Diethyl 1-[(4-methyl-2-phenyl-4,5-di­hydro-1,3-oxazol-4-yl)meth­yl]-1H-1,2,3-triazole-4,5-di­carboxyl­ate

Boukhssas, S.; Aouine, Y.; Faraj, H.; Alami, A.; El Hallaoui, A.; Zouihri, H.

doi:10.1107/S2414314617017011

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 11| November 2017| x171701

https://doi.org/10.1107/S2414314617017011

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Diethyl 1-[(4-methyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methyl]-1H-1,2,3-triazole-4,5-dicarboxylate

Salaheddine Boukhssas,^a,^b Younas Aouine,^b Hassane Faraj,^b Anouar Alami,^b ^* Abdelilah El Hallaoui ^b and Hafid Zouihri ^c

^aFormation Doctorale Molécules Bioactives, Santé et Biotechnologies, Centre détudes Doctorales Sciences et Technologies, Faculté des Sciences Dhar El Marhaz, Fès, Morocco, ^bLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, and ^cLaboratoire de Chimie des Matériaux et Biotechnologie des Produits Naturels, E.Ma.Me.P.S., Université Moulay Ismail, Faculté des Sciences, Meknès, Morocco
^*Correspondence e-mail: anouar.alami@usmba.ac.ma

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 10 November 2017; accepted 26 November 2017; online 28 November 2017)

In the title compound, C₁₉H₂₂N₄O₅, the central triazole ring makes dihedral angles of 56.15 (8) and 43.25 (9)° with the oxazole and benzene rings, respectively. The mean planes of the two ethoxycarbonyl groups make dihedral angles of 24.16 (11) and 51.90 (10)° with the triazole ring. Globally, the molecule has a U-shape. In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into supramolecular layers in the bc plane.

Keywords: crystal structure; 1,2,3-triazole moiety; hydrogen bonds.

CCDC reference: 1587658

Structure description

Azide–alkyne cycloaddition is a useful and convenient method for the preparation of 1,2,3-triazoles (Lutz et al., 2008 ; Oliva et al., 2008 ; Kiss et al., 2010 ). The approach for the synthesis of 1,2,3-triazole-substituted compounds involves transformation of the azide function in a 1,3-dipolar cycloaddition reaction with acetylene derivatives. In this context, the title compound was obtained with good yield (Boukhssas et al., 2017 ).

In the title compound, Fig. 1, the central triazole ring is planar (r.m.s deviation = 0.0054 (13) Å) and makes dihedral angles of 56.15 (8) and 43.25 (9)° with the oxazol and benzene rings, respectively. The mean planes of the two ethoxycarbonyl groups make dihedral angles of 24.16 (11) and 51.90 (10)° with the triazole ring.

Figure 1
The structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level. H atoms are represented as small spheres of arbitrary radii.

In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into supramolecular layers in the bc plane, Table 1 and Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯N3ⁱ	0.97	2.59	3.454 (2)	149
C11—H11A⋯O1ⁱⁱ	0.96	2.56	3.392 (2)	145
Symmetry codes: (i) $[x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
A view of the molecular packing along the c axis. Hydrogen bonds are drawn as dashed lines.

Synthesis and crystallization

A mixture of 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole (0.65 mmol) and diethyl acetylenedicarboxylate (0.65 mmol) was stirred for 12 h. The crude product was treated with ethyl acetate, the organic layer was washed with water, dried with Na₂SO₄, and the solvent removed. The product was purified by recrystallization from ether–hexane to afford the pure product. Suitable crystals of the title compound were obtained by recrystallization from its CHCl₃ solution. The structure of the product was established on the basis of NMR spectroscopy (¹H and ¹³C) and MS data.

Yield = 75% (white solid); m.p. = 92–94°C; R_f = 0.23 (ether/hexane). ¹H NMR (300.13 MHz; CDCl₃): 1.30 (3H, CH₃–CH₂, t, J = 7.15 Hz); 1.38 (3H, CH₃–CH₂, t, J = 7.14 Hz); 1.41 (3H, CH₃–Oxaz, s); 4.13–4.53 (2H, CH₂–Oxaz, AB, J = 9.05 Hz); 4.24–4.38 (2H, –CH₂–CH₃, q, J = 7.15 Hz); 4.27–4.42 (2H, –CH₂–CH₃, q, J = 7.15 Hz); 4.76–4.93 (2H, --CH₂–triazole, AB, J = 13.76 Hz); 7.35–7.84 (5Harom, m). ¹³C NMR (75.47 MHz; CDCl₃): 13.66 (CH₃–CH₂); 14.14 (CH₃–CH₂); 25.22 (CH₃–Oxaz); 56.38 (CH₂–triazole); 61.71 (CH₃–CH₂); 62.76 (CH₃–CH₂); 70.77 (C_q–Oxaz); 75.13 (CH₂–Oxaz); 127.00 (C-5, of triazole ring); 128.21; 128.46; 131.74 and 132.06 (6 Carom); 139.60 (C-4, of triazole ring); 158.73 and 159.93 (CO); 164.46 (CN). MS–EI: [M+1]⁺= 387.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₂₂N₄O₅
M_r	386.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.9450 (9), 16.3245 (10), 9.0473 (6)
β (°)	104.066 (2)
V (Å³)	1997.8 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.21 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	33174, 3529, 2938
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.108, 1.07
No. of reflections	3529
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.26
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXS2013 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1587658

