Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044157/hb2536sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044157/hb2536Isup2.hkl |
CCDC reference: 663778
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- R factor = 0.072
- wR factor = 0.128
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.75 Ratio PLAT430_ALERT_2_B Short Inter D...A Contact O122 .. O122 .. 2.74 Ang.
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Cl
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 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 3 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
The appropriate benzyl amine derivative was prepared in four steps by classical coupling reactions starting from piperidine and 3-chloropropanol. Alcohol chlorination, ether formation with 4-cyanophenol, and catalytic reduction led to the primary benzylamine which then was reacted with Sanger's reagent (1-fluoro-2,4-dinitrobenzen) in a nucleophilic aromatic substitution (Amon et al., 2007). The reaction product was purified chromatographically over silica gel with dichloromethane/methanol (95:5) and NH3 gas. Yellow blocks of (I) were obtained from a mixture of ethanol/diethyl ether (1:6 v/v) with three drops of HCl at approximately 280 K.
The H atoms bonded to C were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The H atoms bonded to N were located in difference maps and their positions and Uiso values were freely refined.
Histamine H3 receptors are important targets for different central nervous system disorders (Celanire et al., 2007). Within a recently developed series of novel potent histamine H3 receptor antagonists having additional fluorescent properties the title compound can be taken as one of the parent molecules (Amon et al., 2007). The compound showed subnanomolar affinity at human histamine H3 receptors (Ki value of 0.6nM) and a good Stokes shift of 100 nm.
The structure of the title compound, C21H27N4O5+ Cl-, (I), is composed of discrete cations and anions. The bond lengths and angles in (I) are in the usual ranges. The piperidine ring adopts a chair conformation with the amino H atom in an axial position. Whereas one of the methylene C—C single bonds is in an antiperiplanar conformation [C2—C3—C4—N41 = 172.9 (3)°], the other one adopts a synclinal conformation [O1—C2—C3—C4 = 68.3 (4)°]. Both nitro groups are slightly tilted with respect to the aromatic ring to which they are attached: the dihedral angles between the planes of the nitro groups and the aromatic ring are 11.1 (5)° and 11.5 (6)° for the nitro groups N12, O121, O122 and N14, O141, O142, respectively. The dihedral angle between the two aromatic rings is 64.20 (11)°.
