)	H25A—C25—H25B	109.5
C13—C12—H12	120.0	C22—C25—H25C	109.5
C11—C12—H12	120.0	H25A—C25—H25C	109.5
C12—C13—C14	120.57 (15)	H25B—C25—H25C	109.5
C12—C13—H13	119.7

C6—C1—C2—C3	−1.6 (2)	O2—S1—N15—C1	34.08 (12)
N15—C1—C2—C3	178.67 (12)	C19—S1—N15—C1	−81.09 (11)
C1—C2—C3—C4	0.9 (2)	O1—S1—N15—C16	−34.38 (12)
C2—C3—C4—C5	0.7 (2)	O2—S1—N15—C16	−163.53 (10)
C3—C4—C5—C6	−1.6 (2)	C19—S1—N15—C16	81.30 (11)
C4—C5—C6—C1	1.0 (2)	C1—N15—C16—C17	−72.93 (16)
C4—C5—C6—C7	−178.24 (13)	S1—N15—C16—C17	124.65 (12)
C2—C1—C6—C5	0.64 (19)	O1—S1—C19—C24	−149.20 (11)
N15—C1—C6—C5	−179.61 (12)	O2—S1—C19—C24	−17.83 (12)
C2—C1—C6—C7	179.79 (12)	N15—S1—C19—C24	96.28 (11)
N15—C1—C6—C7	−0.4 (2)	O1—S1—C19—C20	32.94 (12)
C14—C9—C10—C11	1.5 (2)	O2—S1—C19—C20	164.32 (10)
C8—C9—C10—C11	−178.23 (13)	N15—S1—C19—C20	−81.58 (11)
C9—C10—C11—C12	−1.4 (2)	C24—C19—C20—C21	−0.3 (2)
C10—C11—C12—C13	0.2 (2)	S1—C19—C20—C21	177.52 (10)
C11—C12—C13—C14	0.9 (2)	C19—C20—C21—C22	−2.3 (2)
C12—C13—C14—C9	−0.7 (2)	C20—C21—C22—C23	3.3 (2)
C10—C9—C14—C13	−0.5 (2)	C20—C21—C22—C25	−175.95 (13)
C8—C9—C14—C13	179.28 (13)	C21—C22—C23—C24	−1.7 (2)
C2—C1—N15—C16	114.85 (14)	C25—C22—C23—C24	177.51 (13)
C6—C1—N15—C16	−64.91 (17)	C20—C19—C24—C23	1.9 (2)
C2—C1—N15—S1	−82.57 (14)	S1—C19—C24—C23	−175.95 (10)
C6—C1—N15—S1	97.67 (13)	C22—C23—C24—C19	−0.8 (2)
O1—S1—N15—C1	163.23 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2ⁱ	0.95	2.44	3.3110 (18)	152
C18—H18···O2ⁱⁱ	0.95	2.45	3.231 (2)	139

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x+1/2, −y+3/2, z+1/2.

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