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

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ISSN: 2056-9890

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

CROSSMARK_Color_square_no_text.svg

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[Ohgi, T., Kondo, T. & Goto, T. (1979). J. Am. Chem. Soc. 101, 3629-3633.]; Tolmann et al., 1968[Tolmann, R. L., Robins, R. K. & Townsend, L. B. (1968). J. Am. Chem. Soc. 90, 524-526.]). 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[Hutzenlaub, W., Tolman, R. L. & Robins, R. K. (1972). J. Med. Chem. 15, 879-883.]; Smith et al., 1972[Smith, C. W., Sidwell, R. W., Robins, R. K. & Tolman, R. L. (1972). J. Med. Chem. 15, 883-887.]).

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

[Scheme 1]

Fig. 1[link] shows the mol­ecular structure of (2)[link], 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[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) 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[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L. & Orpen, A. G. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

The structure is stabilized by intra- and inter­molecular C—H⋯O hydrogen bonds (Table 1[link]). 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[link]).

[Figure 1]
Figure 1
The mol­ecular structure of (2)[link], with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted.
[Figure 2]
Figure 2
Packing diagram of (2)[link]; 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[Hökelek, T., Sarıpınar, E., Yıldırım, I., Akkurt, M. & Akçamur, Y. (2002). Acta Cryst. E58, o30-o32.]). 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

  • Mr = 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

  • Dx = 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[Bruker (1997). SMART, SAINT, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])Tmin = 0.968, Tmax = 0.991

  • 18940 measured reflections

  • 7331 independent reflections

  • 4028 reflections with I > 2σ(I)

