Ethidium benzoate methanol monosolvate

Shimazaki, R.; Sadakiyo, M.

doi:10.1107/S241431462400302X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 4| April 2024| x240302

https://doi.org/10.1107/S241431462400302X

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Ethidium benzoate methanol monosolvate

Runa Shimazaki ^a and Masaaki Sadakiyo ^a ^*

^aDepartment of Applied Chemistry, Faculty of Science Division I, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan
^*Correspondence e-mail: sadakiyo@rs.tus.ac.jp

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 27 March 2024; accepted 8 April 2024; online 18 April 2024)

In the title salt solvate (systematic name: 8-amino-5-ethyl-6-phenylphenanthridin-5-ium benzoate methanol monosolvate), C₂₁H₂₀N₃⁺·C₆H₅CO₂⁻·CH₃OH, two ethidium cations, C₂₁H₂₀N₃⁺, dimerize about a twofold axis through π–π interactions [inter-centroid separation = 3.6137 (4) Å]. The benzoate anions are connected through hydrogen bonding with the –NH₂ groups of the ethidium cations and the –OH group of the MeOH molecule. The MeOH molecule also accepts a hydrogen bond from the –NH₂ group of the ethidium cation. The result is a one-dimensional hydrogen-bonded chain along the b-axis direction.

Keywords: crystal structure; ethidium salt; benzoate; hydrogen bonding.

CCDC reference: 2347501

Structure description

Ethidium salts have various applications such as an intercalator for DNA (Chen et al., 2000 ) and as a building block for covalent organic frameworks (Ma et al., 2016 ). In this study, the structure of a new ethidium salt solvate, C₂₁H₂₀N₃⁺·C₆H₅CO₂⁻·MeOH, is reported (Fig. 1). The dihedral angle between the pendant ring and the fused ring system is 77.01 (6)°. Two ethidium cations associate about a twofold axis via π–π stacking (Fig. 2). The closest separation between the molecular planes is approximately 3.4 Å [the Cg⋯Cg separation is 3.6137 (4) Å], indicating the presence of π–π interactions. The three components of C₂₁H₂₀N₃⁺·C₆H₅CO₂⁻·CH₃OH are connected by hydrogen bonds (Table 1) formed along the b-axis direction, resulting in the formation of a one-dimensional hydrogen-bonded chain (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.84	1.85	2.6636 (17)	163
N2—H2⋯O1ⁱⁱ	0.88	2.09	2.8741 (18)	148
N2—H2A⋯O2ⁱⁱⁱ	0.88	2.06	2.9271 (17)	169
N3—H3A⋯O1	0.88	2.18	2.9264 (18)	142
N3—H3B⋯O3^iv	0.88	2.09	2.939 (2)	162
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+1, y-1, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Figure 1
The structure of the crystallographically independent molecules in C₂₁H₂₀N₃⁺·C₆H₅CO₂⁻·CH₃OH with displacement ellipsoids drawn at the 50% probability level.

Figure 2
The dimer formed by two ethidium cations. The Cg⋯Cg separations [inter-centroid separation: 3.6137 (4) Å] are indicated as purple dotted lines.

Figure 3
An illustration of the hydrogen-bonding network. Hydrogen bonds are shown as dotted lines.

Synthesis and crystallization

An aqueous solution (120 ml) of silver(I) benzoate (45.8 mg 0.20 mmol) was mixed with an aqueous solution (200 ml) of ethidium bromide (78.9 mg, 0.20 mmol) and then the mixture was stirred overnight at room temperature. After that, the precipitate was removed by centrifugation. The remaining solution was evaporated to obtain a crude powder. The powder was dissolved in methanol (4 ml) and the remaining precipitate was again removed by centrifugation. By evaporation of the remaining solution, a red powder was obtained. Red single crystals of [C₂₁H₂₀N₃][C₆H₅CO₂]·MeOH were obtained by slow evaporation (for 11 days) of a solution of the powder (7 mg) dissolved in 1 ml of a mixed solvent system, H₂O/MeOH (1:1).

