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

Jin, D.-C.; Zhang, W.-B.; Piao, F.-Y.; Han, R.-B.

doi:10.1107/S1600536811024470

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1821

doi:10.1107/S1600536811024470

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

Da-Cheng Jin,^a Wen-Bin Zhang,^b Feng-Yu Piao ^b and Rong-Bi Han ^c ^*

^aInstitute of Chemical Technology of Yanbian University, Yanji 133002, Jilin Province, People's Republic of China, ^bDepartment of Chemistry, College of Science, Yanbian University, Yanji 133002, Jilin Province, People's Republic of China, and ^cKey Laboratory of Natural Resources of Changbai Mountain & Functional Molecules (Yanbian University), Ministry of Education, Yanji 133002, Jilin Province, People's Republic of China
^*Correspondence e-mail: rongbihan@ybu.edu.cn

(Received 7 June 2011; accepted 22 June 2011; online 25 June 2011)

In the title molecule, C₁₈H₁₆ClN₃O₂, 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. Intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing also exhibits weak intermolecular C—H⋯N hydrogen bonds and π–π interactions with a short distance of 3.734 (3) Å between the centroids of the aromatic rings of neighbouring molecules.

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_r = 341.79
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.113
S = 1.07
3569 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) $[-x+{\script{3\over 2}}, -y+{\script{5\over 2}}, -z+1]$ ; (ii) $[x, -y+2, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024470/cv5117sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811024470/cv5117Isup3.cml

checkCIF report

Comment top

The title compound (I) was obtained from the reaction of 7-alkoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-thione and methyl hydrazinocarboylate in n-butanol (Piao et al. 2011; Jin et al. 2006), but its structure can not be confirmed with ¹³C-NMR spectra. Herein we report its crystal structure.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those reported for the related compounds (Han et al. 2010; Jin et al. 2010). Except C15, all non-hydrogen atoms lie in a plane with r.m.s of 0.0406 (9) Å. Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. The crystal packing exhibits weak intermolecular C—H···N hydrogen bonds (Table 1) and π—π interactions with the short distence of 3.734 (3) Å between the centroids of aromatic rings from the neighbouring molecules.

Related literature top

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 top

The title compound was prepared according to the literature (Piao et al., 2011; Jin et al., 2006). Single crystals suitable for X-ray diffraction were prepared by slow evaporation a mixture of n-butanol and ethanol (1:1) at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with the atom numbering. Displacement ellipsoids are drawn at the 30% probalility level.

9-(2-Chlorobenzyloxy)-6,7-dihydro-2H- benzo[c][1,2,4]triazolo[4,3-a]azepin-3(5H)-one top

Crystal data top

C₁₈H₁₆ClN₃O₂	F(000) = 1424
M_r = 341.79	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0667P)² + 1.2865P] where P = (F_o² + 2F_c²)/3
3569 reflections	(Δ/σ)_max = 0.002
217 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₈H₁₆ClN₃O₂	V = 3129 (3) Å³
M_r = 341.79	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.421 (11) Å	µ = 0.26 mm⁻¹
b = 8.009 (4) Å	T = 291 K
c = 14.896 (8) Å	0.35 × 0.28 × 0.25 mm
β = 112.654 (18)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3569 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3033 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.938	R_int = 0.019
14713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.07	Δρ_max = 0.21 e Å⁻³
3569 reflections	Δρ_min = −0.36 e Å⁻³
217 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, −y+5/2, −z+1; (ii) x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆ClN₃O₂
M_r	341.79
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	291
a, b, c (Å)	28.421 (11), 8.009 (4), 14.896 (8)
β (°)	112.654 (18)
V (Å³)	3129 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.35 × 0.28 × 0.25

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.914, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	14713, 3569, 3033
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.113, 1.07
No. of reflections	3569
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.36

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, −y+5/2, −z+1; (ii) x, −y+2, z−1/2.

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20662010) and the Specialized Research Fund for the Doctoral Progam of Higher Education (grant No. 2006184001).

References

Han, R.-B., Zhang, B. & Piao, F.-Y. (2010). Acta Cryst. E66, o2775. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 67| Part 7| July 2011| Page o1821

doi:10.1107/S1600536811024470

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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