Methyl 1-benzyl-5-methyl-2,4-diphenyl-1H-pyrrole-3-carboxyl­ate

Lopchuk, J.M.; Gribble, G.W.; Jasinski, J.P.

doi:10.1107/S1600536814003316

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o338-o339

doi:10.1107/S1600536814003316

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Methyl 1-benzyl-5-methyl-2,4-diphenyl-1H-pyrrole-3-carboxylate

Justin M. Lopchuk,^a Gordon W. Gribble ^a and Jerry P. Jasinski ^b ^*

^aDepartment of Chemistry, Dartmouth College, Hanover, New Hampshire 03755-3564, USA, and ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

(Received 12 February 2014; accepted 13 February 2014; online 22 February 2014)

In the title compound, C₂₆H₂₃NO₂, the dihedral angles between the pyrrole ring and the two phenyl rings are 58.1 (6) and 71.5 (5)°. The mean planes of the 5-methylbenzene ring and the carboxyl group are twisted by 89.5 (3) and 22.1 (9)°, respectively, from the pyrrole ring. In the crystal, weak C—H⋯O interactions lead to supramolecular layers in the ab plane.

CCDC reference: 986712

Related literature

For previous münchnone-based approaches to atorvastatin, see: Pandey & Rao (2004 ); Park et al. (2008 ); Roth et al. (1991 ). For other examples of the synthesis of pyrroles via 1,3-dipolar cycloadditions with münchnones, see: Lopchuk & Gribble (2011a ,b ); Lopchuk et al. (2013 ). For related crystal structures, see: Grassi et al. (2002 ); Fang et al. (2012 ); Donohoe et al. (2010 ); Sun et al. (2004 ); Zhang et al. (2011 ).

Experimental

Crystal data

C₂₆H₂₃NO₂
M_r = 381.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.8056 (2) Å
b = 10.6638 (2) Å
c = 21.8315 (5) Å
V = 2050.00 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.61 mm⁻¹
T = 173 K
0.28 × 0.22 × 0.12 mm

Data collection

Agilent Xcalibur (Eos Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.720, T_max = 1.000
12873 measured reflections
3991 independent reflections
3525 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.06
3991 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack parameter determined using 1348 quotients (Parsons et al., 2013 )
Absolute structure parameter: 0.02 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯O1ⁱ	0.99	2.56	3.177 (3)	120
C26—H26A⋯O2ⁱⁱ	0.98	2.59	3.383 (3)	138
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus et al., 2012 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 986712

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814003316/tk5295sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003316/tk5295Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814003316/tk5295Isup3.cml

checkCIF report

Structural commentary top

During the course of our studies toward a total synthesis of atorvastatin, methyl 1-benzyl-5-methyl-2,4-diphenyl-1H-pyrrole-3-carboxylate (I), a pentasubstituted pyrrole, was generated from the reaction of a münchnone with methyl 3-phenylpropiolate. Previously published work on münchnone-based routes toward atorvastatin found that the key münchnone cycloadditions were either low yielding or unselective and delivered 1:1 mixtures of regioisomers (Pandey et al., 2004; Park et al., 2008; Roth et al., 1991). However, our recent studies on the 1,3-dipolar cycloaddition of münchnones showed that high regioselectivies can be obtained by proper selection and combination of the münchnone, dipolarophile, and solvent (Lopchuk et al., 2011a, Lopchuk et al., 2011b; Lopchuk et al., 2013).

A variety of related highly substituted pyrrole crystal structures have been reported including N-((2-methyl-4,5-diphenyl-1H-pyrrole-3-carbonyl)oxy)benzamide (Grassi et al., 2002), N,1,5-tribenzyl-4-(2-chlorophenyl)-2-methyl-1H-pyrrole-3-carbothioamide (Fang et al., 2012), 1-(2-benzyl-5-isopropyl-4-phenyl-1H-pyrrol-3-yl)-2-methylpropan-1-one (Sun et al., 2004), 5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide (Donohoe et al., 2010), and 1-(2-benzoyl-5-isopropyl-4-phenyl-1H-pyrrol-3-yl)-2-methylpropan-1-one (Zhang et al., 2011). In continuation of our work on münchnone-based routes this paper reports the crystal structure of the title compound, (I), C₂₆H₂₃NO₂,

In (I), the dihedral angles between the mean planes of the two phenyl rings (C5–C10 and C11–C16) with that of the pyrrole ring (N1/C1–C4) are 58.1 (6) and 71.5 (5)°, respectively (Fig. 1). The mean planes of the 5-methyl benzene ring (C18–C23) and carboxyl group (O1/O2/C24/C25) are also twisted by 89.5 (3) and 22.1 (9)°, respectively, from that of the pyrrole ring. In the crystal, while no classical hydrogen bonds are observed, weak C—H···O intermolecular interactions are observed (Table 1) which lead to supramolecular layers in the ab plane.