  • Rint = 0.054

  • θmax = 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(Fo2) + (0.054P)2 + 0.1342P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A DA 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⋯O4iv 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 Uiso(H) values of 1.2 (1.5 for meth­yl) times Ueq.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART, SAINT, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SHELXTL (Bruker, 1997[Bruker (1997). SMART, SAINT, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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
C41H35N3O5Z = 2
Mr = 649.72F(000) = 684
Triclinic, P1Dx = 1.322 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1797 (12) ÅCell parameters from 3062 reflections
b = 12.5347 (14) Åθ = 4.7–50.5°
c = 13.6855 (16) ŵ = 0.09 mm1
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 tube4028 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 100 pixels mm-1θmax = 27.6°, θmin = 1.6°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
k = 1616
Tmin = 0.968, Tmax = 0.991l = 1717
18940 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.054P)2 + 0.1342P]
where P = (Fo2 + 2Fc2)/3
7331 reflections(Δ/σ)max < 0.001
445 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
xyzUiso*/Ueq
N10.44303 (17)0.76941 (14)0.35720 (13)0.0225 (4)
N20.26565 (17)0.80260 (14)0.23849 (13)0.0224 (4)
N30.60522 (17)0.64263 (14)0.28048 (13)0.0236 (4)
O10.38721 (15)0.45850 (12)0.06781 (12)0.0318 (4)
O20.62192 (15)0.45004 (12)0.21556 (12)0.0298 (4)
O30.27951 (15)0.88193 (13)0.41620 (12)0.0318 (4)
O40.11979 (15)0.52626 (13)0.19218 (12)0.0324 (4)
O50.66647 (17)1.05878 (13)0.09981 (13)0.0406 (4)
C10.5081 (2)0.72444 (17)0.26482 (16)0.0224 (5)
C20.4005 (2)0.65493 (17)0.17695 (16)0.0213 (5)
C30.4375 (2)0.54068 (18)0.14025 (17)0.0248 (5)
C40.5655 (2)0.53540 (18)0.21550 (17)0.0242 (5)
C50.3282 (2)0.82213 (17)0.34428 (17)0.0232 (5)
C60.2842 (2)0.70480 (17)0.16055 (16)0.0226 (5)
C70.1781 (2)0.66148 (16)0.06802 (16)0.0217 (5)
C80.0421 (2)0.66904 (16)0.07351 (17)0.0233 (5)
H8A0.01670.70600.13860.028*
C90.0554 (2)0.62364 (17)0.01428 (17)0.0245 (5)
H9A0.14730.62790.00960.029*
C100.0170 (2)0.57146 (17)0.10992 (17)0.0249 (5)
C110.1167 (2)0.56659 (17)0.11805 (17)0.0242 (5)
H11A0.14190.53300.18390.029*
C120.2132 (2)0.61127 (17)0.02897 (16)0.0243 (5)
H12A0.30500.60760.03410.029*
C130.1911 (2)0.89035 (17)0.21112 (16)0.0225 (5)
C140.2316 (2)0.93196 (17)0.13800 (16)0.0247 (5)
H14A0.30560.90270.10690.030*
C150.1637 (2)1.01653 (18)0.11028 (17)0.0273 (5)
H15A0.19081.04380.05890.033*
C160.0568 (2)1.06241 (18)0.15605 (17)0.0267 (5)
C170.0171 (2)1.01765 (18)0.22822 (17)0.0284 (5)
H17A0.05731.04620.25910.034*
C180.0831 (2)0.93267 (18)0.25615 (17)0.0275 (5)
H18A0.05450.90350.30590.033*
C190.4964 (2)0.75896 (17)0.45847 (16)0.0225 (5)
C200.5933 (2)0.83576 (18)0.52888 (17)0.0260 (5)
H20A0.62320.89940.51290.031*
C210.6467 (2)0.81931 (18)0.62289 (17)0.0274 (5)
H21A0.71390.87190.67080.033*
C220.6039 (2)0.72734 (18)0.64869 (17)0.0259 (5)
C230.5041 (2)0.65289 (19)0.57750 (18)0.0314 (6)
H23A0.47190.59040.59390.038*
C240.4509 (2)0.66830 (18)0.48307 (17)0.0273 (5)
H24A0.38300.61640.43520.033*
