7,8,9,10-Tetra­hydro-11H-pyrido­[2,3-a]­carbazol-1-ium chloride

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.

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


 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

---

S1. Comment

NO COMMENT

S2. Experimental

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

S3. Refinement

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

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

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'

Crystal data

C15H15N2^+·Cl^−	Dx = 1.370 Mg m^−3
Mr = 258.74	Melting point: 430 - 431 K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.9111 (6) Å	Cell parameters from 3819 reflections
b = 5.0374 (2) Å	θ = 2.9–27.5°
c = 17.1233 (9) Å	µ = 0.29 mm^−1
β = 113.9330 (17)°	T = 150 K
V = 1254.44 (10) Å^3	Needle, orange
Z = 4	0.35 × 0.07 × 0.06 mm
F(000) = 544

Data collection

Enraf-Nonius KappaCCD area-detector diffractometer	2868 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode	1761 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ and ω scans	h = −20→18
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −5→6
Tmin = 0.906, Tmax = 0.983	l = −18→22
8962 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0396P)^2] where P = (Fo^2 + 2Fc^2)/3
2868 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.11456 (4)	0.61271 (10)	0.32677 (3)	0.02965 (19)
N1	−0.12479 (12)	0.5409 (3)	0.14700 (12)	0.0230 (4)
H1	−0.1221 (17)	0.575 (4)	0.2063 (16)	0.051 (7)*
C2	−0.07204 (15)	0.6910 (4)	0.12120 (15)	0.0276 (5)
H2	−0.0335	0.8219	0.1586	0.034*
C3	−0.07244 (15)	0.6598 (4)	0.04124 (15)	0.0297 (6)
H3	−0.0349	0.7688	0.0232	0.037*
C4	−0.12810 (15)	0.4680 (4)	−0.01228 (14)	0.0283 (5)
H4	−0.1281	0.4433	−0.0673	0.035*
C4A	−0.18470 (14)	0.3088 (4)	0.01334 (13)	0.0232 (5)
C5	−0.24482 (15)	0.1120 (4)	−0.04083 (13)	0.0264 (5)
H5	−0.2455	0.0819	−0.0958	0.033*
C6	−0.30104 (15)	−0.0328 (4)	−0.01534 (14)	0.0268 (5)
H6	−0.3411	−0.1616	−0.0525	0.034*
C6A	−0.29979 (14)	0.0088 (4)	0.06704 (13)	0.0204 (5)
C6B	−0.34895 (14)	−0.1054 (4)	0.11187 (13)	0.0215 (5)
C7	−0.42485 (15)	−0.3084 (4)	0.08287 (14)	0.0261 (5)
