Polyfunctionalized pyridinium N-benzoyl­guanidine: N2-benzoyl-N1-(4-methyl­phen­yl)-N3-pyridinioguanidin-3-ide

Cunha, S.; Vencato, I.; Rodrigues, M.T. Jr; Macedo, F.C. Jr; Sabino, J.R.

doi:10.1107/S1600536806009111

Polyfunctionalized pyridinium N-benzoylguanidine: N²-benzoyl-N¹-(4-methylphenyl)-N³-pyridinioguanidin-3-ide

S. Cunha, I. Vencato, M. T. Rodrigues Jr, F. C. Macedo Jr and J. R. Sabino

The title compound, C₂₀H₁₈N₄O, is an example of a recently described pyridinium N-benzoylguanidine. This work represents the second structural study of this kind of compound. The structure is stabilized by C—H

π, C—H

N and C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009111/kp2002sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009111/kp2002Isup2.hkl Contains datablock I

CCDC reference: 605246

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.006 Å
R factor = 0.046
wR factor = 0.154
Data-to-parameter ratio = 6.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.61
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           67.93
           From the CIF: _reflns_number_total               1586
           Count of symmetry unique reflns         1593
           Completeness (_total/calc)             99.56%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4-PC Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N²-benzoyl-N¹-(4-methylphenyl)-N³-pyridinioguanidin-3-ide top

Crystal data top

C₂₀H₁₈N₄O	D_x = 1.302 Mg m⁻³
M_r = 330.38	Melting point = 227–228 K
Orthorhombic, Pna2₁	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 17.182 (3) Å	θ = 16.1–36.7°
b = 6.660 (1) Å	µ = 0.67 mm⁻¹
c = 14.730 (3) Å	T = 297 K
V = 1685.6 (5) Å³	Prism, colorless
Z = 4	0.35 × 0.25 × 0.18 mm
F(000) = 696

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.038
Radiation source: fine-focus sealed tube	θ_max = 67.9°, θ_min = 5.2°
Graphite monochromator	h = −1→20
non–profiled ω/2θ scans	k = −8→0
1690 measured reflections	l = 0→17
1586 independent reflections	2 standard reflections every 120 min
1513 reflections with I > 2σ(I)	intensity decay: <1%

Refinement top

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0865P)² + 0.6464P] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max < 0.001
1586 reflections	Δρ_max = 0.21 e Å⁻³
240 parameters	Δρ_min = −0.30 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.054 (5)

Special details top

Experimental. IR (KBr) ν_max/cm^-1: 3236, 1601, 1558; ¹H (DMSO-d₆/CDCl₃): δ 7.09 (2H, t, J = 7.8 Hz), 7.21 (2H, t, J = 6.9 Hz), 7.30 (1H, d, J = 5.7 Hz), 7.54 (2H, d, J = 7.5 Hz), 7.72 (2H, d, J = 7.8 Hz), 7.92 (2H, t, J = 6.6 Hz), 8.25 (1H, t, J = 7.5 Hz), 8.78 (2H, d, J = 5.7 Hz), 12.06 (1H, s). ¹³C (DMSO-d₆/CDCl₃): δ 20.3 (CH₃), 120.1 (CH), 126.5 (CH), 127.4 (CH), 128.1 (CH), 129.0 (CH), 130.0 (CH), 130.5 (C), 138.9 (CH), 144.6 (CH), 162.2 (C), 172.5 (C).

