1-(Pyrrolidin-1-yl)ethan-1-iminium chloride

The title compound, C₆H₁₃N₂⁺·Cl⁻, is as an amidinium salt that was isolated as unexpected product from the reaction between aceto­nitrile, chloro­form and pyrrolidine under refluxing conditions. The packing features two N—H...Cl hydrogen bonds to generate centrosymmetric tetra­mers (two cations and two anions) and van der Waals inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 300 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.033
• wR factor = 0.100
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9 Note
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00010 Ang.
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          5 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        25% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         12 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          7 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   6 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 1.171.42.84a (Rigaku OD, 2023); cell refinement: CrysAlis PRO 1.171.42.84a (Rigaku OD, 2023); data reduction: CrysAlis PRO 1.171.42.84a (Rigaku OD, 2023); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

1-(Pyrrolidin-1-yl)ethan-1-iminium chloride

Crystal data

C6H13N2^+·Cl^−	F(000) = 320
Mr = 148.63	Dx = 1.221 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 5.7234 (1) Å	Cell parameters from 5627 reflections
b = 11.2961 (1) Å	θ = 3.5–69.3°
c = 12.6591 (2) Å	µ = 3.53 mm^−1
β = 98.820 (1)°	T = 300 K
V = 808.76 (2) Å^3	Needle, clear light yellow
Z = 4	0.3 × 0.1 × 0.1 mm

Data collection

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	1514 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1343 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 10.0000 pixels mm^-1	θmax = 69.8°, θmin = 5.3°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2023)	k = −13→13
Tmin = 0.326, Tmax = 1.000	l = −15→15
8326 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0521P)^2 + 0.1032P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.100	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.20 e Å^−3
1514 reflections	Δρmin = −0.17 e Å^−3
111 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
7 restraints	Extinction coefficient: 0.0060 (11)
Primary atom site location: dual

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.5387 (2)	0.28640 (11)	0.42307 (9)	0.0501 (3)
N2	0.2421 (3)	0.41737 (13)	0.44168 (12)	0.0639 (4)
C1	0.3772 (3)	0.36286 (13)	0.38250 (12)	0.0493 (4)
C2	0.3413 (3)	0.38872 (15)	0.26616 (13)	0.0610 (4)
H2C	0.485848	0.418222	0.246373	0.091*
H2D	0.219266	0.447140	0.249911	0.091*
H2E	0.295598	0.317535	0.226955	0.091*
C3	0.6948 (3)	0.22165 (16)	0.36067 (14)	0.0637 (4)
H3AA	0.823737	0.271321	0.345347	0.076*	0.590 (11)
H3AB	0.607714	0.192420	0.293987	0.076*	0.590 (11)
H3BC	0.774587	0.275324	0.318169	0.076*	0.410 (11)
H3BD	0.607101	0.163573	0.313957	0.076*	0.410 (11)
C6	0.5776 (3)	0.25090 (17)	0.53598 (13)	0.0645 (5)
H6AA	0.442485	0.207796	0.553965	0.077*	0.590 (11)
H6AB	0.606325	0.319377	0.582389	0.077*	0.590 (11)
H6BC	0.429154	0.235374	0.561480	0.077*	0.410 (11)
H6BD	0.664313	0.311035	0.580605	0.077*	0.410 (11)
C4	0.7858 (13)	0.1195 (5)	0.4355 (4)	0.0712 (14)	0.590 (11)
H4A	0.679085	0.052351	0.425390	0.085*	0.590 (11)
H4B	0.941834	0.094355	0.423829	0.085*	0.590 (11)
C5	0.7933 (11)	0.1725 (6)	0.5457 (4)	0.0648 (14)	0.590 (11)
H5A	0.786343	0.111081	0.598645	0.078*	0.590 (11)
H5B	0.936561	0.218358	0.565710	0.078*	0.590 (11)
C4A	0.8700 (14)	0.1621 (8)	0.4477 (6)	0.0741 (19)	0.410 (11)
H4AA	0.930051	0.088867	0.422068	0.089*	0.410 (11)
H4AB	1.001716	0.213995	0.472880	0.089*	0.410 (11)
C5A	0.7221 (17)	0.1389 (8)	0.5339 (8)	0.079 (3)	0.410 (11)
H5AA	0.820851	0.125641	0.602236	0.094*	0.410 (11)
H5AB	0.620598	0.070640	0.516567	0.094*	0.410 (11)
Cl1	0.15495 (7)	0.08401 (4)	0.18724 (3)	0.0659 (2)
H2A	0.134 (3)	0.4650 (16)	0.4103 (15)	0.074 (6)*
H2B	0.250 (4)	0.4087 (18)	0.5110 (13)	0.082 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0544 (7)	0.0526 (7)	0.0435 (6)	0.0031 (6)	0.0077 (5)	−0.0016 (5)
N2	0.0708 (10)	0.0699 (9)	0.0509 (8)	0.0214 (7)	0.0092 (7)	0.0035 (7)
C1	0.0526 (8)	0.0470 (8)	0.0477 (8)	−0.0048 (6)	0.0064 (6)	−0.0024 (6)
C2	0.0707 (10)	0.0635 (10)	0.0476 (9)	0.0005 (8)	0.0059 (7)	0.0030 (7)
C3	0.0639 (10)	0.0725 (10)	0.0556 (9)	0.0103 (8)	0.0120 (7)	−0.0083 (8)
C6	0.0732 (11)	0.0722 (11)	0.0474 (8)	0.0148 (8)	0.0077 (8)	0.0055 (7)
C4	0.081 (3)	0.068 (3)	0.063 (2)	0.022 (2)	0.004 (2)	−0.009 (2)
C5	0.066 (3)	0.067 (3)	0.057 (2)	0.011 (2)	−0.0018 (19)	−0.0028 (18)
C4A	0.069 (4)	0.068 (4)	0.084 (4)	0.017 (3)	0.008 (3)	−0.008 (3)
C5A	0.070 (5)	0.068 (5)	0.094 (6)	0.010 (3)	0.003 (4)	0.024 (4)
Cl1	0.0682 (3)	0.0695 (3)	0.0592 (3)	−0.01566 (18)	0.0073 (2)	−0.00212 (17)