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017011/tk4040sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017011/tk4040Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617017011/tk4040Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Diethyl 1-[(4-methyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methyl]-1H-1,2,3-triazole-4,5-dicarboxylate top

Crystal data top

C₁₉H₂₂N₄O₅	F(000) = 816
M_r = 386.41	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 298 reflections
a = 13.9450 (9) Å	θ = 1.4–28.4°
b = 16.3245 (10) Å	µ = 0.10 mm⁻¹
c = 9.0473 (6) Å	T = 173 K
β = 104.066 (2)°	Prism, colourless
V = 1997.8 (2) Å³	0.34 × 0.21 × 0.17 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2938 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
φ and ω scan	h = −16→16
33174 measured reflections	k = −19→19
3529 independent reflections	l = −10→10

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0558P)² + 0.3505P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.108	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 0.24 e Å⁻³
3529 reflections	Δρ_min = −0.26 e Å⁻³
257 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0066 (12)

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
O1	0.91074 (9)	0.92709 (7)	−0.10242 (14)	0.0694 (4)
O2	0.75141 (8)	0.95729 (7)	−0.11812 (12)	0.0566 (3)
O3	0.78857 (14)	1.13220 (8)	−0.14989 (14)	0.0965 (5)
O4	0.76719 (8)	1.21752 (6)	0.03184 (11)	0.0509 (3)
O5	0.75886 (7)	0.88651 (7)	0.37008 (12)	0.0594 (3)
N1	0.92249 (8)	0.98814 (7)	0.22234 (13)	0.0422 (3)
N2	0.93045 (9)	1.05074 (7)	0.32281 (14)	0.0503 (3)
N3	0.88258 (9)	1.11341 (7)	0.25090 (13)	0.0485 (3)
N4	0.82672 (9)	0.82643 (7)	0.19534 (14)	0.0495 (3)
C1	0.86797 (9)	1.01117 (8)	0.08517 (15)	0.0401 (3)
C2	0.84362 (10)	1.09149 (8)	0.10399 (15)	0.0421 (3)
C3	0.84737 (11)	0.95944 (9)	−0.05463 (16)	0.0465 (3)
C4	0.72235 (16)	0.91941 (14)	−0.2678 (2)	0.0810 (6)
H4A	0.7292	0.8604	−0.2587	0.097*
H4B	0.7642	0.9389	−0.3317	0.097*
C5	0.61798 (18)	0.94152 (15)	−0.3363 (2)	0.0955 (7)
H5A	0.5771	0.9219	−0.2723	0.143*
H5B	0.5971	0.9170	−0.4353	0.143*
H5C	0.6121	1.0000	−0.3455	0.143*
C6	0.79680 (12)	1.14840 (9)	−0.01821 (16)	0.0506 (4)
C7	0.72300 (14)	1.27614 (10)	−0.08724 (19)	0.0635 (4)
H7A	0.6618	1.2543	−0.1497	0.076*
H7B	0.7678	1.2865	−0.1522	0.076*
C8	0.7035 (2)	1.35238 (13)	−0.0141 (2)	0.1027 (8)
H8A	0.6570	1.3421	0.0463	0.154*
H8B	0.6768	1.3924	−0.0909	0.154*
H8C	0.7641	1.3726	0.0500	0.154*
C9	0.97441 (10)	0.91127 (9)	0.27105 (18)	0.0484 (4)
H9A	1.0317	0.9228	0.3536	0.058*
H9B	0.9981	0.8892	0.1869	0.058*
C10	0.91134 (10)	0.84644 (8)	0.32417 (17)	0.0480 (4)
C11	0.97659 (14)	0.77174 (10)	0.3755 (2)	0.0743 (5)
H11A	0.9375	0.7284	0.4023	0.111*
H11B	1.0286	0.7859	0.4625	0.111*
