9-(2-Chloro-benz-yloxy)-6,7-dihydro-2H-benzo[c][1,2,4]triazolo[4,3-a]azepin-3(5H)-one.

In the title mol-ecule, C(18)H(16)ClN(3)O(2), the seven-membered ring adopts an envelope conformation with the flap atom deviating by 0.801 (5) Å from the mean plane formed by the remaining non-H atoms. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. The crystal packing also exhibits weak inter-molecular C-H⋯N hydrogen bonds and π-π inter-actions with a short distance of 3.734 (3) Å between the centroids of the aromatic rings of neighbouring mol-ecules.

Related literature

For background and details of the synthesis, see: Piao et al. (2011 ▶); Jin et al. (2006 ▶). For related structures, see: Han et al. (2010 ▶); Jin et al. (2010 ▶).

Experimental

Crystal data

C18H16ClN3O2

M = 341.79

Monoclinic,

a = 28.421 (11) Å

b = 8.009 (4) Å

c = 14.896 (8) Å

β = 112.654 (18)°

V = 3129 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 291 K

0.35 × 0.28 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.914, T max = 0.938

14713 measured reflections

3569 independent reflections

3033 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.07

3569 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.36 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024470/cv5117sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024470/cv5117Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024470/cv5117Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H16ClN3O2	F(000) = 1424
Mr = 341.79	Dx = 1.451 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 12565 reflections
a = 28.421 (11) Å	θ = 3.1–27.6°
b = 8.009 (4) Å	µ = 0.26 mm−1
c = 14.896 (8) Å	T = 291 K
β = 112.654 (18)°	Block, colourless
V = 3129 (3) Å3	0.35 × 0.28 × 0.25 mm
Z = 8

Rigaku R-AXIS RAPID diffractometer	3569 independent reflections
Radiation source: fine-focus sealed tube	3033 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −35→36
Tmin = 0.914, Tmax = 0.938	k = −8→10
14713 measured reflections	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0667P)2 + 1.2865P] where P = (Fo2 + 2Fc2)/3
3569 reflections	(Δ/σ)max = 0.002
217 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Experimental. (See detailed section in the paper)

