4,7a-Bis(4-methoxy­phen­yl)-1,3,7-tris(4-methyl­phen­yl)-2,3,5,6,7,7a-hexa­hydro-1H-pyrrolo[2,3-d]pyrimidine-2,5,6-trione

Adams, H.; Hawxwell, S.M.; Saçmaci, M.; Üngoren, S.H.; Akçamur, Y.; Şahıngöz, R.

doi:10.1107/S1600536805035191

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 11| November 2005| Pages o3953-o3955

https://doi.org/10.1107/S1600536805035191

4,7a-Bis(4-methoxyphenyl)-1,3,7-tris(4-methylphenyl)-2,3,5,6,7,7a-hexahydro-1H-pyrrolo[2,3-d]pyrimidine-2,5,6-trione

Harry Adams,^a ^* Samuel M. Hawxwell,^a Mustafa Saçmaci,^b Şevket Hakan Üngoren,^b Yunus Akçamur ^b and Recep Şahıngöz ^c

^aDepartment of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, England, ^bDepartment of Chemistry, Yozgat Faculty of Arts and Sciences, Erciyes University, 66200-Yozgat, Turkey, and ^cDepartment of Physics, Yozgat Faculty of Arts and Sciences, Erciyes University, 66200-Yozgat, Turkey
^*Correspondence e-mail: h.adams@sheffield.ac.uk

(Received 12 October 2005; accepted 27 October 2005; online 31 October 2005)

The structure of the title compound, C₄₁H₃₅N₃O₅, is stabilized by intra- and intermolecular C—H⋯O hydrogen bonds.

Comment

Pyrrolo[2,3]pyrimidines are an important class of compounds that are structurally and chemically related to nucleosides and some antibiotics (Ohgi et al., 1979 ; Tolmann et al., 1968 ). The well known biological activity of these compounds has led to intensive investigation of their use as antitumor, anti-allergic, antiviral and anti-inflammatory agents (Hutzenlaub et al., 1972 ; Smith et al., 1972 ).

In the light of this, we have synthesized and characterized the title compound, (2), and have determined its structure by X-ray analysis.

Fig. 1 shows the molecular structure of (2), with the atomic numbering scheme. The six-membered non-aromatic ring (C2/C1/N1/C5/N2/C6) has a total puckering amplitude of 0.532 (3) Å (Cremer & Pople, 1975 ) and a boat conformation [φ = 179.5 (4)° and θ = 105.0 (5)°]. The five-membered aromatic ring (C1–C4/N3) and the five benzene rings (C7–C12, C13–C18, C19–C24, C25–C30 and C31–C36) are each essentially planar, with r.m.s. deviations of 0.0296 (13), 0.0104 (14), 0.0069 (15), 0.0067 (15), 0.046 (16) and 0.126 (15) Å, respectively. The bond lengths and angles are in agreement with reported literature values (Allen et al., 1987 ).

The structure is stabilized by intra- and intermolecular C—H⋯O hydrogen bonds (Table 1). In the crystal structure, the C—H⋯O intermolecular hydrogen bonds link the molecules into dimers which are stacked along the b axis (Fig. 2).

Figure 1
The molecular structure of (2)

, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted.

Figure 2
Packing diagram of (2)

; C—H⋯O hydrogen bonds are shown as dashed lines.