H11C	1.0047	0.7539	0.2941	0.111*
C12	0.86204 (11)	0.87770 (11)	0.44759 (17)	0.0558 (4)
H12A	0.8702	0.8387	0.5306	0.067*
H12B	0.8900	0.9299	0.4880	0.067*
C13	0.74973 (10)	0.85130 (8)	0.23094 (16)	0.0448 (3)
C14	0.64819 (10)	0.84697 (9)	0.13450 (17)	0.0477 (4)
C15	0.57447 (12)	0.89708 (11)	0.1616 (2)	0.0630 (4)
H15	0.5883	0.9334	0.2433	0.076*
C16	0.48023 (13)	0.89344 (14)	0.0675 (2)	0.0753 (5)
H16	0.4309	0.9275	0.0857	0.090*
C17	0.45948 (13)	0.83999 (14)	−0.0518 (2)	0.0778 (6)
H17	0.3961	0.8378	−0.1152	0.093*
C18	0.53193 (14)	0.78945 (14)	−0.0784 (2)	0.0795 (6)
H18	0.5172	0.7526	−0.1591	0.095*
C19	0.62626 (13)	0.79287 (11)	0.0134 (2)	0.0630 (4)
H19	0.6753	0.7588	−0.0061	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0646 (7)	0.0756 (8)	0.0763 (8)	−0.0012 (6)	0.0331 (6)	−0.0257 (6)
O2	0.0532 (6)	0.0723 (7)	0.0424 (6)	−0.0056 (5)	0.0080 (5)	−0.0191 (5)
O3	0.1746 (16)	0.0726 (8)	0.0387 (7)	0.0207 (9)	0.0192 (8)	0.0032 (6)
O4	0.0572 (6)	0.0520 (6)	0.0406 (6)	0.0088 (5)	0.0060 (5)	0.0069 (4)
O5	0.0456 (6)	0.0838 (8)	0.0460 (6)	−0.0019 (5)	0.0058 (5)	−0.0103 (5)
N1	0.0384 (6)	0.0426 (6)	0.0439 (6)	−0.0020 (5)	0.0067 (5)	−0.0030 (5)
N2	0.0558 (7)	0.0458 (7)	0.0431 (7)	−0.0008 (6)	−0.0001 (6)	−0.0041 (5)
N3	0.0561 (7)	0.0454 (6)	0.0396 (7)	0.0007 (5)	0.0031 (5)	−0.0038 (5)
N4	0.0424 (7)	0.0503 (7)	0.0520 (7)	−0.0029 (5)	0.0040 (6)	−0.0057 (5)
C1	0.0364 (7)	0.0449 (7)	0.0399 (7)	−0.0048 (6)	0.0110 (6)	−0.0033 (6)
C2	0.0433 (7)	0.0457 (7)	0.0370 (7)	−0.0035 (6)	0.0093 (6)	−0.0027 (6)
C3	0.0515 (9)	0.0460 (7)	0.0458 (8)	−0.0048 (6)	0.0189 (7)	−0.0065 (6)
C4	0.0879 (14)	0.0981 (14)	0.0515 (10)	−0.0074 (11)	0.0062 (10)	−0.0337 (10)
C5	0.0958 (16)	0.1154 (18)	0.0590 (12)	−0.0133 (13)	−0.0128 (11)	−0.0138 (11)
C6	0.0610 (9)	0.0516 (8)	0.0389 (8)	−0.0037 (7)	0.0114 (7)	0.0004 (6)
C7	0.0762 (11)	0.0596 (10)	0.0493 (9)	0.0064 (8)	0.0048 (8)	0.0160 (7)
C8	0.159 (2)	0.0744 (13)	0.0639 (12)	0.0469 (14)	0.0051 (14)	0.0081 (10)
C9	0.0365 (7)	0.0488 (8)	0.0574 (9)	0.0061 (6)	0.0064 (6)	−0.0003 (7)
C10	0.0415 (8)	0.0449 (7)	0.0518 (9)	−0.0004 (6)	0.0002 (6)	−0.0002 (6)
C11	0.0688 (11)	0.0511 (9)	0.0917 (14)	0.0070 (8)	−0.0024 (10)	0.0086 (9)
C12	0.0470 (8)	0.0709 (10)	0.0446 (8)	−0.0075 (7)	0.0018 (7)	0.0023 (7)
C13	0.0461 (8)	0.0425 (7)	0.0440 (8)	−0.0071 (6)	0.0077 (6)	0.0008 (6)
C14	0.0416 (8)	0.0529 (8)	0.0474 (8)	−0.0087 (6)	0.0084 (6)	0.0021 (7)
C15	0.0499 (9)	0.0755 (11)	0.0604 (10)	−0.0015 (8)	0.0073 (8)	−0.0110 (8)
C16	0.0457 (9)	0.1039 (14)	0.0738 (12)	0.0070 (9)	0.0100 (9)	−0.0087 (11)
C17	0.0439 (9)	0.1183 (16)	0.0649 (12)	−0.0127 (10)	0.0011 (8)	−0.0090 (11)
C18	0.0589 (11)	0.1041 (15)	0.0685 (12)	−0.0138 (10)	0.0020 (9)	−0.0284 (11)
C19	0.0492 (9)	0.0733 (11)	0.0633 (10)	−0.0064 (8)	0.0075 (8)	−0.0149 (8)

