4-Pyridylmethyl 1H-pyrrole-2-carboxyl­ate

The title compound, C₁₁H₁₀N₂O₂, has been synthesized by the reaction of 2-(trichloro­acet­yl)pyrrole with 4-(hydroxy­meth­yl)pyridine. In the solid state, the mol­ecules form a one-dimensional infinite ladder structure through inter­molecular N—H...N and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.121
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         41 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C6      ..       5.98 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       5.68 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

4-Pyridylmethyl 1H-pyrrole-2-carboxylate

Crystal data

C11H10N2O2	Dx = 1.275 Mg m^−3
Mr = 202.21	Melting point: 411 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.698 (3) Å	Cell parameters from 951 reflections
b = 15.796 (6) Å	θ = 2.6–21.5°
c = 8.789 (3) Å	µ = 0.09 mm^−1
β = 99.771 (7)°	T = 294 K
V = 1053.2 (7) Å^3	LABLLAR, colorless
Z = 4	0.26 × 0.24 × 0.20 mm
F(000) = 424

Data collection

Bruker SMART CCD area-detector diffractometer	2147 independent reflections
Radiation source: fine-focus sealed tube	884 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→9
Tmin = 0.977, Tmax = 0.982	k = −18→19
5812 measured reflections	l = −7→11

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0526P)^2] where P = (Fo^2 + 2Fc^2)/3
2147 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.15 e Å^−3
1 restraint	Δρmin = −0.15 e Å^−3

Special details

Experimental. ¹H NMR (300 MHz, CDCl₃): δ 9.36 (b, 1H, NH), 8.61 (d, 2H, J = 3 Hz, CH), 7.31 (d, 2H, J = 3 Hz, CH), 7.00–7.04 (m, 2H, –CH═), 6.30–6.33 (m, 1H, –CH═), 5.33 (s, 2H, –CH₂). ESI–MS (m/z): 203 (M + H⁺). Analysis calculated for C₁₁H₁₀N₂O₂: C 65.34, H 4.98, N 13.85%; found: C 65.25, H 5.07, N 13.76%.

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
O1	0.13863 (18)	0.62036 (10)	0.70839 (19)	0.0733 (5)
O2	0.2723 (2)	0.68122 (11)	0.52945 (19)	0.0880 (6)
N1	0.2301 (3)	0.45899 (19)	1.1917 (3)	0.0852 (7)
N2	−0.1841 (3)	0.63798 (13)	0.5375 (2)	0.0698 (6)
C1	0.2951 (3)	0.59320 (18)	1.0912 (4)	0.0843 (8)
H1	0.3227	0.6500	1.1103	0.101*
C2	0.2703 (4)	0.5397 (3)	1.2102 (3)	0.0946 (10)
H2	0.2828	0.5621	1.3093	0.114*
C3	0.2122 (3)	0.43009 (18)	1.0493 (4)	0.0824 (8)
H3	0.1827	0.3734	1.0325	0.099*
C4	0.2341 (3)	0.47806 (17)	0.9251 (3)	0.0726 (7)
H4	0.2191	0.4541	0.8271	0.087*
C5	0.2782 (3)	0.56110 (17)	0.9451 (3)	0.0611 (6)
C6	0.3060 (3)	0.61480 (18)	0.8113 (3)	0.0899 (9)
H6A	0.3463	0.6708	0.8465	0.108*
H6B	0.3940	0.5894	0.7585	0.108*
C7	0.1383 (3)	0.65758 (14)	0.5707 (3)	0.0626 (6)
C8	−0.0373 (3)	0.66576 (14)	0.4843 (2)	0.0568 (6)
C9	−0.0932 (3)	0.70623 (15)	0.3474 (3)	0.0714 (7)
H9	−0.0212	0.7314	0.2855	0.086*
C10	−0.2766 (3)	0.70330 (16)	0.3164 (3)	0.0752 (7)
H10	−0.3494	0.7258	0.2307	0.090*
C11	−0.3282 (3)	0.66119 (17)	0.4357 (3)	0.0768 (7)
H11	−0.4443	0.6500	0.4458	0.092*
H2A	−0.183 (4)	0.6091 (16)	0.626 (2)	0.135 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0468 (10)	0.0967 (13)	0.0776 (12)	0.0001 (8)	0.0136 (8)	0.0202 (9)
O2	0.0619 (12)	0.1079 (15)	0.1027 (13)	−0.0067 (10)	0.0379 (10)	0.0169 (10)
N1	0.0611 (15)	0.117 (2)	0.0776 (19)	−0.0055 (14)	0.0108 (12)	0.0125 (15)
N2	0.0557 (13)	0.0963 (17)	0.0597 (14)	−0.0070 (11)	0.0165 (11)	0.0020 (12)
C1	0.0706 (19)	0.076 (2)	0.104 (2)	−0.0081 (14)	0.0102 (17)	−0.0228 (19)
C2	0.077 (2)	0.139 (3)	0.068 (2)	−0.007 (2)	0.0134 (15)	−0.026 (2)
C3	0.0817 (19)	0.074 (2)	0.089 (2)	−0.0048 (14)	0.0067 (15)	0.0010 (18)
C4	0.0760 (19)	0.075 (2)	0.0666 (18)	−0.0002 (15)	0.0100 (13)	−0.0055 (15)
C5	0.0392 (13)	0.0688 (19)	0.0751 (19)	−0.0010 (12)	0.0091 (11)	0.0059 (14)
C6	0.0486 (16)	0.106 (2)	0.112 (2)	−0.0047 (14)	0.0057 (15)	0.0307 (17)
C7	0.0620 (17)	0.0628 (16)	0.0684 (17)	0.0008 (13)	0.0268 (13)	−0.0014 (13)
C8	0.0555 (14)	0.0631 (15)	0.0555 (14)	−0.0024 (12)	0.0200 (11)	−0.0035 (12)
C9	0.0765 (19)	0.0747 (18)	0.0659 (17)	−0.0067 (15)	0.0207 (13)	0.0035 (13)
C10	0.082 (2)	0.0781 (19)	0.0643 (17)	−0.0015 (15)	0.0079 (14)	−0.0008 (13)
C11	0.0533 (15)	0.105 (2)	0.0709 (17)	−0.0033 (14)	0.0060 (14)	−0.0104 (16)

