2-tert-Butyl 4-methyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxyl-ate.

In the title mol-ecule, C(13)H(19)NO(4), except for two C atoms of the tert-butyl group, the non-H atoms are almost coplanar (r.m.s. deviation = 0.2542 Å). In the crystal, mol-ecules are linked into centrosymmetric dimers by two inter-molecular N-H⋯O hydrogen bonds, forming an R(2) (2)(10) ring motif.

Related literature

For complexes of Schiff bases containing a pyrrole unit, see: Wu et al. (2003 ▶); Wang et al. (2008 ▶). For the synthesis of the title compound, see: Sun et al. (2003 ▶).

Experimental

Crystal data

C13H19NO4

M = 253.29

Monoclinic,

a = 11.788 (4) Å

b = 17.045 (6) Å

c = 7.229 (2) Å

β = 106.420 (7)°

V = 1393.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.19 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.983, T max = 0.986

7149 measured reflections

2458 independent reflections

1334 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.250

S = 1.02

2458 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020120/vm2170sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020120/vm2170Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020120/vm2170Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H19NO4	F(000) = 544
Mr = 253.29	Dx = 1.208 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1135 reflections
a = 11.788 (4) Å	θ = 3.0–21.5°
b = 17.045 (6) Å	µ = 0.09 mm−1
c = 7.229 (2) Å	T = 296 K
β = 106.420 (7)°	Plate, colorless
V = 1393.2 (8) Å3	0.19 × 0.18 × 0.16 mm
Z = 4

Bruker SMART CCD diffractometer	2458 independent reflections
Radiation source: fine-focus sealed tube	1334 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→14
Tmin = 0.983, Tmax = 0.986	k = −19→20
7149 measured reflections	l = −8→7

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.250	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1445P)2] where P = (Fo2 + 2Fc2)/3
2458 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	1.1539 (4)	0.4652 (3)	1.0373 (8)	0.1274 (19)
H1B	1.0961	0.5063	1.0193	0.191*
H1C	1.1953	0.4696	0.9409	0.191*
H1D	1.2091	0.4699	1.1630	0.191*
C2	1.1615 (3)	0.3246 (2)	1.0408 (5)	0.0768 (11)
C3	1.0936 (3)	0.25230 (19)	1.0199 (4)	0.0587 (9)
C4	0.9687 (3)	0.24090 (18)	0.9753 (4)	0.0554 (8)
C5	0.9521 (2)	0.16057 (19)	0.9724 (4)	0.0586 (9)
C6	1.1478 (3)	0.1795 (2)	1.0403 (5)	0.0657 (9)
C7	0.8755 (3)	0.30226 (19)	0.9401 (5)	0.0692 (10)
H7A	0.7992	0.2778	0.9138	0.104*
H7B	0.8788	0.3337	0.8315	0.104*
H7C	0.8881	0.3350	1.0521	0.104*
C8	1.2746 (3)	0.1548 (3)	1.0879 (7)	0.0978 (14)
H8A	1.2792	0.0986	1.0897	0.147*
H8B	1.3167	0.1750	1.2123	0.147*
H8C	1.3092	0.1750	0.9923	0.147*
C9	0.8486 (3)	0.1108 (2)	0.9370 (5)	0.0632 (9)
C10	0.6297 (3)	0.1201 (2)	0.8529 (6)	0.0735 (11)
C11	0.6041 (4)	0.0676 (3)	0.6820 (8)	0.131 (2)
H11A	0.6540	0.0222	0.7116	0.197*
H11B	0.6189	0.0952	0.5753	0.197*
H11C	0.5227	0.0517	0.6488	0.197*
C12	0.6181 (4)	0.0814 (3)	1.0336 (7)	0.1063 (15)
H12A	0.6657	0.0348	1.0584	0.159*
H12B	0.5368	0.0677	1.0175	0.159*
H12C	0.6443	0.1169	1.1403	0.159*
C13	0.5522 (3)	0.1940 (3)	0.8125 (8)	0.1084 (16)
H13A	0.5697	0.2261	0.9261	0.163*
H13B	0.4703	0.1790	0.7776	0.163*
H13C	0.5680	0.2229	0.7086	0.163*
O1	1.0949 (2)	0.38906 (15)	1.0199 (4)	0.0925 (9)
O2	1.2657 (3)	0.32986 (18)	1.0728 (6)	0.1295 (13)
O3	0.74888 (17)	0.15373 (14)	0.8891 (3)	0.0713 (8)
O4	0.85058 (19)	0.03974 (15)	0.9488 (4)	0.0876 (9)
N1	1.0615 (2)	0.12471 (17)	1.0127 (4)	0.0674 (8)
H1A	1.0730	0.0748	1.0192	0.081*

