Crystal structure of 2-{5-[2-(2-hy­droxy­phen­yl)diazen-1-yl]-1-methyl­pyrrol-2-yl}phenol methanol monosolvate

Yang, G.; Feng, H.; Yin, Z.

doi:10.1107/S2056989018007764

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ISSN: 2056-9890

Volume 74| Part 6| June 2018| Pages 871-873

https://doi.org/10.1107/S2056989018007764

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Crystal structure of 2-{5-[2-(2-hydroxyphenyl)diazen-1-yl]-1-methylpyrrol-2-yl}phenol methanol monosolvate

Guiwen Yang,^a Huixiao Feng ^a and Zhenming Yin ^a ^*

^aCollege of Chemistry, Tianjin Key Laboratory of Structure and Performance for, Functional Molecule, Tianjin Normal University, Tianjin 300387, People's Republic of China;, Key Laboratory of Inorganic-Organic Hybrid Functional Materials Chemistry, (Tianjin Normal University), Ministry of Education, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: tjyinzm@aliyun.com

Edited by K. Fejfarova, Institute of Biotechnology CAS, Czech Republic (Received 12 April 2018; accepted 24 May 2018; online 31 May 2018)

In the title azopyrrole compound, C₁₇H₁₅N₃O₂·CH₃OH, the azo N=N bond adopts a trans configuration and the pyrrole N and azo group are in an anti orientation. The dihedral angles between the pyrrole ring and the two phenyl rings are 6.7 (3) and 54.7 (3)°. In the crystal, a supramolecular ring structure is formed between two azopyrrole and two methanol solvent molecules through four O—H⋯O hydrogen bonds.

Keywords: azopyrrole; crystal structure; hydrogen bonding.

CCDC reference: 1845021

1. Chemical context

Recently, azopyrrole dyes have received much attention for their promising use in the design of advanced materials and devices. For example, some thienylpyrrole azo dyes bearing heterocyclic groups have good non-linear optical properties (Raposo et al., 2011 ). Mikroyannidis and coworkers found that many azopyrrole dyes are efficient bulk heterojunction solar cell materials (Sharma et al., 2012 ). In a previous work, we reported the crystal engineering of some 5,5′-bis(phenyldiazo)dipyrromethane compounds and demonstrated their interlocked type self-assemblies in the solid state via quadruple N—H⋯N hydrogen bonds (Yin et al., 2008 , 2009 ). In a continuation of this research, we report herein the crystal structure of 2-{5-[2-(2-hydroxyphenyl)diazen-1-yl]-1-methylpyrrol-2-yl}phenol methanol monosolvate.

2. Structural commentary

The structure of the title compound is shown in Fig. 1. The asymmetric unit contains one azopyrrole molecule and one methanol solvent molecule. The azoylazopyrrole group is almost planar, reflected by the dihedral angle between the pyrrole ring (N3/C7–C10) and the benzene ring (C1–C6) of only 6.7 (3)°, which may be due to the existence of the intramolecular O1—H1⋯N2 hydrogen bond (Table 1) between the hydroxy group and the azo N atom. The dihedral angle between pyrrole ring and the other benzene ring (C12–C17) is 54.7 (3)°, which may be caused by the steric repulsion between hydroxy group and methyl group. The azo N=N bond adopts a trans configuration and its length is 1.286 (2) Å, which is shorter than that in the crystal of 2,5-bis(2-hydroxyphenylazo)-1H-pyrrole (1.293 Å; Li et al. 2009 ). It is worth mentioning that the N1 atom of the azo group and the N3 atom of the pyrrole ring are arranged on opposite sides with respect to the C7—N2 bond, which is the same as in the crystal of 2-phenylazo-1-vinyl pyrrole (Trofimov et al., 2006 ) but different to many other observations (Li et al., 2009; Yin et al., 2008). The bond lengths in the pyrrole ring are more equal compared to those normally observed.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C12-C17 rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.84	1.81	2.530 (2)	143
O2—H2⋯O3ⁱ	0.84	1.81	2.641 (2)	171
O3—H3A⋯O1ⁱⁱ	0.84	1.97	2.763 (2)	157
C11—H11B⋯Cg1ⁱⁱⁱ	0.98	2.73	3.587 (2)	147
C18—H18C⋯Cg2^iv	0.98	2.75	3.483 (3)	132
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x, y, z+1; (iii) -x, -y+1, -z; (iv) -x, -y+2, -z+1.

