tert-Butyl 4-[2-(methoxy­carbonyl)­ethyl]-3,5-di­methyl-1H-pyrrole-2-carboxyl­ate

In the solid state, the title compound, C₁₅H₂₃NO₄, forms centrosymmetric dimers in which individual mol­ecules are linked by intermolecular N—H...O hydrogen bonds. The pyrrole ring is planar within 0.004 (9) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.130
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

tert-Butyl 4-[2-(methoxycarbonyl)ethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate

Crystal data

C15H23NO4	Z = 2
Mr = 281.34	F(000) = 304
Triclinic, P1	Dx = 1.172 Mg m^−3
a = 6.1468 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.261 (2) Å	Cell parameters from 25 reflections
c = 12.9983 (7) Å	θ = 9.7–15.8°
α = 114.775 (10)°	µ = 0.08 mm^−1
β = 92.134 (11)°	T = 293 K
γ = 100.408 (10)°	Plate, colourless
V = 797.0 (2) Å^3	0.34 × 0.25 × 0.09 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.009
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 3.2°
Graphite monochromator	h = −6→7
profile data from ω–2θ scans	k = −13→13
3470 measured reflections	l = −15→15
2836 independent reflections	3 standard reflections every 180 min
2418 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0678P)^2 + 0.194P] where P = (Fo^2 + 2Fc^2)/3
2836 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.19 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
N	0.4397 (2)	0.11540 (13)	0.40420 (11)	0.0470 (3)
H	0.5289	0.0967	0.4450	0.056*
O2	−0.01061 (19)	−0.16918 (11)	0.27029 (10)	0.0553 (3)
C7	−0.1126 (3)	−0.30634 (16)	0.25229 (15)	0.0514 (4)
C3	0.1423 (3)	0.09987 (15)	0.29126 (13)	0.0447 (4)
O1	0.2611 (2)	−0.13009 (13)	0.40954 (12)	0.0686 (4)
O3	0.6716 (2)	0.30831 (15)	0.16712 (12)	0.0741 (4)
O4	0.4673 (2)	0.16400 (16)	0.00318 (11)	0.0754 (4)
C2	0.2374 (3)	0.03498 (15)	0.34564 (12)	0.0445 (4)
C6	0.1664 (3)	−0.09387 (16)	0.34761 (13)	0.0471 (4)
C4	0.2963 (3)	0.22208 (15)	0.31825 (12)	0.0455 (4)
C14	0.4928 (3)	0.25472 (16)	0.11109 (14)	0.0482 (4)
C5	0.4780 (3)	0.22838 (15)	0.38830 (12)	0.0467 (4)
C12	0.2680 (3)	0.32616 (16)	0.27776 (15)	0.0543 (4)
H12A	0.3858	0.4053	0.3183	0.065*
H12B	0.1270	0.3515	0.2970	0.065*
C11	−0.0798 (3)	0.05314 (18)	0.21975 (16)	0.0590 (4)
H11A	−0.0685	−0.0118	0.1444	0.088*
H11B	−0.1254	0.1281	0.2151	0.088*
H11C	−0.1878	0.0131	0.2539	0.088*
C16	0.6860 (3)	0.33383 (18)	0.44264 (16)	0.0624 (5)
