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In the title compound, C
11H
16ClN
2O
+·Cl
−, the chloroethyl side chain is in a synclinal conformation. The tetrahydropyridine ring adopts a half-chair conformation. The crystal structure is stabilized by intermolecular N—H
Cl hydrogen bonds.
Supporting information
CCDC reference: 621381
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.053
- wR factor = 0.131
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.53
PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc.
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 25.00
From the CIF: _reflns_number_total 2200
Count of symmetry unique reflns 1310
Completeness (_total/calc) 167.94%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 890
Fraction of Friedel pairs measured 0.679
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
3-(2-chloroethyl)-2-methyl-4-oxo-6,7,8,9-tetrahydro-4
H-pyrido[1,2-
a]pyrimidin- 1-ium chloride
top
Crystal data top
C11H16ClN2O+·Cl− | F(000) = 552 |
Mr = 263.16 | Dx = 1.385 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4176 reflections |
a = 6.609 (5) Å | θ = 2.3–25.9° |
b = 10.340 (8) Å | µ = 0.50 mm−1 |
c = 18.473 (14) Å | T = 273 K |
V = 1262.5 (17) Å3 | Block, colorless |
Z = 4 | 0.21 × 0.17 × 0.09 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1980 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ω scans | h = −7→7 |
8301 measured reflections | k = −12→11 |
2200 independent reflections | l = −21→21 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0819P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
2200 reflections | Δρmax = 0.68 e Å−3 |
151 parameters | Δρmin = −0.27 e Å−3 |
6 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (10) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.8314 (4) | 0.5794 (2) | 0.75737 (14) | 0.0357 (6) | |
C2 | 0.8076 (5) | 0.5654 (3) | 0.67740 (16) | 0.0514 (8) | |
H2A | 0.6983 | 0.6212 | 0.6616 | 0.062* | |
H2B | 0.7683 | 0.4769 | 0.6669 | 0.062* | |
C3 | 0.9928 (10) | 0.5970 (7) | 0.6344 (2) | 0.0602 (14) | 0.712 (10) |
H3A | 0.9574 | 0.6108 | 0.5840 | 0.072* | 0.712 (10) |
H3B | 1.0890 | 0.5264 | 0.6370 | 0.072* | 0.712 (10) |
C4 | 1.0841 (11) | 0.7183 (6) | 0.6658 (3) | 0.0602 (14) | 0.712 (10) |
H4A | 1.2015 | 0.7425 | 0.6374 | 0.072* | 0.712 (10) |
