Dibenzyl 3,3',4,4'-tetra-methyl-5,5'-(ethynedi-yl)bis-(pyrrole-2-carboxyl-ate).

The title mol-ecule, C(30)H(28)N(2)O(4), has crystallographic twofold rotation symmetry, with the pyrrole planes forming a dihedral angle of 40.49 (4)°. The pyrrole N-H donor and adjacent ester carbonyl acceptor form R(2) (2)(10) hydrogen-bonded rings about inversion centers, leading to chains of hydrogen-bonded mol-ecules along [001].

Related literature

For background literature, see: Chinchilla & Najera (2007 ▶); Black et al. (1999 ▶); Etter (1990 ▶); Vogel (1996 ▶). For related structures, see: Xie et al. (1996 ▶); Weghorn et al. (1995 ▶).

Experimental

Crystal data

C30H28N2O4

M = 480.54

Monoclinic,

a = 19.340 (2) Å

b = 9.8955 (10) Å

c = 13.8495 (15) Å

β = 110.217 (6)°

V = 2487.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 90 K

0.30 × 0.22 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream

Absorption correction: none

28071 measured reflections

4748 independent reflections

3948 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.03

4748 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.39 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061739/dn2299sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061739/dn2299Isup2.hkl

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

C30H28N2O4	F000 = 1016
Mr = 480.54	Dx = 1.283 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4869 reflections
a = 19.340 (2) Å	θ = 2.5–33.1º
b = 9.8955 (10) Å	µ = 0.09 mm−1
c = 13.8495 (15) Å	T = 90 K
β = 110.217 (6)º	Prism, colorless
V = 2487.2 (5) Å3	0.30 × 0.22 × 0.15 mm
Z = 4