The amino H atom of the piperidine ring forms a classical N—H···Cl hydrogen bond (Table 1). The other amino H atom forms a bifurcated hydrogen bond. There is an intramolecular contact to one of the nitro O atoms of the aromatic ring attached to the amino group and there is an intermolecular contact to a symmetry equivalent of the same nitro O atom. As a result, a centrosymmetric dimer is formed (Fig. 2). In addition to these classical hydrogen bonds, the crystal packing is further stabilized by weak C—H···Cl and C—H···O contacts.
For related literature, see: Amon et al. (2007); Celanire et al. (2007).
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C21H27N4O5+·Cl− | F(000) = 952 |
Mr = 450.92 | Dx = 1.320 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9924 reflections |
a = 19.4030 (15) Å | θ = 3.5–25.6° |
b = 7.2300 (5) Å | µ = 0.21 mm−1 |
c = 17.2830 (13) Å | T = 173 K |
β = 110.583 (6)° | Block, yellow |
V = 2269.8 (3) Å3 | 0.27 × 0.12 × 0.11 mm |
Z = 4 |
Stoe IPDS II two-circle diffractometer | 4261 independent reflections |
Radiation source: fine-focus sealed tube | 2776 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
ω scans | θmax = 25.7°, θmin = 3.6° |
Absorption correction: multi-scan [MULABS (Spek, 2003; Blessing, 1995)] | h = −23→23 |
Tmin = 0.946, Tmax = 0.968 | k = −8→8 |
27016 measured reflections | l = −21→21 |
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)] = 0.072 | Hydrogen site location: difmap and geom |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0475P)2] where P = (Fo2 + 2Fc2)/3 |
4261 reflections | (Δ/σ)max < 0.001 |
288 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C21H27N4O5+·Cl− | V = 2269.8 (3) Å3 |
Mr = 450.92 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 19.4030 (15) Å | µ = 0.21 mm−1 |
b = 7.2300 (5) Å | T = 173 K |
c = 17.2830 (13) Å | 0.27 × 0.12 × 0.11 mm |
β = 110.583 (6)° |
Stoe IPDS II two-circle diffractometer | 4261 independent reflections |
Absorption correction: multi-scan [MULABS (Spek, 2003; Blessing, 1995)] | 2776 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.968 | Rint = 0.074 |
27016 measured reflections |
R[F2 > 2σ(F2)] = 0.072 | 0 restraints |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.26 e Å−3 |
4261 reflections | Δρmin = −0.24 e Å−3 |
288 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.06439 (14) | 0.7518 (4) | 0.45674 (16) | 0.0220 (6) | |
H1 | 0.0424 (17) | 0.661 (5) | 0.4681 (19) | 0.012 (8)* | |
C1 | 0.06952 (17) | 0.7550 (4) | 0.37402 (19) | 0.0234 (7) | |
H1A | 0.0679 | 0.8852 | 0.3557 | 0.028* | |
H1B | 0.0260 | 0.6911 | 0.3351 | 0.028* | |
O1 | 0.32321 (13) | 0.4100 (3) | 0.34329 (16) | 0.0323 (6) | |
C2 | 0.34155 (18) | 0.2203 (5) | 0.3692 (2) | 0.0307 (8) | |
H2A | 0.3002 | 0.1372 | 0.3393 | 0.037* | |
H2B | 0.3519 | 0.2077 | 0.4292 | 0.037* | |
C3 | 0.40978 (17) | 0.1709 (5) | 0.3488 (2) | 0.0309 (8) | |
H3A | 0.4009 | 0.2000 | 0.2901 | 0.037* | |