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.05644 (16)	0.1516 (5)	0.7437 (3)	0.0576 (9)
N1	0.15320 (19)	0.3217 (5)	0.8547 (2)	0.0457 (8)
H1	0.105 (3)	0.305 (7)	0.825 (4)	0.055*
N2	0.18414 (18)	0.0406 (5)	0.7637 (2)	0.0403 (7)
N3	0.27541 (18)	0.1863 (5)	0.8631 (3)	0.0472 (8)
N4	0.32227 (18)	0.0244 (5)	0.8356 (3)	0.0434 (8)
C1	0.1128 (2)	0.0390 (6)	0.7268 (3)	0.0406 (9)
C2	0.2051 (2)	0.1792 (5)	0.8269 (3)	0.0384 (8)
C3	0.1614 (2)	0.4729 (6)	0.9213 (3)	0.0412 (9)
C4	0.2101 (3)	0.4577 (6)	0.9964 (3)	0.0481 (10)
H4	0.246 (3)	0.332 (7)	1.007 (4)	0.058*
C5	0.2103 (3)	0.6123 (7)	1.0603 (3)	0.0528 (11)
H5	0.246 (3)	0.593 (8)	1.116 (4)	0.063*
C6	0.1646 (2)	0.7822 (6)	1.0509 (3)	0.0465 (9)
C7	0.1169 (2)	0.7941 (6)	0.9749 (3)	0.0477 (10)
H7	0.0856	0.9065	0.9668	0.057*
C8	0.1152 (2)	0.6424 (6)	0.9115 (3)	0.0451 (9)
H8	0.0826	0.6536	0.8614	0.054*
C9	0.1005 (2)	−0.1247 (6)	0.6576 (3)	0.0410 (8)
C10	0.0451 (3)	−0.0979 (8)	0.5903 (4)	0.0593 (12)
H10	0.0187	0.0237	0.5861	0.071*
C11	0.0287 (3)	−0.2496 (10)	0.5295 (4)	0.0737 (16)
H11	−0.0086	−0.2306	0.4847	0.088*
C12	0.0682 (3)	−0.4299 (8)	0.5356 (4)	0.0663 (14)
H12	0.0567	−0.5334	0.4954	0.080*
C13	0.1239 (3)	−0.4569 (8)	0.6004 (4)	0.0608 (12)
H13	0.1501	−0.5787	0.6041	0.073*
C14	0.1417 (2)	−0.3036 (6)	0.6609 (3)	0.0478 (10)
H14	0.1811	−0.3209	0.7035	0.057*
C15	0.3864 (2)	0.0656 (7)	0.7874 (3)	0.0523 (10)
H15	0.3960	0.1964	0.7684	0.063*
C16	0.4380 (2)	−0.0851 (8)	0.7659 (4)	0.0572 (11)
H16	0.4824	−0.0567	0.7321	0.069*
C17	0.4236 (3)	−0.2767 (7)	0.7947 (3)	0.0539 (11)
H17	0.460 (3)	−0.378 (8)	0.787 (4)	0.065*
C18	0.3589 (2)	−0.3153 (6)	0.8452 (4)	0.0546 (11)
H18	0.3493	−0.4443	0.8665	0.065*
C19	0.3080 (2)	−0.1621 (6)	0.8643 (3)	0.0489 (10)
H19	0.2632	−0.1885	0.8975	0.059*
C20	0.1665 (3)	0.9473 (8)	1.1199 (4)	0.0647 (13)
H20A	0.1156	0.9634	1.1459	0.097*
H20B	0.1820	1.0703	1.0911	0.097*
H20C	0.2030	0.9140	1.1668	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0385 (14)	0.0568 (17)	0.077 (2)	0.0055 (12)	−0.0076 (15)	−0.0172 (16)
N1	0.0427 (16)	0.0449 (17)	0.0494 (19)	0.0058 (13)	−0.0074 (16)	−0.0109 (15)
N2	0.0373 (16)	0.0433 (16)	0.0404 (16)	0.0001 (13)	0.0007 (13)	−0.0081 (14)
N3	0.0384 (16)	0.0436 (17)	0.060 (2)	0.0035 (13)	−0.0013 (16)	−0.0138 (16)
N4	0.0365 (16)	0.0481 (18)	0.0457 (18)	−0.0009 (13)	−0.0009 (13)	−0.0078 (15)
C1	0.0323 (17)	0.046 (2)	0.044 (2)	−0.0041 (14)	0.0026 (15)	−0.0002 (16)
C2	0.0359 (17)	0.0388 (18)	0.0404 (19)	−0.0013 (14)	0.0011 (15)	−0.0020 (15)
C3	0.042 (2)	0.041 (2)	0.040 (2)	−0.0016 (15)	0.0033 (16)	−0.0028 (16)
C4	0.057 (2)	0.046 (2)	0.041 (2)	0.0084 (18)	−0.0021 (19)	0.0021 (17)
C5	0.058 (3)	0.056 (2)	0.044 (2)	0.004 (2)	−0.006 (2)	−0.002 (2)
C6	0.049 (2)	0.048 (2)	0.042 (2)	−0.0025 (17)	0.0062 (17)	−0.0062 (18)
C7	0.047 (2)	0.045 (2)	0.051 (2)	0.0086 (17)	0.0046 (18)	−0.0048 (18)
C8	0.040 (2)	0.050 (2)	0.045 (2)	0.0056 (16)	−0.0045 (17)	−0.0039 (19)
C9	0.0318 (16)	0.049 (2)	0.042 (2)	−0.0039 (15)	0.0027 (15)	−0.0043 (18)
C10	0.054 (2)	0.064 (3)	0.060 (3)	0.008 (2)	−0.014 (2)	−0.010 (2)
C11	0.073 (3)	0.085 (4)	0.064 (3)	0.013 (3)	−0.027 (3)	−0.021 (3)
C12	0.058 (3)	0.076 (3)	0.065 (3)	−0.009 (2)	−0.002 (2)	−0.030 (3)
C13	0.063 (3)	0.053 (3)	0.067 (3)	0.002 (2)	0.005 (2)	−0.013 (2)
C14	0.046 (2)	0.049 (2)	0.048 (2)	−0.0001 (17)	−0.0059 (18)	−0.0050 (18)
C15	0.041 (2)	0.060 (2)	0.056 (3)	−0.0053 (18)	0.0040 (18)	0.005 (2)
C16	0.038 (2)	0.074 (3)	0.060 (3)	0.0032 (19)	0.0116 (19)	−0.002 (2)
C17	0.041 (2)	0.060 (3)	0.061 (3)	0.0072 (19)	−0.0044 (19)	−0.016 (2)
C18	0.045 (2)	0.044 (2)	0.075 (3)	0.0003 (16)	0.006 (2)	−0.007 (2)
C19	0.0381 (18)	0.047 (2)	0.062 (3)	−0.0065 (16)	0.0078 (19)	−0.0067 (19)
C20	0.068 (3)	0.066 (3)	0.060 (3)	0.002 (2)	0.005 (2)	−0.020 (2)

