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The title compound, C11H16NO2+·Cl, was obtained as colorless crystals. The mol­ecular packing is stabilized by strong N—H...Cl hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014869/hg2217sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014869/hg2217Isup2.hkl
Contains datablock I

CCDC reference: 647234

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.114
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.98 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.73 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1C .. O1 .. 2.66 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C11 H16 N O2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 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

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

[(Isopropoxycarbonyl)phenylmethyl]ammonium chloride top
Crystal data top
C11H16NO2+·ClF(000) = 488
Mr = 229.70Dx = 1.270 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4411 reflections
a = 5.5811 (13) Åθ = 2.4–28.3°
b = 12.746 (3) ŵ = 0.30 mm1
c = 16.886 (4) ÅT = 295 K
β = 90.664 (4)°Chunk, colorless
V = 1201.1 (5) Å30.22 × 0.11 × 0.09 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
2086 independent reflections
Radiation source: fine-focus sealed tube1967 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 65
Tmin = 0.937, Tmax = 0.974k = 1513
5855 measured reflectionsl = 2017
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0793P)2 + 0.2301P]
where P = (Fo2 + 2Fc2)/3
2086 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.15 e Å3
Special details top

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
Cl10.21845 (7)0.00955 (3)0.62347 (2)0.04454 (19)
O10.6294 (2)0.16837 (10)0.47758 (8)0.0522 (3)
N10.2724 (2)0.06846 (10)0.55569 (8)0.0385 (3)
H1A0.15460.04630.58750.058*
H1B0.41280.05640.57840.058*
H1C0.26620.03420.50980.058*
C10.2416 (3)0.24380 (12)0.61753 (9)0.0375 (4)
O20.3943 (2)0.30642 (10)0.45266 (7)0.0547 (4)
C20.4311 (3)0.23861 (15)0.66883 (11)0.0525 (4)
H2A0.56180.19590.65710.063*
C30.4268 (4)0.29696 (17)0.73791 (12)0.0609 (5)
H3A0.55500.29370.77250.073*
C40.2348 (4)0.35921 (15)0.75526 (12)0.0582 (5)
H4A0.23280.39840.80170.070*
C50.0466 (4)0.36454 (15)0.70530 (12)0.0593 (5)
H5A0.08420.40690.71770.071*
C60.0496 (3)0.30690 (14)0.63606 (11)0.0504 (4)
H6A0.07930.31080.60180.060*
C70.2448 (3)0.18253 (12)0.54124 (9)0.0377 (4)
H7A0.09290.19430.51410.045*
C80.4484 (3)0.21681 (12)0.48699 (9)0.0391 (4)
C90.5667 (4)0.34892 (16)0.39491 (12)0.0640 (6)
H9A0.64800.29080.36770.077*
C100.4209 (6)0.4079 (3)0.33695 (19)0.1119 (11)
H10A0.30850.36120.31270.168*
H10B0.52420.43750.29700.168*
H10C0.33560.46320.36370.168*
C110.7469 (5)0.4147 (3)0.4349 (2)0.1067 (11)
H11A0.83850.37210.47030.160*
H11B0.66720.46920.46430.160*
H11C0.85190.44560.39600.160*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0382 (3)0.0584 (3)0.0370 (3)0.00127 (15)0.00112 (18)0.00599 (15)