H3B | 0.4195 | 0.0366 | 0.3569 | 0.037* | |
C4 | 0.47691 (17) | 0.2788 (5) | 0.4039 (2) | 0.0249 (7) | |
H4A | 0.4695 | 0.4122 | 0.3906 | 0.030* | |
H4B | 0.4819 | 0.2624 | 0.4624 | 0.030* | |
C11 | 0.09157 (16) | 0.8805 (4) | 0.51601 (19) | 0.0193 (7) | |
C12 | 0.07709 (17) | 0.8840 (4) | 0.5918 (2) | 0.0201 (7) | |
C13 | 0.09925 (16) | 1.0306 (4) | 0.64785 (19) | 0.0217 (7) | |
H13 | 0.0872 | 1.0315 | 0.6966 | 0.026* | |
C14 | 0.13877 (19) | 1.1733 (4) | 0.6314 (2) | 0.0282 (8) | |
C15 | 0.1599 (2) | 1.1705 (5) | 0.5615 (2) | 0.0326 (8) | |
H15 | 0.1906 | 1.2654 | 0.5534 | 0.039* | |
C16 | 0.13618 (18) | 1.0301 (4) | 0.5051 (2) | 0.0276 (7) | |
H16 | 0.1496 | 1.0317 | 0.4572 | 0.033* | |
N12 | 0.03606 (14) | 0.7389 (3) | 0.61389 (16) | 0.0246 (6) | |
O121 | 0.01389 (15) | 0.7619 (4) | 0.67164 (15) | 0.0392 (6) | |
O122 | 0.02439 (16) | 0.5931 (3) | 0.57364 (16) | 0.0428 (7) | |
N14 | 0.15790 (19) | 1.3301 (4) | 0.6881 (2) | 0.0417 (8) | |
O141 | 0.12909 (19) | 1.3407 (4) | 0.74137 (19) | 0.0527 (8) | |
O142 | 0.2012 (2) | 1.4472 (4) | 0.6795 (2) | 0.0675 (10) | |
C21 | 0.26258 (17) | 0.4855 (5) | 0.3546 (2) | 0.0243 (7) | |
C22 | 0.24320 (19) | 0.6651 (5) | 0.3233 (2) | 0.0277 (8) | |
H22 | 0.2719 | 0.7271 | 0.2968 | 0.033* | |
C23 | 0.18216 (17) | 0.7521 (4) | 0.3311 (2) | 0.0247 (7) | |
H23 | 0.1699 | 0.8738 | 0.3100 | 0.030* | |
C24 | 0.13876 (17) | 0.6646 (4) | 0.36916 (19) | 0.0201 (7) | |
C25 | 0.15833 (17) | 0.4860 (5) | 0.3999 (2) | 0.0280 (7) | |
H25 | 0.1287 | 0.4233 | 0.4251 | 0.034* | |
C26 | 0.22036 (18) | 0.3975 (4) | 0.3944 (2) | 0.0290 (8) | |
H26 | 0.2338 | 0.2780 | 0.4177 | 0.035* | |
N41 | 0.54659 (14) | 0.2151 (4) | 0.39226 (16) | 0.0198 (5) | |
H41 | 0.5459 (19) | 0.081 (5) | 0.393 (2) | 0.029 (9)* | |
C42 | 0.55035 (18) | 0.2777 (5) | 0.3111 (2) | 0.0304 (8) | |
H42A | 0.5507 | 0.4146 | 0.3093 | 0.036* | |
H42B | 0.5063 | 0.2336 | 0.2655 | 0.036* | |
C43 | 0.6197 (2) | 0.2028 (6) | 0.2993 (2) | 0.0397 (9) | |
H43A | 0.6175 | 0.0660 | 0.2969 | 0.048* | |
H43B | 0.6219 | 0.2485 | 0.2462 | 0.048* | |
C44 | 0.6888 (2) | 0.2630 (6) | 0.3697 (3) | 0.0476 (10) | |
H44A | 0.6941 | 0.3990 | 0.3686 | 0.057* | |
H44B | 0.7326 | 0.2057 | 0.3629 | 0.057* | |
C45 | 0.68359 (18) | 0.2042 (6) | 0.4524 (2) | 0.0371 (9) | |
H45A | 0.7272 | 0.2508 | 0.4980 | 0.044* | |
H45B | 0.6839 | 0.0674 | 0.4557 | 0.044* | |
C46 | 0.61356 (17) | 0.2785 (5) | 0.4630 (2) | 0.0294 (7) | |
H46A | 0.6107 | 0.2335 | 0.5159 | 0.035* | |
H46B | 0.6151 | 0.4153 | 0.4648 | 0.035* | |
Cl1 | 0.55483 (6) | −0.21420 (11) | 0.40105 (6) | 0.0365 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0251 (14) | 0.0192 (14) | 0.0246 (14) | −0.0060 (11) | 0.0125 (11) | −0.0030 (11) |
C1 | 0.0246 (16) | 0.0261 (17) | 0.0199 (15) | 0.0035 (13) | 0.0085 (12) | 0.0025 (13) |