Experimental

Compound (1) was prepared from the cyclocondensation reaction that occurs between p,p′-dimethoxydibenzoylketene and oxalyl chloride (Hökelek et al., 2002 ). Compound (2) was obtained from (1) (1.0 g, 2.96 mmol) by reaction with an excess of p-tolyl isocyanate in a 25 ml round-bottomed flask equipped with a calcium chloride tube. The mixture was heated at 338 K for 24 h. After cooling to room temperature, the residue was triturated with anhydrous diethyl ether, and the crude product was recrystallized from ethanol (yield 1.26 g, 66%; m.p. 475 K). IR (KBr, cm⁻¹): υ 1727 (C3—O1), 1709 (C4—O2), 1684 (C5—O3); ¹H NMR (CDCl₃, p.p.m..): δ 7.64–6.04 (m, 20H, Ar—H), 3.88, 3.77 (s, 6H, CH₃O), 2.25, 2.18, 2.15 (s, 9H, Ar—CH₃); ¹³C NMR (CDCl₃, p.p.m..): δ 178.51 (C3—O1), 165.58 (C4—O2), 164.47 (C5—O3), 162.35–115.52 (C=C, arom. and aliph.), 81.36 (N1—C1—N2), 57.50 (O4—C38), 57.28 (O5—C37), 23.00, 22.94, 22.92 (Ar—CH₃). Analysis calculated for C₄₁H₃₅N₃O₅: C 75.80, H 5.39, N 6.47%; found: C 76.02, H 5.69, N 6.22%.

Crystal data

C₄₁H₃₅N₃O₅
M_r = 649.72
Triclinic, $[P \overline 1]$
a = 10.1797 (12) Å
b = 12.5347 (14) Å
c = 13.6855 (16) Å
α = 107.999 (2)°
β = 99.985 (2)°
γ = 90.504 (2)°
V = 1632.0 (3) Å³
Z = 2
D_x = 1.322 Mg m⁻³
Mo Kα radiation
Cell parameters from 3062 reflections
θ = 4.7–50.5°
μ = 0.09 mm⁻¹
T = 150 (2) K
Block, yellow
0.38 × 0.21 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
ω scans
Absorption correction: multi-scan(SADABS; Bruker, 1997 )T_min = 0.968, T_max = 0.991
18940 measured reflections
7331 independent reflections
4028 reflections with I > 2σ(I)
R_int = 0.054
θ_max = 27.6°
h = −13 → 13
k = −16 → 16
l = −17 → 17

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.129
S = 0.98
7331 reflections
445 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.054P)² + 0.1342P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1ⁱ	0.95	2.55	3.409 (3)	150
C11—H11A⋯O2ⁱⁱ	0.95	2.53	3.158 (3)	123
C18—H18A⋯O3	0.95	2.58	2.927 (3)	102
C30—H30A⋯O2	0.95	2.55	2.928 (3)	104
C32—H32A⋯N1	0.95	2.51	2.858 (3)	102
C39—H39C⋯O5ⁱⁱⁱ	0.98	2.48	3.422 (3)	160
C40—H40C⋯O4^iv	0.98	2.54	3.341 (3)	139
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) x-1, y, z; (iv) x+1, y, z+1.

H atoms were positioned geometrically [0.95 (CH) and 0.98 Å (CH₃)] and constrained to ride on their parent atoms, with U_iso(H) values of 1.2 (1.5 for methyl) times U_eq.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, 2. DOI: https://doi.org/10.1107/S1600536805035191/hk6047sup1.cif

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S1600536805035191/hk60472sup2.hkl