Figure 1
ORTEP diagram for the title compound, with displacement ellipsoids drawn at the 30% probability level. The methanol solvent molecule was omitted for clarity.

3. Supramolecular features

In the crystal, two azopyrrole molecules are bridged by two methanol solvent molecules through four O—H⋯O hydrogen bonds forming a large supramolecular ring structure, in which the methanol acts as both a hydrogen-bond acceptor and a donor (Fig. 2, Table 1). This type of coordination environment is most populated (occupying 70%) for methanol molecules as revealed by a search of the Cambridge Structural Database (CSD) (Brychczynska et al. 2008 ). The methyl groups point to the inside of the ring. The rings are further held together through C—H⋯π contacts involving the benzene rings (Table 1). There are no π–π interactions between the aromatic rings. The packing is shown in Fig. 3.

Figure 2
O—H⋯O hydrogen-bonded (Table 1

) supramolecular ring structure.

Figure 3
A view of the crystal packing along the b axis.

4. Database survey

A search in the Cambridge Structural Database (Version 5.38; Groom et al., 2016 ) returned 45 entries for azopyrrole derivatives, including three entries for N-vinylphenylazopyrrole (Trofimov et al., 2006; Rusakov et al., 2007 ), four entries for mono- or bisazopyrroles (Li et al., 2009), two entries for azo calix[4]pyrroles (Nishiyabu et al., 2006 ), five entries for pyrrole-azocrown ethers (Wagner-Wysiecka et al., 2011 ; Szczygelska-Tao et al., 2008 ), two entries for azopyrrole boron difluoride complexes (Li et al., 2009; Lee et al., 2012 ), ten entries for metal complexes (Li et al., 2008 ; Li, & Dolphin, 2011 ; Yin et al., 2012 ; Zhang et al., 2015 ; Ghorui et al., 2016 ); the majority are for mono- or bisphenylazodipyrromethanes (Yin et al., 2008, 2009; Chen & Yin, 2014 ; Zhang & Yin, 2014 ).

5. Synthesis and crystallization

A 273 K solution of 2-aminophenol 0.272 g (2.5 mmol) and aqueous HCl (2 mL) in water (2 mL) was treated with another 273 K solution of NaNO₂ (0.18 g, 2.5 mmol) in 3 mL water, and the mixture was stirred at 273 K for 30 min. The diazonium salt solution was added dropwise to a solution of N-methylpyrrole (81 mg, 1 mmol) in acetonitrile (25 mL) and three drops of acetic acid. The combined solution was maintained at 273 K for 2 h with stirring. After that, EtOAc (25 mL) and water (25 mL) were added. The organic layer was separated and washed with water (20 mL) and dried with anhydrous MgSO₄. The solution was evaporated and the residue was purified by column chromatography on silica (ethyl acetate/petroleum ether = 1:2), which gave the title compound as an orange powder (200 mg, 68%, m.p. 404 K).