	U11	U22	U33	U12	U13	U23
C1	0.101 (3)	0.078 (3)	0.197 (6)	−0.040 (3)	0.032 (3)	−0.010 (3)
C2	0.053 (2)	0.083 (3)	0.088 (3)	−0.0142 (19)	0.0105 (18)	0.0009 (19)
C3	0.0448 (18)	0.064 (2)	0.066 (2)	−0.0079 (15)	0.0136 (14)	0.0011 (15)
C4	0.0457 (17)	0.063 (2)	0.0539 (18)	−0.0049 (14)	0.0090 (13)	−0.0018 (14)
C5	0.0379 (16)	0.070 (2)	0.064 (2)	−0.0014 (14)	0.0084 (13)	−0.0017 (16)
C6	0.0442 (18)	0.078 (2)	0.074 (2)	−0.0119 (16)	0.0149 (15)	−0.0050 (16)
C7	0.0512 (19)	0.060 (2)	0.091 (2)	0.0005 (16)	0.0119 (17)	0.0041 (17)
C8	0.043 (2)	0.099 (3)	0.146 (4)	0.005 (2)	0.019 (2)	−0.001 (3)
C9	0.0475 (19)	0.058 (2)	0.083 (2)	−0.0048 (15)	0.0169 (16)	−0.0033 (17)
C10	0.0416 (18)	0.074 (2)	0.102 (3)	−0.0111 (16)	0.0146 (17)	−0.009 (2)
C11	0.067 (3)	0.164 (5)	0.141 (4)	−0.010 (3)	−0.005 (3)	−0.062 (4)
C12	0.075 (3)	0.098 (3)	0.152 (4)	−0.020 (2)	0.041 (3)	0.009 (3)
C13	0.050 (2)	0.110 (4)	0.159 (4)	0.008 (2)	0.018 (2)	0.002 (3)
O1	0.0673 (17)	0.0635 (16)	0.145 (3)	−0.0193 (14)	0.0268 (16)	−0.0068 (15)
O2	0.0530 (18)	0.103 (2)	0.215 (4)	−0.0239 (15)	0.0100 (19)	0.007 (2)
O3	0.0359 (12)	0.0687 (15)	0.1046 (19)	−0.0050 (10)	0.0120 (11)	0.0016 (12)
O4	0.0523 (14)	0.0607 (17)	0.144 (2)	−0.0030 (11)	0.0180 (14)	−0.0099 (14)
N1	0.0442 (15)	0.0624 (16)	0.093 (2)	−0.0020 (13)	0.0149 (13)	−0.0030 (14)