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(2) top

Crystal data top

C₄₁H₃₅N₃O₅	Z = 2
M_r = 649.72	F(000) = 684
Triclinic, P1	D_x = 1.322 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1797 (12) Å	Cell parameters from 3062 reflections
b = 12.5347 (14) Å	θ = 4.7–50.5°
c = 13.6855 (16) Å	µ = 0.09 mm⁻¹
α = 107.999 (2)°	T = 150 K
β = 99.985 (2)°	Block, yellow
γ = 90.504 (2)°	0.38 × 0.21 × 0.10 mm
V = 1632.0 (3) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	7331 independent reflections
Radiation source: fine-focus sealed tube	4028 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 100 pixels mm^-1	θ_max = 27.6°, θ_min = 1.6°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 1997)	k = −16→16
T_min = 0.968, T_max = 0.991	l = −17→17
18940 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.054P)² + 0.1342P] where P = (F_o² + 2F_c²)/3
7331 reflections	(Δ/σ)_max < 0.001
445 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N1	0.44303 (17)	0.76941 (14)	0.35720 (13)	0.0225 (4)
N2	0.26565 (17)	0.80260 (14)	0.23849 (13)	0.0224 (4)
N3	0.60522 (17)	0.64263 (14)	0.28048 (13)	0.0236 (4)
O1	0.38721 (15)	0.45850 (12)	0.06781 (12)	0.0318 (4)
O2	0.62192 (15)	0.45004 (12)	0.21556 (12)	0.0298 (4)
O3	0.27951 (15)	0.88193 (13)	0.41620 (12)	0.0318 (4)
O4	−0.11979 (15)	0.52626 (13)	−0.19218 (12)	0.0324 (4)
O5	0.66647 (17)	1.05878 (13)	0.09981 (13)	0.0406 (4)
C1	0.5081 (2)	0.72444 (17)	0.26482 (16)	0.0224 (5)
C2	0.4005 (2)	0.65493 (17)	0.17695 (16)	0.0213 (5)
C3	0.4375 (2)	0.54068 (18)	0.14025 (17)	0.0248 (5)
C4	0.5655 (2)	0.53540 (18)	0.21550 (17)	0.0242 (5)
C5	0.3282 (2)	0.82213 (17)	0.34428 (17)	0.0232 (5)
C6	0.2842 (2)	0.70480 (17)	0.16055 (16)	0.0226 (5)
C7	0.1781 (2)	0.66148 (16)	0.06802 (16)	0.0217 (5)
C8	0.0421 (2)	0.66904 (16)	0.07351 (17)	0.0233 (5)
H8A	0.0167	0.7060	0.1386	0.028*
C9	−0.0554 (2)	0.62364 (17)	−0.01428 (17)	0.0245 (5)
H9A	−0.1473	0.6279	−0.0096	0.029*
C10	−0.0170 (2)	0.57146 (17)	−0.10992 (17)	0.0249 (5)
C11	0.1167 (2)	0.56659 (17)	−0.11805 (17)	0.0242 (5)
H11A	0.1419	0.5330	−0.1839	0.029*
C12	0.2132 (2)	0.61127 (17)	−0.02897 (16)	0.0243 (5)
H12A	0.3050	0.6076	−0.0341	0.029*
C13	0.1911 (2)	0.89035 (17)	0.21112 (16)	0.0225 (5)
C14	0.2316 (2)	0.93196 (17)	0.13800 (16)	0.0247 (5)
H14A	0.3056	0.9027	0.1069	0.030*
C15	0.1637 (2)	1.01653 (18)	0.11028 (17)	0.0273 (5)
H15A	0.1908	1.0438	0.0589	0.033*
C16	0.0568 (2)	1.06241 (18)	0.15605 (17)	0.0267 (5)
C17	0.0171 (2)	1.01765 (18)	0.22822 (17)	0.0284 (5)
H17A	−0.0573	1.0462	0.2591	0.034*
C18	0.0831 (2)	0.93267 (18)	0.25615 (17)	0.0275 (5)
H18A	0.0545	0.9035	0.3059	0.033*
C19	0.4964 (2)	0.75896 (17)	0.45847 (16)	0.0225 (5)
C20	0.5933 (2)	0.83576 (18)	0.52888 (17)	0.0260 (5)
H20A	0.6232	0.8994	0.5129	0.031*
C21	0.6467 (2)	0.81931 (18)	0.62289 (17)	0.0274 (5)
H21A	0.7139	0.8719	0.6708	0.033*
C22	0.6039 (2)	0.72734 (18)	0.64869 (17)	0.0259 (5)
C23	0.5041 (2)	0.65289 (19)	0.57750 (18)	0.0314 (6)
H23A	0.4719	0.5904	0.5939	0.038*
C24	0.4509 (2)	0.66830 (18)	0.48307 (17)	0.0273 (5)
H24A	0.3830	0.6164	0.4352	0.033*
C25	0.7300 (2)	0.66768 (18)	0.35408 (17)	0.0238 (5)
C26	0.8186 (2)	0.75658 (19)	0.36299 (17)	0.0302 (5)
H26A	0.7978	0.8031	0.3199	0.036*
C27	0.9381 (2)	0.7774 (2)	0.43537 (18)	0.0338 (6)
H27A	0.9972	0.8393	0.4420	0.041*
C28	0.9725 (2)	0.7101 (2)	0.49759 (18)	0.0311 (6)
C29	0.8827 (2)	0.6213 (2)	0.48674 (18)	0.0336 (6)
H29A	0.9043	0.5738	0.5286	0.040*
C30	0.7630 (2)	0.60021 (19)	0.41695 (18)	0.0305 (6)
H30A	0.7031	0.5394	0.4119	0.037*
C31	0.5647 (2)	0.81932 (17)	0.23188 (16)	0.0226 (5)
C32	0.5630 (2)	0.93195 (18)	0.28642 (17)	0.0257 (5)
H32A	0.5371	0.9533	0.3529	0.031*
C33	0.5985 (2)	1.01516 (18)	0.24588 (18)	0.0288 (5)
H33A	0.5966	1.0923	0.2845	0.035*
C34	0.6365 (2)	0.98506 (19)	0.14950 (18)	0.0300 (5)
C35	0.6441 (2)	0.87138 (19)	0.09558 (18)	0.0334 (6)
H35A	0.6742	0.8502	0.0307	0.040*
C36	0.6081 (2)	0.79005 (18)	0.13603 (18)	0.0294 (5)
H36A	0.6128	0.7130	0.0984	0.035*
C37	0.6344 (3)	1.1725 (2)	0.1420 (2)	0.0442 (7)
H37A	0.6609	1.2169	0.1000	0.066*
H37B	0.6823	1.2038	0.2143	0.066*
H37C	0.5379	1.1750	0.1406	0.066*
C38	−0.0837 (3)	0.4640 (2)	−0.28888 (19)	0.0488 (7)
H38A	−0.1647	0.4356	−0.3418	0.073*
H38B	−0.0328	0.4006	−0.2797	0.073*