O1 | 0.0265 (13) | 0.0330 (12) | 0.0454 (16) | 0.0112 (10) | 0.0224 (11) | 0.0127 (11) |
C2 | 0.0217 (16) | 0.0248 (16) | 0.045 (2) | 0.0040 (14) | 0.0114 (15) | 0.0001 (16) |
C3 | 0.0214 (17) | 0.0348 (19) | 0.035 (2) | 0.0043 (14) | 0.0087 (15) | −0.0092 (15) |
C4 | 0.0255 (16) | 0.0261 (15) | 0.0256 (17) | 0.0028 (14) | 0.0121 (13) | −0.0029 (14) |
C11 | 0.0185 (16) | 0.0155 (14) | 0.0214 (16) | 0.0041 (11) | 0.0037 (13) | 0.0018 (12) |
C12 | 0.0190 (15) | 0.0174 (15) | 0.0234 (17) | −0.0002 (12) | 0.0068 (13) | 0.0035 (12) |
C13 | 0.0228 (16) | 0.0212 (15) | 0.0184 (16) | 0.0012 (12) | 0.0040 (13) | −0.0023 (13) |
C14 | 0.0346 (19) | 0.0202 (16) | 0.0232 (17) | −0.0062 (14) | 0.0020 (15) | −0.0015 (13) |
C15 | 0.038 (2) | 0.0248 (17) | 0.034 (2) | −0.0115 (15) | 0.0110 (16) | 0.0034 (15) |
C16 | 0.0318 (18) | 0.0276 (17) | 0.0251 (18) | −0.0077 (14) | 0.0120 (14) | 0.0005 (14) |
N12 | 0.0292 (14) | 0.0220 (14) | 0.0232 (14) | −0.0078 (12) | 0.0100 (11) | −0.0048 (11) |
O121 | 0.0519 (15) | 0.0431 (15) | 0.0337 (14) | −0.0181 (13) | 0.0291 (12) | −0.0121 (12) |
O122 | 0.073 (2) | 0.0291 (13) | 0.0383 (16) | −0.0257 (13) | 0.0346 (14) | −0.0162 (12) |
N14 | 0.056 (2) | 0.0226 (16) | 0.042 (2) | −0.0121 (14) | 0.0116 (17) | −0.0057 (14) |
O141 | 0.091 (2) | 0.0304 (14) | 0.0421 (17) | −0.0175 (14) | 0.0300 (17) | −0.0156 (13) |
O142 | 0.098 (3) | 0.0437 (17) | 0.069 (2) | −0.0476 (18) | 0.041 (2) | −0.0229 (16) |
C21 | 0.0229 (16) | 0.0280 (16) | 0.0247 (17) | 0.0043 (14) | 0.0114 (13) | 0.0042 (14) |
C22 | 0.0316 (18) | 0.0292 (17) | 0.0312 (19) | 0.0018 (14) | 0.0219 (15) | 0.0107 (14) |
C23 | 0.0299 (17) | 0.0187 (16) | 0.0285 (17) | 0.0031 (13) | 0.0139 (13) | 0.0072 (13) |
C24 | 0.0207 (16) | 0.0207 (15) | 0.0174 (16) | 0.0012 (12) | 0.0048 (13) | 0.0013 (12) |
C25 | 0.0231 (17) | 0.0269 (16) | 0.039 (2) | 0.0003 (14) | 0.0169 (15) | 0.0106 (15) |
C26 | 0.0255 (18) | 0.0217 (16) | 0.042 (2) | 0.0035 (13) | 0.0149 (16) | 0.0112 (15) |
N41 | 0.0222 (13) | 0.0190 (12) | 0.0202 (13) | 0.0005 (11) | 0.0099 (11) | 0.0008 (11) |
C42 | 0.0313 (18) | 0.0391 (18) | 0.0240 (17) | 0.0090 (16) | 0.0139 (14) | 0.0092 (16) |
C43 | 0.038 (2) | 0.057 (2) | 0.033 (2) | 0.0114 (18) | 0.0238 (17) | 0.0091 (19) |
C44 | 0.035 (2) | 0.052 (3) | 0.065 (3) | 0.0037 (19) | 0.0290 (19) | 0.011 (2) |
C45 | 0.0201 (17) | 0.045 (2) | 0.041 (2) | 0.0007 (16) | 0.0042 (15) | −0.0030 (18) |
C46 | 0.0256 (17) | 0.0300 (16) | 0.0277 (18) | −0.0040 (14) | 0.0034 (14) | −0.0081 (15) |
Cl1 | 0.0588 (6) | 0.0208 (4) | 0.0265 (4) | 0.0016 (4) | 0.0107 (4) | 0.0010 (4) |
N1—C11 | 1.346 (4) | N14—O141 | 1.236 (4) |
N1—C1 | 1.468 (4) | N14—O142 | 1.238 (4) |
N1—H1 | 0.84 (3) | C21—C26 | 1.396 (5) |
C1—C24 | 1.523 (4) | C21—C22 | 1.406 (5) |
C1—H1A | 0.9900 | C22—C23 | 1.389 (5) |