Refinement

Details of crystal data, data collection and structure refinement are given in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₂₀N₃⁺·C₇H₅O₂⁻·CH₄O
M_r	467.55
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	90
a, b, c (Å)	22.0407 (6), 12.4642 (3), 18.0706 (5)
β (°)	107.4952 (10)
V (Å³)	4734.7 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.15 × 0.10

Data collection
Diffractometer	Bruker PHOTON II CPAD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.691, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	29963, 6087, 4736
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.150, 1.05
No. of reflections	6087
No. of parameters	319
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.27
Computer programs: APEX4 and SAINT (Bruker, 2021 ), SIR2019 (Burla et al., 2015 ), SHELXL2018/3 (Sheldrick, 2015 ), DIAMOND (Brandenburg, 2014 ) and Yadokari-XG (Kabuto et al., 2009 ).

Structural data

CCDC reference: 2347501

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431462400302X/tk4103sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462400302X/tk4103Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431462400302X/tk4103Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S241431462400302X/tk4103sup4.txt

Supporting information file. DOI: https://doi.org/10.1107/S241431462400302X/tk4103Isup5.cml

checkCIF report

Computing details top

8-Amino-5-ethyl-6-phenylphenanthridin-5-ium benzoate methanol monosolvate top

Crystal data top

C₂₁H₂₀N₃⁺·C₇H₅O₂⁻·CH₄O	F(000) = 1984
M_r = 467.55	D_x = 1.312 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
a = 22.0407 (6) Å	Cell parameters from 6092 reflections
b = 12.4642 (3) Å	θ = 2.8–28.6°
c = 18.0706 (5) Å	µ = 0.09 mm⁻¹
β = 107.4952 (10)°	T = 90 K
V = 4734.7 (2) Å³	Block, red
Z = 8	0.30 × 0.15 × 0.10 mm

Data collection top

Bruker PHOTON II CPAD diffractometer	4736 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.064
φ and ω scans	θ_max = 29.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −29→27
T_min = 0.691, T_max = 0.746	k = −16→15
29963 measured reflections	l = −24→24
6087 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.0683P)² + 4.3384P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
6087 reflections	Δρ_max = 0.51 e Å⁻³
319 parameters	Δρ_min = −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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

All hydrogen atoms are geometrically fixed using a riding-model approximation with C—H = 0.95 (for phenyl), 0.98 (for methyl), 0.99 (for methylene), O—H = 0.84 and N—H = 0.88 Å.

