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The title compound, C15H15N2+·Cl, (I), comprises the hydro­chloride of an essentially planar tetra­cyclic mol­ecule, which is protonated on the pyridine N atom. The Cl anion resides in the plane of the mol­ecule and is bound by N—H...Cl interactions from both heterocyclic NH groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800019644/cf6018sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800019644/cf6018Isup2.hkl
Contains datablock I

CCDC reference: 155882

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.105
  • Data-to-parameter ratio = 16.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.287 Value of mu given = 0.290 PLAT_353 Alert C Long N-H Bond (0.87A) N(1) - H(1) = 1.01 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

NO COMMENT

Experimental top

The title compound, (I), was prepared by Spa Contract Synthesis and was recrystallized from dilute HCl solution.

Refinement top

All H atoms were included in the refinement at calculated positions as riding models, with C—H set to 0.95 (Ar—H) and 0.99 Å (CH2), except for the N—H atoms, which were located on difference syntheses and for which both positional and displacement parameters were refined.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for (I), showing 30% probability ellipsoids.
'11H-Pyridinium[2,3 h]-7,8,9,10-tetrahydrocarbazole chloride' top
Crystal data top
C15H15N2+·ClDx = 1.370 Mg m3
Mr = 258.74Melting point: 430 - 431 K K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.9111 (6) ÅCell parameters from 3819 reflections
b = 5.0374 (2) Åθ = 2.9–27.5°
c = 17.1233 (9) ŵ = 0.29 mm1
β = 113.9330 (17)°T = 150 K
V = 1254.44 (10) Å3Needle, orange
Z = 40.35 × 0.07 × 0.06 mm
F(000) = 544
Data collection top
Enraf-Nonius KappaCCD area-detector
diffractometer
2868 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode1761 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
ϕ and ω scansh = 2018
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 56
Tmin = 0.906, Tmax = 0.983l = 1822
8962 measured reflections
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0396P)2]
where P = (Fo2 + 2Fc2)/3
2868 reflections(Δ/σ)max < 0.001
171 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C15H15N2+·ClV = 1254.44 (10) Å3
Mr = 258.74Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.9111 (6) ŵ = 0.29 mm1
b = 5.0374 (2) ÅT = 150 K
c = 17.1233 (9) Å0.35 × 0.07 × 0.06 mm
β = 113.9330 (17)°
Data collection top
Enraf-Nonius KappaCCD area-detector
diffractometer
2868 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
1761 reflections with I > 2σ(I)
Tmin = 0.906, Tmax = 0.983Rint = 0.064
8962 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.23 e Å3
2868 reflectionsΔρmin = 0.31 e Å3
171 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.11456 (4)0.61271 (10)0.32677 (3)0.02965 (19)
N10.12479 (12)0.5409 (3)0.14700 (12)0.0230 (4)
H10.1221 (17)0.575 (4)0.2063 (16)0.051 (7)*
C20.07204 (15)0.6910 (4)0.12120 (15)0.0276 (5)