C1—H1B | 0.9900 | C22—H22 | 0.9500 |
O1—C21 | 1.371 (4) | C23—C24 | 1.390 (4) |
O1—C2 | 1.448 (4) | C23—H23 | 0.9500 |
C2—C3 | 1.527 (5) | C24—C25 | 1.397 (4) |
C2—H2A | 0.9900 | C25—C26 | 1.395 (5) |
C2—H2B | 0.9900 | C25—H25 | 0.9500 |
C3—C4 | 1.530 (4) | C26—H26 | 0.9500 |
C3—H3A | 0.9900 | N41—C42 | 1.500 (4) |
C3—H3B | 0.9900 | N41—C46 | 1.509 (4) |
C4—N41 | 1.507 (4) | N41—H41 | 0.97 (4) |
C4—H4A | 0.9900 | C42—C43 | 1.529 (5) |
C4—H4B | 0.9900 | C42—H42A | 0.9900 |
C11—C12 | 1.434 (5) | C42—H42B | 0.9900 |
C11—C16 | 1.439 (4) | C43—C44 | 1.523 (6) |
C12—C13 | 1.397 (4) | C43—H43A | 0.9900 |
C12—N12 | 1.447 (4) | C43—H43B | 0.9900 |
C13—C14 | 1.374 (5) | C44—C45 | 1.528 (6) |
C13—H13 | 0.9500 | C44—H44A | 0.9900 |
C14—C15 | 1.406 (5) | C44—H44B | 0.9900 |
C14—N14 | 1.459 (4) | C45—C46 | 1.531 (5) |
C15—C16 | 1.370 (5) | C45—H45A | 0.9900 |
C15—H15 | 0.9500 | C45—H45B | 0.9900 |
C16—H16 | 0.9500 | C46—H46A | 0.9900 |
N12—O121 | 1.229 (4) | C46—H46B | 0.9900 |
N12—O122 | 1.239 (3) | ||
C11—N1—C1 | 126.0 (3) | O1—C21—C22 | 116.1 (3) |
C11—N1—H1 | 117 (2) | C26—C21—C22 | 119.1 (3) |
C1—N1—H1 | 117 (2) | C23—C22—C21 | 120.2 (3) |
N1—C1—C24 | 114.2 (3) | C23—C22—H22 | 119.9 |
N1—C1—H1A | 108.7 | C21—C22—H22 | 119.9 |
C24—C1—H1A | 108.7 | C22—C23—C24 | 121.2 (3) |
N1—C1—H1B | 108.7 | C22—C23—H23 | 119.4 |
C24—C1—H1B | 108.7 | C24—C23—H23 | 119.4 |
H1A—C1—H1B | 107.6 | C23—C24—C25 | 118.2 (3) |
C21—O1—C2 | 117.6 (3) | C23—C24—C1 | 121.6 (3) |
O1—C2—C3 | 106.8 (3) | C25—C24—C1 | 120.2 (3) |
O1—C2—H2A | 110.4 | C26—C25—C24 | 121.6 (3) |
C3—C2—H2A | 110.4 | C26—C25—H25 | 119.2 |
O1—C2—H2B | 110.4 | C24—C25—H25 | 119.2 |
C3—C2—H2B | 110.4 | C25—C26—C21 | 119.6 (3) |
H2A—C2—H2B | 108.6 | C25—C26—H26 | 120.2 |
C2—C3—C4 | 110.8 (3) | C21—C26—H26 | 120.2 |
C2—C3—H3A | 109.5 | C42—N41—C4 | 111.9 (2) |
C4—C3—H3A | 109.5 | C42—N41—C46 | 110.8 (3) |
C2—C3—H3B | 109.5 | C4—N41—C46 | 110.9 (2) |
C4—C3—H3B | 109.5 | C42—N41—H41 | 109 (2) |
H3A—C3—H3B | 108.1 | C4—N41—H41 | 107 (2) |
N41—C4—C3 | 111.6 (3) | C46—N41—H41 | 108 (2) |
N41—C4—H4A | 109.3 | N41—C42—C43 | 110.6 (3) |
C3—C4—H4A | 109.3 | N41—C42—H42A | 109.5 |
N41—C4—H4B | 109.3 | C43—C42—H42A | 109.5 |
C3—C4—H4B | 109.3 | N41—C42—H42B | 109.5 |
H4A—C4—H4B | 108.0 | C43—C42—H42B | 109.5 |
N1—C11—C12 | 123.9 (3) | H42A—C42—H42B | 108.1 |
N1—C11—C16 | 120.8 (3) | C44—C43—C42 | 111.1 (3) |
C12—C11—C16 | 115.3 (3) | C44—C43—H43A | 109.4 |
C13—C12—C11 | 122.4 (3) | C42—C43—H43A | 109.4 |
C13—C12—N12 | 115.5 (3) | C44—C43—H43B | 109.4 |
C11—C12—N12 | 122.1 (3) | C42—C43—H43B | 109.4 |
C14—C13—C12 | 119.0 (3) | H43A—C43—H43B | 108.0 |
C14—C13—H13 | 120.5 | C43—C44—C45 | 109.8 (3) |
C12—C13—H13 | 120.5 | C43—C44—H44A | 109.7 |
C13—C14—C15 | 121.3 (3) | C45—C44—H44A | 109.7 |
C13—C14—N14 | 118.2 (3) | C43—C44—H44B | 109.7 |