Geometric parameters (Å, º) top

O1—C3	1.1969 (17)	C7—H7B	0.9700
O2—C3	1.3222 (18)	C8—H8A	0.9600
O2—C4	1.4543 (19)	C8—H8B	0.9600
O3—C6	1.1983 (18)	C8—H8C	0.9600
O4—C6	1.3190 (18)	C9—C10	1.526 (2)
O4—C7	1.4606 (18)	C9—H9A	0.9700
O5—C13	1.3614 (17)	C9—H9B	0.9700
O5—C12	1.4464 (18)	C10—C11	1.525 (2)
N1—C1	1.3419 (17)	C10—C12	1.534 (2)
N1—N2	1.3542 (16)	C11—H11A	0.9600
N1—C9	1.4622 (18)	C11—H11B	0.9600
N2—N3	1.3055 (16)	C11—H11C	0.9600
N3—C2	1.3561 (17)	C12—H12A	0.9700
N4—C13	1.2607 (18)	C12—H12B	0.9700
N4—C10	1.4795 (19)	C13—C14	1.473 (2)
C1—C2	1.3753 (19)	C14—C15	1.382 (2)
C1—C3	1.4896 (19)	C14—C19	1.383 (2)
C2—C6	1.470 (2)	C15—C16	1.383 (2)
C4—C5	1.481 (3)	C15—H15	0.9300
C4—H4A	0.9700	C16—C17	1.364 (3)
C4—H4B	0.9700	C16—H16	0.9300
C5—H5A	0.9600	C17—C18	1.370 (3)
C5—H5B	0.9600	C17—H17	0.9300
C5—H5C	0.9600	C18—C19	1.376 (3)
C7—C8	1.465 (3)	C18—H18	0.9300
C7—H7A	0.9700	C19—H19	0.9300

C3—O2—C4	116.06 (12)	N1—C9—C10	114.14 (11)
C6—O4—C7	114.73 (12)	N1—C9—H9A	108.7
C13—O5—C12	105.35 (11)	C10—C9—H9A	108.7
C1—N1—N2	110.18 (11)	N1—C9—H9B	108.7
C1—N1—C9	130.31 (12)	C10—C9—H9B	108.7
N2—N1—C9	119.44 (11)	H9A—C9—H9B	107.6
N3—N2—N1	107.95 (11)	N4—C10—C11	111.47 (12)
N2—N3—C2	108.44 (11)	N4—C10—C9	108.38 (12)
C13—N4—C10	107.05 (12)	C11—C10—C9	107.67 (13)
N1—C1—C2	104.72 (11)	N4—C10—C12	103.54 (11)
N1—C1—C3	125.13 (12)	C11—C10—C12	112.58 (14)
C2—C1—C3	130.02 (13)	C9—C10—C12	113.14 (12)
N3—C2—C1	108.70 (12)	C10—C11—H11A	109.5
N3—C2—C6	124.71 (12)	C10—C11—H11B	109.5
C1—C2—C6	125.97 (12)	H11A—C11—H11B	109.5
O1—C3—O2	126.13 (14)	C10—C11—H11C	109.5
O1—C3—C1	123.36 (14)	H11A—C11—H11C	109.5
O2—C3—C1	110.48 (11)	H11B—C11—H11C	109.5
O2—C4—C5	107.98 (16)	O5—C12—C10	104.43 (11)
O2—C4—H4A	110.1	O5—C12—H12A	110.9
C5—C4—H4A	110.1	C10—C12—H12A	110.9
O2—C4—H4B	110.1	O5—C12—H12B	110.9
C5—C4—H4B	110.1	C10—C12—H12B	110.9
H4A—C4—H4B	108.4	H12A—C12—H12B	108.9
C4—C5—H5A	109.5	N4—C13—O5	118.56 (13)
C4—C5—H5B	109.5	N4—C13—C14	126.07 (13)
H5A—C5—H5B	109.5	O5—C13—C14	115.36 (12)
C4—C5—H5C	109.5	C15—C14—C19	119.22 (15)
H5A—C5—H5C	109.5	C15—C14—C13	121.06 (14)
H5B—C5—H5C	109.5	C19—C14—C13	119.71 (14)
O3—C6—O4	124.59 (14)	C14—C15—C16	120.15 (16)
O3—C6—C2	121.74 (14)	C14—C15—H15	119.9
O4—C6—C2	113.66 (12)	C16—C15—H15	119.9
O4—C7—C8	108.35 (14)	C17—C16—C15	120.13 (18)
O4—C7—H7A	110.0	C17—C16—H16	119.9
C8—C7—H7A	110.0	C15—C16—H16	119.9
O4—C7—H7B	110.0	C16—C17—C18	120.06 (17)
C8—C7—H7B	110.0	C16—C17—H17	120.0
H7A—C7—H7B	108.4	C18—C17—H17	120.0
C7—C8—H8A	109.5	C17—C18—C19	120.48 (18)
C7—C8—H8B	109.5	C17—C18—H18	119.8
H8A—C8—H8B	109.5	C19—C18—H18	119.8
C7—C8—H8C	109.5	C18—C19—C14	119.95 (17)
H8A—C8—H8C	109.5	C18—C19—H19	120.0
H8B—C8—H8C	109.5	C14—C19—H19	120.0