H20.03350.82190.15860.034*
C30.07244 (15)0.6598 (4)0.04124 (15)0.0297 (6)
H30.03490.76880.02320.037*
C40.12810 (15)0.4680 (4)0.01228 (14)0.0283 (5)
H40.12810.44330.06730.035*
C4A0.18470 (14)0.3088 (4)0.01334 (13)0.0232 (5)
C50.24482 (15)0.1120 (4)0.04083 (13)0.0264 (5)
H50.24550.08190.09580.033*
C60.30104 (15)0.0328 (4)0.01534 (14)0.0268 (5)
H60.34110.16160.05250.034*
C6A0.29979 (14)0.0088 (4)0.06704 (13)0.0204 (5)
C6B0.34895 (14)0.1054 (4)0.11187 (13)0.0215 (5)
C70.42485 (15)0.3084 (4)0.08287 (14)0.0261 (5)
H710.39910.48600.08100.033*
H720.47010.26400.02460.033*
C80.47227 (16)0.3127 (4)0.14443 (15)0.0334 (6)
H810.51100.47370.13370.042*
H820.51300.15590.13360.042*
C90.40327 (15)0.3108 (4)0.23758 (14)0.0297 (6)
H910.36180.46570.24800.037*
H920.43680.32840.27500.037*
C100.34565 (16)0.0564 (4)0.26098 (14)0.0257 (5)
H1010.38260.09150.26870.032*
H1020.29110.08200.31530.032*
C10A0.31589 (14)0.0086 (4)0.19137 (13)0.0211 (5)
N110.24950 (12)0.1908 (3)0.19764 (12)0.0216 (4)
H110.2208 (14)0.277 (4)0.2418 (13)0.025 (6)*
C11A0.23865 (14)0.1947 (4)0.12257 (13)0.0197 (5)
C11B0.18204 (14)0.3499 (4)0.09616 (13)0.0207 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0291 (4)0.0308 (3)0.0287 (3)0.0001 (2)0.0114 (3)0.0069 (2)
N10.0216 (11)0.0222 (9)0.0261 (11)0.0009 (7)0.0104 (9)0.0004 (7)
C20.0225 (13)0.0236 (11)0.0384 (15)0.0003 (9)0.0141 (12)0.0059 (9)
C30.0246 (14)0.0323 (13)0.0364 (15)0.0014 (10)0.0168 (12)0.0101 (10)
C40.0282 (14)0.0343 (13)0.0254 (13)0.0107 (10)0.0140 (11)0.0096 (10)
C4A0.0215 (13)0.0263 (12)0.0235 (13)0.0069 (9)0.0107 (11)0.0051 (9)
C50.0264 (14)0.0317 (12)0.0202 (13)0.0052 (10)0.0084 (11)0.0006 (9)
C60.0265 (14)0.0275 (12)0.0238 (13)0.0013 (9)0.0075 (11)0.0026 (9)
C6A0.0174 (12)0.0185 (10)0.0223 (13)0.0028 (8)0.0048 (10)0.0005 (8)
C6B0.0195 (12)0.0175 (10)0.0267 (13)0.0006 (8)0.0087 (10)0.0001 (9)
C70.0206 (13)0.0251 (12)0.0308 (14)0.0031 (9)0.0085 (11)0.0024 (9)
C80.0259 (14)0.0297 (13)0.0458 (16)0.0062 (10)0.0157 (13)0.0027 (10)
C90.0320 (15)0.0246 (12)0.0384 (16)0.0039 (9)0.0204 (12)0.0009 (9)
C100.0278 (14)0.0236 (12)0.0295 (13)0.0016 (9)0.0155 (11)0.0011 (9)
C10A0.0209 (12)0.0188 (10)0.0252 (13)0.0012 (8)0.0110 (10)0.0026 (9)
N110.0211 (11)0.0220 (10)0.0218 (11)0.0054 (8)0.0090 (9)0.0040 (8)
C11A0.0208 (12)0.0191 (11)0.0194 (12)0.0021 (8)0.0083 (10)0.0006 (8)
C11B0.0177 (12)0.0185 (11)0.0245 (13)0.0041 (8)0.0072 (10)0.0025 (8)
Geometric parameters (Å, º) top
N1—C21.331 (3)C6B—C71.505 (3)
N1—C11B1.367 (2)C7—C81.525 (3)
N1—H11.01 (2)C7—H710.990
C2—C31.376 (3)C7—H720.990
C2—H20.950C8—C91.526 (3)
C3—C41.378 (3)C8—H810.990
C3—H30.950C8—H820.990
C4—C4A1.403 (3)C9—C101.532 (3)
C4—H40.950C9—H910.990
C4A—C11B1.417 (3)C9—H920.990
C4A—C51.428 (3)C10—C10A1.487 (3)
C5—C61.356 (3)C10—H1010.990
C5—H50.950C10—H1020.990
C6—C6A1.418 (3)C10A—N111.370 (3)
C6—H60.950N11—C11A1.365 (3)
C6A—C11A1.406 (3)N11—H110.83 (2)
C6A—C6B1.421 (3)C11A—C11B1.399 (3)
C6B—C10A1.371 (3)
C2—N1—C11B122.4 (2)H71—C7—H72108.2
C2—N1—H1117.5 (13)C7—C8—C9111.99 (18)
C11B—N1—H1120.1 (13)C7—C8—H81109.2
N1—C2—C3121.1 (2)C9—C8—H81109.2