H16A	0.7009	0.3950	0.4082	0.094*
H16B	0.8124	0.2927	0.4318	0.094*
H16C	0.6787	0.3817	0.5229	0.094*
C13	0.2729 (3)	0.27932 (19)	0.14933 (15)	0.0574 (4)
H13A	0.1607	0.1973	0.1090	0.069*
H13B	0.2334	0.3465	0.1283	0.069*
C9	0.0547 (4)	−0.3940 (2)	0.2163 (2)	0.0781 (6)
H9A	0.1150	−0.3895	0.1507	0.117*
H9B	−0.0173	−0.4849	0.1976	0.117*
H9C	0.1729	−0.3637	0.2778	0.117*
C8	−0.2096 (4)	−0.3044 (3)	0.3569 (2)	0.0880 (7)
H8A	−0.0918	−0.2749	0.4184	0.132*
H8B	−0.2894	−0.3929	0.3413	0.132*
H8C	−0.3098	−0.2442	0.3780	0.132*
C15	0.6672 (4)	0.1353 (3)	−0.0474 (2)	0.0992 (8)
H15A	0.7561	0.2157	−0.0458	0.149*
H15B	0.6282	0.0688	−0.1251	0.149*
H15C	0.7507	0.1024	−0.0051	0.149*
C10	−0.2954 (4)	−0.3483 (2)	0.1548 (2)	0.0900 (8)
H10A	−0.3956	−0.2881	0.1775	0.135*
H10B	−0.3760	−0.4377	0.1356	0.135*
H10C	−0.2307	−0.3457	0.0896	0.135*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0523 (8)	0.0466 (7)	0.0401 (7)	0.0050 (6)	−0.0003 (5)	0.0197 (6)
O2	0.0556 (7)	0.0452 (6)	0.0624 (7)	−0.0002 (5)	−0.0110 (5)	0.0265 (5)
C7	0.0480 (9)	0.0439 (8)	0.0605 (10)	0.0009 (7)	0.0014 (7)	0.0250 (8)
C3	0.0497 (8)	0.0420 (8)	0.0410 (8)	0.0138 (7)	0.0089 (6)	0.0149 (6)
O1	0.0733 (8)	0.0625 (8)	0.0714 (8)	−0.0064 (6)	−0.0207 (7)	0.0412 (7)
O3	0.0575 (8)	0.0766 (9)	0.0709 (9)	−0.0007 (7)	0.0020 (7)	0.0222 (7)
O4	0.0662 (8)	0.0994 (11)	0.0477 (7)	0.0241 (7)	0.0057 (6)	0.0171 (7)
C2	0.0478 (8)	0.0428 (8)	0.0394 (8)	0.0066 (6)	0.0038 (6)	0.0158 (6)
C6	0.0485 (8)	0.0470 (8)	0.0442 (8)	0.0059 (7)	0.0022 (7)	0.0204 (7)
C4	0.0565 (9)	0.0396 (8)	0.0388 (8)	0.0130 (7)	0.0110 (6)	0.0140 (6)
C14	0.0543 (9)	0.0472 (8)	0.0485 (9)	0.0086 (7)	0.0036 (7)	0.0271 (7)
C5	0.0558 (9)	0.0425 (8)	0.0374 (8)	0.0061 (7)	0.0080 (7)	0.0147 (6)
C12	0.0661 (10)	0.0452 (9)	0.0569 (10)	0.0208 (8)	0.0162 (8)	0.0231 (8)
C11	0.0527 (10)	0.0569 (10)	0.0686 (11)	0.0146 (8)	−0.0002 (8)	0.0279 (9)
C16	0.0683 (11)	0.0520 (10)	0.0544 (10)	−0.0047 (8)	−0.0015 (8)	0.0192 (8)
C13	0.0620 (10)	0.0639 (10)	0.0589 (10)	0.0221 (8)	0.0084 (8)	0.0350 (9)
C9	0.0673 (12)	0.0535 (11)	0.1042 (17)	0.0122 (9)	0.0147 (11)	0.0253 (11)
C8	0.0860 (15)	0.0877 (15)	0.0811 (15)	−0.0065 (12)	0.0255 (12)	0.0367 (13)
C15	0.0896 (17)	0.140 (2)	0.0694 (14)	0.0488 (16)	0.0322 (13)	0.0349 (15)
C10	0.0798 (15)	0.0710 (14)	0.1050 (18)	−0.0167 (11)	−0.0339 (13)	0.0414 (13)

