Crystal structure of 4-benzyl­carbamoyl-1-methyl­pyridin-1-ium iodide: an efficient multimodal anti­viral drug

Polymorph screening of the title compound, an efficient multimodal anti­viral drug, revealed only a single polymorph, for which the crystal structure is determined in this work.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.024
• wR factor = 0.053
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X       H2     ..  H10     ..       1.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A   ..  I1      ..       3.08 Ang.

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         69 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

4-Benzylcarbamoyl-1-methylpyridin-1-ium iodide

Crystal data

C14H15N2O^+·I^−	Dx = 1.629 Mg m^−3
Mr = 354.18	Melting point: 464(2) K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 9.2867 (2) Å	Cell parameters from 9574 reflections
b = 10.8741 (2) Å	θ = 2.4–26.3°
c = 14.3038 (3) Å	µ = 2.21 mm^−1
V = 1444.46 (5) Å^3	T = 295 K
Z = 4	Block, yellow
F(000) = 696	0.25 × 0.17 × 0.07 mm

Data collection

Rigaku OD Xcalibur, Ruby, Gemini ultra diffractometer	3388 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	3115 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.3°, θmin = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −14→13
Tmin = 0.910, Tmax = 1.000	l = −18→18
18978 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.053	w = 1/[σ^2(Fo^2) + (0.0267P)^2 + 0.0479P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3388 reflections	Δρmax = 0.53 e Å^−3
168 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Absolute structure: Flack x determined using 1207 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.033 (11)

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1886 (4)	0.0803 (3)	0.9728 (2)	0.0423 (8)
C2	0.2939 (4)	0.0665 (4)	1.0407 (3)	0.0475 (9)
H1	0.3631	0.0054	1.0338	0.057*
C3	0.2982 (5)	0.1404 (4)	1.1172 (3)	0.0583 (11)
H3	0.3702	0.1296	1.1617	0.070*
C4	0.1975 (6)	0.2307 (5)	1.1293 (3)	0.0739 (13)
H4	0.2012	0.2817	1.1814	0.089*
C5	0.0909 (6)	0.2452 (5)	1.0639 (4)	0.0805 (16)
H5	0.0210	0.3054	1.0723	0.097*
C6	0.0869 (5)	0.1713 (4)	0.9858 (3)	0.0654 (12)
H6	0.0149	0.1827	0.9414	0.078*
C7	0.1838 (5)	−0.0028 (4)	0.8892 (3)	0.0555 (10)
H7A	0.2008	−0.0868	0.9093	0.067*
H7B	0.0882	0.0006	0.8619	0.067*
C8	0.4168 (4)	−0.0275 (3)	0.8098 (3)	0.0456 (8)
C9	0.5104 (4)	0.0078 (3)	0.7283 (3)	0.0407 (8)
C10	0.4765 (4)	0.0948 (4)	0.6614 (3)	0.0477 (9)
H10	0.3906	0.1385	0.6656	0.057*
C11	0.5694 (5)	0.1168 (4)	0.5888 (3)	0.0504 (9)
H11	0.5455	0.1751	0.5439	0.060*
C12	0.7303 (5)	−0.0274 (5)	0.6477 (3)	0.0677 (13)
H12	0.8177	−0.0686	0.6432	0.081*
C13	0.6423 (5)	−0.0514 (5)	0.7198 (3)	0.0627 (12)
H13	0.6700	−0.1084	0.7648	0.075*
C14	0.7913 (5)	0.0782 (5)	0.5020 (3)	0.0705 (13)
H14A	0.7477	0.1364	0.4602	0.106*
H14B	0.8087	0.0025	0.4694	0.106*
H14C	0.8810	0.1107	0.5246	0.106*
N1	0.6942 (4)	0.0555 (3)	0.5815 (2)	0.0494 (8)
N2	0.2902 (3)	0.0295 (3)	0.8172 (2)	0.0475 (7)
H2	0.262 (7)	0.085 (6)	0.766 (4)	0.12 (2)*
O1	0.4598 (4)	−0.1053 (3)	0.86557 (19)	0.0634 (8)
I1	0.06127 (3)	0.22276 (3)	0.68164 (2)	0.05375 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0396 (19)	0.0438 (18)	0.0435 (18)	−0.0051 (15)	0.0082 (17)	0.0088 (16)
C2	0.0350 (19)	0.057 (2)	0.050 (2)	0.0010 (16)	0.0021 (18)	0.0085 (19)
C3	0.055 (3)	0.075 (3)	0.044 (2)	−0.014 (2)	0.002 (2)	0.003 (2)
C4	0.103 (4)	0.069 (3)	0.050 (2)	−0.011 (3)	0.018 (3)	−0.011 (2)
C5	0.096 (4)	0.069 (3)	0.076 (3)	0.033 (3)	0.016 (3)	0.000 (2)
C6	0.059 (3)	0.078 (3)	0.059 (3)	0.023 (2)	−0.002 (2)	0.015 (2)
C7	0.052 (2)	0.063 (3)	0.051 (2)	−0.015 (2)	0.002 (2)	−0.0028 (19)
C8	0.051 (2)	0.0456 (19)	0.0401 (18)	−0.0024 (16)	−0.011 (2)	−0.0033 (16)
C9	0.0420 (19)	0.042 (2)	0.0382 (19)	−0.0002 (15)	−0.0065 (16)	−0.0043 (15)
C10	0.048 (2)	0.047 (2)	0.048 (2)	0.0084 (16)	−0.0015 (17)	−0.0013 (16)
C11	0.054 (2)	0.048 (2)	0.049 (2)	0.002 (2)	−0.004 (2)	0.0057 (16)
C12	0.046 (3)	0.087 (4)	0.070 (3)	0.020 (2)	0.002 (2)	0.012 (3)
C13	0.056 (3)	0.076 (3)	0.055 (2)	0.021 (2)	−0.002 (2)	0.018 (2)
C14	0.058 (3)	0.097 (4)	0.057 (3)	−0.001 (3)	0.010 (2)	0.004 (3)
N1	0.0408 (17)	0.061 (2)	0.0463 (17)	−0.0012 (15)	−0.0045 (15)	−0.0002 (15)
N2	0.0472 (18)	0.0553 (19)	0.0400 (16)	0.0010 (14)	0.0006 (18)	−0.0012 (17)
O1	0.068 (2)	0.0664 (18)	0.0562 (15)	0.0077 (17)	−0.0044 (16)	0.0181 (15)
I1	0.05146 (14)	0.05593 (15)	0.05386 (14)	0.01142 (12)	−0.00363 (13)	−0.00252 (12)

