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

The title compound, C₁₉H₁₇NO₂, forms dimeric aggregates in the solid state due to the pyrrole-NH-carboxyl-O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.060
• wR factor = 0.171
• Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSMU_01  Alert C The ratio of given/expected absorption coefficient lies
          outside the range 0.99 <> 1.01
          Calculated value of mu =     0.081
          Value of mu given      =     0.080

RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.102


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO (Otwinowski & Minor, 1997), COLLECT and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).

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

Crystal data

C19H17NO2	F(000) = 2464
Mr = 291.34	Dx = 1.255 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 34.1913 (12) Å	Cell parameters from 28010 reflections
b = 10.7042 (4) Å	θ = 3.3–25.0°
c = 19.1129 (9) Å	µ = 0.08 mm^−1
β = 118.186 (2)°	T = 120 K
V = 6165.6 (4) Å^3	Plate, colourless
Z = 16	0.10 × 0.10 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	5420 independent reflections
Radiation source: Nonius FR591 Rotating anode	3071 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.102
Detector resolution: 9.091 pixels mm^1 pixels mm^-1	θmax = 25.0°, θmin = 3.3°
φ and ω scans to fill the asymmetric unit	h = −40→40
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	k = −12→12
Tmin = 0.992, Tmax = 0.996	l = −22→22
28010 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.171	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0881P)^2 + 0.4211P] where P = (Fo^2 + 2Fc^2)/3
5420 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.18316 (10)	−0.2849 (3)	0.1393 (2)	0.0387 (8)
H1A	0.2111	−0.2737	0.1375	0.058*
H1B	0.1608	−0.3208	0.0891	0.058*
H1C	0.1879	−0.3413	0.1830	0.058*
C2	0.16731 (10)	−0.1613 (3)	0.15216 (17)	0.0308 (7)
C3	0.12978 (9)	−0.1280 (3)	0.15895 (16)	0.0283 (7)
C4	0.12983 (9)	0.0051 (3)	0.16501 (16)	0.0276 (7)
C5	0.16766 (9)	0.0479 (3)	0.16284 (17)	0.0300 (7)
C6	0.18825 (10)	0.1682 (3)	0.17113 (17)	0.0308 (7)
C7	0.18855 (11)	0.3832 (3)	0.1993 (2)	0.0423 (8)
H7A	0.1710	0.4447	0.2106	0.063*
H7B	0.1900	0.4077	0.1512	0.063*
H7C	0.2186	0.3795	0.2441	0.063*
C8	0.09577 (9)	−0.2166 (3)	0.15584 (17)	0.0287 (7)
C9	0.10818 (10)	−0.3274 (3)	0.19974 (17)	0.0345 (7)
H9	0.1387	−0.3439	0.2335	0.041*
C10	0.07689 (11)	−0.4131 (3)	0.19489 (18)	0.0390 (8)
H10	0.0860	−0.4881	0.2250	0.047*
C11	0.03201 (11)	−0.3899 (3)	0.14597 (19)	0.0404 (8)
H11	0.0104	−0.4490	0.1421	0.048*
C12	0.01920 (10)	−0.2803 (3)	0.10311 (19)	0.0396 (8)
H12	−0.0114	−0.2638	0.0700	0.048*
C13	0.05045 (10)	−0.1941 (3)	0.10771 (18)	0.0348 (7)
H13	0.0411	−0.1189	0.0779	0.042*
C14	0.09599 (9)	0.0843 (3)	0.17112 (17)	0.0278 (7)