H38C	−0.0286	0.5129	−0.3116	0.073*
C39	−0.0105 (2)	1.15993 (19)	0.13091 (19)	0.0367 (6)
H39A	0.0251	1.1752	0.0741	0.055*
H39B	0.0066	1.2267	0.1931	0.055*
H39C	−0.1071	1.1413	0.1092	0.055*
C40	0.6651 (3)	0.7067 (2)	0.74888 (18)	0.0388 (6)
H40A	0.6011	0.6616	0.7682	0.058*
H40B	0.6880	0.7788	0.8045	0.058*
H40C	0.7462	0.6662	0.7392	0.058*
C41	1.1049 (2)	0.7299 (2)	0.57156 (19)	0.0424 (7)
H41A	1.1536	0.7965	0.5691	0.064*
H41B	1.1576	0.6643	0.5509	0.064*
H41C	1.0897	0.7417	0.6428	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0229 (10)	0.0235 (10)	0.0218 (10)	0.0032 (8)	0.0037 (8)	0.0084 (8)
N2	0.0232 (10)	0.0216 (9)	0.0215 (10)	0.0029 (8)	0.0017 (8)	0.0068 (8)
N3	0.0215 (10)	0.0218 (10)	0.0258 (10)	0.0008 (8)	0.0017 (8)	0.0067 (8)
O1	0.0299 (9)	0.0230 (8)	0.0345 (10)	−0.0005 (7)	0.0029 (7)	−0.0008 (7)
O2	0.0276 (9)	0.0221 (8)	0.0397 (10)	0.0039 (7)	0.0053 (7)	0.0102 (7)
O3	0.0335 (9)	0.0336 (9)	0.0274 (9)	0.0088 (7)	0.0084 (7)	0.0068 (7)
O4	0.0280 (9)	0.0376 (10)	0.0274 (9)	0.0028 (7)	−0.0040 (7)	0.0091 (7)
O5	0.0518 (11)	0.0304 (10)	0.0498 (11)	0.0014 (8)	0.0225 (9)	0.0202 (8)
C1	0.0218 (12)	0.0204 (11)	0.0266 (12)	0.0040 (9)	0.0065 (10)	0.0087 (9)
C2	0.0223 (12)	0.0193 (11)	0.0227 (12)	−0.0008 (9)	0.0048 (9)	0.0069 (9)
C3	0.0225 (12)	0.0222 (12)	0.0309 (13)	−0.0003 (9)	0.0090 (10)	0.0081 (10)
C4	0.0220 (12)	0.0216 (12)	0.0307 (13)	0.0011 (9)	0.0089 (10)	0.0084 (10)
C5	0.0271 (13)	0.0195 (11)	0.0233 (12)	−0.0020 (9)	0.0036 (10)	0.0078 (9)
C6	0.0248 (12)	0.0198 (11)	0.0237 (12)	−0.0016 (9)	0.0053 (10)	0.0074 (9)
C7	0.0236 (12)	0.0166 (11)	0.0261 (12)	0.0001 (9)	0.0031 (10)	0.0093 (9)
C8	0.0286 (13)	0.0157 (11)	0.0268 (12)	0.0003 (9)	0.0063 (10)	0.0079 (9)
C9	0.0221 (12)	0.0215 (11)	0.0325 (13)	0.0027 (9)	0.0041 (10)	0.0129 (10)
C10	0.0266 (13)	0.0229 (12)	0.0253 (12)	0.0003 (10)	−0.0016 (10)	0.0110 (10)
C11	0.0295 (13)	0.0222 (12)	0.0222 (12)	0.0018 (10)	0.0044 (10)	0.0089 (9)
C12	0.0241 (12)	0.0205 (11)	0.0304 (13)	0.0006 (9)	0.0057 (10)	0.0110 (10)
C13	0.0250 (12)	0.0166 (11)	0.0248 (12)	−0.0009 (9)	0.0014 (10)	0.0066 (9)
C14	0.0269 (13)	0.0222 (12)	0.0239 (12)	0.0001 (9)	0.0064 (10)	0.0047 (10)