¹H NMR (400MHz, DMSO-d₆): δ 3.73 (s, 3H, –CH₃), 6.32 (d, J = 4 Hz, 1H, pyrrole C—H), 6.86 (d, J = 4 Hz, 1H, pyrrole C–H), 6.90–6.95 (m, 2H, Ar C-H), 6.99 (t, 2H, J = 8 Hz, Ar C—H), 7.23–7.31 (m, 3H, Ar C-H), 7.65 (d, J = 8Hz, 1H, Ar C—H), 9.95 (s, 1H, –OH), 10.43 (s, 1H, –OH) . Crystals suitable X-ray diffraction analysis were obtained by the slow evaporation of a CHCl₃/CH₃OH solution of the title compound.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. O—H atoms were located in a difference-Fourier map and refined freely. Other H atoms were positioned geometrically (C—H = 0.95 or 0.98 Å) and included in the final cycles of refinement using a riding model, with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(Cmethyl).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₃O₂·CH₄O
M_r	325.36
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	7.1597 (11), 9.8762 (16), 12.243 (2)
α, β, γ (°)	110.426 (3), 94.051 (3), 93.378 (3)
V (Å³)	806.0 (2)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.14 × 0.13 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005 )
T_min, T_max	0.987, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	4168, 2830, 2071
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.109, 1.03
No. of reflections	2830
No. of parameters	222
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23
Computer programs: APEX2 and SAINT (Bruker, 2005), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 1845021

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018007764/ff2153sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018007764/ff2153Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018007764/ff2153Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-{5-[2-(2-Hydroxyphenyl)diazen-1-yl]-1-methylpyrrol-2-yl}phenol methanol monosolvate top

Crystal data top

C₁₇H₁₅N₃O₂·CH₄O	Z = 2
M_r = 325.36	F(000) = 344
Triclinic, P1	D_x = 1.341 Mg m⁻³
a = 7.1597 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8762 (16) Å	Cell parameters from 1104 reflections
c = 12.243 (2) Å	θ = 2.3–28.1°
α = 110.426 (3)°	µ = 0.09 mm⁻¹
β = 94.051 (3)°	T = 173 K
γ = 93.378 (3)°	BLOCK, yellow
V = 806.0 (2) Å³	0.14 × 0.13 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	2830 independent reflections
Radiation source: fine-focus sealed tube	2071 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.987, T_max = 0.989	k = −11→9
4168 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0437P)² + 0.2373P] where P = (F_o² + 2F_c²)/3
2830 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 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.