Geometric parameters (Å, º)

N—C5	1.354 (2)	C12—H12B	0.9700
N—C2	1.375 (2)	C11—H11A	0.9600
N—H	0.8600	C11—H11B	0.9600
O2—C6	1.3356 (19)	C11—H11C	0.9600
O2—C7	1.4729 (19)	C16—H16A	0.9600
C7—C8	1.498 (3)	C16—H16B	0.9600
C7—C9	1.505 (3)	C16—H16C	0.9600
C7—C10	1.514 (3)	C13—H13A	0.9700
C3—C2	1.390 (2)	C13—H13B	0.9700
C3—C4	1.419 (2)	C9—H9A	0.9600
C3—C11	1.497 (2)	C9—H9B	0.9600
O1—C6	1.2164 (19)	C9—H9C	0.9600
O3—C14	1.197 (2)	C8—H8A	0.9600
O4—C14	1.327 (2)	C8—H8B	0.9600
O4—C15	1.440 (3)	C8—H8C	0.9600
C2—C6	1.449 (2)	C15—H15A	0.9600
C4—C5	1.387 (2)	C15—H15B	0.9600
C4—C12	1.505 (2)	C15—H15C	0.9600
C14—C13	1.490 (2)	C10—H10A	0.9600
C5—C16	1.492 (2)	C10—H10B	0.9600
C12—C13	1.529 (2)	C10—H10C	0.9600
C12—H12A	0.9700
C5—N—C2	110.06 (13)	H11A—C11—H11C	109.5
C5—N—H	125.0	H11B—C11—H11C	109.5
C2—N—H	125.0	C5—C16—H16A	109.5
C6—O2—C7	122.62 (12)	C5—C16—H16B	109.5
O2—C7—C8	110.33 (15)	H16A—C16—H16B	109.5
O2—C7—C9	110.17 (14)	C5—C16—H16C	109.5
C8—C7—C9	112.85 (19)	H16A—C16—H16C	109.5
O2—C7—C10	101.85 (14)	H16B—C16—H16C	109.5
C8—C7—C10	110.62 (19)	C14—C13—C12	114.04 (14)
C9—C7—C10	110.48 (18)	C14—C13—H13A	108.7
C2—C3—C4	106.42 (14)	C12—C13—H13A	108.7
C2—C3—C11	127.54 (15)	C14—C13—H13B	108.7
C4—C3—C11	126.04 (14)	C12—C13—H13B	108.7
C14—O4—C15	116.96 (17)	H13A—C13—H13B	107.6
N—C2—C3	107.90 (13)	C7—C9—H9A	109.5
N—C2—C6	119.30 (14)	C7—C9—H9B	109.5
C3—C2—C6	132.78 (15)	H9A—C9—H9B	109.5
O1—C6—O2	124.45 (15)	C7—C9—H9C	109.5
O1—C6—C2	123.99 (15)	H9A—C9—H9C	109.5
O2—C6—C2	111.52 (13)	H9B—C9—H9C	109.5
C5—C4—C3	107.83 (14)	C7—C8—H8A	109.5
C5—C4—C12	126.07 (15)	C7—C8—H8B	109.5
C3—C4—C12	126.10 (15)	H8A—C8—H8B	109.5
O3—C14—O4	122.88 (16)	C7—C8—H8C	109.5
O3—C14—C13	126.34 (16)	H8A—C8—H8C	109.5
O4—C14—C13	110.78 (15)	H8B—C8—H8C	109.5
N—C5—C4	107.79 (14)	O4—C15—H15A	109.5
N—C5—C16	121.37 (15)	O4—C15—H15B	109.5
C4—C5—C16	130.84 (15)	H15A—C15—H15B	109.5
C4—C12—C13	113.71 (13)	O4—C15—H15C	109.5
C4—C12—H12A	108.8	H15A—C15—H15C	109.5
C13—C12—H12A	108.8	H15B—C15—H15C	109.5
C4—C12—H12B	108.8	C7—C10—H10A	109.5
C13—C12—H12B	108.8	C7—C10—H10B	109.5
H12A—C12—H12B	107.7	H10A—C10—H10B	109.5
C3—C11—H11A	109.5	C7—C10—H10C	109.5
C3—C11—H11B	109.5	H10A—C10—H10C	109.5
H11A—C11—H11B	109.5	H10B—C10—H10C	109.5
C3—C11—H11C	109.5
C6—O2—C7—C8	64.8 (2)	C11—C3—C4—C5	178.60 (15)
C6—O2—C7—C9	−60.4 (2)	C2—C3—C4—C12	179.36 (14)
C6—O2—C7—C10	−177.70 (17)	C11—C3—C4—C12	−1.6 (2)
C5—N—C2—C3	−0.58 (17)	C15—O4—C14—O3	−2.6 (3)
C5—N—C2—C6	177.84 (13)	C15—O4—C14—C13	176.72 (18)
C4—C3—C2—N	0.63 (17)	C2—N—C5—C4	0.28 (17)
C11—C3—C2—N	−178.41 (15)	C2—N—C5—C16	179.83 (15)
C4—C3—C2—C6	−177.49 (16)	C3—C4—C5—N	0.12 (17)
C11—C3—C2—C6	3.5 (3)	C12—C4—C5—N	−179.71 (14)
C7—O2—C6—O1	0.5 (3)	C3—C4—C5—C16	−179.37 (16)
C7—O2—C6—C2	178.28 (13)	C12—C4—C5—C16	0.8 (3)
N—C2—C6—O1	9.6 (2)	C5—C4—C12—C13	112.33 (18)
C3—C2—C6—O1	−172.45 (17)	C3—C4—C12—C13	−67.5 (2)
N—C2—C6—O2	−168.20 (13)	O3—C14—C13—C12	−27.9 (3)
C3—C2—C6—O2	9.7 (3)	O4—C14—C13—C12	152.77 (15)
C2—C3—C4—C5	−0.46 (17)	C4—C12—C13—C14	−66.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H···O1^i	0.86	2.10	2.9142 (18)	157

Symmetry code: (i) −x+1, −y, −z+1.