Geometric parameters (Å, º)

C1—C6	1.381 (6)	C8—C9	1.504 (5)
C1—C2	1.387 (5)	C9—C10	1.383 (5)
C1—C7	1.500 (5)	C9—C13	1.389 (6)
C2—C3	1.358 (6)	C10—C11	1.371 (5)
C2—H1	0.9300	C10—H10	0.9300
C3—C4	1.367 (7)	C11—N1	1.341 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.371 (7)	C12—C13	1.342 (6)
C4—H4	0.9300	C12—N1	1.349 (5)
C5—C6	1.376 (7)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—N1	1.472 (5)
C7—N2	1.469 (5)	C14—H14A	0.9600
C7—H7A	0.9700	C14—H14B	0.9600
C7—H7B	0.9700	C14—H14C	0.9600
C8—O1	1.229 (4)	N2—H2	0.98 (6)
C8—N2	1.334 (5)
C6—C1—C2	117.7 (4)	C10—C9—C13	117.2 (4)
C6—C1—C7	121.3 (4)	C10—C9—C8	125.5 (3)
C2—C1—C7	121.0 (4)	C13—C9—C8	117.3 (4)
C3—C2—C1	121.4 (4)	C11—C10—C9	120.0 (4)
C3—C2—H1	119.3	C11—C10—H10	120.0
C1—C2—H1	119.3	C9—C10—H10	120.0
C2—C3—C4	120.4 (4)	N1—C11—C10	121.1 (4)
C2—C3—H3	119.8	N1—C11—H11	119.4
C4—C3—H3	119.8	C10—C11—H11	119.4
C3—C4—C5	119.4 (4)	C13—C12—N1	121.2 (4)
C3—C4—H4	120.3	C13—C12—H12	119.4
C5—C4—H4	120.3	N1—C12—H12	119.4
C4—C5—C6	120.4 (4)	C12—C13—C9	120.9 (4)
C4—C5—H5	119.8	C12—C13—H13	119.5
C6—C5—H5	119.8	C9—C13—H13	119.5
C5—C6—C1	120.6 (4)	N1—C14—H14A	109.5
C5—C6—H6	119.7	N1—C14—H14B	109.5
C1—C6—H6	119.7	H14A—C14—H14B	109.5
N2—C7—C1	113.2 (3)	N1—C14—H14C	109.5
N2—C7—H7A	108.9	H14A—C14—H14C	109.5
C1—C7—H7A	108.9	H14B—C14—H14C	109.5
N2—C7—H7B	108.9	C11—N1—C12	119.4 (4)
C1—C7—H7B	108.9	C11—N1—C14	120.4 (3)
H7A—C7—H7B	107.8	C12—N1—C14	120.2 (4)
O1—C8—N2	123.7 (4)	C8—N2—C7	122.5 (4)
O1—C8—C9	119.4 (4)	C8—N2—H2	118 (4)
N2—C8—C9	116.9 (3)	C7—N2—H2	119 (4)
C6—C1—C2—C3	−0.6 (6)	C13—C9—C10—C11	2.1 (6)
C7—C1—C2—C3	−179.3 (4)	C8—C9—C10—C11	−178.4 (3)
C1—C2—C3—C4	0.3 (6)	C9—C10—C11—N1	−0.4 (6)
C2—C3—C4—C5	0.6 (7)	N1—C12—C13—C9	0.5 (8)
C3—C4—C5—C6	−1.2 (8)	C10—C9—C13—C12	−2.2 (7)
C4—C5—C6—C1	0.9 (8)	C8—C9—C13—C12	178.2 (4)
C2—C1—C6—C5	0.0 (6)	C10—C11—N1—C12	−1.4 (6)
C7—C1—C6—C5	178.7 (4)	C10—C11—N1—C14	178.7 (4)
C6—C1—C7—N2	103.1 (4)	C13—C12—N1—C11	1.3 (7)
C2—C1—C7—N2	−78.2 (5)	C13—C12—N1—C14	−178.7 (5)
O1—C8—C9—C10	−179.0 (4)	O1—C8—N2—C7	−5.2 (6)
N2—C8—C9—C10	0.6 (5)	C9—C8—N2—C7	175.1 (3)
O1—C8—C9—C13	0.5 (5)	C1—C7—N2—C8	97.8 (4)
N2—C8—C9—C13	−179.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···I1	0.98 (6)	2.68 (6)	3.563 (3)	150 (5)
C14—H14A···I1^i	0.96	3.08	4.018 (5)	168
C14—H14C···I1^ii	0.96	3.06	3.919 (5)	150

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