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

	x	y	z	U_iso*/U_eq
O1	0.2218 (2)	0.53355 (15)	−0.07978 (12)	0.0254 (4)
H1	0.2260	0.5941	−0.0113	0.038*
O2	0.4830 (2)	1.13606 (14)	0.27561 (13)	0.0221 (4)
H2	0.5527	1.1998	0.2636	0.033*
O3	0.2725 (2)	0.68674 (17)	0.77244 (15)	0.0304 (4)
H3A	0.2900	0.6375	0.8154	0.046*
N1	0.2920 (2)	0.48800 (18)	0.14369 (15)	0.0191 (4)
N2	0.2614 (2)	0.61395 (18)	0.14132 (14)	0.0181 (4)
N3	0.2453 (2)	0.86125 (17)	0.24967 (14)	0.0166 (4)
C1	0.2840 (3)	0.3796 (2)	0.03169 (18)	0.0180 (5)
C2	0.2539 (3)	0.4013 (2)	−0.07572 (18)	0.0196 (5)
C3	0.2592 (3)	0.2857 (2)	−0.18007 (19)	0.0247 (5)
H3	0.2390	0.3001	−0.2526	0.030*
C4	0.2933 (3)	0.1506 (2)	−0.17897 (19)	0.0243 (5)
H4	0.2988	0.0728	−0.2508	0.029*
C5	0.3199 (3)	0.1269 (2)	−0.07380 (19)	0.0235 (5)
H5	0.3407	0.0329	−0.0735	0.028*
C6	0.3159 (3)	0.2406 (2)	0.02965 (19)	0.0206 (5)
H6	0.3353	0.2244	0.1015	0.025*
C7	0.2752 (3)	0.7239 (2)	0.24820 (17)	0.0170 (5)
C8	0.3197 (3)	0.7316 (2)	0.36227 (17)	0.0190 (5)
H8	0.3478	0.6533	0.3870	0.023*
C9	0.3152 (3)	0.8753 (2)	0.43346 (18)	0.0190 (5)
H9	0.3386	0.9128	0.5164	0.023*
C10	0.2708 (3)	0.9552 (2)	0.36319 (17)	0.0172 (5)
C11	0.1888 (3)	0.8954 (2)	0.14600 (18)	0.0210 (5)
H11A	0.1466	0.9933	0.1702	0.032*
H11B	0.0858	0.8251	0.0986	0.032*
H11C	0.2959	0.8908	0.0997	0.032*
C12	0.2552 (3)	1.1127 (2)	0.39959 (17)	0.0167 (5)
C13	0.3645 (3)	1.2011 (2)	0.35662 (17)	0.0166 (5)
C14	0.3540 (3)	1.3501 (2)	0.39739 (17)	0.0184 (5)
H14	0.4266	1.4092	0.3664	0.022*
C15	0.2372 (3)	1.4124 (2)	0.48346 (18)	0.0203 (5)
H15	0.2299	1.5144	0.5113	0.024*
C16	0.1314 (3)	1.3269 (2)	0.52895 (18)	0.0211 (5)
H16	0.0526	1.3699	0.5886	0.025*
C17	0.1411 (3)	1.1790 (2)	0.48707 (18)	0.0201 (5)
H17	0.0682	1.1207	0.5187	0.024*
C18	0.0860 (3)	0.7274 (3)	0.7761 (2)	0.0310 (6)
H18A	0.0712	0.7970	0.8541	0.046*
H18B	−0.0020	0.6411	0.7594	0.046*
H18C	0.0596	0.7720	0.7173	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0358 (9)	0.0192 (8)	0.0215 (8)	0.0050 (7)	0.0042 (7)	0.0068 (7)
O2	0.0216 (8)	0.0161 (8)	0.0286 (8)	0.0020 (6)	0.0093 (7)	0.0066 (7)
O3	0.0220 (8)	0.0362 (10)	0.0448 (10)	0.0055 (7)	0.0064 (7)	0.0279 (8)
N1	0.0188 (9)	0.0144 (9)	0.0233 (10)	0.0014 (7)	0.0030 (8)	0.0053 (8)
N2	0.0164 (9)	0.0155 (10)	0.0216 (9)	0.0004 (7)	0.0024 (7)	0.0057 (8)
N3	0.0157 (9)	0.0155 (9)	0.0188 (9)	0.0018 (7)	0.0022 (7)	0.0062 (7)
C1	0.0120 (10)	0.0167 (11)	0.0226 (11)	0.0005 (8)	0.0008 (9)	0.0040 (9)
C2	0.0165 (11)	0.0176 (12)	0.0253 (12)	0.0020 (9)	0.0015 (9)	0.0083 (9)
C3	0.0235 (12)	0.0296 (13)	0.0199 (11)	0.0021 (10)	0.0022 (10)	0.0072 (10)
C4	0.0209 (11)	0.0210 (12)	0.0236 (12)	0.0036 (9)	0.0026 (9)	−0.0015 (10)
C5	0.0212 (12)	0.0160 (12)	0.0304 (13)	0.0036 (9)	0.0001 (10)	0.0049 (10)
C6	0.0172 (11)	0.0211 (12)	0.0230 (11)	0.0008 (9)	−0.0021 (9)	0.0080 (9)
C7	0.0152 (10)	0.0136 (11)	0.0215 (11)	0.0004 (8)	0.0032 (9)	0.0052 (9)
C8	0.0222 (11)	0.0143 (11)	0.0216 (11)	0.0022 (9)	0.0025 (9)	0.0077 (9)
C9	0.0198 (11)	0.0184 (11)	0.0179 (11)	0.0012 (9)	0.0031 (9)	0.0051 (9)
C10	0.0143 (10)	0.0160 (11)	0.0195 (11)	0.0004 (8)	0.0028 (9)	0.0042 (9)
C11	0.0239 (12)	0.0176 (11)	0.0198 (11)	0.0019 (9)	−0.0034 (9)	0.0054 (9)
C12	0.0151 (10)	0.0142 (11)	0.0197 (11)	0.0000 (8)	−0.0022 (9)	0.0055 (9)
C13	0.0148 (10)	0.0174 (11)	0.0160 (10)	0.0031 (8)	−0.0001 (8)	0.0040 (9)
C14	0.0181 (11)	0.0154 (11)	0.0211 (11)	−0.0006 (8)	−0.0010 (9)	0.0066 (9)
C15	0.0210 (11)	0.0141 (11)	0.0227 (11)	0.0027 (9)	−0.0009 (9)	0.0031 (9)
C16	0.0206 (11)	0.0200 (12)	0.0216 (11)	0.0047 (9)	0.0048 (9)	0.0050 (9)
C17	0.0171 (11)	0.0202 (12)	0.0239 (11)	−0.0005 (9)	0.0028 (9)	0.0090 (9)
C18	0.0216 (12)	0.0363 (14)	0.0367 (14)	0.0030 (10)	0.0015 (11)	0.0153 (12)