Geometric parameters (Å, º)

N1—C1	1.3107 (18)	C6—H6AA	0.9700
N1—C3	1.4746 (19)	C6—H6AB	0.9700
N1—C6	1.4682 (19)	C6—H6BC	0.9700
N2—C1	1.310 (2)	C6—H6BD	0.9700
N2—H2A	0.870 (15)	C6—C5	1.509 (6)
N2—H2B	0.877 (16)	C6—C5A	1.514 (9)
C1—C2	1.485 (2)	C4—H4A	0.9700
C2—H2C	0.9600	C4—H4B	0.9700
C2—H2D	0.9600	C4—C5	1.512 (6)
C2—H2E	0.9600	C5—H5A	0.9700
C3—H3AA	0.9700	C5—H5B	0.9700
C3—H3AB	0.9700	C4A—H4AA	0.9700
C3—H3BC	0.9700	C4A—H4AB	0.9700
C3—H3BD	0.9700	C4A—C5A	1.503 (10)
C3—C4	1.533 (5)	C5A—H5AA	0.9700
C3—C4A	1.527 (7)	C5A—H5AB	0.9700
C1—N1—C3	124.45 (13)	N1—C6—C5A	102.3 (4)
C1—N1—C6	123.65 (13)	H6AA—C6—H6AB	109.0
C6—N1—C3	111.85 (12)	H6BC—C6—H6BD	109.2
C1—N2—H2A	118.2 (13)	C5—C6—H6AA	111.0
C1—N2—H2B	125.1 (14)	C5—C6—H6AB	111.0
H2A—N2—H2B	116.7 (19)	C5A—C6—H6BC	111.3
N1—C1—C2	120.03 (14)	C5A—C6—H6BD	111.3
N2—C1—N1	121.89 (14)	C3—C4—H4A	111.1
N2—C1—C2	118.08 (14)	C3—C4—H4B	111.1
C1—C2—H2C	109.5	H4A—C4—H4B	109.1
C1—C2—H2D	109.5	C5—C4—C3	103.4 (4)
C1—C2—H2E	109.5	C5—C4—H4A	111.1
H2C—C2—H2D	109.5	C5—C4—H4B	111.1
H2C—C2—H2E	109.5	C6—C5—C4	104.5 (4)
H2D—C2—H2E	109.5	C6—C5—H5A	110.9
N1—C3—H3AA	111.2	C6—C5—H5B	110.9
N1—C3—H3AB	111.2	C4—C5—H5A	110.9
N1—C3—H3BC	111.3	C4—C5—H5B	110.9
N1—C3—H3BD	111.3	H5A—C5—H5B	108.9
N1—C3—C4	102.6 (2)	C3—C4A—H4AA	111.2
N1—C3—C4A	102.5 (3)	C3—C4A—H4AB	111.2
H3AA—C3—H3AB	109.2	H4AA—C4A—H4AB	109.1
H3BC—C3—H3BD	109.2	C5A—C4A—C3	102.7 (6)
C4—C3—H3AA	111.2	C5A—C4A—H4AA	111.2
C4—C3—H3AB	111.2	C5A—C4A—H4AB	111.2
C4A—C3—H3BC	111.3	C6—C5A—H5AA	111.0
C4A—C3—H3BD	111.3	C6—C5A—H5AB	111.0
N1—C6—H6AA	111.0	C4A—C5A—C6	103.7 (6)
N1—C6—H6AB	111.0	C4A—C5A—H5AA	111.0
N1—C6—H6BC	111.3	C4A—C5A—H5AB	111.0
N1—C6—H6BD	111.3	H5AA—C5A—H5AB	109.0
N1—C6—C5	103.9 (2)
N1—C3—C4—C5	−31.8 (6)	C3—N1—C1—C2	0.3 (2)
N1—C3—C4A—C5A	32.2 (9)	C3—N1—C6—C5	8.1 (3)
N1—C6—C5—C4	−28.2 (6)	C3—N1—C6—C5A	−13.8 (4)
N1—C6—C5A—C4A	34.0 (9)	C3—C4—C5—C6	37.6 (8)
C1—N1—C3—C4	−162.4 (3)	C3—C4A—C5A—C6	−41.7 (11)
C1—N1—C3—C4A	171.2 (4)	C6—N1—C1—N2	2.5 (2)
C1—N1—C6—C5	−174.6 (3)	C6—N1—C1—C2	−176.66 (15)
C1—N1—C6—C5A	163.5 (4)	C6—N1—C3—C4	14.9 (3)
C3—N1—C1—N2	179.53 (16)	C6—N1—C3—C4A	−11.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^i	0.87 (2)	2.33 (2)	3.1988 (16)	175 (2)
N2—H2B···Cl1^ii	0.88 (2)	2.38 (2)	3.2230 (16)	162 (2)

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