Methyl 1-benzyl-5-methyl-2,4-diphenyl-1H-pyrrole-3-carboxyl-ate.

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-methyl-benzene 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 inter-actions lead to supra-molecular layers in the ab plane.

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 = 381.45

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.06

3991 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack parameter determined using 1348 quotients (Parsons et al., 2013 ▶)

Absolute structure parameter: 0.02 (18)

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.

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

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

Click here for additional data file.

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

CCDC reference: 986712

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H23NO2	Dx = 1.236 Mg m−3
Mr = 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

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

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(Fo2) + (0.0691P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.119	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.24 e Å−3
3991 reflections	Δρmin = −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

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .