N-Benzyl­propan-2-aminium chloride

In the crystal structure of title salt, C₁₀H₁₆N⁺·Cl⁻, the amino H atoms are involved in inter­molecular N—H...Cl hydrogen bonding, generating a zigzag chain propagating in [100].

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.021
• wR factor = 0.057
• Data-to-parameter ratio = 22.9

checkCIF/PLATON results

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Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         10
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          2

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           29.00
           From the CIF: _reflns_number_total               2720
           Count of symmetry unique reflns         1501
           Completeness (_total/calc)            181.21%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1219
           Fraction of Friedel pairs measured     0.812
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   3 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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S1. Comment

In the previous works, the structure determination of [NH₂(CH₂C₆H₅)(CH(CH₃)₂)][CCl₃C(O)NHP(O)(O)(OCH₃)] (Pourayoubi & Sabbaghi, 2007) and [NH₂(CH₂C₆H₅)(CH(CH₃)₂)] [CF₃C(O)NHP(O)(O)(N(CH₂C₆H₅)(CH(CH₃)₂)] (Yazdanbakhsh & Sabbaghi, 2007) have been investigated; we report here on the crystal structure of title compound, the chloride salt of N-benzyl-2-propanaminium cation (Fig. 1). Both hydrogen atoms of NH₂ groups are involved in intermolecular N—H···Cl hydrogen bonding with neighbouring Cl^- anions [N1···Cl1 = 3.1296 (9) Å, N1···Cl2 = 3.1257 (9) Å] into an extended 1-D zigzag chain (Fig. 2).

Related literature

For related structures, see: Pourayoubi & Sabbaghi (2007); Yazdanbakhsh & Sabbaghi (2007).

S2. Experimental

The title compound is a by-product of the preparation of P(O)[OC₆H₅][N(CH₂C₆H₅)(CH(CH₃)₂)]₂ [from the reaction between P(O)[OC₆H₅]Cl₂ and NH(CH₂C₆H₅)(CH(CH₃)₂), with 1:4 mole ratio] which is crystallized in CH₃C(O)CH₃.

S3. Refinement

The H atoms of the NH2 group were located from the difference Fourier synthesis and refined isotropically, no restraints were used. Finally, the geometrical and thermal parameters obtained for these H-atoms, as well as parameters of the hydrogen bonds for these H-atoms included, were rather realistic. The H(C) atom positions were calculated and refined in isotropic approximation in riding model with the Uiso(H) parameters equal to 1.2 Ueq(Ci), for methyl groups equal to 1.5 Ueq(Cii), where U(Ci) and U(Cii) are respectively the equivalent thermal parameters of the carbon atoms to which corresponding H atoms are bonded.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title salt, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50 % probability level.
	Fig. 2. Fragment of crystal packing (projection along c crystal axis), the hydrogen bonds are shown by dash line.

N-Benzylpropan-2-aminium chloride

Crystal data

C10H16N^+·Cl^−	F(000) = 400
Mr = 185.69	Dx = 1.197 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8636 reflections
a = 9.9666 (6) Å	θ = 2.3–34.0°
b = 18.0379 (11) Å	µ = 0.32 mm^−1
c = 5.7307 (4) Å	T = 100 K
V = 1030.25 (11) Å^3	Prism, colourless
Z = 4	0.50 × 0.40 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	2662 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ϕ and ω scans	θmax = 29.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.818, Tmax = 0.910	k = −24→24
11694 measured reflections	l = −7→7

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.057	w = 1/[σ^2(Fo^2) + (0.0336P)^2 + 0.1229P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2720 reflections	Δρmax = 0.25 e Å^−3
119 parameters	Δρmin = −0.15 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1229 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (4)

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.

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
Cl1	0.212804 (19)	0.282008 (11)	0.24289 (5)	0.01590 (6)
N1	0.47016 (8)	0.26697 (4)	0.55218 (15)	0.01274 (15)
H1	0.3950 (14)	0.2666 (7)	0.481 (2)	0.013 (3)*
H2	0.5322 (12)	0.2517 (7)	0.455 (3)	0.014 (3)*
C1	0.47024 (10)	0.21793 (5)	0.7630 (2)	0.01667 (19)
H1A	0.4181	0.2423	0.8884	0.020*
H1B	0.5636	0.2123	0.8190	0.020*
C2	0.41198 (9)	0.14208 (5)	0.71879 (19)	0.01422 (17)
C3	0.32866 (10)	0.11207 (6)	0.88949 (19)	0.01721 (19)
H3A	0.3064	0.1405	1.0235	0.021*
C4	0.27777 (10)	0.04055 (6)	0.8647 (2)	0.0205 (2)
H4A	0.2218	0.0202	0.9826	0.025*
C5	0.30877 (11)	−0.00100 (6)	0.6679 (2)	0.0192 (2)
H5A	0.2743	−0.0498	0.6512	0.023*
C6	0.39045 (10)	0.02910 (5)	0.49499 (19)	0.0188 (2)
H6A	0.4105	0.0010	0.3591	0.023*
C7	0.44277 (10)	0.10012 (5)	0.52059 (18)	0.01675 (18)
H7A	0.4995	0.1202	0.4033	0.020*
C8	0.50162 (11)	0.34699 (5)	0.6084 (2)	0.0195 (2)
H8A	0.5825	0.3487	0.7116	0.023*
C9	0.38428 (13)	0.38228 (5)	0.7366 (2)	0.0281 (2)
H9A	0.3631	0.3530	0.8758	0.042*
H9B	0.3059	0.3837	0.6335	0.042*
H9C	0.4083	0.4329	0.7830	0.042*
C10	0.53322 (12)	0.38753 (6)	0.3829 (2)	0.0256 (2)
H10A	0.6057	0.3617	0.3007	0.038*
H10B	0.5613	0.4384	0.4184	0.038*
H10C	0.4530	0.3887	0.2840	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01334 (10)	0.01922 (10)	0.01515 (10)	0.00008 (7)	−0.00118 (9)	0.00016 (10)
N1	0.0131 (4)	0.0111 (3)	0.0140 (4)	−0.0004 (3)	−0.0017 (3)	0.0011 (3)
C1	0.0237 (4)	0.0127 (4)	0.0136 (5)	−0.0013 (3)	−0.0044 (4)	0.0014 (3)
C2	0.0155 (4)	0.0114 (4)	0.0157 (4)	0.0011 (3)	−0.0018 (4)	0.0034 (4)
C3	0.0181 (4)	0.0173 (4)	0.0162 (4)	0.0020 (3)	0.0013 (4)	0.0012 (4)
C4	0.0197 (5)	0.0199 (5)	0.0221 (6)	−0.0024 (4)	0.0022 (4)	0.0062 (4)
C5	0.0189 (4)	0.0143 (4)	0.0243 (5)	−0.0027 (4)	−0.0041 (4)	0.0029 (3)
C6	0.0209 (4)	0.0163 (4)	0.0192 (5)	−0.0003 (4)	−0.0018 (4)	−0.0021 (4)
C7	0.0187 (4)	0.0154 (4)	0.0162 (4)	−0.0016 (3)	0.0008 (4)	0.0003 (4)
C8	0.0234 (5)	0.0113 (4)	0.0238 (5)	−0.0048 (4)	−0.0083 (4)	0.0010 (4)
C9	0.0512 (6)	0.0125 (4)	0.0205 (5)	0.0038 (4)	0.0042 (6)	−0.0007 (5)
C10	0.0241 (5)	0.0171 (5)	0.0355 (6)	−0.0021 (4)	0.0051 (5)	0.0084 (4)

Geometric parameters (Å, º)

N1—C1	1.4974 (13)	C5—H5A	0.9500
N1—C8	1.5118 (13)	C6—C7	1.3910 (14)
N1—H1	0.853 (14)	C6—H6A	0.9500
N1—H2	0.877 (14)	C7—H7A	0.9500
C1—C2	1.5076 (12)	C8—C10	1.5178 (16)
C1—H1A	0.9900	C8—C9	1.5207 (17)
C1—H1B	0.9900	C8—H8A	1.0000
C2—C3	1.3927 (14)	C9—H9A	0.9800
C2—C7	1.3990 (14)	C9—H9B	0.9800
C3—C4	1.3934 (15)	C9—H9C	0.9800
C3—H3A	0.9500	C10—H10A	0.9800
C4—C5	1.3892 (16)	C10—H10B	0.9800
C4—H4A	0.9500	C10—H10C	0.9800
C5—C6	1.3925 (15)
C1—N1—C8	113.08 (8)	C7—C6—C5	120.21 (10)
C1—N1—H1	112.4 (9)	C7—C6—H6A	119.9
C8—N1—H1	107.0 (8)	C5—C6—H6A	119.9
C1—N1—H2	109.1 (9)	C6—C7—C2	120.11 (9)
C8—N1—H2	106.8 (8)	C6—C7—H7A	119.9
H1—N1—H2	108.2 (14)	C2—C7—H7A	119.9
N1—C1—C2	113.60 (9)	N1—C8—C10	108.76 (9)
N1—C1—H1A	108.8	N1—C8—C9	110.07 (8)
C2—C1—H1A	108.8	C10—C8—C9	111.67 (9)
N1—C1—H1B	108.8	N1—C8—H8A	108.8
C2—C1—H1B	108.8	C10—C8—H8A	108.8
H1A—C1—H1B	107.7	C9—C8—H8A	108.8
C3—C2—C7	119.39 (8)	C8—C9—H9A	109.5
C3—C2—C1	117.67 (9)	C8—C9—H9B	109.5
C7—C2—C1	122.88 (9)	H9A—C9—H9B	109.5
C2—C3—C4	120.36 (9)	C8—C9—H9C	109.5
C2—C3—H3A	119.8	H9A—C9—H9C	109.5
C4—C3—H3A	119.8	H9B—C9—H9C	109.5
C5—C4—C3	120.08 (9)	C8—C10—H10A	109.5
C5—C4—H4A	120.0	C8—C10—H10B	109.5
C3—C4—H4A	120.0	H10A—C10—H10B	109.5
C4—C5—C6	119.83 (9)	C8—C10—H10C	109.5
C4—C5—H5A	120.1	H10A—C10—H10C	109.5
C6—C5—H5A	120.1	H10B—C10—H10C	109.5
C8—N1—C1—C2	168.17 (8)	C4—C5—C6—C7	1.03 (16)
N1—C1—C2—C3	−138.75 (10)	C5—C6—C7—C2	−0.91 (15)
N1—C1—C2—C7	44.10 (12)	C3—C2—C7—C6	−0.02 (14)
C7—C2—C3—C4	0.83 (15)	C1—C2—C7—C6	177.09 (9)
C1—C2—C3—C4	−176.43 (9)	C1—N1—C8—C10	166.04 (8)
C2—C3—C4—C5	−0.71 (16)	C1—N1—C8—C9	−71.33 (11)
C3—C4—C5—C6	−0.22 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.853 (13)	2.288 (13)	3.1296 (9)	168.8 (11)
N1—H2···Cl1^i	0.877 (14)	2.255 (14)	3.1257 (9)	171.9 (13)

Symmetry code: (i) x+1/2, −y+1/2, z.