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In the crystal structure of the title compound, N-benzyl-N-methyl­prop-2-yn-1-aminium chloride, C11H14N+·Cl, the asymmetric unit contains two independent enantiomeric cations with a pseudo-inversion center between them. In both mol­ecules, the protonation occurs at the N atom, and the side chains are extended in a direction roughly perpendicular to the benzene rings. The mol­ecules are arranged head-to-head and tail-to-tail, producing hydro­philic and hydro­phobic regions. In addition to the ordinary N—H...Cl hydrogen bonds, numerous weak non-standard hydrogen bonds of the type C—H...Cl also contribute to the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013292/lh6415sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013292/lh6415Isup2.hkl
Contains datablock I

CCDC reference: 274577

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.065
  • wR factor = 0.167
  • Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 64.97 Deg.
Author Response: ...'see _exptl_special_details'

Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 12
Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5877 Proportion of unique data used 1.0000 Ratio reflections to parameters 7.9170 STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.450 From the CIF: _refine_ls_abs_structure_Flack_su 0.080 THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5877 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 64.97 Deg. PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.45 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.92 PLAT128_ALERT_4_C Non-standard setting of Space group Pca21 .... Pbc21 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N8B PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 Cl
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 64.97 From the CIF: _reflns_number_total 1908 Count of symmetry unique reflns 1908 Completeness (_total/calc) 100.00% 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 yes
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Picker Operating Manual (Picker, 1967); cell refinement: Picker; data reduction: DATRDN (Stewart, 1976); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N-benzyl-N-methylprop-2-yn-1-aminium chloride top
Crystal data top
C11H14N+·ClDx = 1.176 Mg m3
Mr = 195.68Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbc21Cell parameters from 32 reflections
a = 5.958 (2) Åθ = 22–37°
b = 11.039 (3) ŵ = 2.68 mm1
c = 33.596 (5) ÅT = 294 K
V = 2209.6 (10) Å3Needle, colorless
Z = 80.31 × 0.07 × 0.03 mm
F(000) = 832
Data collection top
Picker FACS-1 four-circle
diffractometer
1636 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Ni filtered radiation monochromatorθmax = 65.0°, θmin = 2.6°
ω/2θ scansh = 07