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
C1	1.12595 (5)	0.48226 (18)	0.42519 (11)	0.0357 (3)
C2	1.17285 (6)	0.4037 (2)	0.45532 (13)	0.0466 (4)
H2	1.1863	0.3715	0.4102	0.056*
C3	1.19933 (6)	0.3737 (2)	0.55289 (14)	0.0499 (4)
H3	1.2310	0.3217	0.5740	0.060*
C4	1.17895 (5)	0.4207 (2)	0.61950 (12)	0.0441 (4)
H4	1.1965	0.3982	0.6853	0.053*
C5	1.13222 (5)	0.50153 (17)	0.58801 (11)	0.0348 (3)
H5	1.1189	0.5342	0.6334	0.042*
C6	1.10491 (5)	0.53472 (15)	0.49043 (10)	0.0285 (3)
C7	1.05452 (5)	0.62455 (16)	0.45363 (9)	0.0302 (3)
H7A	1.0568	0.7245	0.4188	0.036*
H7B	1.0283	0.5531	0.4091	0.036*
C8	0.99692 (4)	0.75568 (15)	0.51182 (9)	0.0280 (3)
C9	0.98445 (5)	0.80010 (17)	0.58989 (9)	0.0321 (3)
H9	1.0058	0.7714	0.6530	0.038*
C10	0.94008 (5)	0.88719 (17)	0.57312 (9)	0.0305 (3)
H10	0.9319	0.9164	0.6257	0.037*
C11	0.90681 (4)	0.93338 (15)	0.47889 (9)	0.0256 (2)
C12	0.91964 (5)	0.88864 (16)	0.40076 (9)	0.0283 (3)
C13	0.96483 (5)	0.79982 (17)	0.41914 (9)	0.0300 (3)
H13	0.9734	0.7697	0.3671	0.036*
C14	0.88795 (6)	0.9227 (2)	0.29509 (10)	0.0419 (4)
H14A	0.8630	0.8338	0.2711	0.050*
H14B	0.9101	0.9166	0.2594	0.050*
C15	0.85993 (5)	1.08733 (19)	0.27128 (10)	0.0378 (3)
H15A	0.8820	1.1745	0.3106	0.045*
H15B	0.8521	1.1141	0.2035	0.045*
C16	0.81139 (6)	1.0853 (2)	0.28893 (10)	0.0455 (4)
H16A	0.7919	1.1848	0.2605	0.055*
H16B	0.7913	0.9893	0.2563	0.055*
C17	0.86043 (4)	1.02428 (15)	0.47298 (9)	0.0261 (2)
C18	0.78474 (5)	1.15106 (18)	0.42277 (10)	0.0325 (3)
Cl1	1.091807 (19)	0.51334 (6)	0.30151 (3)	0.05919 (16)
N1	0.81980 (4)	1.07857 (14)	0.39169 (8)	0.0305 (2)
N2	0.85271 (4)	1.05951 (16)	0.55146 (8)	0.0359 (3)
N3	0.80577 (4)	1.13648 (16)	0.51955 (9)	0.0377 (3)
H3A	0.7916	1.1713	0.5577	0.045*
O1	1.04149 (3)	0.66817 (13)	0.53366 (7)	0.0348 (2)
O2	0.74323 (4)	1.21405 (16)	0.37020 (7)	0.0452 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0366 (7)	0.0354 (7)	0.0399 (7)	0.0023 (5)	0.0201 (6)	−0.0008 (6)
C2	0.0399 (8)	0.0489 (9)	0.0607 (10)	0.0052 (6)	0.0300 (7)	−0.0076 (7)
C3	0.0278 (7)	0.0536 (9)	0.0658 (11)	0.0099 (6)	0.0153 (7)	−0.0039 (8)
C4	0.0295 (7)	0.0483 (9)	0.0469 (8)	0.0033 (6)	0.0065 (6)	0.0015 (7)
C5	0.0297 (6)	0.0379 (7)	0.0374 (7)	0.0015 (5)	0.0136 (5)	−0.0019 (5)
C6	0.0268 (6)	0.0254 (6)	0.0361 (7)	0.0002 (4)	0.0152 (5)	−0.0015 (5)
C7	0.0297 (6)	0.0309 (6)	0.0319 (6)	0.0050 (5)	0.0140 (5)	0.0004 (5)
C8	0.0246 (6)	0.0266 (6)	0.0338 (6)	0.0033 (4)	0.0124 (5)	−0.0002 (5)
C9	0.0298 (6)	0.0386 (7)	0.0265 (6)	0.0061 (5)	0.0094 (5)	0.0021 (5)
C10	0.0302 (6)	0.0379 (7)	0.0259 (6)	0.0049 (5)	0.0136 (5)	−0.0007 (5)
C11	0.0251 (6)	0.0261 (6)	0.0271 (6)	0.0012 (4)	0.0119 (4)	−0.0007 (4)
C12	0.0288 (6)	0.0311 (6)	0.0268 (6)	0.0047 (5)	0.0127 (5)	0.0017 (5)
C13	0.0310 (6)	0.0338 (7)	0.0294 (6)	0.0057 (5)	0.0163 (5)	−0.0007 (5)
C14	0.0463 (8)	0.0545 (9)	0.0259 (7)	0.0207 (7)	0.0149 (6)	0.0019 (6)
C15	0.0440 (8)	0.0460 (8)	0.0253 (6)	0.0127 (6)	0.0154 (5)	0.0060 (5)
C16	0.0358 (7)	0.0739 (11)	0.0235 (6)	0.0178 (7)	0.0077 (5)	−0.0028 (6)
C17	0.0257 (6)	0.0277 (6)	0.0264 (6)	0.0021 (4)	0.0119 (4)	0.0002 (4)
C18	0.0277 (6)	0.0399 (7)	0.0325 (6)	0.0050 (5)	0.0145 (5)	−0.0021 (5)
Cl1	0.0724 (3)	0.0747 (3)	0.0384 (2)	0.0194 (2)	0.0300 (2)	0.00614 (19)
N1	0.0249 (5)	0.0410 (6)	0.0260 (5)	0.0065 (4)	0.0101 (4)	−0.0024 (4)
N2	0.0334 (6)	0.0482 (7)	0.0292 (6)	0.0144 (5)	0.0156 (5)	0.0031 (5)
N3	0.0325 (6)	0.0529 (7)	0.0325 (6)	0.0155 (5)	0.0179 (5)	0.0019 (5)
O1	0.0293 (5)	0.0439 (6)	0.0324 (5)	0.0127 (4)	0.0133 (4)	0.0010 (4)
O2	0.0291 (5)	0.0698 (7)	0.0355 (5)	0.0178 (5)	0.0113 (4)	−0.0014 (5)