Nonius KappaCCD (with Oxford Cryostream) diffractometer	3948 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Monochromator: graphite	θmax = 33.2º
T = 90 K	θmin = 2.6º
ω scans with κ offsets	h = −29→29
Absorption correction: none	k = −15→15
28071 measured reflections	l = −21→21
4748 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.067P)2 + 1.378P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4748 reflections	Δρmax = 0.46 e Å−3
168 parameters	Δρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.38808 (4)	0.18151 (7)	0.63308 (5)	0.01536 (14)
O2	0.45716 (4)	0.03182 (7)	0.58415 (5)	0.01670 (14)
N1	0.46808 (4)	0.21012 (7)	0.43512 (5)	0.01204 (14)
H1N	0.4897 (7)	0.1328 (14)	0.4339 (10)	0.014*
C1	0.43250 (5)	0.24465 (9)	0.50220 (6)	0.01179 (15)
C2	0.40633 (5)	0.37712 (9)	0.48108 (6)	0.01253 (15)
C3	0.42701 (5)	0.42307 (8)	0.39832 (6)	0.01261 (15)
C4	0.46445 (5)	0.31725 (8)	0.37111 (6)	0.01224 (15)
C5	0.49073 (5)	0.31065 (9)	0.28744 (6)	0.01342 (15)
C6	0.42810 (5)	0.14317 (8)	0.57551 (6)	0.01202 (15)
C7	0.36367 (5)	0.45910 (9)	0.53229 (7)	0.01701 (17)
H7A	0.3974	0.5187	0.5838	0.026*
H7B	0.3389	0.3985	0.5660	0.026*
H7C	0.3268	0.5137	0.4806	0.026*
C8	0.40864 (6)	0.55667 (9)	0.34548 (7)	0.01793 (17)
H8A	0.4358	0.5673	0.2979	0.027*
H8B	0.4225	0.6292	0.3968	0.027*
H8C	0.3556	0.5612	0.3071	0.027*
C9	0.37901 (5)	0.07780 (9)	0.70202 (7)	0.01577 (16)
H9A	0.4274	0.0553	0.7543	0.019*
H9B	0.3584	−0.0052	0.6627	0.019*
C10	0.32768 (5)	0.13018 (9)	0.75362 (6)	0.01280 (15)
C11	0.26606 (5)	0.20803 (9)	0.70116 (7)	0.01592 (16)
H11	0.2572	0.2337	0.6318	0.019*
C12	0.21747 (5)	0.24831 (10)	0.74984 (8)	0.01892 (18)
H12	0.1761	0.3027	0.7141	0.023*
C13	0.22929 (6)	0.20909 (11)	0.85086 (8)	0.0228 (2)
H13	0.1954	0.2346	0.8835	0.027*
C14	0.29082 (6)	0.13248 (11)	0.90349 (8)	0.0235 (2)
H14	0.2992	0.1058	0.9725	0.028*
C15	0.34045 (5)	0.09438 (10)	0.85570 (7)	0.01773 (17)
H15	0.3831	0.0438	0.8928	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0226 (3)	0.0130 (3)	0.0161 (3)	0.0032 (2)	0.0138 (2)	0.0026 (2)
O2	0.0229 (3)	0.0139 (3)	0.0171 (3)	0.0063 (2)	0.0118 (2)	0.0028 (2)
N1	0.0154 (3)	0.0107 (3)	0.0129 (3)	0.0023 (2)	0.0085 (2)	0.0010 (2)
C1	0.0147 (3)	0.0117 (3)	0.0115 (3)	0.0011 (3)	0.0077 (3)	−0.0001 (3)
C2	0.0151 (3)	0.0117 (3)	0.0128 (3)	0.0017 (3)	0.0074 (3)	−0.0004 (3)
C3	0.0151 (4)	0.0111 (3)	0.0132 (3)	0.0015 (3)	0.0069 (3)	0.0005 (3)
C4	0.0145 (3)	0.0119 (3)	0.0124 (3)	0.0002 (3)	0.0073 (3)	0.0006 (3)
C5	0.0149 (4)	0.0125 (3)	0.0147 (3)	0.0001 (3)	0.0075 (3)	0.0000 (3)
C6	0.0142 (3)	0.0127 (3)	0.0107 (3)	0.0010 (3)	0.0063 (3)	0.0001 (3)
C7	0.0224 (4)	0.0148 (4)	0.0183 (4)	0.0043 (3)	0.0127 (3)	−0.0008 (3)
C8	0.0241 (4)	0.0128 (4)	0.0192 (4)	0.0035 (3)	0.0105 (3)	0.0038 (3)
C9	0.0220 (4)	0.0145 (4)	0.0152 (3)	0.0034 (3)	0.0119 (3)	0.0038 (3)
C10	0.0159 (4)	0.0120 (3)	0.0128 (3)	−0.0016 (3)	0.0080 (3)	−0.0005 (3)
C11	0.0158 (4)	0.0180 (4)	0.0145 (3)	−0.0009 (3)	0.0060 (3)	−0.0004 (3)
C12	0.0155 (4)	0.0186 (4)	0.0248 (4)	−0.0006 (3)	0.0095 (3)	−0.0019 (3)
C13	0.0274 (5)	0.0211 (4)	0.0285 (5)	−0.0009 (4)	0.0209 (4)	−0.0028 (4)
C14	0.0351 (5)	0.0238 (5)	0.0190 (4)	0.0027 (4)	0.0188 (4)	0.0021 (4)
C15	0.0240 (4)	0.0169 (4)	0.0150 (4)	0.0026 (3)	0.0101 (3)	0.0020 (3)