Synthesis and crystallization top

A round bottom flask was charged with N-benzoyl-N-benzylalanine (424 mg, 1.5 mmol), methyl 3-phenylpropiolate (80 mg, 0.5 mmol), and dry THF (20 ml). The reaction was placed under nitrogen and N,N'-diisopropylcarbodiimide (234 ml, 1.5 mmol) added at room temperature. The mixture was heated to reflux for 24 h (Fig. 2). The reaction was cooled to room temperature and concentrated in vacuo. The residue was directly purified by flash chromatography to afford pyrrole I as a clear, colorless oil which solidified upon standing (158 mg, 83%). Pyrrole I was obtained as the major isomer (96:4 ratio of I:II). Single crystals suitable for diffraction were grown from dichloromethane (slow evaporation) at ambient temperature [M.pt. 454- 455 K].

Refinement top

All of the H atoms were placed in their calculated positions and then refined using the riding model with atom—H lengths of 0.95 Å (CH), 0.99 Å (CH₂) or 0.98 Å (CH₃). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH₂) or 1.5 (CH₃) times U_eq of the parent atom. Idealized methyl groups were refined as rotating.

Related literature top

For previous münchnone-based approaches to atorvastatin, see: Pandey & Rao (2004); Park et al. (2008); Roth et al. (1991). For other examples of the synthesis of pyrroles via 1,3-dipolar cycloadditions with münchnones, see: Lopchuk & Gribble (2011a,b); Lopchuk et al. (2013). For related crystal structures, see: Grassi et al. (2002); Fang et al. (2012); Donohoe et al. (2010); Sun et al. (2004); Zhang et al. (2011).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus et al., 2012); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of (I), C₂₆H₂₃NO₂, showing the labeling scheme with 30% probability displacement ellipsoids.
	Fig. 2. Reaction scheme for C₂₆H₂₃NO₂.

Methyl 1-benzyl-5-methyl-2,4-diphenyl-1H-pyrrole-3-carboxylate top

Crystal data top

C₂₆H₂₃NO₂	D_x = 1.236 Mg m⁻³
M_r = 381.45	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 4659 reflections
a = 8.8056 (2) Å	θ = 4.1–72.4°
b = 10.6638 (2) Å	µ = 0.61 mm⁻¹
c = 21.8315 (5) Å	T = 173 K
V = 2050.00 (8) Å³	Irregular, colourless
Z = 4	0.28 × 0.22 × 0.12 mm
F(000) = 808

Data collection top

Agilent Xcalibur (Eos Gemini) diffractometer	3991 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3525 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 16.0416 pixels mm^-1	θ_max = 72.6°, θ_min = 4.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −13→11
T_min = 0.720, T_max = 1.000	l = −26→26
12873 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0691P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.119	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.24 e Å⁻³
3991 reflections	Δρ_min = −0.20 e Å⁻³
264 parameters	Absolute structure: Flack parameter determined using 1348 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.02 (18)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₆H₂₃NO₂	V = 2050.00 (8) Å³
M_r = 381.45	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 8.8056 (2) Å	µ = 0.61 mm⁻¹
b = 10.6638 (2) Å	T = 173 K
c = 21.8315 (5) Å	0.28 × 0.22 × 0.12 mm

Data collection top

Agilent Xcalibur (Eos Gemini) diffractometer	3991 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	3525 reflections with I > 2σ(I)
T_min = 0.720, T_max = 1.000	R_int = 0.041
12873 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.119	Δρ_max = 0.24 e Å⁻³
S = 1.06	Δρ_min = −0.20 e Å⁻³
3991 reflections	Absolute structure: Flack parameter determined using 1348 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
264 parameters	Absolute structure parameter: 0.02 (18)
0 restraints

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.