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

	x	y	z	U_iso*/U_eq
N1	0.41329 (6)	0.45032 (9)	0.33925 (7)	0.0185 (3)
O1	0.69273 (5)	0.72829 (8)	0.31166 (7)	0.0271 (3)
C1	0.52679 (7)	0.33972 (11)	0.35270 (8)	0.0188 (3)
C2	0.52645 (7)	0.45352 (11)	0.35874 (8)	0.0187 (3)
C3	0.46802 (7)	0.28272 (11)	0.33491 (8)	0.0189 (3)
O2	0.69837 (6)	0.89712 (9)	0.27351 (7)	0.0308 (3)
C4	0.41035 (7)	0.33857 (11)	0.32620 (8)	0.0190 (3)
C5	0.58308 (7)	0.51335 (11)	0.36914 (8)	0.0203 (3)
H5	0.581926	0.589338	0.372557	0.024*
C6	0.46801 (7)	0.50549 (11)	0.35457 (8)	0.0184 (3)
O3	0.29255 (6)	0.86288 (10)	0.36827 (7)	0.0333 (3)
H3	0.297556	0.860786	0.324012	0.050*
N2	0.29253 (6)	0.12236 (10)	0.26776 (8)	0.0271 (3)
H2	0.256774	0.157719	0.261451	0.033*
H2A	0.291688	0.052819	0.259098	0.033*
C7	0.35174 (7)	0.28527 (12)	0.30498 (9)	0.0209 (3)
H7	0.313740	0.324333	0.300220	0.025*
C8	0.58634 (7)	0.28949 (12)	0.36280 (8)	0.0209 (3)
H8	0.588537	0.213396	0.361985	0.025*
C9	0.40670 (7)	0.11801 (12)	0.30101 (9)	0.0230 (3)
H9	0.405605	0.042653	0.292810	0.028*
C10	0.64007 (7)	0.46248 (12)	0.37438 (8)	0.0206 (3)
N3	0.69510 (7)	0.51611 (11)	0.38180 (9)	0.0291 (3)
H3A	0.695708	0.586676	0.383493	0.035*
H3B	0.730214	0.480361	0.384930	0.035*
C11	0.64045 (7)	0.34775 (12)	0.37364 (8)	0.0217 (3)
H11	0.679646	0.311216	0.380930	0.026*
C12	0.46366 (7)	0.17005 (12)	0.32241 (9)	0.0213 (3)
H12	0.501570	0.129871	0.329174	0.026*
C13	0.34882 (7)	0.17493 (12)	0.29078 (8)	0.0213 (3)
C14	0.35344 (7)	0.50599 (12)	0.33950 (9)	0.0218 (3)
H14	0.317546	0.478366	0.296421	0.026*
H14A	0.357563	0.583836	0.331271	0.026*
C15	0.46851 (7)	0.62318 (11)	0.36976 (8)	0.0195 (3)
C16	0.68832 (7)	0.82758 (12)	0.31927 (9)	0.0223 (3)
C17	0.67009 (7)	0.86787 (12)	0.38850 (9)	0.0236 (3)
C18	0.49149 (8)	0.66099 (13)	0.44535 (9)	0.0255 (3)
H18	0.503879	0.611805	0.487379	0.031*
C19	0.33973 (8)	0.48795 (14)	0.41613 (10)	0.0298 (4)
H19	0.340212	0.410852	0.426940	0.045*
H19A	0.297811	0.517464	0.412963	0.045*
H19B	0.372324	0.523897	0.457891	0.045*
C20	0.65307 (9)	0.97436 (14)	0.39351 (10)	0.0342 (4)
H20	0.652014	1.022597	0.352441	0.041*
C21	0.45042 (8)	0.69580 (12)	0.30839 (9)	0.0240 (3)
H21	0.434456	0.670472	0.256566	0.029*
C22	0.49639 (9)	0.77075 (13)	0.45959 (10)	0.0300 (4)
H22	0.511866	0.796341	0.511400	0.036*
C23	0.47885 (8)	0.84285 (13)	0.39869 (10)	0.0289 (4)
H23	0.482578	0.917811	0.408518	0.035*
C24	0.67216 (9)	0.79923 (14)	0.44987 (10)	0.0324 (4)
H24	0.683412	0.726078	0.447166	0.039*
C25	0.45578 (8)	0.80517 (13)	0.32318 (10)	0.0278 (3)
H25	0.443564	0.854601	0.281290	0.033*
C26	0.64006 (9)	0.94195 (15)	0.51899 (10)	0.0340 (4)
H26	0.629493	0.967049	0.563207	0.041*
C27	0.63763 (10)	1.01061 (15)	0.45818 (11)	0.0374 (4)
H27	0.625279	1.083222	0.460647	0.045*