O1—C6	1.3436 (10)	C8—H8A	0.9800
O1—C9	1.4530 (10)	C8—H8B	0.9800
O2—C6	1.2240 (10)	C8—H8C	0.9800
N1—C4	1.3680 (11)	C9—C10	1.5018 (12)
N1—C1	1.3767 (10)	C9—H9A	0.9900
N1—H1N	0.875 (14)	C9—H9B	0.9900
C1—C2	1.3992 (12)	C10—C11	1.3940 (12)
C1—C6	1.4514 (11)	C10—C15	1.3941 (12)
C2—C3	1.4133 (11)	C11—C12	1.3910 (13)
C2—C7	1.4987 (12)	C11—H11	0.9500
C3—C4	1.3969 (12)	C12—C13	1.3925 (15)
C3—C8	1.4932 (12)	C12—H12	0.9500
C4—C5	1.4185 (12)	C13—C14	1.3866 (16)
C5—C5i	1.2088 (17)	C13—H13	0.9500
C7—H7A	0.9800	C14—C15	1.3931 (13)
C7—H7B	0.9800	C14—H14	0.9500
C7—H7C	0.9800	C15—H15	0.9500
C6—O1—C9	114.55 (7)	H8A—C8—H8B	109.5
C4—N1—C1	108.62 (7)	C3—C8—H8C	109.5
C4—N1—H1N	125.7 (8)	H8A—C8—H8C	109.5
C1—N1—H1N	125.7 (8)	H8B—C8—H8C	109.5
N1—C1—C2	108.70 (7)	O1—C9—C10	108.58 (7)
N1—C1—C6	117.66 (7)	O1—C9—H9A	110.0
C2—C1—C6	133.63 (7)	C10—C9—H9A	110.0
C1—C2—C3	106.71 (7)	O1—C9—H9B	110.0
C1—C2—C7	128.81 (8)	C10—C9—H9B	110.0
C3—C2—C7	124.47 (8)	H9A—C9—H9B	108.4
C4—C3—C2	107.22 (7)	C11—C10—C15	119.27 (8)
C4—C3—C8	126.09 (8)	C11—C10—C9	121.96 (7)
C2—C3—C8	126.60 (8)	C15—C10—C9	118.70 (8)
N1—C4—C3	108.75 (7)	C12—C11—C10	120.32 (8)
N1—C4—C5	122.75 (8)	C12—C11—H11	119.8
C3—C4—C5	128.34 (8)	C10—C11—H11	119.8
C5i—C5—C4	175.61 (10)	C11—C12—C13	120.22 (9)
O2—C6—O1	122.38 (8)	C11—C12—H12	119.9
O2—C6—C1	123.73 (8)	C13—C12—H12	119.9
O1—C6—C1	113.89 (7)	C14—C13—C12	119.58 (9)
C2—C7—H7A	109.5	C14—C13—H13	120.2
C2—C7—H7B	109.5	C12—C13—H13	120.2
H7A—C7—H7B	109.5	C13—C14—C15	120.35 (9)
C2—C7—H7C	109.5	C13—C14—H14	119.8
H7A—C7—H7C	109.5	C15—C14—H14	119.8
H7B—C7—H7C	109.5	C14—C15—C10	120.22 (9)
C3—C8—H8A	109.5	C14—C15—H15	119.9
C3—C8—H8B	109.5	C10—C15—H15	119.9
C4—N1—C1—C2	−0.61 (10)	C9—O1—C6—C1	176.08 (7)
C4—N1—C1—C6	178.33 (7)	N1—C1—C6—O2	3.67 (13)
N1—C1—C2—C3	0.08 (10)	C2—C1—C6—O2	−177.72 (9)
C6—C1—C2—C3	−178.63 (9)	N1—C1—C6—O1	−175.51 (7)
N1—C1—C2—C7	179.36 (9)	C2—C1—C6—O1	3.10 (14)
C6—C1—C2—C7	0.65 (16)	C6—O1—C9—C10	−174.76 (7)
C1—C2—C3—C4	0.47 (10)	O1—C9—C10—C11	38.88 (11)
C7—C2—C3—C4	−178.85 (8)	O1—C9—C10—C15	−144.09 (8)
C1—C2—C3—C8	177.24 (9)	C15—C10—C11—C12	−0.68 (14)
C7—C2—C3—C8	−2.09 (14)	C9—C10—C11—C12	176.33 (9)
C1—N1—C4—C3	0.92 (10)	C10—C11—C12—C13	−1.15 (14)
C1—N1—C4—C5	−174.76 (8)	C11—C12—C13—C14	1.62 (16)
C2—C3—C4—N1	−0.86 (10)	C12—C13—C14—C15	−0.25 (16)
C8—C3—C4—N1	−177.64 (8)	C13—C14—C15—C10	−1.59 (16)
C2—C3—C4—C5	174.51 (8)	C11—C10—C15—C14	2.04 (14)
C8—C3—C4—C5	−2.28 (15)	C9—C10—C15—C14	−175.07 (9)
C9—O1—C6—O2	−3.12 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ii	0.875 (14)	1.987 (14)	2.8565 (10)	172.1 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.875 (14)	1.987 (14)	2.8565 (10)	172.1 (12)

Symmetry code: (i) .