Geometric parameters (Å, º) top

O1—C1	1.250 (5)	C9—C10	1.386 (6)
N1—C2	1.365 (5)	C10—C11	1.379 (7)
N1—C3	1.413 (5)	C10—H10	0.9300
N1—H1	0.95 (5)	C11—C12	1.382 (8)
N2—C1	1.340 (5)	C11—H11	0.9300
N2—C2	1.360 (5)	C12—C13	1.363 (8)
N3—C2	1.321 (5)	C12—H12	0.9300
N3—N4	1.406 (5)	C13—C14	1.389 (6)
N4—C19	1.334 (6)	C13—H13	0.9300
N4—C15	1.339 (5)	C14—H14	0.9300
C1—C9	1.508 (5)	C15—C16	1.376 (7)
C3—C8	1.388 (5)	C15—H15	0.9300
C3—C4	1.390 (6)	C16—C17	1.368 (7)
C4—C5	1.395 (6)	C16—H16	0.9300
C4—H4	1.05 (5)	C17—C18	1.362 (7)
C5—C6	1.384 (6)	C17—H17	0.93 (6)
C5—H5	1.03 (6)	C18—C19	1.373 (6)
C6—C7	1.390 (6)	C18—H18	0.9300
C6—C20	1.497 (6)	C19—H19	0.9300
C7—C8	1.376 (6)	C20—H20A	0.9600
C7—H7	0.9300	C20—H20B	0.9600
C8—H8	0.9300	C20—H20C	0.9600
C9—C14	1.386 (6)

