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In the title compound, C11H16ClN2O+·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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603056X/kj2018sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603056X/kj2018Isup2.hkl
Contains datablock I

CCDC reference: 621381

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](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

Computing details top

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-4H-pyrido[1,2-a]pyrimidin- 1-ium chloride top
Crystal data top
C11H16ClN2O+·ClF(000) = 552
Mr = 263.16Dx = 1.385 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4176 reflections
a = 6.609 (5) Åθ = 2.3–25.9°
b = 10.340 (8) ŵ = 0.50 mm1
c = 18.473 (14) ÅT = 273 K
V = 1262.5 (17) Å3Block, colorless
Z = 40.21 × 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 tubeRint = 0.056
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω scansh = 77
8301 measured reflectionsk = 1211
2200 independent reflectionsl = 2121
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H 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 reflectionsΔρmax = 0.68 e Å3
151 parametersΔρmin = 0.27 e Å3
6 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/UeqOcc. (<1)
C10.8314 (4)0.5794 (2)0.75737 (14)0.0357 (6)
C20.8076 (5)0.5654 (3)0.67740 (16)0.0514 (8)
H2A0.69830.62120.66160.062*
H2B0.76830.47690.66690.062*
C30.9928 (10)0.5970 (7)0.6344 (2)0.0602 (14)0.712 (10)
H3A0.95740.61080.58400.072*0.712 (10)
H3B1.08900.52640.63700.072*0.712 (10)
C41.0841 (11)0.7183 (6)0.6658 (3)0.0602 (14)0.712 (10)
H4A1.20150.74250.63740.072*0.712 (10)
H4B0.98640.78800.66240.072*0.712 (10)
C310.9280 (18)0.6608 (16)0.6356 (6)0.0602 (14)0.288 (10)
H31A0.85650.74270.63550.072*0.288 (10)
H31B0.93760.63150.58590.072*0.288 (10)
C411.1357 (18)0.6824 (19)0.6639 (5)0.0602 (14)0.288 (10)
H41A1.21880.60840.65140.072*0.288 (10)
H41B1.19290.75760.64000.072*0.288 (10)
C51.1457 (5)0.7024 (3)0.74275 (16)0.0565 (8)
H5A1.26650.64930.74500.068*
H5B1.17830.78640.76290.068*
C60.9965 (5)0.6612 (3)0.86271 (15)0.0434 (7)
C70.8414 (4)0.6034 (2)0.90617 (14)0.0406 (6)
C80.6915 (4)0.5376 (3)0.87322 (15)0.0397 (6)
C90.8573 (5)0.6237 (3)0.98624 (15)0.0545 (7)
H9A0.87070.71570.99540.065*
H9B0.73180.59541.00840.065*
C101.0286 (6)0.5556 (3)1.02274 (16)0.0588 (8)
H10A1.02920.57761.07380.071*
H10B1.15550.58461.00200.071*
C110.5159 (5)0.4741 (4)0.9097 (2)0.0620 (9)
H11A0.56210.39950.93590.093*
H11B0.41870.44800.87400.093*
H11C0.45420.53400.94270.093*
Cl11.00872 (19)0.38447 (10)1.01307 (5)0.0818 (4)
N10.6915 (4)0.5274 (2)0.79943 (13)0.0405 (6)
H1N0.604 (5)0.483 (3)0.7777 (17)0.048 (9)*
N20.9847 (3)0.64161 (19)0.78680 (11)0.0363 (5)
O11.1383 (4)0.7238 (3)0.88617 (12)0.0712 (7)
Cl20.36262 (12)0.37058 (8)0.72785 (5)0.0617 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0384 (15)0.0310 (12)0.0376 (13)0.0012 (11)0.0023 (12)0.0010 (10)
C20.0627 (19)0.0517 (16)0.0398 (15)0.0091 (16)0.0055 (15)0.0001 (13)
C30.062 (3)0.079 (3)0.0388 (14)0.016 (2)0.0097 (15)0.0012 (18)
C40.062 (3)0.079 (3)0.0388 (14)0.016 (2)0.0097 (15)0.0012 (18)
C310.062 (3)0.079 (3)0.0388 (14)0.016 (2)0.0097 (15)0.0012 (18)
C410.062 (3)0.079 (3)0.0388 (14)0.016 (2)0.0097 (15)0.0012 (18)
C50.0503 (18)0.0676 (19)0.0516 (18)0.0227 (17)0.0040 (15)0.0023 (15)
C60.0490 (17)0.0406 (14)0.0404 (14)0.0030 (13)0.0061 (13)0.0023 (11)
C70.0443 (16)0.0386 (14)0.0387 (15)0.0100 (13)0.0034 (12)0.0006 (11)