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

	x	y	z	U_iso*/U_eq
O1	0.9445 (2)	0.4206 (2)	0.84521 (12)	0.0598 (7)
O2	0.7077 (2)	0.43820 (19)	0.87973 (9)	0.0393 (5)
N1	0.7361 (2)	0.1689 (2)	0.72021 (10)	0.0315 (5)
C1	0.6106 (3)	0.1444 (2)	0.75598 (12)	0.0309 (5)
C2	0.6162 (3)	0.2209 (2)	0.80673 (12)	0.0286 (5)
C3	0.7518 (3)	0.2943 (2)	0.80125 (11)	0.0288 (5)
C4	0.8227 (3)	0.2603 (2)	0.74693 (12)	0.0310 (6)
C5	0.5074 (3)	0.2152 (2)	0.85815 (12)	0.0307 (5)
C6	0.3528 (3)	0.2348 (3)	0.84848 (13)	0.0366 (6)
H6	0.3174	0.2554	0.8086	0.044*
C7	0.2498 (3)	0.2246 (3)	0.89631 (15)	0.0451 (7)
H7	0.1448	0.2385	0.8890	0.054*
C8	0.2991 (4)	0.1945 (3)	0.95452 (15)	0.0467 (7)
H8	0.2284	0.1861	0.9871	0.056*
C9	0.4528 (4)	0.1765 (3)	0.96491 (14)	0.0458 (7)
H9	0.4876	0.1573	1.0050	0.055*
C10	0.5561 (3)	0.1864 (3)	0.91732 (13)	0.0369 (6)
H10	0.6611	0.1734	0.9250	0.044*
C11	0.9580 (3)	0.3149 (2)	0.71660 (11)	0.0319 (6)
C12	0.9505 (3)	0.4354 (3)	0.69197 (14)	0.0402 (6)
H12	0.8580	0.4811	0.6938	0.048*
C13	1.0765 (4)	0.4889 (3)	0.66490 (15)	0.0437 (7)
H13	1.0706	0.5715	0.6488	0.052*
C14	1.2107 (3)	0.4232 (3)	0.66111 (13)	0.0413 (7)
H14	1.2972	0.4604	0.6425	0.050*
C15	1.2193 (3)	0.3033 (3)	0.68443 (14)	0.0419 (7)
H15	1.3114	0.2573	0.6813	0.050*
C16	1.0935 (3)	0.2494 (3)	0.71249 (14)	0.0386 (6)
H16	1.1005	0.1672	0.7290	0.046*
C17	0.7718 (3)	0.1039 (3)	0.66289 (12)	0.0355 (6)
H17A	0.7508	0.0134	0.6684	0.043*
H17B	0.8818	0.1131	0.6546	0.043*
C18	0.6847 (3)	0.1500 (3)	0.60767 (13)	0.0357 (6)
C19	0.6183 (4)	0.2672 (3)	0.60486 (15)	0.0450 (7)
H19	0.6225	0.3213	0.6394	0.054*
C20	0.5454 (4)	0.3065 (4)	0.55163 (18)	0.0598 (9)
H20	0.5000	0.3873	0.5500	0.072*
C21	0.5387 (5)	0.2287 (4)	0.50119 (17)	0.0668 (11)
H21	0.4888	0.2555	0.4649	0.080*
C22	0.6049 (5)	0.1122 (4)	0.50404 (16)	0.0688 (11)
H22	0.6016	0.0585	0.4694	0.083*
C23	0.6765 (4)	0.0727 (3)	0.55703 (15)	0.0529 (8)
H23	0.7205	−0.0086	0.5586	0.063*
C24	0.8137 (3)	0.3888 (2)	0.84308 (12)	0.0316 (5)
C25	0.7587 (4)	0.5348 (3)	0.92114 (14)	0.0446 (7)
H25A	0.7974	0.6061	0.8975	0.067*
H25B	0.8397	0.5016	0.9473	0.067*
H25C	0.6736	0.5623	0.9467	0.067*
C26	0.5022 (3)	0.0412 (3)	0.73991 (14)	0.0387 (6)
H26A	0.4606	0.0560	0.6989	0.058*
H26B	0.4192	0.0394	0.7698	0.058*