H71	−0.3991	−0.4860	0.0810	0.033*
H72	−0.4701	−0.2640	0.0246	0.033*
C8	−0.47227 (16)	−0.3127 (4)	0.14443 (15)	0.0334 (6)
H81	−0.5110	−0.4737	0.1337	0.042*
H82	−0.5130	−0.1559	0.1336	0.042*
C9	−0.40327 (15)	−0.3108 (4)	0.23758 (14)	0.0297 (6)
H91	−0.3618	−0.4657	0.2480	0.037*
H92	−0.4368	−0.3284	0.2750	0.037*
C10	−0.34565 (16)	−0.0564 (4)	0.26098 (14)	0.0257 (5)
H101	−0.3826	0.0915	0.2687	0.032*
H102	−0.2911	−0.0820	0.3153	0.032*
C10A	−0.31589 (14)	0.0086 (4)	0.19137 (13)	0.0211 (5)
N11	−0.24950 (12)	0.1908 (3)	0.19764 (12)	0.0216 (4)
H11	−0.2208 (14)	0.277 (4)	0.2418 (13)	0.025 (6)*
C11A	−0.23865 (14)	0.1947 (4)	0.12257 (13)	0.0197 (5)
C11B	−0.18204 (14)	0.3499 (4)	0.09616 (13)	0.0207 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0291 (4)	0.0308 (3)	0.0287 (3)	−0.0001 (2)	0.0114 (3)	−0.0069 (2)
N1	0.0216 (11)	0.0222 (9)	0.0261 (11)	−0.0009 (7)	0.0104 (9)	0.0004 (7)
C2	0.0225 (13)	0.0236 (11)	0.0384 (15)	0.0003 (9)	0.0141 (12)	0.0059 (9)
C3	0.0246 (14)	0.0323 (13)	0.0364 (15)	0.0014 (10)	0.0168 (12)	0.0101 (10)
C4	0.0282 (14)	0.0343 (13)	0.0254 (13)	0.0107 (10)	0.0140 (11)	0.0096 (10)
C4A	0.0215 (13)	0.0263 (12)	0.0235 (13)	0.0069 (9)	0.0107 (11)	0.0051 (9)
C5	0.0264 (14)	0.0317 (12)	0.0202 (13)	0.0052 (10)	0.0084 (11)	−0.0006 (9)
C6	0.0265 (14)	0.0275 (12)	0.0238 (13)	0.0013 (9)	0.0075 (11)	−0.0026 (9)
C6A	0.0174 (12)	0.0185 (10)	0.0223 (13)	0.0028 (8)	0.0048 (10)	−0.0005 (8)
C6B	0.0195 (12)	0.0175 (10)	0.0267 (13)	0.0006 (8)	0.0087 (10)	−0.0001 (9)
C7	0.0206 (13)	0.0251 (12)	0.0308 (14)	−0.0031 (9)	0.0085 (11)	−0.0024 (9)
C8	0.0259 (14)	0.0297 (13)	0.0458 (16)	−0.0062 (10)	0.0157 (13)	−0.0027 (10)
C9	0.0320 (15)	0.0246 (12)	0.0384 (16)	−0.0039 (9)	0.0204 (12)	0.0009 (9)
C10	0.0278 (14)	0.0236 (12)	0.0295 (13)	−0.0016 (9)	0.0155 (11)	−0.0011 (9)
C10A	0.0209 (12)	0.0188 (10)	0.0252 (13)	0.0012 (8)	0.0110 (10)	0.0026 (9)
N11	0.0211 (11)	0.0220 (10)	0.0218 (11)	−0.0054 (8)	0.0090 (9)	−0.0040 (8)
C11A	0.0208 (12)	0.0191 (11)	0.0194 (12)	0.0021 (8)	0.0083 (10)	−0.0006 (8)
C11B	0.0177 (12)	0.0185 (11)	0.0245 (13)	0.0041 (8)	0.0072 (10)	0.0025 (8)