H4B | 0.9864 | 0.7880 | 0.6624 | 0.072* | 0.712 (10) |
C31 | 0.9280 (18) | 0.6608 (16) | 0.6356 (6) | 0.0602 (14) | 0.288 (10) |
H31A | 0.8565 | 0.7427 | 0.6355 | 0.072* | 0.288 (10) |
H31B | 0.9376 | 0.6315 | 0.5859 | 0.072* | 0.288 (10) |
C41 | 1.1357 (18) | 0.6824 (19) | 0.6639 (5) | 0.0602 (14) | 0.288 (10) |
H41A | 1.2188 | 0.6084 | 0.6514 | 0.072* | 0.288 (10) |
H41B | 1.1929 | 0.7576 | 0.6400 | 0.072* | 0.288 (10) |
C5 | 1.1457 (5) | 0.7024 (3) | 0.74275 (16) | 0.0565 (8) | |
H5A | 1.2665 | 0.6493 | 0.7450 | 0.068* | |
H5B | 1.1783 | 0.7864 | 0.7629 | 0.068* | |
C6 | 0.9965 (5) | 0.6612 (3) | 0.86271 (15) | 0.0434 (7) | |
C7 | 0.8414 (4) | 0.6034 (2) | 0.90617 (14) | 0.0406 (6) | |
C8 | 0.6915 (4) | 0.5376 (3) | 0.87322 (15) | 0.0397 (6) | |
C9 | 0.8573 (5) | 0.6237 (3) | 0.98624 (15) | 0.0545 (7) | |
H9A | 0.8707 | 0.7157 | 0.9954 | 0.065* | |
H9B | 0.7318 | 0.5954 | 1.0084 | 0.065* | |
C10 | 1.0286 (6) | 0.5556 (3) | 1.02274 (16) | 0.0588 (8) | |
H10A | 1.0292 | 0.5776 | 1.0738 | 0.071* | |
H10B | 1.1555 | 0.5846 | 1.0020 | 0.071* | |
C11 | 0.5159 (5) | 0.4741 (4) | 0.9097 (2) | 0.0620 (9) | |
H11A | 0.5621 | 0.3995 | 0.9359 | 0.093* | |
H11B | 0.4187 | 0.4480 | 0.8740 | 0.093* | |
H11C | 0.4542 | 0.5340 | 0.9427 | 0.093* | |
Cl1 | 1.00872 (19) | 0.38447 (10) | 1.01307 (5) | 0.0818 (4) | |
N1 | 0.6915 (4) | 0.5274 (2) | 0.79943 (13) | 0.0405 (6) | |
H1N | 0.604 (5) | 0.483 (3) | 0.7777 (17) | 0.048 (9)* | |
N2 | 0.9847 (3) | 0.64161 (19) | 0.78680 (11) | 0.0363 (5) | |
O1 | 1.1383 (4) | 0.7238 (3) | 0.88617 (12) | 0.0712 (7) | |
Cl2 | 0.36262 (12) | 0.37058 (8) | 0.72785 (5) | 0.0617 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0384 (15) | 0.0310 (12) | 0.0376 (13) | 0.0012 (11) | −0.0023 (12) | 0.0010 (10) |
C2 | 0.0627 (19) | 0.0517 (16) | 0.0398 (15) | −0.0091 (16) | −0.0055 (15) | 0.0001 (13) |
C3 | 0.062 (3) | 0.079 (3) | 0.0388 (14) | −0.016 (2) | 0.0097 (15) | −0.0012 (18) |
C4 | 0.062 (3) | 0.079 (3) | 0.0388 (14) | −0.016 (2) | 0.0097 (15) | −0.0012 (18) |
C31 | 0.062 (3) | 0.079 (3) | 0.0388 (14) | −0.016 (2) | 0.0097 (15) | −0.0012 (18) |
C41 | 0.062 (3) | 0.079 (3) | 0.0388 (14) | −0.016 (2) | 0.0097 (15) | −0.0012 (18) |
C5 | 0.0503 (18) | 0.0676 (19) | 0.0516 (18) | −0.0227 (17) | 0.0040 (15) | 0.0023 (15) |
C6 | 0.0490 (17) | 0.0406 (14) | 0.0404 (14) | −0.0030 (13) | −0.0061 (13) | −0.0023 (11) |
