Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045813/hg2293sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045813/hg2293Isup2.hkl |
CCDC reference: 664210
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.115
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Haria et al. (1994); Lin et al. (2005); Stampa et al. (2000).
The title compound was synthesized according to the method described by Stampa et al. (2000). Colorless blocks of (I) were grown by slow evaporation of a methanol solution (m.p. 372–374 K).
All H atoms were positioned geometrically (C—H = 0.93–0.97 Å), and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5eq(methyl groups).
Loratadine is a long-acting tricyclic antihistamine with selective peripheral histamine H1-receptor antagonistic activity (Haria et al., 1994). The title compound, (I), was unexpectedly obtained in the preparation of loratadine by the cross reductive coupling between 8-chloro-10,11-dihydro-4-aza-5H- dibenzo[a,d] cyclohepten-5-one and ethyl 4-oxopiperidine-1-carboxylate. We report here the crystal structure of (I) (Fig. 1).
The molecule contains a tricyclic fused-ring system composed of a benzene ring, a pyridine ring and a central non-planar seven-membered ring whose conformation was found in a similar system in 8-chloro-10,11-dihydro-4-aza-5H- dibenzo[a,d] cyclohepten-5-one (Lin et al., 2005).
For related literature, see: Haria et al. (1994); Lin et al. (2005); Stampa et al. (2000).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
Fig. 1. A view of the molecular of (I). Displacement ellopsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. |
C14H12ClN | F(000) = 480 |
Mr = 229.70 | Dx = 1.329 Mg m−3 |
Monoclinic, P21/c | Melting point = 372–374 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.609 (3) Å | Cell parameters from 3781 reflections |
b = 13.588 (3) Å | θ = 2.5–26.2° |
c = 8.1997 (18) Å | µ = 0.30 mm−1 |
β = 103.841 (4)° | T = 294 K |
V = 1147.8 (5) Å3 | Block, colorless |
Z = 4 | 0.22 × 0.20 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 2027 independent reflections |
Radiation source: fine-focus sealed tube | 1638 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −12→12 |
Tmin = 0.937, Tmax = 0.948 | k = −16→16 |
8106 measured reflections | l = −9→9 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0446P)2 + 0.6828P] where P = (Fo2 + 2Fc2)/3 |
2027 reflections | (Δ/σ)max = 0.005 |
145 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
C14H12ClN | V = 1147.8 (5) Å3 |
Mr = 229.70 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.609 (3) Å | µ = 0.30 mm−1 |
b = 13.588 (3) Å | T = 294 K |
c = 8.1997 (18) Å | 0.22 × 0.20 × 0.18 mm |
β = 103.841 (4)° |
Bruker SMART CCD area-detector diffractometer | 2027 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1638 reflections with I > 2σ(I) |
Tmin = 0.937, Tmax = 0.948 | Rint = 0.021 |
8106 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.44 e Å−3 |
2027 reflections | Δρmin = −0.55 e Å−3 |
145 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 | ||
Cl1 | 0.41484 (7) | 0.65806 (6) | 0.24910 (9) | 0.0848 (3) | |
N1 | 1.09198 (17) | 0.58490 (13) | 0.8124 (2) | 0.0509 (5) | |
C1 | 1.1725 (2) | 0.65826 (18) | 0.8727 (3) | 0.0582 (6) | |
H1 | 1.2574 | 0.6547 | 0.8611 | 0.070* | |
C2 | 1.1368 (3) | 0.73863 (18) | 0.9510 (3) | 0.0632 (6) | |