Absorption correction: ψ scan
(North et al., 1968)
k = 012
Tmin = 0.794, Tmax = 0.919l = 039
1908 measured reflections3 standard reflections every 100 reflections
1908 independent reflections intensity decay: 1.2%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.065 w = 1/[σ2(Fo2) + (0.1152P)2 + 0.9636P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.167(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.49 e Å3
1908 reflectionsΔρmin = 0.39 e Å3
241 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0071 (9)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 0 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.45 (8)
Special details top

Experimental. PICKER FACS-1 mechanical limit does not allow for data collection above θ = 65°

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
xyzUiso*/Ueq
C1A0.3868 (11)0.4459 (6)0.2602 (2)0.0556 (15)
C2A0.1829 (12)0.3982 (7)0.2471 (2)0.0655 (17)
H2A0.13470.32300.25620.089 (5)*
C3A0.0531 (14)0.4630 (9)0.2206 (3)0.082 (2)
H3A0.08100.43000.21150.089 (5)*
C4A0.1170 (16)0.5736 (9)0.2077 (3)0.086 (2)
H4A0.02540.61610.19020.089 (5)*
C5A0.3153 (16)0.6241 (7)0.2201 (3)0.076 (2)
H5A0.35780.70060.21130.089 (5)*
C6A0.4522 (13)0.5595 (7)0.2460 (2)0.0670 (18)
H6A0.58860.59240.25410.089 (5)*
C7A0.5291 (12)0.3767 (6)0.2885 (2)0.0581 (16)
H71A0.46690.29600.29140.089 (5)*
H72A0.67790.36840.27710.089 (5)*
N8A0.5508 (8)0.4318 (4)0.32872 (17)0.0467 (11)
H8A0.62880.50220.32610.089 (5)*
C9A0.6825 (14)0.3504 (6)0.3543 (3)0.067 (2)
H91A0.59680.27880.35990.079 (9)*
H92A0.71790.39090.37880.079 (9)*
H93A0.81900.32830.34100.079 (9)*
C10A0.3273 (10)0.4616 (6)0.3467 (2)0.0502 (14)
H10A0.24560.51470.32890.089 (5)*
H11A0.24090.38770.34980.089 (5)*
C11A0.3496 (10)0.5205 (6)0.3856 (2)0.0519 (15)
C12A0.3669 (11)0.5675 (7)0.4162 (2)0.0586 (16)
H12A0.38070.60530.44080.089 (5)*
C1B0.0797 (12)0.3558 (6)0.5816 (2)0.0579 (16)
C2B0.2807 (13)0.4022 (8)0.5956 (3)0.0723 (19)
H2B0.33270.47660.58640.089 (5)*
C3B0.4024 (16)0.3382 (10)0.6229 (3)0.095 (3)
H3B0.53730.36920.63240.089 (5)*
C4B0.3261 (18)0.2281 (11)0.6364 (3)0.098 (3)
H4B0.41120.18400.65460.089 (5)*
C5B0.1224 (18)0.1826 (9)0.6231 (3)0.095 (3)
H5B0.06930.10900.63280.089 (5)*
C6B0.0002 (15)0.2459 (7)0.5958 (2)0.0702 (18)
H6B0.13610.21550.58670.089 (5)*
C7B0.0506 (12)0.4273 (6)0.5509 (2)0.0584 (16)
H71B0.20130.44060.56090.089 (5)*
H72B0.01980.50600.54780.089 (5)*
N8B0.0661 (8)0.3685 (4)0.51102 (17)0.0458 (11)
H8B0.14440.29840.51440.089 (5)*
C9B0.1956 (13)0.4436 (7)0.4829 (3)0.069 (2)
H91B0.33820.46360.49440.079 (9)*
H92B0.21870.39930.45860.079 (9)*
H93B0.11410.51660.47730.079 (9)*
C10B0.1625 (11)0.3336 (7)0.4948 (3)0.0577 (19)
H10B0.25520.40550.49250.089 (5)*
H11B0.23540.27850.51320.089 (5)*
C11B0.1434 (10)0.2764 (5)0.4564 (2)0.0506 (14)
C12B0.1338 (12)0.2300 (6)0.4252 (2)0.0607 (17)