H26C	0.5558	−0.0393	0.7405	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0366 (12)	0.0751 (16)	0.0676 (15)	−0.0174 (11)	0.0058 (11)	−0.0342 (14)
O2	0.0370 (11)	0.0398 (11)	0.0411 (10)	−0.0007 (8)	0.0007 (8)	−0.0131 (9)
N1	0.0321 (11)	0.0329 (11)	0.0294 (11)	−0.0004 (9)	−0.0020 (8)	−0.0042 (9)
C1	0.0296 (12)	0.0307 (13)	0.0324 (13)	−0.0007 (10)	−0.0031 (10)	−0.0002 (10)
C2	0.0284 (12)	0.0276 (12)	0.0299 (12)	0.0008 (10)	−0.0038 (10)	0.0016 (10)
C3	0.0283 (12)	0.0273 (12)	0.0308 (12)	0.0015 (10)	−0.0030 (10)	−0.0002 (10)
C4	0.0301 (13)	0.0303 (13)	0.0325 (13)	0.0006 (10)	−0.0016 (10)	−0.0015 (10)
C5	0.0318 (13)	0.0263 (12)	0.0339 (13)	−0.0025 (10)	0.0008 (10)	−0.0031 (10)
C6	0.0329 (14)	0.0388 (15)	0.0382 (15)	−0.0016 (11)	−0.0021 (11)	0.0008 (12)
C7	0.0303 (14)	0.0480 (18)	0.0569 (19)	−0.0003 (13)	0.0058 (13)	−0.0027 (14)
C8	0.0483 (17)	0.0467 (17)	0.0452 (17)	−0.0068 (13)	0.0180 (14)	−0.0043 (14)
C9	0.0546 (19)	0.0511 (18)	0.0317 (14)	−0.0035 (15)	0.0047 (13)	0.0018 (13)
C10	0.0349 (14)	0.0403 (15)	0.0354 (14)	−0.0021 (12)	−0.0004 (11)	0.0008 (11)
C11	0.0321 (13)	0.0350 (14)	0.0285 (12)	−0.0026 (10)	0.0000 (10)	−0.0051 (10)
C12	0.0409 (15)	0.0354 (15)	0.0443 (15)	−0.0004 (12)	0.0041 (12)	−0.0057 (13)
C13	0.0517 (18)	0.0359 (16)	0.0436 (16)	−0.0072 (12)	0.0050 (14)	0.0007 (12)
C14	0.0412 (16)	0.0508 (17)	0.0320 (13)	−0.0128 (12)	0.0068 (11)	−0.0053 (13)
C15	0.0316 (15)	0.0529 (17)	0.0413 (15)	0.0013 (12)	0.0022 (11)	−0.0034 (13)
C16	0.0351 (14)	0.0402 (15)	0.0406 (15)	0.0010 (11)	−0.0015 (11)	0.0052 (12)
C17	0.0365 (14)	0.0373 (14)	0.0328 (13)	0.0038 (11)	−0.0005 (11)	−0.0079 (11)
C18	0.0338 (14)	0.0413 (15)	0.0319 (14)	−0.0047 (12)	0.0047 (10)	0.0002 (11)
C19	0.0449 (16)	0.0459 (18)	0.0443 (16)	−0.0021 (14)	0.0027 (13)	0.0018 (13)
C20	0.058 (2)	0.062 (2)	0.060 (2)	−0.0049 (17)	−0.0040 (17)	0.0243 (18)
C21	0.069 (2)	0.094 (3)	0.0374 (17)	−0.016 (2)	−0.0051 (16)	0.0245 (19)
C22	0.086 (3)	0.090 (3)	0.0295 (16)	−0.013 (2)	−0.0009 (17)	−0.0045 (17)
C23	0.064 (2)	0.058 (2)	0.0362 (15)	0.0005 (16)	0.0042 (14)	−0.0082 (15)
C24	0.0309 (13)	0.0313 (13)	0.0325 (13)	−0.0025 (10)	−0.0015 (10)	0.0001 (11)
C25	0.0581 (19)	0.0387 (16)	0.0369 (15)	0.0006 (14)	−0.0044 (14)	−0.0110 (12)
C26	0.0351 (14)	0.0369 (14)	0.0440 (16)	−0.0066 (11)	−0.0027 (12)	−0.0084 (12)