C28	0.65795 (10)	0.83670 (15)	0.51494 (11)	0.0391 (4)
H28	0.660563	0.789493	0.557056	0.047*
C29	0.30916 (9)	0.76352 (14)	0.40501 (11)	0.0351 (4)
H29	0.354249	0.749124	0.412005	0.053*
H29A	0.283218	0.706941	0.372969	0.053*
H29B	0.301619	0.764985	0.455754	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0208 (6)	0.0152 (6)	0.0197 (6)	0.0019 (4)	0.0063 (5)	0.0003 (4)
O1	0.0308 (6)	0.0187 (5)	0.0341 (6)	0.0025 (4)	0.0133 (5)	0.0023 (4)
C1	0.0236 (7)	0.0166 (7)	0.0165 (6)	0.0012 (5)	0.0064 (5)	0.0007 (5)
C2	0.0223 (7)	0.0171 (7)	0.0160 (6)	0.0022 (5)	0.0048 (5)	0.0008 (5)
C3	0.0224 (7)	0.0166 (7)	0.0188 (7)	0.0010 (5)	0.0077 (6)	0.0001 (5)
O2	0.0429 (7)	0.0208 (6)	0.0331 (6)	−0.0014 (5)	0.0181 (5)	0.0030 (4)
C4	0.0244 (7)	0.0146 (7)	0.0179 (6)	0.0012 (5)	0.0064 (5)	−0.0007 (5)
C5	0.0243 (7)	0.0152 (7)	0.0212 (7)	0.0007 (5)	0.0065 (6)	0.0011 (5)
C6	0.0234 (7)	0.0155 (7)	0.0162 (6)	0.0011 (5)	0.0056 (5)	0.0010 (5)
O3	0.0448 (7)	0.0262 (6)	0.0324 (6)	0.0095 (5)	0.0169 (6)	0.0010 (5)
N2	0.0233 (7)	0.0180 (6)	0.0405 (8)	−0.0020 (5)	0.0102 (6)	−0.0053 (5)
C7	0.0209 (7)	0.0184 (7)	0.0247 (7)	0.0018 (5)	0.0085 (6)	0.0003 (5)
C8	0.0241 (7)	0.0159 (7)	0.0220 (7)	0.0031 (5)	0.0057 (6)	−0.0001 (5)
C9	0.0289 (8)	0.0157 (7)	0.0254 (7)	0.0003 (6)	0.0099 (6)	−0.0015 (5)
C10	0.0222 (7)	0.0201 (7)	0.0194 (7)	0.0001 (5)	0.0061 (6)	0.0016 (5)
N3	0.0231 (7)	0.0198 (6)	0.0457 (9)	0.0012 (5)	0.0122 (6)	0.0026 (6)
C11	0.0218 (7)	0.0209 (7)	0.0225 (7)	0.0039 (5)	0.0066 (6)	0.0013 (5)
C12	0.0236 (7)	0.0174 (7)	0.0232 (7)	0.0023 (5)	0.0077 (6)	−0.0002 (5)
C13	0.0248 (7)	0.0192 (7)	0.0209 (7)	−0.0012 (5)	0.0085 (6)	−0.0014 (5)
C14	0.0209 (7)	0.0158 (7)	0.0294 (8)	0.0030 (5)	0.0086 (6)	−0.0010 (5)
C15	0.0195 (7)	0.0157 (7)	0.0237 (7)	0.0012 (5)	0.0069 (6)	−0.0008 (5)
C16	0.0204 (7)	0.0200 (7)	0.0260 (7)	0.0001 (5)	0.0062 (6)	0.0009 (6)
C17	0.0238 (7)	0.0222 (7)	0.0239 (7)	−0.0019 (6)	0.0059 (6)	0.0005 (6)
C18	0.0320 (8)	0.0208 (7)	0.0221 (7)	0.0018 (6)	0.0059 (6)	0.0005 (6)
C19	0.0331 (9)	0.0253 (8)	0.0361 (9)	0.0038 (6)	0.0178 (7)	−0.0020 (6)
C20	0.0497 (11)	0.0247 (8)	0.0302 (9)	0.0074 (7)	0.0153 (8)	0.0053 (7)
C21	0.0282 (8)	0.0194 (7)	0.0225 (7)	0.0026 (6)	0.0048 (6)	0.0007 (5)
C22	0.0408 (10)	0.0232 (8)	0.0240 (8)	−0.0001 (7)	0.0068 (7)	−0.0048 (6)
C23	0.0345 (9)	0.0161 (7)	0.0347 (9)	0.0008 (6)	0.0082 (7)	−0.0033 (6)
C24	0.0453 (10)	0.0225 (8)	0.0312 (9)	0.0001 (7)	0.0140 (8)	0.0025 (6)
C25	0.0335 (9)	0.0185 (7)	0.0296 (8)	0.0043 (6)	0.0070 (7)	0.0036 (6)
C26	0.0395 (10)	0.0354 (9)	0.0285 (8)	−0.0029 (7)	0.0125 (7)	−0.0045 (7)
C27	0.0518 (12)	0.0271 (9)	0.0335 (9)	0.0075 (8)	0.0133 (8)	−0.0013 (7)
C28	0.0572 (12)	0.0304 (9)	0.0322 (9)	−0.0039 (8)	0.0174 (9)	0.0040 (7)
C29	0.0366 (10)	0.0297 (9)	0.0391 (10)	0.0067 (7)	0.0117 (8)	0.0031 (7)