C7 | 0.0443 (16) | 0.0386 (14) | 0.0387 (15) | 0.0100 (13) | 0.0034 (12) | −0.0006 (11) |
C8 | 0.0362 (15) | 0.0380 (14) | 0.0448 (16) | 0.0086 (12) | 0.0032 (12) | 0.0049 (11) |
C9 | 0.0628 (18) | 0.0595 (16) | 0.0411 (16) | 0.0095 (19) | 0.0082 (14) | −0.0061 (14) |
C10 | 0.0607 (19) | 0.083 (2) | 0.0322 (15) | −0.0061 (18) | 0.0003 (14) | −0.0019 (14) |
C11 | 0.0457 (19) | 0.083 (2) | 0.058 (2) | −0.0048 (19) | 0.0106 (16) | 0.0085 (17) |
Cl1 | 0.1077 (8) | 0.0768 (6) | 0.0609 (6) | 0.0220 (6) | −0.0093 (5) | 0.0060 (4) |
N1 | 0.0374 (13) | 0.0414 (13) | 0.0427 (13) | −0.0072 (11) | −0.0044 (11) | 0.0003 (10) |
N2 | 0.0380 (11) | 0.0352 (10) | 0.0358 (12) | −0.0036 (10) | 0.0019 (9) | 0.0013 (9) |
O1 | 0.0786 (16) | 0.0863 (16) | 0.0487 (12) | −0.0444 (15) | −0.0092 (12) | −0.0044 (12) |
Cl2 | 0.0508 (4) | 0.0540 (4) | 0.0802 (6) | −0.0168 (4) | −0.0115 (4) | 0.0014 (4) |
Geometric parameters (Å, º) top
C1—N2 | 1.317 (3) | C5—H5A | 0.9700 |
C1—N1 | 1.322 (4) | C5—H5B | 0.9700 |
C1—C2 | 1.493 (4) | C6—O1 | 1.218 (4) |
C2—C31 | 1.485 (8) | C6—N2 | 1.419 (4) |
C2—C3 | 1.496 (6) | C6—C7 | 1.432 (4) |
C2—H2A | 0.9700 | C7—C8 | 1.348 (4) |
C2—H2B | 0.9700 | C7—C9 | 1.497 (4) |
C3—C4 | 1.508 (7) | C8—N1 | 1.367 (4) |
C3—H3A | 0.9700 | C8—C11 | 1.494 (4) |
C3—H3B | 0.9700 | C9—C10 | 1.494 (5) |
C4—C5 | 1.487 (6) | C9—H9A | 0.9700 |
C4—H4A | 0.9700 | C9—H9B | 0.9700 |
C4—H4B | 0.9700 | C10—Cl1 | 1.783 (4) |
C31—C41 | 1.486 (10) | C10—H10A | 0.9700 |
C31—H31A | 0.9700 | C10—H10B | 0.9700 |
C31—H31B | 0.9700 | C11—H11A | 0.9600 |
C41—C5 | 1.472 (9) | C11—H11B | 0.9600 |
C41—H41A | 0.9700 | C11—H11C | 0.9600 |
C41—H41B | 0.9700 | N1—H1N | 0.84 (3) |
C5—N2 | 1.480 (4) | | |
| | | |
N2—C1—N1 | 119.6 (2) | N2—C5—H5A | 109.2 |
N2—C1—C2 | 122.5 (2) | C4—C5—H5A | 109.2 |
N1—C1—C2 | 117.9 (2) | C41—C5—H5B | 121.0 |
C31—C2—C1 | 113.2 (5) | N2—C5—H5B | 109.2 |
C1—C2—C3 | 114.7 (3) | C4—C5—H5B | 109.2 |
C31—C2—H2A | 81.2 | H5A—C5—H5B | 107.9 |
C1—C2—H2A | 108.6 | O1—C6—N2 | 118.0 (3) |
C3—C2—H2A | 108.6 | O1—C6—C7 | 124.9 (3) |
C31—C2—H2B | 131.7 | N2—C6—C7 | 117.0 (3) |
C1—C2—H2B | 108.6 | C8—C7—C6 | 118.9 (2) |
C3—C2—H2B | 108.6 | C8—C7—C9 | 124.6 (3) |
H2A—C2—H2B | 107.6 | C6—C7—C9 | 116.4 (3) |
C2—C3—C4 | 107.8 (5) | C7—C8—N1 | 119.3 (3) |
C2—C3—H3A | 110.2 | C7—C8—C11 | 126.1 (3) |