C15—C14—N14 | 120.5 (3) | C45—C44—H44B | 109.7 |
C16—C15—C14 | 119.7 (3) | H44A—C44—H44B | 108.2 |
C16—C15—H15 | 120.2 | C44—C45—C46 | 111.6 (3) |
C14—C15—H15 | 120.2 | C44—C45—H45A | 109.3 |
C15—C16—C11 | 122.1 (3) | C46—C45—H45A | 109.3 |
C15—C16—H16 | 119.0 | C44—C45—H45B | 109.3 |
C11—C16—H16 | 119.0 | C46—C45—H45B | 109.3 |
O121—N12—O122 | 121.6 (3) | H45A—C45—H45B | 108.0 |
O121—N12—C12 | 119.9 (3) | N41—C46—C45 | 110.1 (3) |
O122—N12—C12 | 118.5 (3) | N41—C46—H46A | 109.6 |
O141—N14—O142 | 123.5 (3) | C45—C46—H46A | 109.6 |
O141—N14—C14 | 118.3 (3) | N41—C46—H46B | 109.6 |
O142—N14—C14 | 118.2 (3) | C45—C46—H46B | 109.6 |
O1—C21—C26 | 124.8 (3) | H46A—C46—H46B | 108.2 |
C11—N1—C1—C24 | 88.5 (4) | C15—C14—N14—O142 | −9.5 (5) |
C21—O1—C2—C3 | 179.2 (3) | C2—O1—C21—C26 | 4.8 (5) |
O1—C2—C3—C4 | 68.3 (4) | C2—O1—C21—C22 | −175.5 (3) |
C2—C3—C4—N41 | 172.9 (3) | O1—C21—C22—C23 | 179.4 (3) |
C1—N1—C11—C12 | 171.6 (3) | C26—C21—C22—C23 | −0.9 (5) |
C1—N1—C11—C16 | −6.3 (5) | C21—C22—C23—C24 | −0.4 (5) |
N1—C11—C12—C13 | −172.7 (3) | C22—C23—C24—C25 | 0.3 (5) |
C16—C11—C12—C13 | 5.3 (4) | C22—C23—C24—C1 | −176.8 (3) |
N1—C11—C12—N12 | 5.0 (5) | N1—C1—C24—C23 | −131.3 (3) |
C16—C11—C12—N12 | −177.0 (3) | N1—C1—C24—C25 | 51.7 (4) |
C11—C12—C13—C14 | −2.5 (5) | C23—C24—C25—C26 | 1.2 (5) |
N12—C12—C13—C14 | 179.7 (3) | C1—C24—C25—C26 | 178.3 (3) |
C12—C13—C14—C15 | −2.9 (5) | C24—C25—C26—C21 | −2.5 (5) |
C12—C13—C14—N14 | 176.6 (3) | O1—C21—C26—C25 | −178.0 (3) |
C13—C14—C15—C16 | 5.1 (5) | C22—C21—C26—C25 | 2.4 (5) |
N14—C14—C15—C16 | −174.4 (3) | C3—C4—N41—C42 | 72.8 (3) |
C14—C15—C16—C11 | −1.9 (5) | C3—C4—N41—C46 | −162.9 (3) |
N1—C11—C16—C15 | 175.0 (3) | C4—N41—C42—C43 | −177.2 (3) |
C12—C11—C16—C15 | −3.0 (5) | C46—N41—C42—C43 | 58.5 (4) |
C13—C12—N12—O121 | 10.4 (4) | N41—C42—C43—C44 | −57.5 (4) |
C11—C12—N12—O121 | −167.4 (3) | C42—C43—C44—C45 | 55.4 (4) |
C13—C12—N12—O122 | −169.4 (3) | C43—C44—C45—C46 | −55.4 (4) |
C11—C12—N12—O122 | 12.8 (4) | C42—N41—C46—C45 | −58.0 (4) |
C13—C14—N14—O141 | −10.2 (5) | C4—N41—C46—C45 | 177.1 (3) |
C15—C14—N14—O141 | 169.2 (3) | C44—C45—C46—N41 | 56.7 (4) |
C13—C14—N14—O142 | 171.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N41—H41···Cl1 | 0.97 (4) | 2.14 (4) | 3.109 (3) | 175 (3) |
N1—H1···O122 | 0.84 (3) | 2.03 (3) | 2.665 (4) | 131 (3) |
N1—H1···O122i | 0.84 (3) | 2.22 (3) | 2.971 (4) | 149 (3) |
C4—H4B···Cl1ii | 0.99 | 2.72 | 3.664 (3) | 161 |
C23—H23···O141iii | 0.95 | 2.37 | 3.318 (4) | 173 |
C42—H42B···Cl1iv | 0.99 | 2.73 | 3.514 (3) | 137 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, −y+5/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H27N4O5+·Cl− |
Mr | 450.92 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 19.4030 (15), 7.2300 (5), 17.2830 (13) |
β (°) | 110.583 (6) |