Geometric parameters (Å, º) top

N1—C6	1.3428 (19)	C12—H12	0.9500
N1—C4	1.4109 (18)	C14—C19	1.520 (2)
N1—C14	1.4917 (18)	C14—H14	0.9900
O1—C16	1.2523 (18)	C14—H14A	0.9900
C1—C8	1.416 (2)	C15—C18	1.389 (2)
C1—C2	1.423 (2)	C15—C21	1.394 (2)
C1—C3	1.427 (2)	C16—C17	1.510 (2)
C2—C5	1.417 (2)	C17—C20	1.390 (2)
C2—C6	1.423 (2)	C17—C24	1.390 (2)
C3—C4	1.416 (2)	C18—C22	1.390 (2)
C3—C12	1.421 (2)	C18—H18	0.9500
O2—C16	1.2626 (19)	C19—H19	0.9800
C4—C7	1.400 (2)	C19—H19A	0.9800
C5—C10	1.385 (2)	C19—H19B	0.9800
C5—H5	0.9500	C20—C27	1.387 (3)
C6—C15	1.4918 (19)	C20—H20	0.9500
O3—C29	1.401 (2)	C21—C25	1.387 (2)
O3—H3	0.8400	C21—H21	0.9500
N2—C13	1.353 (2)	C22—C23	1.383 (2)
N2—H2	0.8800	C22—H22	0.9500
N2—H2A	0.8800	C23—C25	1.387 (2)
C7—C13	1.397 (2)	C23—H23	0.9500
C7—H7	0.9500	C24—C28	1.386 (3)
C8—C11	1.359 (2)	C24—H24	0.9500
C8—H8	0.9500	C25—H25	0.9500
C9—C12	1.362 (2)	C26—C28	1.378 (3)
C9—C13	1.422 (2)	C26—C27	1.381 (3)
C9—H9	0.9500	C26—H26	0.9500
C10—N3	1.356 (2)	C27—H27	0.9500
C10—C11	1.430 (2)	C28—H28	0.9500
N3—H3A	0.8800	C29—H29	0.9800
N3—H3B	0.8800	C29—H29A	0.9800
C11—H11	0.9500	C29—H29B	0.9800

