The title compound, C
11H
16NO
2+·Cl
−, was obtained as colorless crystals. The molecular packing is stabilized by strong N—H
Cl hydrogen-bonding interactions.
Supporting information
CCDC reference: 647234
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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+·Cl− | F(000) = 488 |
Mr = 229.70 | Dx = 1.270 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4411 reflections |
a = 5.5811 (13) Å | θ = 2.4–28.3° |
b = 12.746 (3) Å | µ = 0.30 mm−1 |
c = 16.886 (4) Å | T = 295 K |
β = 90.664 (4)° | Chunk, colorless |
V = 1201.1 (5) Å3 | 0.22 × 0.11 × 0.09 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 2086 independent reflections |
Radiation source: fine-focus sealed tube | 1967 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −6→5 |
Tmin = 0.937, Tmax = 0.974 | k = −15→13 |
5855 measured reflections | l = −20→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-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 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.21845 (7) | 0.00955 (3) | 0.62347 (2) | 0.04454 (19) | |
O1 | −0.6294 (2) | −0.16837 (10) | 0.47758 (8) | 0.0522 (3) | |
N1 | −0.2724 (2) | −0.06846 (10) | 0.55569 (8) | 0.0385 (3) | |
H1A | −0.1546 | −0.0463 | 0.5875 | 0.058* | |
H1B | −0.4128 | −0.0564 | 0.5784 | 0.058* | |
H1C | −0.2662 | −0.0342 | 0.5098 | 0.058* | |
C1 | −0.2416 (3) | −0.24380 (12) | 0.61753 (9) | 0.0375 (4) | |
O2 | −0.3943 (2) | −0.30642 (10) | 0.45266 (7) | 0.0547 (4) | |
C2 | −0.4311 (3) | −0.23861 (15) | 0.66883 (11) | 0.0525 (4) | |
H2A | −0.5618 | −0.1959 | 0.6571 | 0.063* | |
C3 | −0.4268 (4) | −0.29696 (17) | 0.73791 (12) | 0.0609 (5) | |
H3A | −0.5550 | −0.2937 | 0.7725 | 0.073* | |
C4 | −0.2348 (4) | −0.35921 (15) | 0.75526 (12) | 0.0582 (5) | |
H4A | −0.2328 | −0.3984 | 0.8017 | 0.070* | |
C5 | −0.0466 (4) | −0.36454 (15) | 0.70530 (12) | 0.0593 (5) | |
H5A | 0.0842 | −0.4069 | 0.7177 | 0.071* | |
C6 | −0.0496 (3) | −0.30690 (14) | 0.63606 (11) | 0.0504 (4) | |
H6A | 0.0793 | −0.3108 | 0.6018 | 0.060* | |
C7 | −0.2448 (3) | −0.18253 (12) | 0.54124 (9) | 0.0377 (4) | |
H7A | −0.0929 | −0.1943 | 0.5141 | 0.045* | |
C8 | −0.4484 (3) | −0.21681 (12) | 0.48699 (9) | 0.0391 (4) | |
C9 | −0.5667 (4) | −0.34892 (16) | 0.39491 (12) | 0.0640 (6) | |
H9A | −0.6480 | −0.2908 | 0.3677 | 0.077* | |
C10 | −0.4209 (6) | −0.4079 (3) | 0.33695 (19) | 0.1119 (11) | |
H10A | −0.3085 | −0.3612 | 0.3127 | 0.168* | |
H10B | −0.5242 | −0.4375 | 0.2970 | 0.168* | |
H10C | −0.3356 | −0.4632 | 0.3637 | 0.168* | |
C11 | −0.7469 (5) | −0.4147 (3) | 0.4349 (2) | 0.1067 (11) | |
H11A | −0.8385 | −0.3721 | 0.4703 | 0.160* | |
H11B | −0.6672 | −0.4692 | 0.4643 | 0.160* | |
H11C | −0.8519 | −0.4456 | 0.3960 | 0.160* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0382 (3) | 0.0584 (3) | 0.0370 (3) | −0.00127 (15) | −0.00112 (18) | −0.00599 (15) |
O1 | 0.0441 (7) | 0.0536 (7) | 0.0585 (8) | 0.0038 (5) | −0.0136 (6) | −0.0120 (6) |
N1 | 0.0368 (7) | 0.0415 (7) | 0.0373 (7) | −0.0055 (5) | −0.0043 (5) | 0.0011 (5) |
C1 | 0.0356 (8) | 0.0388 (8) | 0.0378 (8) | −0.0032 (6) | −0.0067 (6) | −0.0009 (6) |
O2 | 0.0599 (8) | 0.0490 (7) | 0.0547 (8) | 0.0082 (6) | −0.0169 (6) | −0.0145 (6) |
C2 | 0.0412 (9) | 0.0626 (11) | 0.0538 (10) | 0.0037 (8) | 0.0005 (7) | 0.0125 (8) |
C3 | 0.0574 (11) | 0.0736 (13) | 0.0519 (11) | −0.0066 (10) | 0.0060 (9) | 0.0151 (9) |