C1—N1—N2—N3	−0.62 (15)	N2—N1—C9—C10	95.08 (15)
C9—N1—N2—N3	176.55 (11)	C13—N4—C10—C11	128.55 (15)
N1—N2—N3—C2	−0.01 (15)	C13—N4—C10—C9	−113.13 (13)
N2—N1—C1—C2	0.96 (14)	C13—N4—C10—C12	7.27 (15)
C9—N1—C1—C2	−175.80 (12)	N1—C9—C10—N4	61.10 (16)
N2—N1—C1—C3	177.17 (12)	N1—C9—C10—C11	−178.19 (13)
C9—N1—C1—C3	0.4 (2)	N1—C9—C10—C12	−53.13 (16)
N2—N3—C2—C1	0.61 (16)	C13—O5—C12—C10	9.24 (15)
N2—N3—C2—C6	−170.79 (13)	N4—C10—C12—O5	−10.01 (15)
N1—C1—C2—N3	−0.96 (15)	C11—C10—C12—O5	−130.54 (13)
C3—C1—C2—N3	−176.90 (13)	C9—C10—C12—O5	107.10 (13)
N1—C1—C2—C6	170.31 (13)	C10—N4—C13—O5	−1.56 (17)
C3—C1—C2—C6	−5.6 (2)	C10—N4—C13—C14	177.70 (13)
C4—O2—C3—O1	−7.0 (2)	C12—O5—C13—N4	−5.31 (17)
C4—O2—C3—C1	170.88 (14)	C12—O5—C13—C14	175.35 (12)
N1—C1—C3—O1	−53.3 (2)	N4—C13—C14—C15	−159.58 (16)
C2—C1—C3—O1	121.89 (18)	O5—C13—C14—C15	19.7 (2)
N1—C1—C3—O2	128.71 (14)	N4—C13—C14—C19	19.4 (2)
C2—C1—C3—O2	−56.09 (19)	O5—C13—C14—C19	−161.28 (14)
C3—O2—C4—C5	−165.55 (16)	C19—C14—C15—C16	−0.6 (3)
C7—O4—C6—O3	−0.8 (2)	C13—C14—C15—C16	178.45 (16)
C7—O4—C6—C2	178.29 (13)	C14—C15—C16—C17	0.4 (3)
N3—C2—C6—O3	158.83 (17)	C15—C16—C17—C18	0.3 (3)
C1—C2—C6—O3	−11.1 (2)	C16—C17—C18—C19	−0.9 (3)
N3—C2—C6—O4	−20.2 (2)	C17—C18—C19—C14	0.7 (3)
C1—C2—C6—O4	169.83 (13)	C15—C14—C19—C18	0.0 (3)
C6—O4—C7—C8	−174.17 (17)	C13—C14—C19—C18	−179.03 (17)
C1—N1—C9—C10	−88.40 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···N3ⁱ	0.97	2.59	3.454 (2)	149
C11—H11A···O1ⁱⁱ	0.96	2.56	3.392 (2)	145

Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) x, −y+3/2, z+1/2.

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