C6—N1—C4	122.23 (12)	C19—C14—H14A	109.5
C6—N1—C14	120.09 (12)	H14—C14—H14A	108.1
C4—N1—C14	117.61 (12)	C18—C15—C21	119.65 (14)
C8—C1—C2	117.20 (13)	C18—C15—C6	119.68 (13)
C8—C1—C3	123.55 (13)	C21—C15—C6	120.51 (13)
C2—C1—C3	119.23 (13)	O1—C16—O2	124.88 (15)
C5—C2—C1	120.66 (13)	O1—C16—C17	117.93 (13)
C5—C2—C6	120.96 (13)	O2—C16—C17	117.19 (13)
C1—C2—C6	118.38 (13)	C20—C17—C24	118.72 (15)
C4—C3—C12	116.91 (13)	C20—C17—C16	121.05 (14)
C4—C3—C1	120.27 (13)	C24—C17—C16	120.19 (14)
C12—C3—C1	122.78 (13)	C15—C18—C22	120.07 (14)
C7—C4—N1	120.44 (13)	C15—C18—H18	120.0
C7—C4—C3	121.39 (13)	C22—C18—H18	120.0
N1—C4—C3	118.17 (13)	C14—C19—H19	109.5
C10—C5—C2	120.85 (13)	C14—C19—H19A	109.5
C10—C5—H5	119.6	H19—C19—H19A	109.5
C2—C5—H5	119.6	C14—C19—H19B	109.5
N1—C6—C2	121.34 (13)	H19—C19—H19B	109.5
N1—C6—C15	119.87 (13)	H19A—C19—H19B	109.5
C2—C6—C15	118.77 (13)	C27—C20—C17	120.36 (16)
C29—O3—H3	109.5	C27—C20—H20	119.8
C13—N2—H2	120.0	C17—C20—H20	119.8
C13—N2—H2A	120.0	C25—C21—C15	119.84 (14)
H2—N2—H2A	120.0	C25—C21—H21	120.1
C13—C7—C4	120.35 (13)	C15—C21—H21	120.1
C13—C7—H7	119.8	C23—C22—C18	120.30 (15)
C4—C7—H7	119.8	C23—C22—H22	119.8
C11—C8—C1	121.44 (14)	C18—C22—H22	119.8
C11—C8—H8	119.3	C22—C23—C25	119.67 (15)
C1—C8—H8	119.3	C22—C23—H23	120.2
C12—C9—C13	120.90 (14)	C25—C23—H23	120.2
C12—C9—H9	119.5	C28—C24—C17	120.51 (16)
C13—C9—H9	119.5	C28—C24—H24	119.7
N3—C10—C5	123.17 (14)	C17—C24—H24	119.7
N3—C10—C11	119.10 (14)	C23—C25—C21	120.46 (15)
C5—C10—C11	117.71 (13)	C23—C25—H25	119.8
C10—N3—H3A	120.0	C21—C25—H25	119.8
C10—N3—H3B	120.0	C28—C26—C27	119.40 (17)
H3A—N3—H3B	120.0	C28—C26—H26	120.3
C8—C11—C10	121.88 (14)	C27—C26—H26	120.3
C8—C11—H11	119.1	C26—C27—C20	120.51 (17)
C10—C11—H11	119.1	C26—C27—H27	119.7
C9—C12—C3	121.90 (14)	C20—C27—H27	119.7
C9—C12—H12	119.1	C26—C28—C24	120.48 (17)
C3—C12—H12	119.1	C26—C28—H28	119.8
N2—C13—C7	121.36 (14)	C24—C28—H28	119.8
N2—C13—C9	120.13 (13)	O3—C29—H29	109.5
C7—C13—C9	118.51 (13)	O3—C29—H29A	109.5
N1—C14—C19	110.62 (12)	H29—C29—H29A	109.5
N1—C14—H14	109.5	O3—C29—H29B	109.5
C19—C14—H14	109.5	H29—C29—H29B	109.5
N1—C14—H14A	109.5	H29A—C29—H29B	109.5