C15	0.0327 (14)	0.0256 (12)	0.0237 (12)	−0.0050 (10)	0.0023 (10)	0.0095 (10)
C16	0.0285 (13)	0.0203 (11)	0.0276 (13)	−0.0015 (10)	−0.0031 (10)	0.0069 (10)
C17	0.0267 (13)	0.0255 (12)	0.0343 (14)	0.0050 (10)	0.0098 (11)	0.0088 (10)
C18	0.0297 (13)	0.0270 (12)	0.0289 (13)	0.0022 (10)	0.0092 (11)	0.0113 (10)
C19	0.0197 (12)	0.0233 (12)	0.0253 (12)	0.0032 (9)	0.0040 (10)	0.0087 (10)
C20	0.0294 (13)	0.0210 (12)	0.0279 (13)	−0.0010 (10)	0.0056 (10)	0.0079 (10)
C21	0.0258 (13)	0.0250 (12)	0.0257 (13)	−0.0010 (10)	−0.0009 (10)	0.0029 (10)
C22	0.0258 (12)	0.0265 (12)	0.0262 (13)	0.0066 (10)	0.0043 (10)	0.0094 (10)
C23	0.0310 (14)	0.0293 (13)	0.0383 (15)	−0.0022 (11)	0.0013 (11)	0.0200 (11)
C24	0.0217 (12)	0.0258 (12)	0.0315 (13)	−0.0051 (10)	−0.0031 (10)	0.0094 (10)
C25	0.0207 (12)	0.0232 (11)	0.0260 (12)	0.0017 (9)	0.0051 (10)	0.0050 (9)
C26	0.0277 (13)	0.0333 (13)	0.0306 (13)	−0.0017 (11)	0.0024 (11)	0.0131 (11)
C27	0.0275 (13)	0.0364 (14)	0.0339 (14)	−0.0052 (11)	0.0023 (11)	0.0080 (11)
C28	0.0231 (13)	0.0381 (14)	0.0273 (13)	0.0066 (11)	0.0027 (10)	0.0043 (11)
C29	0.0314 (14)	0.0365 (14)	0.0353 (14)	0.0088 (11)	0.0042 (11)	0.0157 (11)
C30	0.0254 (13)	0.0297 (13)	0.0395 (15)	0.0042 (10)	0.0071 (11)	0.0146 (11)
C31	0.0187 (11)	0.0227 (11)	0.0247 (12)	−0.0009 (9)	0.0011 (9)	0.0066 (9)
C32	0.0274 (13)	0.0259 (12)	0.0244 (12)	−0.0006 (10)	0.0060 (10)	0.0082 (10)
C33	0.0297 (13)	0.0226 (12)	0.0338 (14)	−0.0006 (10)	0.0073 (11)	0.0076 (10)
C34	0.0269 (13)	0.0289 (13)	0.0369 (14)	−0.0014 (10)	0.0059 (11)	0.0142 (11)
C35	0.0366 (15)	0.0330 (14)	0.0323 (14)	−0.0004 (11)	0.0144 (11)	0.0083 (11)
C36	0.0306 (13)	0.0224 (12)	0.0329 (14)	−0.0016 (10)	0.0077 (11)	0.0046 (10)
C37	0.0514 (18)	0.0315 (14)	0.0617 (19)	0.0095 (12)	0.0194 (14)	0.0269 (13)
C38	0.0387 (16)	0.069 (2)	0.0269 (15)	0.0036 (14)	−0.0053 (12)	0.0046 (14)
C39	0.0378 (15)	0.0307 (14)	0.0419 (15)	0.0048 (11)	−0.0007 (12)	0.0162 (12)
C40	0.0410 (16)	0.0408 (15)	0.0368 (15)	0.0034 (12)	0.0000 (12)	0.0195 (12)
C41	0.0346 (15)	0.0514 (17)	0.0348 (15)	0.0056 (12)	−0.0027 (12)	0.0093 (13)