C250.7300 (2)0.66768 (18)0.35408 (17)0.0238 (5)
C260.8186 (2)0.75658 (19)0.36299 (17)0.0302 (5)
H26A0.79780.80310.31990.036*
C270.9381 (2)0.7774 (2)0.43537 (18)0.0338 (6)
H27A0.99720.83930.44200.041*
C280.9725 (2)0.7101 (2)0.49759 (18)0.0311 (6)
C290.8827 (2)0.6213 (2)0.48674 (18)0.0336 (6)
H29A0.90430.57380.52860.040*
C300.7630 (2)0.60021 (19)0.41695 (18)0.0305 (6)
H30A0.70310.53940.41190.037*
C310.5647 (2)0.81932 (17)0.23188 (16)0.0226 (5)
C320.5630 (2)0.93195 (18)0.28642 (17)0.0257 (5)
H32A0.53710.95330.35290.031*
C330.5985 (2)1.01516 (18)0.24588 (18)0.0288 (5)
H33A0.59661.09230.28450.035*
C340.6365 (2)0.98506 (19)0.14950 (18)0.0300 (5)
C350.6441 (2)0.87138 (19)0.09558 (18)0.0334 (6)
H35A0.67420.85020.03070.040*
C360.6081 (2)0.79005 (18)0.13603 (18)0.0294 (5)
H36A0.61280.71300.09840.035*
C370.6344 (3)1.1725 (2)0.1420 (2)0.0442 (7)
H37A0.66091.21690.10000.066*
H37B0.68231.20380.21430.066*
H37C0.53791.17500.14060.066*
C380.0837 (3)0.4640 (2)0.28888 (19)0.0488 (7)
H38A0.16470.43560.34180.073*
H38B0.03280.40060.27970.073*
H38C0.02860.51290.31160.073*
C390.0105 (2)1.15993 (19)0.13091 (19)0.0367 (6)
H39A0.02511.17520.07410.055*
H39B0.00661.22670.19310.055*
H39C0.10711.14130.10920.055*
C400.6651 (3)0.7067 (2)0.74888 (18)0.0388 (6)
H40A0.60110.66160.76820.058*
H40B0.68800.77880.80450.058*
H40C0.74620.66620.73920.058*
C411.1049 (2)0.7299 (2)0.57156 (19)0.0424 (7)
H41A1.15360.79650.56910.064*
H41B1.15760.66430.55090.064*
H41C1.08970.74170.64280.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0229 (10)0.0235 (10)0.0218 (10)0.0032 (8)0.0037 (8)0.0084 (8)
N20.0232 (10)0.0216 (9)0.0215 (10)0.0029 (8)0.0017 (8)0.0068 (8)
N30.0215 (10)0.0218 (10)0.0258 (10)0.0008 (8)0.0017 (8)0.0067 (8)
O10.0299 (9)0.0230 (8)0.0345 (10)0.0005 (7)0.0029 (7)0.0008 (7)
O20.0276 (9)0.0221 (8)0.0397 (10)0.0039 (7)0.0053 (7)0.0102 (7)
O30.0335 (9)0.0336 (9)0.0274 (9)0.0088 (7)0.0084 (7)0.0068 (7)
O40.0280 (9)0.0376 (10)0.0274 (9)0.0028 (7)0.0040 (7)0.0091 (7)
O50.0518 (11)0.0304 (10)0.0498 (11)0.0014 (8)0.0225 (9)0.0202 (8)
C10.0218 (12)0.0204 (11)0.0266 (12)0.0040 (9)0.0065 (10)0.0087 (9)
C20.0223 (12)0.0193 (11)0.0227 (12)0.0008 (9)0.0048 (9)0.0069 (9)
C30.0225 (12)0.0222 (12)0.0309 (13)0.0003 (9)0.0090 (10)0.0081 (10)
C40.0220 (12)0.0216 (12)0.0307 (13)0.0011 (9)0.0089 (10)0.0084 (10)
C50.0271 (13)0.0195 (11)0.0233 (12)0.0020 (9)0.0036 (10)0.0078 (9)
C60.0248 (12)0.0198 (11)0.0237 (12)0.0016 (9)0.0053 (10)0.0074 (9)
C70.0236 (12)0.0166 (11)0.0261 (12)0.0001 (9)0.0031 (10)0.0093 (9)
C80.0286 (13)0.0157 (11)0.0268 (12)0.0003 (9)0.0063 (10)0.0079 (9)
C90.0221 (12)0.0215 (11)0.0325 (13)0.0027 (9)0.0041 (10)0.0129 (10)
C100.0266 (13)0.0229 (12)0.0253 (12)0.0003 (10)0.0016 (10)0.0110 (10)
C110.0295 (13)0.0222 (12)0.0222 (12)0.0018 (10)0.0044 (10)0.0089 (9)
C120.0241 (12)0.0205 (11)0.0304 (13)0.0006 (9)0.0057 (10)0.0110 (10)
C130.0250 (12)0.0166 (11)0.0248 (12)0.0009 (9)0.0014 (10)0.0066 (9)
C140.0269 (13)0.0222 (12)0.0239 (12)0.0001 (9)0.0064 (10)0.0047 (10)
C150.0327 (14)0.0256 (12)0.0237 (12)0.0050 (10)0.0023 (10)0.0095 (10)
C160.0285 (13)0.0203 (11)0.0276 (13)0.0015 (10)0.0031 (10)0.0069 (10)
C170.0267 (13)0.0255 (12)0.0343 (14)0.0050 (10)0.0098 (11)0.0088 (10)
