8-Chloro-10,11-di­hydro-4-aza-5H-dibenzo­[a,d]­cyclo­hepten-5-one

The title compound, C₁₄H₁₀ClNO, is the key intermediate in the synthesis of the antihistaminic drug loratadine. The mol­ecule contains a tricyclic fused-ring system composed of a benzene ring, a pyridine ring and a central non-planar seven-membered ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.142
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: CrystalStructure.

8-Chloro-10,11-dihydro-4-aza-5H-dibenzo[a,d]cyclohepten-5-one

Crystal data

C14H10ClNO	F(000) = 504.00
Mr = 243.69	Dx = 1.406 Mg m^−3
Monoclinic, P21/n	Melting point: 373 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.7107 Å
a = 6.8221 (3) Å	Cell parameters from 7263 reflections
b = 23.023 (1) Å	θ = 2.9–27.4°
c = 7.6719 (3) Å	µ = 0.31 mm^−1
β = 107.176 (2)°	T = 293 K
V = 1151.2 (1) Å^3	Block, colorless
Z = 4	0.52 × 0.50 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1871 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.025
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi,1995)	h = −8→7
Tmin = 0.770, Tmax = 0.883	k = −29→29
8508 measured reflections	l = −9→9
2554 independent reflections

Refinement

Refinement on F^2	w = 1/[0.004Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.041	(Δ/σ)max < 0.001
wR(F^2) = 0.142	Δρmax = 0.20 e Å^−3
S = 1.00	Δρmin = −0.26 e Å^−3
1871 reflections	Extinction correction: Larson (1970), equation 22
155 parameters	Extinction coefficient: 246 (55)
H-atom parameters constrained

Special details

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 using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.2973 (1)	0.38736 (2)	0.58020 (8)	0.0780 (2)
O1	0.9062 (2)	0.59633 (6)	1.0202 (2)	0.0607 (4)
N1	0.8241 (3)	0.69819 (7)	0.8186 (3)	0.0559 (5)
C1	0.7392 (3)	0.60450 (7)	0.9104 (3)	0.0418 (4)
C2	0.6758 (3)	0.66636 (7)	0.8551 (2)	0.0410 (4)
C3	0.7803 (4)	0.7537 (1)	0.7749 (3)	0.0685 (7)
C4	0.5984 (4)	0.7796 (1)	0.7693 (4)	0.0740 (7)
C5	0.4495 (4)	0.74639 (9)	0.8093 (3)	0.0670 (6)
C6	0.4864 (3)	0.68803 (8)	0.8534 (3)	0.0482 (5)
C7	0.3303 (3)	0.64971 (8)	0.8978 (3)	0.0564 (6)
C8	0.2529 (3)	0.60225 (9)	0.7577 (3)	0.0620 (6)
C9	0.3962 (3)	0.55204 (8)	0.7577 (2)	0.0446 (5)
C10	0.3043 (3)	0.49931 (9)	0.6857 (2)	0.0522 (5)
C11	0.4188 (3)	0.45142 (8)	0.6734 (2)	0.0517 (5)
C12	0.6300 (3)	0.45281 (8)	0.7345 (3)	0.0525 (5)
C13	0.7238 (3)	0.50361 (7)	0.8128 (2)	0.0461 (5)
C14	0.6100 (3)	0.55362 (7)	0.8249 (2)	0.0395 (4)
H10	0.1543	0.4965	0.6427	0.061*
H12	0.7104	0.4187	0.7217	0.064*
H13	0.8736	0.5051	0.8616	0.055*
H71	0.3937	0.6312	1.0145	0.070*
H72	0.2157	0.6734	0.9061	0.070*
H3	0.8857	0.7774	0.7457	0.082*
H4	0.5732	0.8206	0.7356	0.085*
H81	0.2213	0.6208	0.6390	0.074*
H82	0.1283	0.5863	0.7749	0.074*
H5	0.3180	0.7639	0.8079	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1060 (6)	0.0508 (4)	0.0711 (4)	−0.0291 (3)	0.0167 (4)	−0.0095 (2)
O1	0.0411 (8)	0.0452 (7)	0.083 (1)	0.0055 (6)	−0.0016 (7)	−0.0033 (7)
N1	0.0505 (9)	0.0450 (9)	0.073 (1)	−0.0064 (7)	0.0197 (8)	0.0031 (7)
C1	0.0355 (8)	0.0382 (9)	0.0530 (9)	0.0032 (6)	0.0148 (8)	−0.0006 (7)
C2	0.0422 (9)	0.0352 (8)	0.0459 (8)	0.0019 (6)	0.0133 (7)	0.0010 (6)
C3	0.073 (1)	0.047 (1)	0.084 (1)	−0.012 (1)	0.020 (1)	0.012 (1)
C4	0.079 (2)	0.042 (1)	0.092 (2)	0.005 (1)	0.011 (1)	0.020 (1)
C5	0.062 (1)	0.046 (1)	0.089 (1)	0.0171 (9)	0.016 (1)	0.010 (1)
C6	0.047 (1)	0.0400 (9)	0.057 (1)	0.0071 (7)	0.0154 (9)	0.0023 (7)
C7	0.047 (1)	0.051 (1)	0.078 (1)	0.0110 (8)	0.029 (1)	0.0027 (9)
C8	0.0359 (9)	0.056 (1)	0.092 (2)	0.0044 (8)	0.015 (1)	0.002 (1)
C9	0.0414 (9)	0.0448 (9)	0.0473 (9)	−0.0014 (7)	0.0125 (7)	0.0043 (7)
C10	0.049 (1)	0.051 (1)	0.053 (1)	−0.0099 (8)	0.0091 (8)	0.0046 (8)
C11	0.070 (1)	0.041 (1)	0.0430 (9)	−0.0138 (8)	0.0155 (8)	0.0013 (7)
C12	0.069 (1)	0.0367 (9)	0.054 (1)	0.0022 (8)	0.0215 (9)	0.0021 (7)
C13	0.047 (1)	0.0367 (9)	0.0544 (9)	0.0042 (7)	0.0149 (8)	0.0045 (7)
C14	0.0388 (9)	0.0368 (9)	0.0427 (8)	0.0010 (6)	0.0119 (7)	0.0038 (6)