C4—C3—H3A | 110.2 | N1—C8—C11 | 114.6 (3) |
C2—C3—H3B | 110.2 | C10—C9—C7 | 115.6 (3) |
C4—C3—H3B | 110.2 | C10—C9—H9A | 108.4 |
H3A—C3—H3B | 108.5 | C7—C9—H9A | 108.4 |
C5—C4—C3 | 112.7 (5) | C10—C9—H9B | 108.4 |
C5—C4—H4A | 109.1 | C7—C9—H9B | 108.4 |
C3—C4—H4A | 109.1 | H9A—C9—H9B | 107.4 |
C5—C4—H4B | 109.1 | C9—C10—Cl1 | 111.5 (3) |
C3—C4—H4B | 109.1 | C9—C10—H10A | 109.3 |
H4A—C4—H4B | 107.8 | Cl1—C10—H10A | 109.3 |
C2—C31—C41 | 114.4 (11) | C9—C10—H10B | 109.3 |
C2—C31—H31A | 108.7 | Cl1—C10—H10B | 109.3 |
C41—C31—H31A | 108.7 | H10A—C10—H10B | 108.0 |
C2—C31—H31B | 108.7 | C8—C11—H11A | 109.5 |
C41—C31—H31B | 108.7 | C8—C11—H11B | 109.5 |
H31A—C31—H31B | 107.6 | H11A—C11—H11B | 109.5 |
C5—C41—C31 | 114.2 (10) | C8—C11—H11C | 109.5 |
C5—C41—H41A | 108.7 | H11A—C11—H11C | 109.5 |
C31—C41—H41A | 108.7 | H11B—C11—H11C | 109.5 |
C5—C41—H41B | 108.7 | C1—N1—C8 | 123.7 (3) |
C31—C41—H41B | 108.7 | C1—N1—H1N | 115 (2) |
H41A—C41—H41B | 107.6 | C8—N1—H1N | 121 (2) |
C41—C5—N2 | 116.9 (6) | C1—N2—C6 | 121.3 (2) |
N2—C5—C4 | 112.1 (4) | C1—N2—C5 | 122.2 (2) |
C41—C5—H5A | 90.0 | C6—N2—C5 | 116.3 (2) |
| | | |
N2—C1—C2—C31 | −18.9 (8) | C9—C7—C8—C11 | 0.3 (4) |
N1—C1—C2—C31 | 160.8 (8) | C8—C7—C9—C10 | 111.9 (3) |
N2—C1—C2—C3 | 14.6 (5) | C6—C7—C9—C10 | −69.3 (4) |
N1—C1—C2—C3 | −165.7 (4) | C7—C9—C10—Cl1 | −61.4 (3) |
C31—C2—C3—C4 | 51.1 (10) | N2—C1—N1—C8 | 2.3 (4) |
C1—C2—C3—C4 | −43.1 (7) | C2—C1—N1—C8 | −177.4 (2) |
C2—C3—C4—C5 | 61.0 (9) | C7—C8—N1—C1 | −0.3 (4) |
C1—C2—C31—C41 | 42.0 (17) | C11—C8—N1—C1 | 178.5 (3) |
C3—C2—C31—C41 | −57.8 (12) | N1—C1—N2—C6 | −4.1 (4) |
C2—C31—C41—C5 | −47 (2) | C2—C1—N2—C6 | 175.6 (3) |
C31—C41—C5—N2 | 27.6 (18) | N1—C1—N2—C5 | −179.8 (2) |
C31—C41—C5—C4 | −52.7 (15) | C2—C1—N2—C5 | −0.1 (4) |
C3—C4—C5—C41 | 61 (2) | O1—C6—N2—C1 | −177.2 (3) |
C3—C4—C5—N2 | −47.9 (7) | C7—C6—N2—C1 | 3.9 (4) |
O1—C6—C7—C8 | 179.3 (3) | O1—C6—N2—C5 | −1.3 (4) |
N2—C6—C7—C8 | −1.8 (4) | C7—C6—N2—C5 | 179.8 (2) |
O1—C6—C7—C9 | 0.5 (4) | C41—C5—N2—C1 | −4.3 (9) |
N2—C6—C7—C9 | 179.3 (2) | C4—C5—N2—C1 | 16.7 (5) |
C6—C7—C8—N1 | 0.1 (4) | C41—C5—N2—C6 | 179.8 (8) |
C9—C7—C8—N1 | 178.9 (3) | C4—C5—N2—C6 | −159.2 (4) |
C6—C7—C8—C11 | −178.5 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl2 | 0.84 (3) | 2.18 (4) | 3.017 (3) | 176 (3) |
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