N1—C2—H2119.5C7—C8—H82109.2
C3—C2—H2119.5C9—C8—H82109.2
C2—C3—C4119.0 (2)H81—C8—H82107.9
C2—C3—H3120.5C8—C9—C10112.28 (17)
C4—C3—H3120.5C8—C9—H91109.1
C3—C4—C4A120.9 (2)C10—C9—H91109.1
C3—C4—H4119.5C8—C9—H92109.1
C4A—C4—H4119.5C10—C9—H92109.1
C4—C4A—C11B117.9 (2)H91—C9—H92107.9
C4—C4A—C5122.7 (2)C10A—C10—C9109.03 (17)
C11B—C4A—C5119.46 (19)C10A—C10—H101109.9
C6—C5—C4A121.3 (2)C9—C10—H101109.9
C6—C5—H5119.3C10A—C10—H102109.9
C4A—C5—H5119.3C9—C10—H102109.9
C5—C6—C6A119.7 (2)H101—C10—H102108.3
C5—C6—H6120.2N11—C10A—C6B109.36 (18)
C6A—C6—H6120.2N11—C10A—C10124.80 (18)
C11A—C6A—C6119.86 (19)C6B—C10A—C10125.83 (19)
C11A—C6A—C6B106.60 (18)C11A—N11—C10A108.89 (17)
C6—C6A—C6B133.53 (19)C11A—N11—H11128.1 (15)
C10A—C6B—C6A107.06 (18)C10A—N11—H11123.0 (15)
C10A—C6B—C7123.08 (19)N11—C11A—C11B131.03 (18)
C6A—C6B—C7129.85 (19)N11—C11A—C6A108.08 (18)
C6B—C7—C8109.71 (17)C11B—C11A—C6A120.87 (19)
C6B—C7—H71109.7N1—C11B—C11A122.50 (19)
C8—C7—H71109.7N1—C11B—C4A118.80 (19)
C6B—C7—H72109.7C11A—C11B—C4A118.70 (18)
C8—C7—H72109.7
C11B—N1—C2—C30.3 (3)C7—C6B—C10A—C102.9 (3)
N1—C2—C3—C40.5 (3)C9—C10—C10A—N11166.73 (19)
C2—C3—C4—C4A0.9 (3)C9—C10—C10A—C6B12.2 (3)
C3—C4—C4A—C11B0.6 (3)C6B—C10A—N11—C11A0.4 (2)
C3—C4—C4A—C5178.59 (19)C10—C10A—N11—C11A178.66 (19)
C4—C4A—C5—C6177.7 (2)C10A—N11—C11A—C11B177.9 (2)
C11B—C4A—C5—C61.4 (3)C10A—N11—C11A—C6A0.2 (2)
C4A—C5—C6—C6A0.7 (3)C6—C6A—C11A—N11178.33 (17)
C5—C6—C6A—C11A1.7 (3)C6B—C6A—C11A—N110.7 (2)
C5—C6—C6A—C6B179.6 (2)C6—C6A—C11A—C11B3.3 (3)
C11A—C6A—C6B—C10A0.9 (2)C6B—C6A—C11A—C11B177.64 (18)
C6—C6A—C6B—C10A177.9 (2)C2—N1—C11B—C11A178.95 (19)
C11A—C6A—C6B—C7177.87 (18)C2—N1—C11B—C4A0.6 (3)
C6—C6A—C6B—C73.3 (4)N11—C11A—C11B—N10.9 (3)
C10A—C6B—C7—C813.7 (3)C6A—C11A—C11B—N1176.98 (18)
C6A—C6B—C7—C8165.0 (2)N11—C11A—C11B—C4A179.56 (19)
C6B—C7—C8—C945.1 (2)C6A—C11A—C11B—C4A2.5 (3)
C7—C8—C9—C1063.4 (2)C4—C4A—C11B—N10.1 (3)
C8—C9—C10—C10A43.7 (2)C5—C4A—C11B—N1179.36 (18)
C6A—C6B—C10A—N110.9 (2)C4—C4A—C11B—C11A179.41 (18)
C7—C6B—C10A—N11178.05 (17)C5—C4A—C11B—C11A0.2 (3)
C6A—C6B—C10A—C10178.22 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl11.01 (2)2.03 (2)3.038 (2)175.7 (18)
N11—H11···Cl10.83 (2)2.42 (2)3.1880 (19)155.2 (19)

Experimental details

Crystal data
Chemical formulaC15H15N2+·Cl
Mr258.74
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)15.9111 (6), 5.0374 (2), 17.1233 (9)
β (°) 113.9330 (17)
V3)1254.44 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.29
Crystal size (mm)0.35 × 0.07 × 0.06
Data collection
DiffractometerEnraf-Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.906, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
8962, 2868, 1761
Rint0.064
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.105, 0.99
No. of reflections2868
No. of parameters171
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.31

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl11.01 (2)2.03 (2)3.038 (2)175.7 (18)
N11—H11···Cl10.83 (2)2.42 (2)3.1880 (19)155.2 (19)
 

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