H2 | 1.1952 | 0.7893 | 0.9897 | 0.076* | |
C3 | 1.0125 (3) | 0.74217 (18) | 0.9706 (3) | 0.0606 (6) | |
H3 | 0.9862 | 0.7960 | 1.0242 | 0.073* | |
C4 | 0.9251 (2) | 0.66698 (15) | 0.9120 (2) | 0.0485 (5) | |
C5 | 0.7909 (2) | 0.6772 (2) | 0.9426 (3) | 0.0687 (7) | |
H5A | 0.7602 | 0.7428 | 0.9069 | 0.082* | |
H5B | 0.8000 | 0.6742 | 1.0630 | 0.082* | |
C6 | 0.6847 (2) | 0.60588 (19) | 0.8626 (3) | 0.0593 (6) | |
H6A | 0.7029 | 0.5426 | 0.9180 | 0.071* | |
H6B | 0.6030 | 0.6294 | 0.8813 | 0.071* | |
C7 | 0.6700 (2) | 0.59178 (15) | 0.6771 (3) | 0.0456 (5) | |
C8 | 0.5626 (2) | 0.62711 (16) | 0.5612 (3) | 0.0524 (5) | |
H8 | 0.4978 | 0.6605 | 0.5976 | 0.063* | |
C9 | 0.5514 (2) | 0.61297 (17) | 0.3926 (3) | 0.0550 (6) | |
C10 | 0.6447 (2) | 0.56352 (18) | 0.3355 (3) | 0.0592 (6) | |
H10 | 0.6358 | 0.5537 | 0.2211 | 0.071* | |
C11 | 0.7528 (2) | 0.52821 (16) | 0.4512 (3) | 0.0534 (5) | |
H11 | 0.8171 | 0.4950 | 0.4135 | 0.064* | |
C12 | 0.76631 (19) | 0.54171 (14) | 0.6219 (2) | 0.0436 (5) | |
C13 | 0.8840 (2) | 0.50542 (16) | 0.7484 (3) | 0.0511 (5) | |
H13A | 0.9334 | 0.4621 | 0.6932 | 0.061* | |
H13B | 0.8565 | 0.4676 | 0.8341 | 0.061* | |
C14 | 0.9696 (2) | 0.58905 (15) | 0.8304 (2) | 0.0440 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0748 (5) | 0.0773 (5) | 0.0845 (5) | −0.0125 (3) | −0.0162 (4) | 0.0282 (4) |
N1 | 0.0510 (10) | 0.0547 (11) | 0.0462 (10) | 0.0076 (9) | 0.0102 (8) | 0.0002 (8) |
C1 | 0.0524 (13) | 0.0702 (16) | 0.0489 (12) | −0.0005 (12) | 0.0059 (10) | 0.0044 (11) |
C2 | 0.0681 (16) | 0.0580 (14) | 0.0560 (14) | −0.0079 (12) | 0.0000 (12) | −0.0047 (11) |
C3 | 0.0727 (16) | 0.0530 (13) | 0.0503 (13) | 0.0083 (12) | 0.0033 (11) | −0.0131 (10) |
C4 | 0.0569 (13) | 0.0498 (12) | 0.0368 (10) | 0.0080 (10) | 0.0068 (9) | −0.0032 (9) |
C5 | 0.0668 (16) | 0.0806 (17) | 0.0610 (15) | 0.0077 (13) | 0.0202 (12) | −0.0243 (13) |
C6 | 0.0608 (14) | 0.0718 (15) | 0.0504 (13) | 0.0045 (12) | 0.0237 (11) | −0.0025 (11) |
C7 | 0.0499 (12) | 0.0434 (11) | 0.0461 (11) | −0.0013 (9) | 0.0165 (9) | 0.0010 (9) |
C8 | 0.0491 (12) | 0.0462 (12) | 0.0627 (14) | −0.0005 (10) | 0.0150 (11) | 0.0015 (10) |
C9 | 0.0557 (13) | 0.0485 (12) | 0.0563 (13) | −0.0113 (10) | 0.0045 (11) | 0.0103 (10) |
C10 | 0.0721 (16) | 0.0648 (15) | 0.0396 (11) | −0.0208 (12) | 0.0110 (11) | 0.0002 (10) |
C11 | 0.0591 (13) | 0.0521 (13) | 0.0531 (13) | −0.0086 (10) | 0.0221 (11) | −0.0125 (10) |
C12 | 0.0505 (12) | 0.0356 (10) | 0.0456 (11) | −0.0033 (9) | 0.0135 (9) | −0.0015 (8) |
C13 | 0.0559 (13) | 0.0407 (11) | 0.0567 (13) | 0.0070 (9) | 0.0135 (10) | −0.0045 (9) |
C14 | 0.0513 (12) | 0.0434 (11) | 0.0358 (10) | 0.0082 (9) | 0.0075 (9) | 0.0043 (8) |
Cl1—C9 | 1.745 (2) | C6—H6A | 0.9700 |
N1—C1 | 1.329 (3) | C6—H6B | 0.9700 |
N1—C14 | 1.342 (3) | C7—C8 | 1.384 (3) |
C1—C2 | 1.365 (3) | C7—C12 | 1.390 (3) |
C1—H1 | 0.9300 | C8—C9 | 1.373 (3) |
C2—C3 | 1.367 (4) | C8—H8 | 0.9300 |
C2—H2 | 0.9300 | C9—C10 | 1.368 (3) |
C3—C4 | 1.386 (3) | C10—C11 | 1.387 (3) |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
C4—C14 | 1.394 (3) | C11—C12 | 1.385 (3) |
C4—C5 | 1.510 (3) | C11—H11 | 0.9300 |
C5—C6 | 1.511 (3) | C12—C13 | 1.503 (3) |
C5—H5A | 0.9700 | C13—C14 | 1.509 (3) |
C5—H5B | 0.9700 | C13—H13A | 0.9700 |
C6—C7 | 1.504 (3) | C13—H13B | 0.9700 |
C1—N1—C14 | 118.67 (19) | C8—C7—C6 | 121.29 (19) |