C1—C2	1.383 (2)	C11—C12	1.3938 (18)
C1—C6	1.3879 (19)	C11—C17	1.4785 (16)
C1—Cl1	1.7379 (18)	C12—C13	1.4000 (17)
C2—C3	1.376 (3)	C12—C14	1.5071 (19)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.380 (2)	C14—C15	1.510 (2)
C3—H3	0.9300	C14—H14A	0.9700
C4—C5	1.387 (2)	C14—H14B	0.9700
C4—H4	0.9300	C15—C16	1.501 (2)
C5—C6	1.384 (2)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C6—C7	1.5048 (17)	C16—N1	1.4565 (19)
C7—O1	1.4214 (17)	C16—H16A	0.9700
C7—H7A	0.9700	C16—H16B	0.9700
C7—H7B	0.9700	C17—N2	1.3008 (18)
C8—O1	1.3726 (15)	C17—N1	1.3827 (16)
C8—C13	1.3759 (19)	C18—O2	1.2441 (16)
C8—C9	1.3865 (19)	C18—N3	1.3363 (19)
C9—C10	1.3770 (18)	C18—N1	1.3782 (16)
C9—H9	0.9300	N2—N3	1.3774 (15)
C10—C11	1.4066 (18)	N3—H3A	0.8600
C10—H10	0.9300
C2—C1—C6	122.12 (14)	C11—C12—C14	125.62 (11)
C2—C1—Cl1	118.94 (12)	C13—C12—C14	115.49 (11)
C6—C1—Cl1	118.93 (11)	C8—C13—C12	122.04 (11)
C3—C2—C1	119.25 (14)	C8—C13—H13	119.0
C3—C2—H2	120.4	C12—C13—H13	119.0
C1—C2—H2	120.4	C12—C14—C15	116.89 (12)
C2—C3—C4	120.11 (14)	C12—C14—H14A	108.1
C2—C3—H3	119.9	C15—C14—H14A	108.1
C4—C3—H3	119.9	C12—C14—H14B	108.1
C3—C4—C5	119.77 (15)	C15—C14—H14B	108.1
C3—C4—H4	120.1	H14A—C14—H14B	107.3
C5—C4—H4	120.1	C16—C15—C14	112.75 (14)
C6—C5—C4	121.43 (14)	C16—C15—H15A	109.0
C6—C5—H5	119.3	C14—C15—H15A	109.0
C4—C5—H5	119.3	C16—C15—H15B	109.0
C5—C6—C1	117.29 (12)	C14—C15—H15B	109.0
C5—C6—C7	122.98 (11)	H15A—C15—H15B	107.8
C1—C6—C7	119.72 (12)	N1—C16—C15	113.26 (11)
O1—C7—C6	109.31 (11)	N1—C16—H16A	108.9
O1—C7—H7A	109.8	C15—C16—H16A	108.9
C6—C7—H7A	109.8	N1—C16—H16B	108.9
O1—C7—H7B	109.8	C15—C16—H16B	108.9
C6—C7—H7B	109.8	H16A—C16—H16B	107.7
H7A—C7—H7B	108.3	N2—C17—N1	110.23 (11)
O1—C8—C13	124.30 (11)	N2—C17—C11	120.56 (11)
O1—C8—C9	116.29 (11)	N1—C17—C11	129.18 (11)
C13—C8—C9	119.40 (12)	O2—C18—N3	129.51 (12)
C10—C9—C8	119.33 (12)	O2—C18—N1	126.32 (13)
C10—C9—H9	120.3	N3—C18—N1	104.16 (11)
C8—C9—H9	120.3	C18—N1—C17	107.84 (11)
C9—C10—C11	122.07 (12)	C18—N1—C16	119.35 (11)
C9—C10—H10	119.0	C17—N1—C16	132.51 (11)
C11—C10—H10	119.0	C17—N2—N3	105.25 (11)
C12—C11—C10	118.30 (11)	C18—N3—N2	112.51 (10)
C12—C11—C17	126.21 (11)	C18—N3—H3A	123.7
C10—C11—C17	115.48 (11)	N2—N3—H3A	123.7
C11—C12—C13	118.86 (11)	C8—O1—C7	116.19 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2i	0.86	1.95	2.7986 (17)	170
C15—H15B···N2ii	0.97	2.66	3.410 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2i	0.86	1.95	2.7986 (17)	170
C15—H15B⋯N2ii	0.97	2.66	3.410 (2)	134

Symmetry codes: (i) ; (ii) .