Geometric parameters (Å, º) top

N1—C5	1.360 (3)	C20—C21	1.384 (3)
N1—C19	1.444 (3)	C20—H20A	0.9500
N1—C1	1.487 (3)	C21—C22	1.392 (3)
N2—C6	1.393 (3)	C21—H21A	0.9500
N2—C5	1.421 (3)	C22—C23	1.389 (3)
N2—C13	1.448 (3)	C22—C40	1.504 (3)
N3—C4	1.374 (3)	C23—C24	1.384 (3)
N3—C25	1.442 (3)	C23—H23A	0.9500
N3—C1	1.468 (3)	C24—H24A	0.9500
O1—C3	1.220 (2)	C25—C30	1.387 (3)
O2—C4	1.219 (2)	C25—C26	1.389 (3)
O3—C5	1.223 (2)	C26—C27	1.395 (3)
O4—C10	1.368 (2)	C26—H26A	0.9500
O4—C38	1.425 (3)	C27—C28	1.380 (3)
O5—C34	1.365 (3)	C27—H27A	0.9500
O5—C37	1.427 (3)	C28—C29	1.389 (3)
C1—C2	1.511 (3)	C28—C41	1.506 (3)
C1—C31	1.536 (3)	C29—C30	1.379 (3)
C2—C6	1.360 (3)	C29—H29A	0.9500
C2—C3	1.441 (3)	C30—H30A	0.9500
C3—C4	1.530 (3)	C31—C32	1.380 (3)
C6—C7	1.468 (3)	C31—C36	1.399 (3)
C7—C12	1.392 (3)	C32—C33	1.395 (3)
C7—C8	1.402 (3)	C32—H32A	0.9500
C8—C9	1.381 (3)	C33—C34	1.380 (3)
C8—H8A	0.9500	C33—H33A	0.9500
C9—C10	1.395 (3)	C34—C35	1.397 (3)
C9—H9A	0.9500	C35—C36	1.376 (3)
C10—C11	1.385 (3)	C35—H35A	0.9500
C11—C12	1.385 (3)	C36—H36A	0.9500
C11—H11A	0.9500	C37—H37A	0.9800
C12—H12A	0.9500	C37—H37B	0.9800
C13—C14	1.380 (3)	C37—H37C	0.9800
C13—C18	1.383 (3)	C38—H38A	0.9800
C14—C15	1.384 (3)	C38—H38B	0.9800
C14—H14A	0.9500	C38—H38C	0.9800
C15—C16	1.391 (3)	C39—H39A	0.9800
C15—H15A	0.9500	C39—H39B	0.9800
C16—C17	1.389 (3)	C39—H39C	0.9800
C16—C39	1.508 (3)	C40—H40A	0.9800
C17—C18	1.381 (3)	C40—H40B	0.9800
C17—H17A	0.9500	C40—H40C	0.9800
C18—H18A	0.9500	C41—H41A	0.9800
C19—C24	1.379 (3)	C41—H41B	0.9800
C19—C20	1.382 (3)	C41—H41C	0.9800