C15	0.08629 (10)	0.0709 (3)	0.23329 (18)	0.0349 (8)
H15	0.1005	0.0072	0.2716	0.042*
C16	0.05599 (11)	0.1495 (3)	0.2404 (2)	0.0402 (8)
H16	0.0498	0.1398	0.2835	0.048*
C17	0.03497 (10)	0.2416 (3)	0.18471 (19)	0.0360 (8)
H17	0.0149	0.2970	0.1901	0.043*
C18	0.04326 (10)	0.2528 (3)	0.12127 (19)	0.0356 (8)
H18	0.0281	0.3147	0.0820	0.043*
C19	0.07334 (10)	0.1753 (3)	0.11396 (18)	0.0337 (7)
H19	0.0787	0.1839	0.0697	0.040*
C20	0.28778 (11)	0.3862 (3)	0.12216 (19)	0.0367 (8)
H20A	0.2616	0.3719	0.1292	0.055*
H20B	0.2800	0.4424	0.0770	0.055*
H20C	0.3113	0.4241	0.1704	0.055*
C21	0.30371 (9)	0.2643 (3)	0.10665 (17)	0.0298 (7)
C22	0.33940 (9)	0.2377 (3)	0.09254 (16)	0.0290 (7)
C23	0.34072 (9)	0.1051 (3)	0.08523 (16)	0.0293 (7)
C24	0.30615 (9)	0.0562 (3)	0.09607 (17)	0.0294 (7)
C25	0.28822 (10)	−0.0669 (3)	0.09481 (18)	0.0325 (7)
C26	0.30009 (13)	−0.2860 (3)	0.0947 (2)	0.0501 (9)
H26A	0.3182	−0.3449	0.0830	0.075*
H26B	0.2686	−0.3029	0.0596	0.075*
H26C	0.3065	−0.2957	0.1501	0.075*
C27	0.37110 (10)	0.3290 (3)	0.09083 (17)	0.0298 (7)
C28	0.35697 (10)	0.4332 (3)	0.04101 (17)	0.0337 (7)
H28	0.3261	0.4471	0.0084	0.040*
C29	0.38728 (11)	0.5168 (3)	0.03829 (19)	0.0391 (8)
H29	0.3771	0.5872	0.0040	0.047*
C30	0.43201 (11)	0.4977 (3)	0.0851 (2)	0.0406 (8)
H30	0.4528	0.5537	0.0823	0.049*
C31	0.44675 (11)	0.3968 (3)	0.13635 (19)	0.0367 (8)
H31	0.4776	0.3850	0.1698	0.044*
C32	0.41665 (10)	0.3131 (3)	0.13905 (18)	0.0344 (7)
H32	0.4271	0.2438	0.1742	0.041*
C33	0.37190 (9)	0.0390 (3)	0.06410 (18)	0.0295 (7)
C34	0.37957 (10)	0.0885 (3)	0.00430 (17)	0.0335 (7)
H34	0.3652	0.1639	−0.0212	0.040*
C35	0.40780 (10)	0.0300 (3)	−0.0187 (2)	0.0388 (8)
H35	0.4127	0.0655	−0.0595	0.047*
C36	0.42864 (10)	−0.0790 (3)	0.0170 (2)	0.0412 (8)
H36	0.4475	−0.1203	0.0005	0.049*
C37	0.42189 (10)	−0.1281 (3)	0.0773 (2)	0.0400 (8)
H37	0.4365	−0.2033	0.1027	0.048*
C38	0.39424 (9)	−0.0696 (3)	0.10128 (18)	0.0343 (7)
H38	0.3905	−0.1038	0.1436	0.041*
N1	0.18954 (8)	−0.0552 (2)	0.15491 (14)	0.0314 (6)
H1	0.2145	−0.0523	0.1520	0.038*
N2	0.28444 (8)	0.1557 (2)	0.10873 (14)	0.0324 (6)
H2	0.2613	0.1489	0.1170	0.039*
O1	0.22208 (7)	0.18485 (19)	0.16545 (13)	0.0410 (6)
O2	0.16790 (7)	0.26184 (18)	0.18756 (12)	0.0363 (5)
O3	0.25634 (7)	−0.08671 (19)	0.10541 (13)	0.0394 (5)
O4	0.31039 (7)	−0.15943 (19)	0.08193 (15)	0.0467 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0339 (17)	0.0348 (18)	0.050 (2)	0.0033 (15)	0.0224 (16)	0.0018 (16)
C2	0.0288 (16)	0.0283 (16)	0.0341 (17)	0.0008 (14)	0.0139 (14)	0.0011 (13)
C3	0.0256 (15)	0.0304 (17)	0.0291 (16)	0.0023 (14)	0.0130 (13)	0.0026 (13)
C4	0.0262 (15)	0.0299 (16)	0.0272 (16)	0.0000 (14)	0.0129 (13)	0.0034 (13)
C5	0.0282 (16)	0.0308 (17)	0.0300 (17)	0.0043 (14)	0.0129 (14)	0.0030 (13)
C6	0.0265 (16)	0.0356 (18)	0.0293 (16)	0.0004 (15)	0.0122 (14)	0.0014 (14)
C7	0.046 (2)	0.0297 (17)	0.051 (2)	−0.0079 (16)	0.0222 (17)	−0.0082 (15)