C8—C1—C2—C5	4.2 (2)	C5—C10—C11—C8	4.5 (2)
C3—C1—C2—C5	−174.09 (13)	C13—C9—C12—C3	−0.4 (2)
C8—C1—C2—C6	−175.42 (12)	C4—C3—C12—C9	1.7 (2)
C3—C1—C2—C6	6.3 (2)	C1—C3—C12—C9	−176.06 (14)
C8—C1—C3—C4	179.54 (13)	C4—C7—C13—N2	−177.83 (14)
C2—C1—C3—C4	−2.3 (2)	C4—C7—C13—C9	2.2 (2)
C8—C1—C3—C12	−2.8 (2)	C12—C9—C13—N2	178.47 (14)
C2—C1—C3—C12	175.40 (13)	C12—C9—C13—C7	−1.5 (2)
C6—N1—C4—C7	−175.44 (13)	C6—N1—C14—C19	−98.78 (15)
C14—N1—C4—C7	7.59 (19)	C4—N1—C14—C19	78.27 (16)
C6—N1—C4—C3	4.3 (2)	N1—C6—C15—C18	103.00 (17)
C14—N1—C4—C3	−172.63 (12)	C2—C6—C15—C18	−75.35 (19)
C12—C3—C4—C7	−1.0 (2)	N1—C6—C15—C21	−81.64 (18)
C1—C3—C4—C7	176.79 (13)	C2—C6—C15—C21	100.00 (17)
C12—C3—C4—N1	179.18 (12)	O1—C16—C17—C20	−168.22 (16)
C1—C3—C4—N1	−3.0 (2)	O2—C16—C17—C20	12.2 (2)
C1—C2—C5—C10	−0.6 (2)	O1—C16—C17—C24	14.0 (2)
C6—C2—C5—C10	178.99 (13)	O2—C16—C17—C24	−165.61 (16)
C4—N1—C6—C2	−0.2 (2)	C21—C15—C18—C22	0.0 (2)
C14—N1—C6—C2	176.68 (12)	C6—C15—C18—C22	175.40 (15)
C4—N1—C6—C15	−178.53 (12)	C24—C17—C20—C27	−0.9 (3)
C14—N1—C6—C15	−1.6 (2)	C16—C17—C20—C27	−178.76 (17)
C5—C2—C6—N1	175.22 (13)	C18—C15—C21—C25	0.3 (2)
C1—C2—C6—N1	−5.2 (2)	C6—C15—C21—C25	−175.05 (14)
C5—C2—C6—C15	−6.5 (2)	C15—C18—C22—C23	−0.4 (3)
C1—C2—C6—C15	173.15 (12)	C18—C22—C23—C25	0.5 (3)
N1—C4—C7—C13	178.89 (13)	C20—C17—C24—C28	−0.5 (3)
C3—C4—C7—C13	−0.9 (2)	C16—C17—C24—C28	177.42 (16)
C2—C1—C8—C11	−3.5 (2)	C22—C23—C25—C21	−0.2 (3)
C3—C1—C8—C11	174.73 (14)	C15—C21—C25—C23	−0.2 (3)
C2—C5—C10—N3	177.79 (14)	C28—C26—C27—C20	−0.1 (3)
C2—C5—C10—C11	−3.7 (2)	C17—C20—C27—C26	1.2 (3)
C1—C8—C11—C10	−0.9 (2)	C27—C26—C28—C24	−1.3 (3)
N3—C10—C11—C8	−176.92 (14)	C17—C24—C28—C26	1.6 (3)

Hydrogen-bond geometry (Å, º) top

Hydrogen-bond geometry (Å, °).

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.84	1.85	2.6636 (17)	163
N2—H2···O1ⁱⁱ	0.88	2.09	2.8741 (18)	148
N2—H2A···O2ⁱⁱⁱ	0.88	2.06	2.9271 (17)	169
N3—H3A···O1	0.88	2.18	2.9264 (18)	142
N3—H3B···O3^iv	0.88	2.09	2.939 (2)	162

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

Funding information

Financial support from a JSPS Grant-in-Aid for Scientific Research (grant No. 21 K05089) is gratefully acknowledged.

References

Brandenburg, K. (2014). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2021). APEX4 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Carrozzini, B., Cascarano, G. L., Cuocci, C., Giacovazzo, C., Mallamo, M., Mazzone, A. & Polidori, G. (2015). J. Appl. Cryst. 48, 306–309. Web of Science CrossRef CAS IUCr Journals Google Scholar
Chen, W., Turro, N. J. & Tomalia, D. A. (2000). Langmuir, 16, 15–19. Web of Science CrossRef Google Scholar
Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Crystallogr. Soc. Japan, 51, 218–224. CrossRef 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
Ma, H., Liu, B., Li, B., Zhang, L., Li, Y.-G., Tan, H.-Q., Zang, H.-Y. & Zhu, G. (2016). J. Am. Chem. Soc. 138, 5897–5903. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 9| Part 4| April 2024| x240302

https://doi.org/10.1107/S241431462400302X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethidium benzoate methanol monosolvate

Structure description

Synthesis and crystallization

Refinement

Structural data

Funding information

References

organic compounds