C5—N1—C19	119.39 (17)	C22—C21—H21A	119.3
C5—N1—C1	117.75 (17)	C23—C22—C21	117.8 (2)
C19—N1—C1	122.85 (16)	C23—C22—C40	120.5 (2)
C6—N2—C5	120.94 (17)	C21—C22—C40	121.6 (2)
C6—N2—C13	120.02 (17)	C24—C23—C22	121.1 (2)
C5—N2—C13	118.84 (16)	C24—C23—H23A	119.5
C4—N3—C25	121.79 (17)	C22—C23—H23A	119.5
C4—N3—C1	112.47 (17)	C19—C24—C23	120.0 (2)
C25—N3—C1	125.74 (17)	C19—C24—H24A	120.0
C10—O4—C38	116.51 (18)	C23—C24—H24A	120.0
C34—O5—C37	117.17 (18)	C30—C25—C26	119.1 (2)
N3—C1—N1	111.55 (16)	C30—C25—N3	118.95 (19)
N3—C1—C2	103.72 (16)	C26—C25—N3	121.9 (2)
N1—C1—C2	106.37 (16)	C25—C26—C27	119.8 (2)
N3—C1—C31	114.00 (17)	C25—C26—H26A	120.1
N1—C1—C31	111.61 (16)	C27—C26—H26A	120.1
C2—C1—C31	108.97 (17)	C28—C27—C26	121.6 (2)
C6—C2—C3	133.0 (2)	C28—C27—H27A	119.2
C6—C2—C1	116.01 (18)	C26—C27—H27A	119.2
C3—C2—C1	109.98 (18)	C27—C28—C29	117.5 (2)
O1—C3—C2	133.0 (2)	C27—C28—C41	121.1 (2)
O1—C3—C4	121.84 (19)	C29—C28—C41	121.4 (2)
C2—C3—C4	105.16 (18)	C30—C29—C28	121.9 (2)
O2—C4—N3	126.8 (2)	C30—C29—H29A	119.0
O2—C4—C3	125.02 (19)	C28—C29—H29A	119.0
N3—C4—C3	108.17 (17)	C29—C30—C25	120.1 (2)
O3—C5—N1	124.2 (2)	C29—C30—H30A	120.0
O3—C5—N2	121.0 (2)	C25—C30—H30A	120.0
N1—C5—N2	114.75 (18)	C32—C31—C36	118.3 (2)
C2—C6—N2	116.79 (18)	C32—C31—C1	123.56 (19)
C2—C6—C7	124.41 (19)	C36—C31—C1	117.84 (18)
N2—C6—C7	118.80 (18)	C31—C32—C33	121.3 (2)
C12—C7—C8	118.53 (19)	C31—C32—H32A	119.4
C12—C7—C6	119.09 (19)	C33—C32—H32A	119.4
C8—C7—C6	122.38 (19)	C34—C33—C32	119.8 (2)
C9—C8—C7	121.0 (2)	C34—C33—H33A	120.1
C9—C8—H8A	119.5	C32—C33—H33A	120.1
C7—C8—H8A	119.5	O5—C34—C33	124.9 (2)
C8—C9—C10	119.1 (2)	O5—C34—C35	115.7 (2)
C8—C9—H9A	120.5	C33—C34—C35	119.4 (2)
C10—C9—H9A	120.5	C36—C35—C34	120.3 (2)
O4—C10—C11	123.8 (2)	C36—C35—H35A	119.9
O4—C10—C9	115.23 (19)	C34—C35—H35A	119.9
C11—C10—C9	121.0 (2)	C35—C36—C31	120.9 (2)
C12—C11—C10	119.1 (2)	C35—C36—H36A	119.6
C12—C11—H11A	120.4	C31—C36—H36A	119.6
C10—C11—H11A	120.4	O5—C37—H37A	109.5
C11—C12—C7	121.2 (2)	O5—C37—H37B	109.5
C11—C12—H12A	119.4	H37A—C37—H37B	109.5
C7—C12—H12A	119.4	O5—C37—H37C	109.5
C14—C13—C18	120.2 (2)	H37A—C37—H37C	109.5
C14—C13—N2	117.77 (19)	H37B—C37—H37C	109.5
C18—C13—N2	122.04 (19)	O4—C38—H38A	109.5
C13—C14—C15	119.6 (2)	O4—C38—H38B	109.5
C13—C14—H14A	120.2	H38A—C38—H38B	109.5
C15—C14—H14A	120.2	O4—C38—H38C	109.5
C14—C15—C16	121.4 (2)	H38A—C38—H38C	109.5
C14—C15—H15A	119.3	H38B—C38—H38C	109.5
C16—C15—H15A	119.3	C16—C39—H39A	109.5
C15—C16—C17	117.6 (2)	C16—C39—H39B	109.5
C15—C16—C39	121.1 (2)	H39A—C39—H39B	109.5
C17—C16—C39	121.3 (2)	C16—C39—H39C	109.5
C18—C17—C16	121.6 (2)	H39A—C39—H39C	109.5
C18—C17—H17A	119.2	H39B—C39—H39C	109.5
C16—C17—H17A	119.2	C22—C40—H40A	109.5
C17—C18—C13	119.5 (2)	C22—C40—H40B	109.5
C17—C18—H18A	120.3	H40A—C40—H40B	109.5
C13—C18—H18A	120.3	C22—C40—H40C	109.5
C24—C19—C20	120.1 (2)	H40A—C40—H40C	109.5
C24—C19—N1	118.46 (19)	H40B—C40—H40C	109.5
C20—C19—N1	121.44 (19)	C28—C41—H41A	109.5
C19—C20—C21	119.5 (2)	C28—C41—H41B	109.5
C19—C20—H20A	120.3	H41A—C41—H41B	109.5
C21—C20—H20A	120.3	C28—C41—H41C	109.5
C20—C21—C22	121.4 (2)	H41A—C41—H41C	109.5
C20—C21—H21A	119.3	H41B—C41—H41C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1ⁱ	0.95	2.55	3.409 (3)	150
C11—H11A···O2ⁱⁱ	0.95	2.53	3.158 (3)	123
C18—H18A···O3	0.95	2.58	2.927 (3)	102
C30—H30A···O2	0.95	2.55	2.928 (3)	104
C32—H32A···N1	0.95	2.51	2.858 (3)	102
C39—H39C···O5ⁱⁱⁱ	0.98	2.48	3.422 (3)	160
C40—H40C···O4^iv	0.98	2.54	3.341 (3)	139

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

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