C8	0.0295 (16)	0.0309 (16)	0.0326 (16)	−0.0012 (14)	0.0205 (14)	−0.0043 (14)
C9	0.0364 (17)	0.0341 (18)	0.0341 (17)	−0.0031 (15)	0.0176 (15)	0.0004 (14)
C10	0.049 (2)	0.0325 (17)	0.0393 (18)	−0.0074 (16)	0.0234 (16)	0.0000 (15)
C11	0.043 (2)	0.0384 (19)	0.046 (2)	−0.0149 (17)	0.0267 (17)	−0.0118 (16)
C12	0.0302 (17)	0.046 (2)	0.045 (2)	−0.0059 (16)	0.0206 (15)	−0.0154 (17)
C13	0.0336 (18)	0.0336 (17)	0.0404 (18)	0.0018 (15)	0.0201 (15)	−0.0035 (15)
C14	0.0243 (15)	0.0270 (15)	0.0331 (16)	−0.0026 (14)	0.0143 (13)	0.0020 (14)
C15	0.0360 (17)	0.0335 (17)	0.0375 (18)	0.0027 (15)	0.0191 (15)	0.0073 (14)
C16	0.0442 (19)	0.0428 (19)	0.045 (2)	0.0076 (17)	0.0305 (17)	0.0063 (16)
C17	0.0323 (17)	0.0334 (18)	0.045 (2)	0.0010 (15)	0.0203 (16)	−0.0028 (16)
C18	0.0314 (17)	0.0304 (17)	0.0423 (19)	0.0075 (15)	0.0152 (15)	0.0083 (14)
C19	0.0325 (17)	0.0389 (18)	0.0321 (17)	0.0045 (15)	0.0173 (14)	0.0066 (15)
C20	0.0394 (18)	0.0284 (16)	0.0491 (19)	0.0022 (15)	0.0266 (16)	−0.0024 (15)
C21	0.0274 (15)	0.0280 (17)	0.0339 (17)	−0.0010 (14)	0.0145 (14)	−0.0013 (13)
C22	0.0300 (16)	0.0280 (16)	0.0277 (16)	0.0019 (14)	0.0127 (13)	0.0004 (13)
C23	0.0272 (16)	0.0298 (16)	0.0278 (16)	0.0016 (14)	0.0104 (13)	−0.0011 (13)
C24	0.0286 (16)	0.0267 (16)	0.0351 (17)	0.0031 (14)	0.0168 (14)	−0.0009 (13)
C25	0.0313 (17)	0.0309 (17)	0.0393 (18)	−0.0001 (15)	0.0199 (15)	−0.0033 (14)
C26	0.060 (2)	0.0239 (17)	0.078 (3)	−0.0026 (17)	0.041 (2)	−0.0040 (17)
C27	0.0359 (18)	0.0261 (16)	0.0329 (17)	−0.0004 (14)	0.0208 (15)	−0.0043 (13)
C28	0.0367 (17)	0.0305 (17)	0.0341 (17)	−0.0008 (15)	0.0168 (14)	−0.0026 (14)
C29	0.048 (2)	0.0337 (18)	0.0399 (19)	−0.0027 (17)	0.0248 (17)	0.0006 (15)
C30	0.044 (2)	0.0372 (19)	0.050 (2)	−0.0135 (17)	0.0301 (18)	−0.0124 (17)
C31	0.0333 (17)	0.0381 (19)	0.0440 (19)	−0.0025 (16)	0.0226 (15)	−0.0121 (16)
C32	0.0348 (18)	0.0303 (17)	0.0391 (18)	0.0024 (15)	0.0184 (15)	−0.0056 (14)
C33	0.0260 (15)	0.0261 (16)	0.0370 (17)	−0.0052 (14)	0.0152 (14)	−0.0064 (14)
C34	0.0325 (17)	0.0330 (17)	0.0375 (18)	−0.0020 (15)	0.0187 (15)	−0.0049 (14)
C35	0.0392 (18)	0.0409 (19)	0.0432 (19)	−0.0096 (17)	0.0250 (16)	−0.0131 (16)
C36	0.0300 (17)	0.044 (2)	0.053 (2)	−0.0025 (17)	0.0225 (16)	−0.0156 (18)
C37	0.0317 (17)	0.0312 (17)	0.053 (2)	0.0009 (15)	0.0162 (16)	−0.0085 (16)
C38	0.0282 (16)	0.0318 (17)	0.0401 (18)	−0.0042 (15)	0.0139 (14)	−0.0031 (15)
N1	0.0241 (12)	0.0302 (14)	0.0413 (15)	−0.0004 (12)	0.0167 (12)	0.0018 (11)
N2	0.0298 (14)	0.0303 (14)	0.0419 (15)	−0.0009 (12)	0.0208 (12)	−0.0017 (12)
O1	0.0349 (12)	0.0372 (13)	0.0590 (15)	−0.0052 (10)	0.0287 (11)	−0.0065 (11)
O2	0.0338 (12)	0.0281 (11)	0.0513 (13)	0.0015 (10)	0.0235 (11)	0.0005 (10)
O3	0.0376 (12)	0.0332 (12)	0.0571 (14)	−0.0045 (10)	0.0302 (11)	−0.0043 (11)
O4	0.0509 (14)	0.0260 (12)	0.0778 (17)	−0.0041 (11)	0.0424 (13)	−0.0092 (11)