Geometric parameters (Å, º) top

O1—C24	1.202 (3)	C13—H13	0.9500
O2—C24	1.337 (3)	C13—C14	1.376 (4)
O2—C25	1.442 (3)	C14—H14	0.9500
N1—C1	1.379 (3)	C14—C15	1.378 (4)
N1—C4	1.368 (3)	C15—H15	0.9500
N1—C17	1.465 (3)	C15—C16	1.390 (4)
C1—C2	1.377 (4)	C16—H16	0.9500
C1—C26	1.499 (4)	C17—H17A	0.9900
C2—C3	1.433 (3)	C17—H17B	0.9900
C2—C5	1.477 (4)	C17—C18	1.511 (4)
C3—C4	1.388 (4)	C18—C19	1.381 (4)
C3—C24	1.465 (4)	C18—C23	1.381 (4)
C4—C11	1.482 (4)	C19—H19	0.9500
C5—C6	1.394 (4)	C19—C20	1.392 (5)
C5—C10	1.395 (4)	C20—H20	0.9500
C6—H6	0.9500	C20—C21	1.380 (6)
C6—C7	1.387 (4)	C21—H21	0.9500
C7—H7	0.9500	C21—C22	1.374 (6)
C7—C8	1.381 (5)	C22—H22	0.9500
C8—H8	0.9500	C22—C23	1.383 (5)
C8—C9	1.385 (5)	C23—H23	0.9500
C9—H9	0.9500	C25—H25A	0.9800
C9—C10	1.385 (4)	C25—H25B	0.9800
C10—H10	0.9500	C25—H25C	0.9800
C11—C12	1.394 (4)	C26—H26A	0.9800
C11—C16	1.386 (4)	C26—H26B	0.9800
C12—H12	0.9500	C26—H26C	0.9800
C12—C13	1.381 (4)

C24—O2—C25	116.0 (2)	C14—C15—H15	119.9
C1—N1—C17	124.5 (2)	C14—C15—C16	120.2 (3)
C4—N1—C1	109.9 (2)	C16—C15—H15	119.9
C4—N1—C17	125.6 (2)	C11—C16—C15	120.4 (3)
N1—C1—C26	121.2 (2)	C11—C16—H16	119.8
C2—C1—N1	108.3 (2)	C15—C16—H16	119.8
C2—C1—C26	130.3 (3)	N1—C17—H17A	108.6
C1—C2—C3	106.6 (2)	N1—C17—H17B	108.6
C1—C2—C5	124.3 (2)	N1—C17—C18	114.8 (2)
C3—C2—C5	128.8 (2)	H17A—C17—H17B	107.5
C2—C3—C24	129.3 (2)	C18—C17—H17A	108.6
C4—C3—C2	107.7 (2)	C18—C17—H17B	108.6
C4—C3—C24	123.0 (2)	C19—C18—C17	123.0 (3)
N1—C4—C3	107.4 (2)	C23—C18—C17	118.1 (3)
N1—C4—C11	122.5 (2)	C23—C18—C19	118.9 (3)
C3—C4—C11	129.8 (2)	C18—C19—H19	119.9
C6—C5—C2	120.8 (2)	C18—C19—C20	120.3 (3)
C6—C5—C10	118.2 (2)	C20—C19—H19	119.9
C10—C5—C2	120.9 (2)	C19—C20—H20	119.8
C5—C6—H6	119.6	C21—C20—C19	120.3 (4)
C7—C6—C5	120.9 (3)	C21—C20—H20	119.8
C7—C6—H6	119.6	C20—C21—H21	120.4
C6—C7—H7	119.8	C22—C21—C20	119.3 (3)
C8—C7—C6	120.3 (3)	C22—C21—H21	120.4
C8—C7—H7	119.8	C21—C22—H22	119.8
C7—C8—H8	120.3	C21—C22—C23	120.5 (4)
C7—C8—C9	119.4 (3)	C23—C22—H22	119.8
C9—C8—H8	120.3	C18—C23—C22	120.7 (4)
C8—C9—H9	119.7	C18—C23—H23	119.6
C10—C9—C8	120.5 (3)	C22—C23—H23	119.6
C10—C9—H9	119.7	O1—C24—O2	122.4 (3)
C5—C10—H10	119.7	O1—C24—C3	125.0 (3)
C9—C10—C5	120.6 (3)	O2—C24—C3	112.6 (2)
C9—C10—H10	119.7	O2—C25—H25A	109.5
C12—C11—C4	119.8 (2)	O2—C25—H25B	109.5
C16—C11—C4	121.5 (2)	O2—C25—H25C	109.5
C16—C11—C12	118.7 (3)	H25A—C25—H25B	109.5
C11—C12—H12	119.7	H25A—C25—H25C	109.5
C13—C12—C11	120.5 (3)	H25B—C25—H25C	109.5
C13—C12—H12	119.7	C1—C26—H26A	109.5
C12—C13—H13	119.8	C1—C26—H26B	109.5
C14—C13—C12	120.4 (3)	C1—C26—H26C	109.5
C14—C13—H13	119.8	H26A—C26—H26B	109.5
C13—C14—H14	120.1	H26A—C26—H26C	109.5
C13—C14—C15	119.8 (3)	H26B—C26—H26C	109.5
C15—C14—H14	120.1