Geometric parameters (Å, º)

N1—C2	1.331 (3)	C6B—C7	1.505 (3)
N1—C11B	1.367 (2)	C7—C8	1.525 (3)
N1—H1	1.01 (2)	C7—H71	0.990
C2—C3	1.376 (3)	C7—H72	0.990
C2—H2	0.950	C8—C9	1.526 (3)
C3—C4	1.378 (3)	C8—H81	0.990
C3—H3	0.950	C8—H82	0.990
C4—C4A	1.403 (3)	C9—C10	1.532 (3)
C4—H4	0.950	C9—H91	0.990
C4A—C11B	1.417 (3)	C9—H92	0.990
C4A—C5	1.428 (3)	C10—C10A	1.487 (3)
C5—C6	1.356 (3)	C10—H101	0.990
C5—H5	0.950	C10—H102	0.990
C6—C6A	1.418 (3)	C10A—N11	1.370 (3)
C6—H6	0.950	N11—C11A	1.365 (3)
C6A—C11A	1.406 (3)	N11—H11	0.83 (2)
C6A—C6B	1.421 (3)	C11A—C11B	1.399 (3)
C6B—C10A	1.371 (3)
C2—N1—C11B	122.4 (2)	H71—C7—H72	108.2
C2—N1—H1	117.5 (13)	C7—C8—C9	111.99 (18)
C11B—N1—H1	120.1 (13)	C7—C8—H81	109.2
N1—C2—C3	121.1 (2)	C9—C8—H81	109.2
N1—C2—H2	119.5	C7—C8—H82	109.2
C3—C2—H2	119.5	C9—C8—H82	109.2
C2—C3—C4	119.0 (2)	H81—C8—H82	107.9
C2—C3—H3	120.5	C8—C9—C10	112.28 (17)
C4—C3—H3	120.5	C8—C9—H91	109.1
C3—C4—C4A	120.9 (2)	C10—C9—H91	109.1
C3—C4—H4	119.5	C8—C9—H92	109.1
C4A—C4—H4	119.5	C10—C9—H92	109.1
C4—C4A—C11B	117.9 (2)	H91—C9—H92	107.9
C4—C4A—C5	122.7 (2)	C10A—C10—C9	109.03 (17)
C11B—C4A—C5	119.46 (19)	C10A—C10—H101	109.9
C6—C5—C4A	121.3 (2)	C9—C10—H101	109.9
C6—C5—H5	119.3	C10A—C10—H102	109.9
C4A—C5—H5	119.3	C9—C10—H102	109.9
C5—C6—C6A	119.7 (2)	H101—C10—H102	108.3
C5—C6—H6	120.2	N11—C10A—C6B	109.36 (18)
C6A—C6—H6	120.2	N11—C10A—C10	124.80 (18)
C11A—C6A—C6	119.86 (19)	C6B—C10A—C10	125.83 (19)
C11A—C6A—C6B	106.60 (18)	C11A—N11—C10A	108.89 (17)
C6—C6A—C6B	133.53 (19)	C11A—N11—H11	128.1 (15)
C10A—C6B—C6A	107.06 (18)	C10A—N11—H11	123.0 (15)
C10A—C6B—C7	123.08 (19)	N11—C11A—C11B	131.03 (18)
C6A—C6B—C7	129.85 (19)	N11—C11A—C6A	108.08 (18)
C6B—C7—C8	109.71 (17)	C11B—C11A—C6A	120.87 (19)
C6B—C7—H71	109.7	N1—C11B—C11A	122.50 (19)
C8—C7—H71	109.7	N1—C11B—C4A	118.80 (19)
C6B—C7—H72	109.7	C11A—C11B—C4A	118.70 (18)
C8—C7—H72	109.7
C11B—N1—C2—C3	−0.3 (3)	C7—C6B—C10A—C10	2.9 (3)
N1—C2—C3—C4	−0.5 (3)	C9—C10—C10A—N11	−166.73 (19)
C2—C3—C4—C4A	0.9 (3)	C9—C10—C10A—C6B	12.2 (3)
C3—C4—C4A—C11B	−0.6 (3)	C6B—C10A—N11—C11A	−0.4 (2)
C3—C4—C4A—C5	178.59 (19)	C10—C10A—N11—C11A	178.66 (19)
C4—C4A—C5—C6	−177.7 (2)	C10A—N11—C11A—C11B	177.9 (2)
C11B—C4A—C5—C6	1.4 (3)	C10A—N11—C11A—C6A	−0.2 (2)
C4A—C5—C6—C6A	−0.7 (3)	C6—C6A—C11A—N11	−178.33 (17)
C5—C6—C6A—C11A	−1.7 (3)	C6B—C6A—C11A—N11	0.7 (2)
C5—C6—C6A—C6B	179.6 (2)	C6—C6A—C11A—C11B	3.3 (3)
C11A—C6A—C6B—C10A	−0.9 (2)	C6B—C6A—C11A—C11B	−177.64 (18)
C6—C6A—C6B—C10A	177.9 (2)	C2—N1—C11B—C11A	−178.95 (19)
C11A—C6A—C6B—C7	177.87 (18)	C2—N1—C11B—C4A	0.6 (3)
C6—C6A—C6B—C7	−3.3 (4)	N11—C11A—C11B—N1	−0.9 (3)
C10A—C6B—C7—C8	13.7 (3)	C6A—C11A—C11B—N1	176.98 (18)
C6A—C6B—C7—C8	−165.0 (2)	N11—C11A—C11B—C4A	179.56 (19)
C6B—C7—C8—C9	−45.1 (2)	C6A—C11A—C11B—C4A	−2.5 (3)
C7—C8—C9—C10	63.4 (2)	C4—C4A—C11B—N1	−0.1 (3)
C8—C9—C10—C10A	−43.7 (2)	C5—C4A—C11B—N1	−179.36 (18)
C6A—C6B—C10A—N11	0.9 (2)	C4—C4A—C11B—C11A	179.41 (18)
C7—C6B—C10A—N11	−178.05 (17)	C5—C4A—C11B—C11A	0.2 (3)
C6A—C6B—C10A—C10	−178.22 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	1.01 (2)	2.03 (2)	3.038 (2)	175.7 (18)
N11—H11···Cl1	0.83 (2)	2.42 (2)	3.1880 (19)	155.2 (19)