Geometric parameters (Å, º)

C1—C2	1.493 (4)	C20—C21	1.497 (4)
C2—N1	1.353 (4)	C21—N2	1.346 (4)
C2—C3	1.396 (4)	C21—C22	1.398 (4)
C3—C4	1.430 (4)	C22—C23	1.429 (4)
C3—C8	1.479 (4)	C22—C27	1.471 (4)
C4—C5	1.391 (4)	C23—C24	1.395 (4)
C4—C14	1.483 (4)	C23—C33	1.486 (4)
C5—N1	1.381 (4)	C24—N2	1.383 (4)
C5—C6	1.440 (4)	C24—C25	1.449 (4)
C6—O1	1.225 (3)	C25—O3	1.218 (3)
C6—O2	1.339 (4)	C25—O4	1.339 (4)
C7—O2	1.445 (4)	C26—O4	1.449 (4)
C8—C9	1.398 (4)	C27—C32	1.396 (4)
C8—C13	1.399 (4)	C27—C28	1.396 (4)
C9—C10	1.379 (4)	C28—C29	1.389 (4)
C10—C11	1.391 (5)	C29—C30	1.374 (4)
C11—C12	1.379 (5)	C30—C31	1.383 (5)
C12—C13	1.383 (4)	C31—C32	1.384 (4)
C14—C15	1.384 (4)	C33—C38	1.388 (4)
C14—C19	1.394 (4)	C33—C34	1.393 (4)
C15—C16	1.390 (4)	C34—C35	1.386 (4)
C16—C17	1.377 (4)	C35—C36	1.369 (4)
C17—C18	1.375 (4)	C36—C37	1.383 (5)
C18—C19	1.379 (4)	C37—C38	1.380 (4)
N1—C2—C3	107.9 (3)	C22—C21—C20	130.4 (3)
N1—C2—C1	120.6 (3)	C21—C22—C23	107.0 (3)
C3—C2—C1	131.4 (3)	C21—C22—C27	126.1 (3)
C2—C3—C4	107.2 (2)	C23—C22—C27	126.9 (3)
C2—C3—C8	125.0 (3)	C24—C23—C22	106.9 (2)
C4—C3—C8	127.8 (3)	C24—C23—C33	129.0 (3)
C5—C4—C3	107.0 (2)	C22—C23—C33	124.0 (3)
C5—C4—C14	125.8 (3)	N2—C24—C23	107.4 (2)
C3—C4—C14	127.2 (2)	N2—C24—C25	116.4 (3)
N1—C5—C4	107.4 (2)	C23—C24—C25	136.1 (3)
N1—C5—C6	117.7 (3)	O3—C25—O4	122.1 (3)
C4—C5—C6	134.8 (3)	O3—C25—C24	124.1 (3)
O1—C6—O2	121.9 (3)	O4—C25—C24	113.8 (3)
O1—C6—C5	123.6 (3)	C32—C27—C28	117.8 (3)
O2—C6—C5	114.5 (3)	C32—C27—C22	120.5 (3)
C9—C8—C13	117.9 (3)	C28—C27—C22	121.6 (3)
C9—C8—C3	120.6 (3)	C29—C28—C27	121.1 (3)
C13—C8—C3	121.4 (3)	C30—C29—C28	120.0 (3)
C10—C9—C8	121.2 (3)	C29—C30—C31	119.9 (3)
C9—C10—C11	120.0 (3)	C30—C31—C32	120.2 (3)
C12—C11—C10	119.5 (3)	C31—C32—C27	120.9 (3)
C11—C12—C13	120.7 (3)	C38—C33—C34	117.9 (3)
C12—C13—C8	120.6 (3)	C38—C33—C23	123.5 (3)
C15—C14—C19	118.4 (3)	C34—C33—C23	118.6 (3)
C15—C14—C4	121.4 (3)	C35—C34—C33	121.2 (3)
C19—C14—C4	120.2 (3)	C36—C35—C34	120.2 (3)
C14—C15—C16	120.9 (3)	C35—C36—C37	119.2 (3)
C17—C16—C15	120.0 (3)	C38—C37—C36	120.9 (3)
C18—C17—C16	119.6 (3)	C37—C38—C33	120.5 (3)
C17—C18—C19	120.7 (3)	C2—N1—C5	110.6 (2)
C18—C19—C14	120.4 (3)	C21—N2—C24	110.4 (2)
N2—C21—C22	108.3 (2)	C6—O2—C7	116.1 (2)
N2—C21—C20	121.2 (3)	C25—O4—C26	117.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.88	2.05	2.875 (3)	157
N2—H2···O1	0.88	1.99	2.829 (3)	158