O10.0441 (7)0.0536 (7)0.0585 (8)0.0038 (5)0.0136 (6)0.0120 (6)
N10.0368 (7)0.0415 (7)0.0373 (7)0.0055 (5)0.0043 (5)0.0011 (5)
C10.0356 (8)0.0388 (8)0.0378 (8)0.0032 (6)0.0067 (6)0.0009 (6)
O20.0599 (8)0.0490 (7)0.0547 (8)0.0082 (6)0.0169 (6)0.0145 (6)
C20.0412 (9)0.0626 (11)0.0538 (10)0.0037 (8)0.0005 (7)0.0125 (8)
C30.0574 (11)0.0736 (13)0.0519 (11)0.0066 (10)0.0060 (9)0.0151 (9)
C40.0736 (13)0.0517 (10)0.0490 (10)0.0104 (9)0.0132 (9)0.0123 (8)
C50.0683 (13)0.0512 (10)0.0579 (12)0.0112 (9)0.0191 (10)0.0058 (8)
C60.0474 (10)0.0550 (10)0.0486 (10)0.0086 (8)0.0051 (8)0.0021 (8)
C70.0340 (8)0.0421 (8)0.0369 (8)0.0004 (6)0.0012 (6)0.0017 (6)
C80.0430 (9)0.0413 (8)0.0331 (7)0.0007 (7)0.0026 (6)0.0013 (6)
C90.0797 (14)0.0564 (11)0.0551 (12)0.0044 (10)0.0254 (10)0.0173 (9)
C100.128 (3)0.128 (2)0.0798 (18)0.039 (2)0.0230 (17)0.0554 (18)
C110.0841 (19)0.129 (3)0.107 (2)0.0296 (18)0.0085 (16)0.051 (2)
Geometric parameters (Å, º) top
O1—C81.193 (2)C4—H4A0.9300
N1—C71.483 (2)C5—C61.381 (3)
N1—H1A0.8900C5—H5A0.9300
N1—H1B0.8900C6—H6A0.9300
N1—H1C0.8900C7—C81.516 (2)
C1—C61.373 (2)C7—H7A0.9800
C1—C21.376 (2)C9—C111.479 (4)
C1—C71.506 (2)C9—C101.485 (3)
O2—C81.317 (2)C9—H9A0.9800
O2—C91.466 (2)C10—H10A0.9600
C2—C31.383 (3)C10—H10B0.9600
C2—H2A0.9300C10—H10C0.9600
C3—C41.362 (3)C11—H11A0.9600
C3—H3A0.9300C11—H11B0.9600
C4—C51.357 (3)C11—H11C0.9600
C7—N1—H1A109.5N1—C7—C8107.68 (12)
C7—N1—H1B109.5C1—C7—C8111.63 (13)
H1A—N1—H1B109.5N1—C7—H7A108.6
C7—N1—H1C109.5C1—C7—H7A108.6
H1A—N1—H1C109.5C8—C7—H7A108.6
H1B—N1—H1C109.5O1—C8—O2126.02 (15)
C6—C1—C2119.21 (15)O1—C8—C7123.99 (14)
C6—C1—C7119.99 (14)O2—C8—C7109.99 (13)
C2—C1—C7120.80 (14)O2—C9—C11110.53 (19)
C8—O2—C9117.46 (14)O2—C9—C10105.4 (2)
C1—C2—C3119.95 (17)C11—C9—C10113.2 (2)
C1—C2—H2A120.0O2—C9—H9A109.2
C3—C2—H2A120.0C11—C9—H9A109.2
C4—C3—C2120.01 (18)C10—C9—H9A109.2
C4—C3—H3A120.0C9—C10—H10A109.5
C2—C3—H3A120.0C9—C10—H10B109.5
C5—C4—C3120.55 (17)H10A—C10—H10B109.5
C5—C4—H4A119.7C9—C10—H10C109.5
C3—C4—H4A119.7H10A—C10—H10C109.5
C4—C5—C6119.87 (18)H10B—C10—H10C109.5
C4—C5—H5A120.1C9—C11—H11A109.5
C6—C5—H5A120.1C9—C11—H11B109.5
C1—C6—C5120.41 (17)H11A—C11—H11B109.5
C1—C6—H6A119.8C9—C11—H11C109.5
C5—C6—H6A119.8H11A—C11—H11C109.5
N1—C7—C1111.59 (12)H11B—C11—H11C109.5
C6—C1—C2—C30.3 (3)C6—C1—C7—C8116.74 (17)
C7—C1—C2—C3178.81 (17)C2—C1—C7—C862.36 (19)
C1—C2—C3—C40.2 (3)C9—O2—C8—O12.8 (3)
C2—C3—C4—C50.1 (3)C9—O2—C8—C7177.08 (15)
C3—C4—C5—C60.3 (3)N1—C7—C8—O119.5 (2)
C2—C1—C6—C50.1 (3)C1—C7—C8—O1103.32 (19)
C7—C1—C6—C5179.06 (16)N1—C7—C8—O2160.40 (13)
C4—C5—C6—C10.3 (3)C1—C7—C8—O276.79 (17)
C6—C1—C7—N1122.71 (16)C8—O2—C9—C1187.8 (2)
C2—C1—C7—N158.2 (2)C8—O2—C9—C10149.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl10.892.283.1192 (14)158
N1—H1B···Cl1i0.892.363.2327 (15)168
N1—H1C···Cl1ii0.892.293.1349 (15)158
N1—H1C···O1iii0.892.663.1179 (19)113
Symmetry codes: (i) x1, y, z; (ii) x, y, z+1; (iii) x1, y, z+1.
 

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