C1—O1	1.461 (5)	C8—H8B	0.9600
C1—H1B	0.9600	C8—H8C	0.9600
C1—H1C	0.9600	C9—O4	1.215 (4)
C1—H1D	0.9600	C9—O3	1.344 (4)
C2—O2	1.188 (4)	C10—O3	1.470 (4)
C2—O1	1.334 (4)	C10—C11	1.486 (6)
C2—C3	1.454 (5)	C10—C12	1.504 (6)
C3—C6	1.385 (5)	C10—C13	1.534 (5)
C3—C4	1.429 (4)	C11—H11A	0.9600
C4—C5	1.383 (4)	C11—H11B	0.9600
C4—C7	1.486 (4)	C11—H11C	0.9600
C5—N1	1.382 (4)	C12—H12A	0.9600
C5—C9	1.448 (4)	C12—H12B	0.9600
C6—N1	1.354 (4)	C12—H12C	0.9600
C6—C8	1.496 (5)	C13—H13A	0.9600
C7—H7A	0.9600	C13—H13B	0.9600
C7—H7B	0.9600	C13—H13C	0.9600
C7—H7C	0.9600	N1—H1A	0.8600
C8—H8A	0.9600
O1—C1—H1B	109.5	O4—C9—O3	124.0 (3)
O1—C1—H1C	109.5	O4—C9—C5	125.0 (3)
H1B—C1—H1C	109.5	O3—C9—C5	111.0 (3)
O1—C1—H1D	109.5	O3—C10—C11	110.0 (3)
H1B—C1—H1D	109.5	O3—C10—C12	109.5 (3)
H1C—C1—H1D	109.5	C11—C10—C12	114.2 (4)
O2—C2—O1	120.2 (4)	O3—C10—C13	101.7 (3)
O2—C2—C3	126.4 (4)	C11—C10—C13	111.4 (4)
O1—C2—C3	113.4 (3)	C12—C10—C13	109.3 (3)
C6—C3—C4	108.5 (3)	C10—C11—H11A	109.5
C6—C3—C2	121.7 (3)	C10—C11—H11B	109.5
C4—C3—C2	129.8 (3)	H11A—C11—H11B	109.5
C5—C4—C3	105.7 (3)	C10—C11—H11C	109.5
C5—C4—C7	126.9 (3)	H11A—C11—H11C	109.5
C3—C4—C7	127.4 (3)	H11B—C11—H11C	109.5
N1—C5—C4	108.4 (3)	C10—C12—H12A	109.5
N1—C5—C9	117.9 (3)	C10—C12—H12B	109.5
C4—C5—C9	133.7 (3)	H12A—C12—H12B	109.5
N1—C6—C3	107.3 (3)	C10—C12—H12C	109.5
N1—C6—C8	120.0 (3)	H12A—C12—H12C	109.5
C3—C6—C8	132.6 (3)	H12B—C12—H12C	109.5
C4—C7—H7A	109.5	C10—C13—H13A	109.5
C4—C7—H7B	109.5	C10—C13—H13B	109.5
H7A—C7—H7B	109.5	H13A—C13—H13B	109.5
C4—C7—H7C	109.5	C10—C13—H13C	109.5
H7A—C7—H7C	109.5	H13A—C13—H13C	109.5
H7B—C7—H7C	109.5	H13B—C13—H13C	109.5
C6—C8—H8A	109.5	C2—O1—C1	118.1 (3)
C6—C8—H8B	109.5	C9—O3—C10	123.8 (3)
H8A—C8—H8B	109.5	C6—N1—C5	110.1 (3)
C6—C8—H8C	109.5	C6—N1—H1A	124.9
H8A—C8—H8C	109.5	C5—N1—H1A	124.9
H8B—C8—H8C	109.5
O2—C2—C3—C6	1.3 (6)	N1—C5—C9—O4	3.7 (5)
O1—C2—C3—C6	−178.8 (3)	C4—C5—C9—O4	−176.5 (4)
O2—C2—C3—C4	−177.7 (4)	N1—C5—C9—O3	−176.4 (3)
O1—C2—C3—C4	2.2 (5)	C4—C5—C9—O3	3.4 (5)
C6—C3—C4—C5	0.6 (4)	O2—C2—O1—C1	0.1 (6)
C2—C3—C4—C5	179.7 (3)	C3—C2—O1—C1	−179.8 (3)
C6—C3—C4—C7	−179.6 (3)	O4—C9—O3—C10	2.7 (5)
C2—C3—C4—C7	−0.6 (6)	C5—C9—O3—C10	−177.2 (3)
C3—C4—C5—N1	−0.2 (3)	C11—C10—O3—C9	−63.7 (5)
C7—C4—C5—N1	−179.9 (3)	C12—C10—O3—C9	62.6 (4)
C3—C4—C5—C9	180.0 (3)	C13—C10—O3—C9	178.1 (3)
C7—C4—C5—C9	0.2 (6)	C3—C6—N1—C5	0.7 (4)
C4—C3—C6—N1	−0.8 (4)	C8—C6—N1—C5	179.4 (3)
C2—C3—C6—N1	−180.0 (3)	C4—C5—N1—C6	−0.4 (4)
C4—C3—C6—C8	−179.3 (4)	C9—C5—N1—C6	179.5 (3)
C2—C3—C6—C8	1.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.86	2.14	2.974 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.86	2.14	2.974 (4)	165

Symmetry code: (i) .