C2—N1—C3	129.6 (3)	C11—C10—H10	119.7
C2—N1—H1	110 (3)	C9—C10—H10	119.7
C3—N1—H1	120 (3)	C10—C11—C12	119.6 (5)
C1—N2—C2	121.7 (3)	C10—C11—H11	120.2
C2—N3—N4	112.3 (3)	C12—C11—H11	120.2
C19—N4—C15	120.6 (4)	C13—C12—C11	120.3 (5)
C19—N4—N3	121.2 (3)	C13—C12—H12	119.9
C15—N4—N3	117.8 (4)	C11—C12—H12	119.9
O1—C1—N2	128.6 (4)	C12—C13—C14	120.5 (5)
O1—C1—C9	117.4 (3)	C12—C13—H13	119.8
N2—C1—C9	114.1 (3)	C14—C13—H13	119.8
N3—C2—N2	122.9 (3)	C9—C14—C13	119.8 (4)
N3—C2—N1	116.9 (3)	C9—C14—H14	120.1
N2—C2—N1	120.2 (3)	C13—C14—H14	120.1
C8—C3—C4	119.0 (4)	N4—C15—C16	120.2 (4)
C8—C3—N1	116.8 (4)	N4—C15—H15	119.9
C4—C3—N1	124.1 (4)	C16—C15—H15	119.9
C3—C4—C5	119.0 (4)	C17—C16—C15	119.5 (4)
C3—C4—H4	122 (3)	C17—C16—H16	120.3
C5—C4—H4	119 (3)	C15—C16—H16	120.3
C6—C5—C4	122.3 (4)	C18—C17—C16	119.6 (4)
C6—C5—H5	121 (3)	C18—C17—H17	119 (4)
C4—C5—H5	116 (3)	C16—C17—H17	121 (3)
C5—C6—C7	117.5 (4)	C17—C18—C19	119.4 (4)
C5—C6—C20	121.4 (4)	C17—C18—H18	120.3
C7—C6—C20	121.2 (4)	C19—C18—H18	120.3
C8—C7—C6	121.2 (4)	N4—C19—C18	120.7 (4)
C8—C7—H7	119.4	N4—C19—H19	119.7
C6—C7—H7	119.4	C18—C19—H19	119.7
C7—C8—C3	121.0 (4)	C6—C20—H20A	109.5
C7—C8—H8	119.5	C6—C20—H20B	109.5
C3—C8—H8	119.5	H20A—C20—H20B	109.5
C14—C9—C10	119.1 (4)	C6—C20—H20C	109.5
C14—C9—C1	121.8 (4)	H20A—C20—H20C	109.5
C10—C9—C1	119.1 (4)	H20B—C20—H20C	109.5
C11—C10—C9	120.6 (5)

C2—N3—N4—C19	−70.0 (5)	N1—C3—C8—C7	177.4 (4)
C2—N3—N4—C15	116.8 (4)	O1—C1—C9—C14	−151.3 (4)
C2—N2—C1—O1	−1.8 (7)	N2—C1—C9—C14	27.5 (5)
C2—N2—C1—C9	179.6 (3)	O1—C1—C9—C10	27.0 (6)
N4—N3—C2—N2	−5.9 (6)	N2—C1—C9—C10	−154.2 (4)
N4—N3—C2—N1	175.3 (4)	C14—C9—C10—C11	2.5 (7)
C1—N2—C2—N3	−178.7 (4)	C1—C9—C10—C11	−175.8 (5)
C1—N2—C2—N1	0.1 (6)	C9—C10—C11—C12	−0.2 (9)
C3—N1—C2—N3	−4.0 (6)	C10—C11—C12—C13	−1.1 (9)
C3—N1—C2—N2	177.2 (4)	C11—C12—C13—C14	−0.1 (9)
C2—N1—C3—C8	154.6 (4)	C10—C9—C14—C13	−3.6 (7)
C2—N1—C3—C4	−28.0 (7)	C1—C9—C14—C13	174.6 (4)
C8—C3—C4—C5	0.7 (6)	C12—C13—C14—C9	2.4 (8)
N1—C3—C4—C5	−176.6 (4)	C19—N4—C15—C16	0.8 (7)
C3—C4—C5—C6	−1.0 (7)	N3—N4—C15—C16	174.0 (4)
C4—C5—C6—C7	0.6 (7)	N4—C15—C16—C17	−0.4 (7)
C4—C5—C6—C20	−179.3 (5)	C15—C16—C17—C18	−0.9 (8)
C5—C6—C7—C8	0.1 (6)	C16—C17—C18—C19	1.8 (7)
C20—C6—C7—C8	179.9 (4)	C15—N4—C19—C18	0.2 (7)
C6—C7—C8—C3	−0.3 (6)	N3—N4—C19—C18	−172.8 (4)
C4—C3—C8—C7	−0.1 (6)	C17—C18—C19—N4	−1.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.95 (5)	1.78 (5)	2.592 (4)	142 (4)
C4—H4···N3	1.05 (5)	2.39 (5)	2.895 (6)	108 (4)
C5—H5···N2ⁱ	1.03 (6)	2.51 (6)	3.535 (6)	172 (4)
C17—H17···O1ⁱⁱ	0.93 (6)	2.54 (6)	3.465 (6)	172 (5)
C19—H19···Cgⁱⁱⁱ	0.93	2.48	3.37	161

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

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Polyfunctionalized pyridinium N-benzoyl­guanidine: N2-benzoyl-N1-(4-methyl­phen­yl)-N3-pyridinioguanidin-3-ide

Supporting information

Key indicators

checkCIF/PLATON results

Polyfunctionalized pyridinium N-benzoylguanidine: N²-benzoyl-N¹-(4-methylphenyl)-N³-pyridinioguanidin-3-ide