Geometric parameters (Å, º) top

O1—C2	1.357 (2)	C7—C8	1.385 (3)
O1—H1	0.8400	C8—C9	1.386 (3)
O2—C13	1.362 (2)	C8—H8	0.9500
O2—H2	0.8400	C9—C10	1.389 (3)
O3—C18	1.416 (3)	C9—H9	0.9500
O3—H3A	0.8400	C10—C12	1.475 (3)
N1—N2	1.286 (2)	C11—H11A	0.9800
N1—C1	1.410 (2)	C11—H11B	0.9800
N2—C7	1.371 (2)	C11—H11C	0.9800
N3—C10	1.367 (2)	C12—C17	1.393 (3)
N3—C7	1.380 (3)	C12—C13	1.396 (3)
N3—C11	1.460 (3)	C13—C14	1.388 (3)
C1—C6	1.397 (3)	C14—C15	1.386 (3)
C1—C2	1.409 (3)	C14—H14	0.9500
C2—C3	1.390 (3)	C15—C16	1.382 (3)
C3—C4	1.375 (3)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.378 (3)
C4—C5	1.389 (3)	C16—H16	0.9500
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.372 (3)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—H6	0.9500	C18—H18C	0.9800

C2—O1—H1	109.5	C10—C9—H9	125.7
C13—O2—H2	109.5	N3—C10—C9	107.62 (17)
C18—O3—H3A	109.5	N3—C10—C12	124.35 (19)
N2—N1—C1	113.64 (18)	C9—C10—C12	128.03 (18)
N1—N2—C7	115.61 (18)	N3—C11—H11A	109.5
C10—N3—C7	108.49 (17)	N3—C11—H11B	109.5
C10—N3—C11	127.06 (17)	H11A—C11—H11B	109.5
C7—N3—C11	124.41 (17)	N3—C11—H11C	109.5
C6—C1—C2	118.50 (19)	H11A—C11—H11C	109.5
C6—C1—N1	115.80 (19)	H11B—C11—H11C	109.5
C2—C1—N1	125.66 (19)	C17—C12—C13	118.08 (19)
O1—C2—C3	119.0 (2)	C17—C12—C10	119.67 (19)
O1—C2—C1	121.41 (18)	C13—C12—C10	122.00 (19)
C3—C2—C1	119.6 (2)	O2—C13—C14	121.74 (19)
C4—C3—C2	120.4 (2)	O2—C13—C12	117.65 (18)
C4—C3—H3	119.8	C14—C13—C12	120.60 (19)
C2—C3—H3	119.8	C15—C14—C13	119.8 (2)
C3—C4—C5	120.6 (2)	C15—C14—H14	120.1
C3—C4—H4	119.7	C13—C14—H14	120.1
C5—C4—H4	119.7	C16—C15—C14	120.3 (2)
C6—C5—C4	119.3 (2)	C16—C15—H15	119.9
C6—C5—H5	120.3	C14—C15—H15	119.9
C4—C5—H5	120.3	C17—C16—C15	119.5 (2)
C5—C6—C1	121.5 (2)	C17—C16—H16	120.3
C5—C6—H6	119.3	C15—C16—H16	120.3
C1—C6—H6	119.3	C16—C17—C12	121.7 (2)
N2—C7—N3	117.55 (18)	C16—C17—H17	119.2
N2—C7—C8	133.93 (19)	C12—C17—H17	119.2
N3—C7—C8	108.49 (17)	O3—C18—H18A	109.5
C7—C8—C9	106.85 (19)	O3—C18—H18B	109.5
C7—C8—H8	126.6	H18A—C18—H18B	109.5
C9—C8—H8	126.6	O3—C18—H18C	109.5
C8—C9—C10	108.55 (18)	H18A—C18—H18C	109.5
C8—C9—H9	125.7	H18B—C18—H18C	109.5