H12B0.12610.19300.40040.089 (5)*
Cl1A0.8653 (2)0.64654 (12)0.32272 (6)0.0543 (5)
Cl2B0.3734 (3)0.15049 (12)0.51852 (6)0.0557 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.065 (4)0.052 (3)0.050 (3)0.002 (3)0.009 (3)0.002 (3)
C2A0.071 (4)0.065 (4)0.060 (4)0.008 (3)0.001 (3)0.003 (3)
C3A0.071 (5)0.115 (7)0.061 (4)0.006 (5)0.009 (4)0.001 (5)
C4A0.105 (7)0.105 (6)0.048 (4)0.016 (5)0.007 (4)0.005 (4)
C5A0.109 (6)0.064 (4)0.056 (4)0.002 (4)0.008 (4)0.009 (4)
C6A0.080 (5)0.057 (4)0.064 (4)0.008 (4)0.005 (4)0.007 (3)
C7A0.056 (4)0.050 (3)0.068 (4)0.004 (3)0.008 (3)0.006 (3)
N8A0.042 (2)0.039 (2)0.059 (3)0.0024 (19)0.004 (2)0.007 (2)
C9A0.066 (4)0.050 (4)0.087 (6)0.017 (3)0.006 (4)0.006 (3)
C10A0.040 (3)0.055 (3)0.055 (3)0.003 (3)0.005 (3)0.008 (3)
C11A0.052 (4)0.049 (3)0.055 (4)0.004 (2)0.008 (3)0.002 (3)
C12A0.063 (4)0.066 (4)0.047 (4)0.007 (3)0.003 (3)0.002 (3)
C1B0.066 (4)0.056 (4)0.051 (4)0.005 (3)0.001 (3)0.015 (3)
C2B0.068 (4)0.087 (5)0.062 (4)0.012 (4)0.000 (4)0.003 (4)
C3B0.088 (6)0.127 (8)0.070 (5)0.009 (5)0.020 (4)0.010 (5)
C4B0.124 (7)0.108 (8)0.061 (5)0.011 (6)0.030 (5)0.002 (5)
C5B0.152 (10)0.077 (5)0.056 (5)0.012 (5)0.017 (5)0.003 (4)
C6B0.100 (5)0.062 (4)0.049 (3)0.008 (4)0.006 (4)0.002 (3)
C7B0.066 (4)0.053 (3)0.056 (4)0.002 (3)0.004 (3)0.012 (3)
N8B0.042 (2)0.044 (2)0.051 (3)0.005 (2)0.003 (2)0.006 (2)
C9B0.069 (4)0.060 (4)0.080 (5)0.013 (3)0.005 (4)0.015 (4)
C10B0.040 (3)0.058 (4)0.074 (5)0.005 (3)0.001 (3)0.009 (3)
C11B0.051 (3)0.046 (3)0.055 (4)0.002 (2)0.003 (3)0.003 (3)
C12B0.070 (4)0.057 (4)0.055 (4)0.001 (3)0.002 (3)0.003 (3)
Cl1A0.0500 (9)0.0477 (8)0.0651 (11)0.0031 (5)0.0054 (7)0.0007 (7)
Cl2B0.0544 (9)0.0494 (9)0.0634 (11)0.0048 (6)0.0074 (7)0.0027 (7)
Geometric parameters (Å, º) top
C1A—C2A1.395 (9)C1B—C2B1.385 (10)
C1A—C6A1.397 (9)C1B—C6B1.386 (10)
C1A—C7A1.486 (10)C1B—C7B1.511 (10)
C2A—C3A1.380 (11)C2B—C3B1.367 (13)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.350 (12)C3B—C4B1.374 (15)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.371 (13)C4B—C5B1.388 (14)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.389 (11)C5B—C6B1.365 (12)
C5A—H5A0.9300C5B—H5B0.9300
C6A—H6A0.9300C6B—H6B0.9300
C7A—N8A1.486 (9)C7B—N8B1.493 (8)
C7A—H71A0.9700C7B—H71B0.9700
C7A—H72A0.9700C7B—H72B0.9700
N8A—C9A1.471 (9)N8B—C9B1.475 (9)
N8A—C10A1.499 (7)N8B—C10B1.517 (8)
N8A—H8A0.9100N8B—H8B0.9100
C9A—H91A0.9600C9B—H91B0.9600
C9A—H92A0.9600C9B—H92B0.9600
C9A—H93A0.9600C9B—H93B0.9600
C10A—C11A1.465 (10)C10B—C11B1.442 (11)
C10A—H10A0.9700C10B—H10B0.9700
C10A—H11A0.9700C10B—H11B0.9700
C11A—C12A1.155 (10)C11B—C12B1.166 (9)
C12A—H12A0.9300C12B—H12B0.9300
C2A—C1A—C6A118.4 (7)C2B—C1B—C6B120.1 (7)
C2A—C1A—C7A120.3 (6)C2B—C1B—C7B118.8 (6)
C6A—C1A—C7A121.3 (6)C6B—C1B—C7B121.1 (6)
C1A—C2A—C3A119.7 (7)C1B—C2B—C3B119.7 (8)