N1—C1—C2—C3	−0.3 (3)	C5—C2—C3—C24	−4.4 (4)
N1—C1—C2—C5	−175.1 (2)	C5—C6—C7—C8	−0.2 (5)
N1—C4—C11—C12	105.7 (3)	C6—C5—C10—C9	0.5 (4)
N1—C4—C11—C16	−74.9 (4)	C6—C7—C8—C9	1.1 (5)
N1—C17—C18—C19	21.3 (4)	C7—C8—C9—C10	−1.2 (5)
N1—C17—C18—C23	−161.1 (3)	C8—C9—C10—C5	0.4 (5)
C1—N1—C4—C3	0.5 (3)	C10—C5—C6—C7	−0.6 (4)
C1—N1—C4—C11	−174.4 (2)	C11—C12—C13—C14	0.9 (5)
C1—N1—C17—C18	80.0 (3)	C12—C11—C16—C15	0.1 (4)
C1—C2—C3—C4	0.6 (3)	C12—C13—C14—C15	0.0 (5)
C1—C2—C3—C24	−179.0 (3)	C13—C14—C15—C16	−0.9 (4)
C1—C2—C5—C6	−59.7 (4)	C14—C15—C16—C11	0.8 (5)
C1—C2—C5—C10	118.3 (3)	C16—C11—C12—C13	−1.0 (4)
C2—C3—C4—N1	−0.7 (3)	C17—N1—C1—C2	178.6 (2)
C2—C3—C4—C11	173.8 (3)	C17—N1—C1—C26	3.4 (4)
C2—C3—C24—O1	157.7 (3)	C17—N1—C4—C3	−178.2 (2)
C2—C3—C24—O2	−22.4 (4)	C17—N1—C4—C11	6.9 (4)
C2—C5—C6—C7	177.4 (3)	C17—C18—C19—C20	177.1 (3)
C2—C5—C10—C9	−177.5 (3)	C17—C18—C23—C22	−176.7 (3)
C3—C2—C5—C6	126.6 (3)	C18—C19—C20—C21	0.0 (5)
C3—C2—C5—C10	−55.4 (4)	C19—C18—C23—C22	0.9 (5)
C3—C4—C11—C12	−67.9 (4)	C19—C20—C21—C22	−0.1 (6)
C3—C4—C11—C16	111.5 (3)	C20—C21—C22—C23	0.6 (6)
C4—N1—C1—C2	−0.1 (3)	C21—C22—C23—C18	−1.0 (6)
C4—N1—C1—C26	−175.3 (2)	C23—C18—C19—C20	−0.4 (5)
C4—N1—C17—C18	−101.5 (3)	C24—C3—C4—N1	178.9 (2)
C4—C3—C24—O1	−21.8 (4)	C24—C3—C4—C11	−6.7 (4)
C4—C3—C24—O2	158.1 (2)	C25—O2—C24—O1	1.6 (4)
C4—C11—C12—C13	178.4 (3)	C25—O2—C24—C3	−178.3 (2)
C4—C11—C16—C15	−179.3 (3)	C26—C1—C2—C3	174.3 (3)
C5—C2—C3—C4	175.1 (2)	C26—C1—C2—C5	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O1ⁱ	0.99	2.56	3.177 (3)	120
C26—H26A···O2ⁱⁱ	0.98	2.59	3.383 (3)	138

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O1ⁱ	0.99	2.56	3.177 (3)	120
C26—H26A···O2ⁱⁱ	0.98	2.59	3.383 (3)	138

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

Acknowledgements

JML acknowledges support from a Graduate Assistance in Areas of National Need (GAANN) fellowship. GWG acknowledges support by the Donors of the Petroleum Research Fund (PRF), administered by the American Chemical Society, and by Wyeth. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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Volume 70| Part 3| March 2014| Pages o338-o339

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