V (Å3) | 2269.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.27 × 0.12 × 0.11 |
Data collection | |
Diffractometer | Stoe IPDS II two-circle |
Absorption correction | Multi-scan [MULABS (Spek, 2003; Blessing, 1995)] |
Tmin, Tmax | 0.946, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27016, 4261, 2776 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.072, 0.128, 1.07 |
No. of reflections | 4261 |
No. of parameters | 288 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.24 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N41—H41···Cl1 | 0.97 (4) | 2.14 (4) | 3.109 (3) | 175 (3) |
N1—H1···O122 | 0.84 (3) | 2.03 (3) | 2.665 (4) | 131 (3) |
N1—H1···O122i | 0.84 (3) | 2.22 (3) | 2.971 (4) | 149 (3) |
C4—H4B···Cl1ii | 0.99 | 2.72 | 3.664 (3) | 160.6 |
C23—H23···O141iii | 0.95 | 2.37 | 3.318 (4) | 172.6 |
C42—H42B···Cl1iv | 0.99 | 2.73 | 3.514 (3) | 136.8 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, −y+5/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2. |
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Histamine H3 receptors are important targets for different central nervous system disorders (Celanire et al., 2007). Within a recently developed series of novel potent histamine H3 receptor antagonists having additional fluorescent properties the title compound can be taken as one of the parent molecules (Amon et al., 2007). The compound showed subnanomolar affinity at human histamine H3 receptors (Ki value of 0.6nM) and a good Stokes shift of 100 nm.
The structure of the title compound, C21H27N4O5+ Cl-, (I), is composed of discrete cations and anions. The bond lengths and angles in (I) are in the usual ranges. The piperidine ring adopts a chair conformation with the amino H atom in an axial position. Whereas one of the methylene C—C single bonds is in an antiperiplanar conformation [C2—C3—C4—N41 = 172.9 (3)°], the other one adopts a synclinal conformation [O1—C2—C3—C4 = 68.3 (4)°]. Both nitro groups are slightly tilted with respect to the aromatic ring to which they are attached: the dihedral angles between the planes of the nitro groups and the aromatic ring are 11.1 (5)° and 11.5 (6)° for the nitro groups N12, O121, O122 and N14, O141, O142, respectively. The dihedral angle between the two aromatic rings is 64.20 (11)°.
The amino H atom of the piperidine ring forms a classical N—H···Cl hydrogen bond (Table 1). The other amino H atom forms a bifurcated hydrogen bond. There is an intramolecular contact to one of the nitro O atoms of the aromatic ring attached to the amino group and there is an intermolecular contact to a symmetry equivalent of the same nitro O atom. As a result, a centrosymmetric dimer is formed (Fig. 2). In addition to these classical hydrogen bonds, the crystal packing is further stabilized by weak C—H···Cl and C—H···O contacts.