C180.0297 (13)0.0270 (12)0.0289 (13)0.0022 (10)0.0092 (11)0.0113 (10)
C190.0197 (12)0.0233 (12)0.0253 (12)0.0032 (9)0.0040 (10)0.0087 (10)
C200.0294 (13)0.0210 (12)0.0279 (13)0.0010 (10)0.0056 (10)0.0079 (10)
C210.0258 (13)0.0250 (12)0.0257 (13)0.0010 (10)0.0009 (10)0.0029 (10)
C220.0258 (12)0.0265 (12)0.0262 (13)0.0066 (10)0.0043 (10)0.0094 (10)
C230.0310 (14)0.0293 (13)0.0383 (15)0.0022 (11)0.0013 (11)0.0200 (11)
C240.0217 (12)0.0258 (12)0.0315 (13)0.0051 (10)0.0031 (10)0.0094 (10)
C250.0207 (12)0.0232 (11)0.0260 (12)0.0017 (9)0.0051 (10)0.0050 (9)
C260.0277 (13)0.0333 (13)0.0306 (13)0.0017 (11)0.0024 (11)0.0131 (11)
C270.0275 (13)0.0364 (14)0.0339 (14)0.0052 (11)0.0023 (11)0.0080 (11)
C280.0231 (13)0.0381 (14)0.0273 (13)0.0066 (11)0.0027 (10)0.0043 (11)
C290.0314 (14)0.0365 (14)0.0353 (14)0.0088 (11)0.0042 (11)0.0157 (11)
C300.0254 (13)0.0297 (13)0.0395 (15)0.0042 (10)0.0071 (11)0.0146 (11)
C310.0187 (11)0.0227 (11)0.0247 (12)0.0009 (9)0.0011 (9)0.0066 (9)
C320.0274 (13)0.0259 (12)0.0244 (12)0.0006 (10)0.0060 (10)0.0082 (10)
C330.0297 (13)0.0226 (12)0.0338 (14)0.0006 (10)0.0073 (11)0.0076 (10)
C340.0269 (13)0.0289 (13)0.0369 (14)0.0014 (10)0.0059 (11)0.0142 (11)
C350.0366 (15)0.0330 (14)0.0323 (14)0.0004 (11)0.0144 (11)0.0083 (11)
C360.0306 (13)0.0224 (12)0.0329 (14)0.0016 (10)0.0077 (11)0.0046 (10)
C370.0514 (18)0.0315 (14)0.0617 (19)0.0095 (12)0.0194 (14)0.0269 (13)
C380.0387 (16)0.069 (2)0.0269 (15)0.0036 (14)0.0053 (12)0.0046 (14)
C390.0378 (15)0.0307 (14)0.0419 (15)0.0048 (11)0.0007 (12)0.0162 (12)
C400.0410 (16)0.0408 (15)0.0368 (15)0.0034 (12)0.0000 (12)0.0195 (12)
C410.0346 (15)0.0514 (17)0.0348 (15)0.0056 (12)0.0027 (12)0.0093 (13)
Geometric parameters (Å, º) top
N1—C51.360 (3)C20—C211.384 (3)
N1—C191.444 (3)C20—H20A0.9500
N1—C11.487 (3)C21—C221.392 (3)
N2—C61.393 (3)C21—H21A0.9500
N2—C51.421 (3)C22—C231.389 (3)
N2—C131.448 (3)C22—C401.504 (3)
N3—C41.374 (3)C23—C241.384 (3)
N3—C251.442 (3)C23—H23A0.9500
N3—C11.468 (3)C24—H24A0.9500
O1—C31.220 (2)C25—C301.387 (3)
O2—C41.219 (2)C25—C261.389 (3)
O3—C51.223 (2)C26—C271.395 (3)
O4—C101.368 (2)C26—H26A0.9500
O4—C381.425 (3)C27—C281.380 (3)
O5—C341.365 (3)C27—H27A0.9500
O5—C371.427 (3)C28—C291.389 (3)
C1—C21.511 (3)C28—C411.506 (3)
C1—C311.536 (3)C29—C301.379 (3)
C2—C61.360 (3)C29—H29A0.9500
C2—C31.441 (3)C30—H30A0.9500
C3—C41.530 (3)C31—C321.380 (3)
C6—C71.468 (3)C31—C361.399 (3)
C7—C121.392 (3)C32—C331.395 (3)
C7—C81.402 (3)C32—H32A0.9500
C8—C91.381 (3)C33—C341.380 (3)
C8—H8A0.9500C33—H33A0.9500
C9—C101.395 (3)C34—C351.397 (3)
C9—H9A0.9500C35—C361.376 (3)
C10—C111.385 (3)C35—H35A0.9500
C11—C121.385 (3)C36—H36A0.9500
C11—H11A0.9500C37—H37A0.9800
C12—H12A0.9500C37—H37B0.9800
C13—C141.380 (3)C37—H37C0.9800
C13—C181.383 (3)C38—H38A0.9800
C14—C151.384 (3)C38—H38B0.9800
C14—H14A0.9500C38—H38C0.9800
C15—C161.391 (3)C39—H39A0.9800
C15—H15A0.9500C39—H39B0.9800
C16—C171.389 (3)C39—H39C0.9800
C16—C391.508 (3)C40—H40A0.9800
C17—C181.381 (3)C40—H40B0.9800
C17—H17A0.9500C40—H40C0.9800
C18—H18A0.9500C41—H41A0.9800
C19—C241.379 (3)C41—H41B0.9800
C19—C201.382 (3)C41—H41C0.9800
C5—N1—C19119.39 (17)C22—C21—H21A119.3
C5—N1—C1117.75 (17)C23—C22—C21117.8 (2)
C19—N1—C1122.85 (16)C23—C22—C40120.5 (2)