C4 | 0.0736 (13) | 0.0517 (10) | 0.0490 (10) | −0.0104 (9) | −0.0132 (9) | 0.0123 (8) |
C5 | 0.0683 (13) | 0.0512 (10) | 0.0579 (12) | 0.0112 (9) | −0.0191 (10) | 0.0058 (8) |
C6 | 0.0474 (10) | 0.0550 (10) | 0.0486 (10) | 0.0086 (8) | −0.0051 (8) | −0.0021 (8) |
C7 | 0.0340 (8) | 0.0421 (8) | 0.0369 (8) | −0.0004 (6) | −0.0012 (6) | −0.0017 (6) |
C8 | 0.0430 (9) | 0.0413 (8) | 0.0331 (7) | −0.0007 (7) | −0.0026 (6) | −0.0013 (6) |
C9 | 0.0797 (14) | 0.0564 (11) | 0.0551 (12) | 0.0044 (10) | −0.0254 (10) | −0.0173 (9) |
C10 | 0.128 (3) | 0.128 (2) | 0.0798 (18) | −0.039 (2) | 0.0230 (17) | −0.0554 (18) |
C11 | 0.0841 (19) | 0.129 (3) | 0.107 (2) | −0.0296 (18) | 0.0085 (16) | −0.051 (2) |
Geometric parameters (Å, º) top
O1—C8 | 1.193 (2) | C4—H4A | 0.9300 |
N1—C7 | 1.483 (2) | C5—C6 | 1.381 (3) |
N1—H1A | 0.8900 | C5—H5A | 0.9300 |
N1—H1B | 0.8900 | C6—H6A | 0.9300 |
N1—H1C | 0.8900 | C7—C8 | 1.516 (2) |
C1—C6 | 1.373 (2) | C7—H7A | 0.9800 |
C1—C2 | 1.376 (2) | C9—C11 | 1.479 (4) |
C1—C7 | 1.506 (2) | C9—C10 | 1.485 (3) |
O2—C8 | 1.317 (2) | C9—H9A | 0.9800 |
O2—C9 | 1.466 (2) | C10—H10A | 0.9600 |
C2—C3 | 1.383 (3) | C10—H10B | 0.9600 |
C2—H2A | 0.9300 | C10—H10C | 0.9600 |
C3—C4 | 1.362 (3) | C11—H11A | 0.9600 |
C3—H3A | 0.9300 | C11—H11B | 0.9600 |
C4—C5 | 1.357 (3) | C11—H11C | 0.9600 |
| | | |
C7—N1—H1A | 109.5 | N1—C7—C8 | 107.68 (12) |
C7—N1—H1B | 109.5 | C1—C7—C8 | 111.63 (13) |
H1A—N1—H1B | 109.5 | N1—C7—H7A | 108.6 |
C7—N1—H1C | 109.5 | C1—C7—H7A | 108.6 |
H1A—N1—H1C | 109.5 | C8—C7—H7A | 108.6 |
H1B—N1—H1C | 109.5 | O1—C8—O2 | 126.02 (15) |
C6—C1—C2 | 119.21 (15) | O1—C8—C7 | 123.99 (14) |
C6—C1—C7 | 119.99 (14) | O2—C8—C7 | 109.99 (13) |
C2—C1—C7 | 120.80 (14) | O2—C9—C11 | 110.53 (19) |
C8—O2—C9 | 117.46 (14) | O2—C9—C10 | 105.4 (2) |
C1—C2—C3 | 119.95 (17) | C11—C9—C10 | 113.2 (2) |
C1—C2—H2A | 120.0 | O2—C9—H9A | 109.2 |
C3—C2—H2A | 120.0 | C11—C9—H9A | 109.2 |
C4—C3—C2 | 120.01 (18) | C10—C9—H9A | 109.2 |
C4—C3—H3A | 120.0 | C9—C10—H10A | 109.5 |
C2—C3—H3A | 120.0 | C9—C10—H10B | 109.5 |
C5—C4—C3 | 120.55 (17) | H10A—C10—H10B | 109.5 |
C5—C4—H4A | 119.7 | C9—C10—H10C | 109.5 |
C3—C4—H4A | 119.7 | H10A—C10—H10C | 109.5 |
C4—C5—C6 | 119.87 (18) | H10B—C10—H10C | 109.5 |
C4—C5—H5A | 120.1 | C9—C11—H11A | 109.5 |
C6—C5—H5A | 120.1 | C9—C11—H11B | 109.5 |
C1—C6—C5 | 120.41 (17) | H11A—C11—H11B | 109.5 |
C1—C6—H6A | 119.8 | C9—C11—H11C | 109.5 |
C5—C6—H6A | 119.8 | H11A—C11—H11C | 109.5 |
N1—C7—C1 | 111.59 (12) | H11B—C11—H11C | 109.5 |
| | | |
C6—C1—C2—C3 | −0.3 (3) | C6—C1—C7—C8 | 116.74 (17) |
C7—C1—C2—C3 | 178.81 (17) | C2—C1—C7—C8 | −62.36 (19) |
C1—C2—C3—C4 | 0.2 (3) | C9—O2—C8—O1 | 2.8 (3) |
C2—C3—C4—C5 | 0.1 (3) | C9—O2—C8—C7 | −177.08 (15) |
C3—C4—C5—C6 | −0.3 (3) | N1—C7—C8—O1 | −19.5 (2) |
C2—C1—C6—C5 | 0.1 (3) | C1—C7—C8—O1 | 103.32 (19) |
C7—C1—C6—C5 | −179.06 (16) | N1—C7—C8—O2 | 160.40 (13) |
C4—C5—C6—C1 | 0.3 (3) | C1—C7—C8—O2 | −76.79 (17) |
C6—C1—C7—N1 | −122.71 (16) | C8—O2—C9—C11 | −87.8 (2) |
C2—C1—C7—N1 | 58.2 (2) | C8—O2—C9—C10 | 149.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1 | 0.89 | 2.28 | 3.1192 (14) | 158 |
N1—H1B···Cl1i | 0.89 | 2.36 | 3.2327 (15) | 168 |
N1—H1C···Cl1ii | 0.89 | 2.29 | 3.1349 (15) | 158 |
N1—H1C···O1iii | 0.89 | 2.66 | 3.1179 (19) | 113 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+1; (iii) −x−1, −y, −z+1. |