N1—C1—C2 | 123.3 (2) | C12—C7—C6 | 119.02 (19) |
N1—C1—H1 | 118.3 | C9—C8—C7 | 120.1 (2) |
C2—C1—H1 | 118.3 | C9—C8—H8 | 120.0 |
C1—C2—C3 | 117.9 (2) | C7—C8—H8 | 120.0 |
C1—C2—H2 | 121.1 | C10—C9—C8 | 121.2 (2) |
C3—C2—H2 | 121.1 | C10—C9—Cl1 | 119.61 (18) |
C2—C3—C4 | 121.2 (2) | C8—C9—Cl1 | 119.18 (19) |
C2—C3—H3 | 119.4 | C9—C10—C11 | 118.9 (2) |
C4—C3—H3 | 119.4 | C9—C10—H10 | 120.5 |
C3—C4—C14 | 116.8 (2) | C11—C10—H10 | 120.5 |
C3—C4—C5 | 117.0 (2) | C12—C11—C10 | 120.9 (2) |
C14—C4—C5 | 126.2 (2) | C12—C11—H11 | 119.5 |
C4—C5—C6 | 120.24 (19) | C10—C11—H11 | 119.5 |
C4—C5—H5A | 107.3 | C11—C12—C7 | 119.17 (19) |
C6—C5—H5A | 107.3 | C11—C12—C13 | 121.49 (19) |
C4—C5—H5B | 107.3 | C7—C12—C13 | 119.32 (18) |
C6—C5—H5B | 107.3 | C12—C13—C14 | 111.88 (17) |
H5A—C5—H5B | 106.9 | C12—C13—H13A | 109.2 |
C7—C6—C5 | 113.98 (19) | C14—C13—H13A | 109.2 |
C7—C6—H6A | 108.8 | C12—C13—H13B | 109.2 |
C5—C6—H6A | 108.8 | C14—C13—H13B | 109.2 |
C7—C6—H6B | 108.8 | H13A—C13—H13B | 107.9 |
C5—C6—H6B | 108.8 | N1—C14—C4 | 122.2 (2) |
H6A—C6—H6B | 107.7 | N1—C14—C13 | 114.49 (17) |
C8—C7—C12 | 119.68 (19) | C4—C14—C13 | 123.27 (19) |
C14—N1—C1—C2 | −0.7 (3) | C10—C11—C12—C7 | −0.3 (3) |
N1—C1—C2—C3 | 1.4 (4) | C10—C11—C12—C13 | −178.9 (2) |
C1—C2—C3—C4 | −0.4 (4) | C8—C7—C12—C11 | 0.1 (3) |
C2—C3—C4—C14 | −1.0 (3) | C6—C7—C12—C11 | 179.7 (2) |
C2—C3—C4—C5 | 179.0 (2) | C8—C7—C12—C13 | 178.75 (19) |
C3—C4—C5—C6 | 171.7 (2) | C6—C7—C12—C13 | −1.6 (3) |
C14—C4—C5—C6 | −8.3 (4) | C11—C12—C13—C14 | 109.3 (2) |
C4—C5—C6—C7 | −49.7 (3) | C7—C12—C13—C14 | −69.4 (2) |
C5—C6—C7—C8 | −110.3 (2) | C1—N1—C14—C4 | −0.8 (3) |
C5—C6—C7—C12 | 70.1 (3) | C1—N1—C14—C13 | 176.47 (18) |
C12—C7—C8—C9 | −0.2 (3) | C3—C4—C14—N1 | 1.7 (3) |
C6—C7—C8—C9 | −179.8 (2) | C5—C4—C14—N1 | −178.3 (2) |
C7—C8—C9—C10 | 0.5 (3) | C3—C4—C14—C13 | −175.4 (2) |
C7—C8—C9—Cl1 | 179.90 (16) | C5—C4—C14—C13 | 4.6 (3) |
C8—C9—C10—C11 | −0.7 (3) | C12—C13—C14—N1 | −122.11 (19) |
Cl1—C9—C10—C11 | 179.93 (16) | C12—C13—C14—C4 | 55.2 (3) |
C9—C10—C11—C12 | 0.6 (3) |
Experimental details
Crystal data | |
Chemical formula | C14H12ClN |
Mr | 229.70 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 10.609 (3), 13.588 (3), 8.1997 (18) |
β (°) | 103.841 (4) |
V (Å3) | 1147.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.937, 0.948 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8106, 2027, 1638 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.115, 1.03 |
No. of reflections | 2027 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.55 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
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Loratadine is a long-acting tricyclic antihistamine with selective peripheral histamine H1-receptor antagonistic activity (Haria et al., 1994). The title compound, (I), was unexpectedly obtained in the preparation of loratadine by the cross reductive coupling between 8-chloro-10,11-dihydro-4-aza-5H- dibenzo[a,d] cyclohepten-5-one and ethyl 4-oxopiperidine-1-carboxylate. We report here the crystal structure of (I) (Fig. 1).
The molecule contains a tricyclic fused-ring system composed of a benzene ring, a pyridine ring and a central non-planar seven-membered ring whose conformation was found in a similar system in 8-chloro-10,11-dihydro-4-aza-5H- dibenzo[a,d] cyclohepten-5-one (Lin et al., 2005).