C1—N1—N2—C7	−177.49 (17)	C7—C8—C9—C10	−0.8 (2)
N2—N1—C1—C6	−179.85 (17)	C7—N3—C10—C9	−0.6 (2)
N2—N1—C1—C2	2.6 (3)	C11—N3—C10—C9	177.13 (18)
C6—C1—C2—O1	179.88 (19)	C7—N3—C10—C12	178.51 (18)
N1—C1—C2—O1	−2.6 (3)	C11—N3—C10—C12	−3.7 (3)
C6—C1—C2—C3	−0.9 (3)	C8—C9—C10—N3	0.9 (2)
N1—C1—C2—C3	176.63 (19)	C8—C9—C10—C12	−178.2 (2)
O1—C2—C3—C4	179.32 (19)	N3—C10—C12—C17	128.7 (2)
C1—C2—C3—C4	0.1 (3)	C9—C10—C12—C17	−52.3 (3)
C2—C3—C4—C5	1.1 (3)	N3—C10—C12—C13	−57.2 (3)
C3—C4—C5—C6	−1.4 (3)	C9—C10—C12—C13	121.8 (2)
C4—C5—C6—C1	0.6 (3)	C17—C12—C13—O2	176.58 (17)
C2—C1—C6—C5	0.6 (3)	C10—C12—C13—O2	2.4 (3)
N1—C1—C6—C5	−177.19 (18)	C17—C12—C13—C14	−2.3 (3)
N1—N2—C7—N3	179.37 (17)	C10—C12—C13—C14	−176.47 (18)
N1—N2—C7—C8	1.5 (3)	O2—C13—C14—C15	−177.29 (17)
C10—N3—C7—N2	−178.23 (17)	C12—C13—C14—C15	1.5 (3)
C11—N3—C7—N2	3.9 (3)	C13—C14—C15—C16	0.0 (3)
C10—N3—C7—C8	0.2 (2)	C14—C15—C16—C17	−0.8 (3)
C11—N3—C7—C8	−177.69 (18)	C15—C16—C17—C12	0.0 (3)
N2—C7—C8—C9	178.4 (2)	C13—C12—C17—C16	1.5 (3)
N3—C7—C8—C9	0.4 (2)	C10—C12—C17—C16	175.89 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C12-C17 rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.84	1.81	2.530 (2)	143
O2—H2···O3ⁱ	0.84	1.81	2.641 (2)	171
O3—H3A···O1ⁱⁱ	0.84	1.97	2.763 (2)	157
C11—H11B···Cg1ⁱⁱⁱ	0.98	2.73	3.587 (2)	147
C18—H18C···Cg2^iv	0.98	2.75	3.483 (3)	132

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

Funding information

Funding for this research was provided by: National Natural Science Foundation of China (award No. 21172174).

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