C6—N2—C5120.94 (17)C21—C22—C40121.6 (2)
C6—N2—C13120.02 (17)C24—C23—C22121.1 (2)
C5—N2—C13118.84 (16)C24—C23—H23A119.5
C4—N3—C25121.79 (17)C22—C23—H23A119.5
C4—N3—C1112.47 (17)C19—C24—C23120.0 (2)
C25—N3—C1125.74 (17)C19—C24—H24A120.0
C10—O4—C38116.51 (18)C23—C24—H24A120.0
C34—O5—C37117.17 (18)C30—C25—C26119.1 (2)
N3—C1—N1111.55 (16)C30—C25—N3118.95 (19)
N3—C1—C2103.72 (16)C26—C25—N3121.9 (2)
N1—C1—C2106.37 (16)C25—C26—C27119.8 (2)
N3—C1—C31114.00 (17)C25—C26—H26A120.1
N1—C1—C31111.61 (16)C27—C26—H26A120.1
C2—C1—C31108.97 (17)C28—C27—C26121.6 (2)
C6—C2—C3133.0 (2)C28—C27—H27A119.2
C6—C2—C1116.01 (18)C26—C27—H27A119.2
C3—C2—C1109.98 (18)C27—C28—C29117.5 (2)
O1—C3—C2133.0 (2)C27—C28—C41121.1 (2)
O1—C3—C4121.84 (19)C29—C28—C41121.4 (2)
C2—C3—C4105.16 (18)C30—C29—C28121.9 (2)
O2—C4—N3126.8 (2)C30—C29—H29A119.0
O2—C4—C3125.02 (19)C28—C29—H29A119.0
N3—C4—C3108.17 (17)C29—C30—C25120.1 (2)
O3—C5—N1124.2 (2)C29—C30—H30A120.0
O3—C5—N2121.0 (2)C25—C30—H30A120.0
N1—C5—N2114.75 (18)C32—C31—C36118.3 (2)
C2—C6—N2116.79 (18)C32—C31—C1123.56 (19)
C2—C6—C7124.41 (19)C36—C31—C1117.84 (18)
N2—C6—C7118.80 (18)C31—C32—C33121.3 (2)
C12—C7—C8118.53 (19)C31—C32—H32A119.4
C12—C7—C6119.09 (19)C33—C32—H32A119.4
C8—C7—C6122.38 (19)C34—C33—C32119.8 (2)
C9—C8—C7121.0 (2)C34—C33—H33A120.1
C9—C8—H8A119.5C32—C33—H33A120.1
C7—C8—H8A119.5O5—C34—C33124.9 (2)
C8—C9—C10119.1 (2)O5—C34—C35115.7 (2)
C8—C9—H9A120.5C33—C34—C35119.4 (2)
C10—C9—H9A120.5C36—C35—C34120.3 (2)
O4—C10—C11123.8 (2)C36—C35—H35A119.9
O4—C10—C9115.23 (19)C34—C35—H35A119.9
C11—C10—C9121.0 (2)C35—C36—C31120.9 (2)
C12—C11—C10119.1 (2)C35—C36—H36A119.6
C12—C11—H11A120.4C31—C36—H36A119.6
C10—C11—H11A120.4O5—C37—H37A109.5
C11—C12—C7121.2 (2)O5—C37—H37B109.5
C11—C12—H12A119.4H37A—C37—H37B109.5
C7—C12—H12A119.4O5—C37—H37C109.5
C14—C13—C18120.2 (2)H37A—C37—H37C109.5
C14—C13—N2117.77 (19)H37B—C37—H37C109.5
C18—C13—N2122.04 (19)O4—C38—H38A109.5
C13—C14—C15119.6 (2)O4—C38—H38B109.5
C13—C14—H14A120.2H38A—C38—H38B109.5
C15—C14—H14A120.2O4—C38—H38C109.5
C14—C15—C16121.4 (2)H38A—C38—H38C109.5
C14—C15—H15A119.3H38B—C38—H38C109.5
C16—C15—H15A119.3C16—C39—H39A109.5
C15—C16—C17117.6 (2)C16—C39—H39B109.5
C15—C16—C39121.1 (2)H39A—C39—H39B109.5
C17—C16—C39121.3 (2)C16—C39—H39C109.5
C18—C17—C16121.6 (2)H39A—C39—H39C109.5
C18—C17—H17A119.2H39B—C39—H39C109.5
C16—C17—H17A119.2C22—C40—H40A109.5
C17—C18—C13119.5 (2)C22—C40—H40B109.5
C17—C18—H18A120.3H40A—C40—H40B109.5
C13—C18—H18A120.3C22—C40—H40C109.5
C24—C19—C20120.1 (2)H40A—C40—H40C109.5
C24—C19—N1118.46 (19)H40B—C40—H40C109.5
C20—C19—N1121.44 (19)C28—C41—H41A109.5
C19—C20—C21119.5 (2)C28—C41—H41B109.5
C19—C20—H20A120.3H41A—C41—H41B109.5
C21—C20—H20A120.3C28—C41—H41C109.5
C20—C21—C22121.4 (2)H41A—C41—H41C109.5
C20—C21—H21A119.3H41B—C41—H41C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1i0.952.553.409 (3)150
C11—H11A···O2ii0.952.533.158 (3)123
C18—H18A···O30.952.582.927 (3)102
C30—H30A···O20.952.552.928 (3)104
C32—H32A···N10.952.512.858 (3)102
C39—H39C···O5iii0.982.483.422 (3)160
C40—H40C···O4iv0.982.543.341 (3)139
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x1, y, z; (iv) x+1, y, z+1.
 

References

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