Geometric parameters (Å, º)

Cl1—C11	1.739 (2)	C10—C11	1.371 (3)
O1—C1	1.215 (2)	C11—C12	1.377 (3)
N1—C2	1.344 (3)	C12—C13	1.382 (2)
N1—C3	1.332 (3)	C13—C14	1.407 (2)
C1—C2	1.512 (2)	C3—H3	0.9800
C1—C14	1.496 (2)	C4—H4	0.9800
C2—C6	1.381 (3)	C5—H5	0.9800
C3—C4	1.367 (4)	C7—H71	0.9700
C4—C5	1.377 (4)	C7—H72	0.9700
C5—C6	1.390 (3)	C8—H81	0.9700
C6—C7	1.498 (3)	C8—H82	0.9700
C7—C8	1.514 (3)	C10—H10	0.9800
C8—C9	1.514 (3)	C12—H12	0.9800
C9—C10	1.403 (3)	C13—H13	0.9800
C9—C14	1.397 (2)
Cl1—C11—C10	119.9 (2)	C11—C12—C13	118.1 (2)
Cl1—C11—C12	118.9 (2)	C12—C13—C14	121.9 (2)
O1—C1—C2	118.2 (1)	N1—C3—H3	117.8385
O1—C1—C14	119.5 (1)	H3—C3—C4	118.0048
N1—C2—C1	113.7 (2)	C3—C4—H4	121.0825
N1—C2—C6	124.1 (2)	H4—C4—C5	120.7095
C3—N1—C2	116.7 (2)	C4—C5—H5	120.1502
N1—C3—C4	124.2 (2)	H5—C5—C6	119.9215
C1—C2—C6	122.1 (2)	C6—C7—H71	108.3647
C14—C1—C2	122.1 (1)	C6—C7—H72	108.9981
C1—C14—C13	113.9 (1)	H71—C7—C8	107.8055
C1—C14—C9	126.7 (2)	C7—C8—H81	106.4728
C2—C6—C5	116.9 (2)	H72—C7—C8	109.4416
C2—C6—C7	120.7 (2)	C7—C8—H82	108.2342
C3—C4—C5	118.2 (2)	H72—C7—H71	109.4611
C4—C5—C6	119.9 (2)	H81—C8—C9	107.4585
C5—C6—C7	122.3 (2)	H82—C8—C9	107.5925
C6—C7—C8	112.7 (2)	H82—C8—H81	109.4607
C7—C8—C9	117.5 (1)	C9—C10—H10	119.3193
C8—C9—C10	116.6 (2)	H10—C10—C11	118.9397
C8—C9—C14	125.7 (2)	C11—C12—H12	120.4822
C9—C10—C11	121.7 (2)	H12—C12—C13	121.4332
C14—C9—C10	117.7 (2)	C12—C13—H13	119.4861
C9—C14—C13	119.4 (1)	H13—C13—C14	118.6629
C10—C11—C12	121.2 (2)
C3—N1—C2—C1	−177.9 (2)	C2—C6—C7—C8	−66.0 (2)
C3—N1—C2—C6	−1.4 (3)	C5—C6—C7—C8	114.1 (2)
C2—N1—C3—C4	1.5 (3)	C6—C7—C8—C9	73.6 (2)
O1—C1—C2—N1	45.1 (3)	C7—C8—C9—C10	155.1 (2)
O1—C1—C2—C6	−131.4 (2)	C7—C8—C9—C14	−24.1 (3)
C14—C1—C2—N1	−130.6 (2)	C8—C9—C10—C11	177.9 (2)
C14—C1—C2—C6	52.9 (3)	C14—C9—C10—C11	−2.8 (3)
O1—C1—C14—C9	152.8 (2)	C8—C9—C14—C1	0.4 (3)
O1—C1—C14—C13	−27.9 (3)	C8—C9—C14—C13	−178.9 (2)
C2—C1—C14—C9	−31.6 (3)	C10—C9—C14—C1	−178.8 (2)
C2—C1—C14—C13	147.7 (2)	C10—C9—C14—C13	2.0 (3)
N1—C2—C6—C5	0.6 (3)	C9—C10—C11—Cl1	−179.2 (2)
N1—C2—C6—C7	−179.3 (2)	C9—C10—C11—C12	1.1 (3)
C1—C2—C6—C5	176.7 (2)	Cl1—C11—C12—C13	−178.2 (2)
C1—C2—C6—C7	−3.2 (3)	C10—C11—C12—C13	1.5 (3)
N1—C3—C4—C5	−0.8 (4)	C11—C12—C13—C14	−2.3 (3)
C3—C4—C5—C6	−0.1 (3)	C12—C13—C14—C1	−178.7 (2)
C4—C5—C6—C2	0.2 (3)	C12—C13—C14—C9	0.6 (3)
C4—C5—C6—C7	−179.9 (2)