Geometric parameters (Å, º)

O1—C7	1.345 (2)	C3—H3	0.9300
O1—C6	1.446 (3)	C4—C5	1.359 (3)
O2—C7	1.209 (2)	C4—H4	0.9300
N1—C2	1.315 (3)	C5—C6	1.495 (3)
N1—C3	1.317 (3)	C6—H6A	0.9700
N2—C11	1.352 (3)	C6—H6B	0.9700
N2—C8	1.366 (3)	C7—C8	1.440 (3)
N2—H2A	0.901 (10)	C8—C9	1.366 (3)
C1—C5	1.366 (3)	C9—C10	1.392 (3)
C1—C2	1.383 (4)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.356 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.363 (3)	C11—H11	0.9300
C7—O1—C6	117.04 (18)	O1—C6—H6A	110.3
C2—N1—C3	116.0 (2)	C5—C6—H6A	110.3
C11—N2—C8	108.6 (2)	O1—C6—H6B	110.3
C11—N2—H2A	126.3 (19)	C5—C6—H6B	110.3
C8—N2—H2A	125.0 (19)	H6A—C6—H6B	108.5
C5—C1—C2	118.7 (3)	O2—C7—O1	122.2 (2)
C5—C1—H1	120.6	O2—C7—C8	125.9 (2)
C2—C1—H1	120.6	O1—C7—C8	111.9 (2)
N1—C2—C1	124.0 (3)	C9—C8—N2	107.2 (2)
N1—C2—H2	118.0	C9—C8—C7	129.4 (2)
C1—C2—H2	118.0	N2—C8—C7	123.2 (2)
N1—C3—C4	124.1 (3)	C8—C9—C10	108.3 (2)
N1—C3—H3	117.9	C8—C9—H9	125.8
C4—C3—H3	117.9	C10—C9—H9	125.8
C5—C4—C3	119.7 (2)	C11—C10—C9	106.6 (2)
C5—C4—H4	120.2	C11—C10—H10	126.7
C3—C4—H4	120.2	C9—C10—H10	126.7
C4—C5—C1	117.5 (2)	N2—C11—C10	109.2 (2)
C4—C5—C6	120.8 (2)	N2—C11—H11	125.4
C1—C5—C6	121.7 (3)	C10—C11—H11	125.4
O1—C6—C5	107.15 (19)
C3—N1—C2—C1	−0.6 (4)	C6—O1—C7—C8	−175.1 (2)
C5—C1—C2—N1	−0.4 (4)	C11—N2—C8—C9	−0.3 (3)
C2—N1—C3—C4	0.6 (4)	C11—N2—C8—C7	175.0 (2)
N1—C3—C4—C5	0.3 (4)	O2—C7—C8—C9	−5.6 (4)
C3—C4—C5—C1	−1.3 (3)	O1—C7—C8—C9	173.6 (2)
C3—C4—C5—C6	179.0 (2)	O2—C7—C8—N2	−179.8 (2)
C2—C1—C5—C4	1.3 (3)	O1—C7—C8—N2	−0.5 (3)
C2—C1—C5—C6	−179.0 (2)	N2—C8—C9—C10	0.1 (3)
C7—O1—C6—C5	−172.3 (2)	C7—C8—C9—C10	−174.8 (2)
C4—C5—C6—O1	64.8 (3)	C8—C9—C10—C11	0.1 (3)
C1—C5—C6—O1	−115.0 (2)	C8—N2—C11—C10	0.4 (3)
C6—O1—C7—O2	4.2 (3)	C9—C10—C11—N2	−0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1^i	0.90 (2)	2.01 (2)	2.902 (3)	169
C11—H11···O2^ii	0.93	2.47	3.331 (3)	155

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x−1, y, z.