C1A—C2A—H2A120.2C1B—C2B—H2B120.2
C3A—C2A—H2A120.2C3B—C2B—H2B120.2
C2A—C3A—C4A121.2 (8)C2B—C3B—C4B120.2 (9)
C2A—C3A—H3A119.4C2B—C3B—H3B119.9
C4A—C3A—H3A119.4C4B—C3B—H3B119.9
C5A—C4A—C3A120.8 (8)C5B—C4B—C3B120.2 (9)
C5A—C4A—H4A119.6C5B—C4B—H4B119.9
C3A—C4A—H4A119.6C3B—C4B—H4B119.9
C6A—C5A—C4A119.2 (8)C4B—C5B—C6B119.9 (10)
C6A—C5A—H5A120.4C4B—C5B—H5B120.1
C4A—C5A—H5A120.4C6B—C5B—H5B120.1
C5A—C6A—C1A120.7 (7)C1B—C6B—C5B119.8 (8)
C5A—C6A—H6A119.7C1B—C6B—H6B120.1
C1A—C6A—H6A119.7C5B—C6B—H6B120.1
N8A—C7A—C1A115.0 (5)N8B—C7B—C1B114.6 (5)
N8A—C7A—H71A108.5N8B—C7B—H71B108.6
C1A—C7A—H71A108.5C1B—C7B—H71B108.6
N8A—C7A—H72A108.5N8B—C7B—H72B108.6
C1A—C7A—H72A108.5C1B—C7B—H72B108.6
H71A—C7A—H72A107.5H71B—C7B—H72B107.6
C7A—N8A—C9A109.2 (5)C9B—N8B—C7B111.3 (5)
C7A—N8A—C10A112.3 (5)C9B—N8B—C10B112.5 (6)
C9A—N8A—C10A111.8 (6)C7B—N8B—C10B112.2 (5)
C7A—N8A—H8A107.8C9B—N8B—H8B106.8
C9A—N8A—H8A107.8C7B—N8B—H8B106.8
C10A—N8A—H8A107.8C10B—N8B—H8B106.8
N8A—C9A—H91A109.5N8B—C9B—H91B109.5
N8A—C9A—H92A109.5N8B—C9B—H92B109.5
H91A—C9A—H92A109.5H91B—C9B—H92B109.5
N8A—C9A—H93A109.5N8B—C9B—H93B109.5
H91A—C9A—H93A109.5H91B—C9B—H93B109.5
H92A—C9A—H93A109.5H92B—C9B—H93B109.5
C11A—C10A—N8A112.1 (5)C11B—C10B—N8B111.2 (6)
C11A—C10A—H10A109.2C11B—C10B—H10B109.4
N8A—C10A—H10A109.2N8B—C10B—H10B109.4
C11A—C10A—H11A109.2C11B—C10B—H11B109.4
N8A—C10A—H11A109.2N8B—C10B—H11B109.4
H10A—C10A—H11A107.9H10B—C10B—H11B108.0
C12A—C11A—C10A179.7 (8)C12B—C11B—C10B178.3 (7)
C11A—C12A—H12A180.0C11B—C12B—H12B180.0
C6A—C1A—C2A—C3A0.5 (10)C6B—C1B—C2B—C3B1.2 (12)
C7A—C1A—C2A—C3A179.6 (7)C7B—C1B—C2B—C3B179.2 (8)
C1A—C2A—C3A—C4A1.5 (12)C1B—C2B—C3B—C4B0.1 (15)
C2A—C3A—C4A—C5A1.0 (13)C2B—C3B—C4B—C5B1.5 (16)
C3A—C4A—C5A—C6A0.5 (13)C3B—C4B—C5B—C6B1.6 (15)
C4A—C5A—C6A—C1A1.6 (12)C2B—C1B—C6B—C5B1.2 (11)
C2A—C1A—C6A—C5A1.0 (10)C7B—C1B—C6B—C5B179.3 (7)
C7A—C1A—C6A—C5A178.8 (7)C4B—C5B—C6B—C1B0.2 (13)
C2A—C1A—C7A—N8A112.8 (7)C2B—C1B—C7B—N8B113.6 (7)
C6A—C1A—C7A—N8A67.1 (8)C6B—C1B—C7B—N8B66.8 (8)
C1A—C7A—N8A—C9A176.2 (6)C1B—C7B—N8B—C9B179.9 (6)
C1A—C7A—N8A—C10A51.6 (7)C1B—C7B—N8B—C10B53.0 (7)
C7A—N8A—C10A—C11A177.5 (5)C9B—N8B—C10B—C11B53.9 (8)
C9A—N8A—C10A—C11A59.3 (7)C7B—N8B—C10B—C11B179.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8A—H8A···Cl1A0.912.133.029 (5)169
N8B—H8B···Cl2B0.912.133.034 (5)171
C6B—H6B···Cl2B0.932.793.578 (8)144
C10A—H10A···Cl1Ai0.972.703.521 (7)143
C10B—H11B···Cl2Bii0.972.733.516 (7)138
C12A—H12A···Cl2Biii0.932.663.559 (8)163
C12B—H12B···Cl1Aiv0.932.663.565 (8)165
C7A—H71A···Cl1Aiv0.972.783.647 (7)149
C7B—H72B···Cl2Biii0.972.823.693 (7)150
C9B—H91B···Cl2Bv0.962.803.639 (8)146
C9A—H93A···Cl1Avi0.962.823.667 (8)148
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y+1/2, z; (iv) x+1, y1/2, z; (v) x1, y+1/2, z; (vi) x+2, y1/2, z.
 

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