C80.0362 (15)0.0380 (14)0.0448 (16)0.0086 (12)0.0032 (12)0.0049 (11)
C90.0628 (18)0.0595 (16)0.0411 (16)0.0095 (19)0.0082 (14)0.0061 (14)
C100.0607 (19)0.083 (2)0.0322 (15)0.0061 (18)0.0003 (14)0.0019 (14)
C110.0457 (19)0.083 (2)0.058 (2)0.0048 (19)0.0106 (16)0.0085 (17)
Cl10.1077 (8)0.0768 (6)0.0609 (6)0.0220 (6)0.0093 (5)0.0060 (4)
N10.0374 (13)0.0414 (13)0.0427 (13)0.0072 (11)0.0044 (11)0.0003 (10)
N20.0380 (11)0.0352 (10)0.0358 (12)0.0036 (10)0.0019 (9)0.0013 (9)
O10.0786 (16)0.0863 (16)0.0487 (12)0.0444 (15)0.0092 (12)0.0044 (12)
Cl20.0508 (4)0.0540 (4)0.0802 (6)0.0168 (4)0.0115 (4)0.0014 (4)
Geometric parameters (Å, º) top
C1—N21.317 (3)C5—H5A0.9700
C1—N11.322 (4)C5—H5B0.9700
C1—C21.493 (4)C6—O11.218 (4)
C2—C311.485 (8)C6—N21.419 (4)
C2—C31.496 (6)C6—C71.432 (4)
C2—H2A0.9700C7—C81.348 (4)
C2—H2B0.9700C7—C91.497 (4)
C3—C41.508 (7)C8—N11.367 (4)
C3—H3A0.9700C8—C111.494 (4)
C3—H3B0.9700C9—C101.494 (5)
C4—C51.487 (6)C9—H9A0.9700
C4—H4A0.9700C9—H9B0.9700
C4—H4B0.9700C10—Cl11.783 (4)
C31—C411.486 (10)C10—H10A0.9700
C31—H31A0.9700C10—H10B0.9700
C31—H31B0.9700C11—H11A0.9600
C41—C51.472 (9)C11—H11B0.9600
C41—H41A0.9700C11—H11C0.9600
C41—H41B0.9700N1—H1N0.84 (3)
C5—N21.480 (4)
N2—C1—N1119.6 (2)N2—C5—H5A109.2
N2—C1—C2122.5 (2)C4—C5—H5A109.2
N1—C1—C2117.9 (2)C41—C5—H5B121.0
C31—C2—C1113.2 (5)N2—C5—H5B109.2
C1—C2—C3114.7 (3)C4—C5—H5B109.2
C31—C2—H2A81.2H5A—C5—H5B107.9
C1—C2—H2A108.6O1—C6—N2118.0 (3)
C3—C2—H2A108.6O1—C6—C7124.9 (3)
C31—C2—H2B131.7N2—C6—C7117.0 (3)
C1—C2—H2B108.6C8—C7—C6118.9 (2)
C3—C2—H2B108.6C8—C7—C9124.6 (3)
H2A—C2—H2B107.6C6—C7—C9116.4 (3)
C2—C3—C4107.8 (5)C7—C8—N1119.3 (3)
C2—C3—H3A110.2C7—C8—C11126.1 (3)
C4—C3—H3A110.2N1—C8—C11114.6 (3)
C2—C3—H3B110.2C10—C9—C7115.6 (3)
C4—C3—H3B110.2C10—C9—H9A108.4
H3A—C3—H3B108.5C7—C9—H9A108.4
C5—C4—C3112.7 (5)C10—C9—H9B108.4
C5—C4—H4A109.1C7—C9—H9B108.4
C3—C4—H4A109.1H9A—C9—H9B107.4
C5—C4—H4B109.1C9—C10—Cl1111.5 (3)
C3—C4—H4B109.1C9—C10—H10A109.3
H4A—C4—H4B107.8Cl1—C10—H10A109.3
C2—C31—C41114.4 (11)C9—C10—H10B109.3
C2—C31—H31A108.7Cl1—C10—H10B109.3
C41—C31—H31A108.7H10A—C10—H10B108.0
C2—C31—H31B108.7C8—C11—H11A109.5
C41—C31—H31B108.7C8—C11—H11B109.5
H31A—C31—H31B107.6H11A—C11—H11B109.5
C5—C41—C31114.2 (10)C8—C11—H11C109.5
C5—C41—H41A108.7H11A—C11—H11C109.5
C31—C41—H41A108.7H11B—C11—H11C109.5
C5—C41—H41B108.7C1—N1—C8123.7 (3)
C31—C41—H41B108.7C1—N1—H1N115 (2)
H41A—C41—H41B107.6C8—N1—H1N121 (2)
C41—C5—N2116.9 (6)C1—N2—C6121.3 (2)
N2—C5—C4112.1 (4)C1—N2—C5122.2 (2)
C41—C5—H5A90.0C6—N2—C5116.3 (2)
N2—C1—C2—C3118.9 (8)C9—C7—C8—C110.3 (4)
N1—C1—C2—C31160.8 (8)C8—C7—C9—C10111.9 (3)
N2—C1—C2—C314.6 (5)C6—C7—C9—C1069.3 (4)
N1—C1—C2—C3165.7 (4)C7—C9—C10—Cl161.4 (3)
C31—C2—C3—C451.1 (10)N2—C1—N1—C82.3 (4)
C1—C2—C3—C443.1 (7)C2—C1—N1—C8177.4 (2)
C2—C3—C4—C561.0 (9)C7—C8—N1—C10.3 (4)
C1—C2—C31—C4142.0 (17)C11—C8—N1—C1178.5 (3)
C3—C2—C31—C4157.8 (12)N1—C1—N2—C64.1 (4)
C2—C31—C41—C547 (2)C2—C1—N2—C6175.6 (3)
C31—C41—C5—N227.6 (18)N1—C1—N2—C5179.8 (2)
C31—C41—C5—C452.7 (15)C2—C1—N2—C50.1 (4)
C3—C4—C5—C4161 (2)O1—C6—N2—C1177.2 (3)
C3—C4—C5—N247.9 (7)C7—C6—N2—C13.9 (4)
O1—C6—C7—C8179.3 (3)O1—C6—N2—C51.3 (4)
N2—C6—C7—C81.8 (4)C7—C6—N2—C5179.8 (2)
O1—C6—C7—C90.5 (4)C41—C5—N2—C14.3 (9)
N2—C6—C7—C9179.3 (2)C4—C5—N2—C116.7 (5)
C6—C7—C8—N10.1 (4)C41—C5—N2—C6179.8 (8)
C9—C7—C8—N1178.9 (3)C4—C5—N2—C6159.2 (4)
C6—C7—C8—C11178.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl20.84 (3)2.18 (4)3.017 (3)176 (3)
 

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