1,5-Dimethyl-3-propargyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione.

The asymmetric unit of the title compound, C(14)H(14)N(2)O(2), comprises two independent mol-ecules, which slightly differ in the orientation of the propargyl chain. In both molecules, the diazepine ring adopts a boat conformation with the propargyl-bearing C atom as the prow and the C atoms at the ring junction as the stern. The carbonyl O atom of one independent mol-ecule is hydrogen bonded to the acetyl-enic H atom of the other independent mol-ecule. In the crystal, symmetry-related mol-ecules are linked together by C-H⋯O hydrogen bonds, forming a ribbon-like structure along the c axis.

Related literature

For a related structure, see: Jabli et al. (2009 ▶).

Experimental

Crystal data

C14H14N2O2

M = 242.27

Monoclinic,

a = 16.0768 (3) Å

b = 17.1087 (3) Å

c = 8.9530 (2) Å

β = 93.701 (1)°

V = 2457.42 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.40 × 0.30 × 0.05 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

21953 measured reflections

3580 independent reflections

2637 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.06

3580 reflections

337 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024219/ci5110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024219/ci5110Isup2.hkl

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

C14H14N2O2	F(000) = 1024
Mr = 242.27	Dx = 1.310 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5448 reflections
a = 16.0768 (3) Å	θ = 2.5–29.4°
b = 17.1087 (3) Å	µ = 0.09 mm−1
c = 8.9530 (2) Å	T = 293 K
β = 93.701 (1)°	Plate, colourless
V = 2457.42 (8) Å3	0.40 × 0.30 × 0.05 mm
Z = 8

Bruker X8 APEXII area-detector diffractometer	2637 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
graphite	θmax = 30.0°, θmin = 2.8°
φ and ω scans	h = −22→22
21953 measured reflections	k = −24→23
3580 independent reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.5357P] where P = (Fo2 + 2Fc2)/3
3580 reflections	(Δ/σ)max = 0.001
337 parameters	Δρmax = 0.22 e Å−3
4 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.50007 (11)	0.33109 (11)	0.5000 (2)	0.0339 (4)
O2	0.34014 (11)	0.41769 (12)	0.21819 (19)	0.0332 (4)
O3	0.99978 (11)	0.63153 (11)	0.9419 (2)	0.0363 (4)
O4	0.78408 (12)	0.58439 (13)	0.74162 (19)	0.0380 (5)
N1	0.39120 (12)	0.33841 (12)	0.6473 (2)	0.0268 (4)
N2	0.26570 (12)	0.39080 (12)	0.4189 (2)	0.0253 (4)
N3	0.91197 (13)	0.68624 (13)	1.1007 (2)	0.0293 (5)
N4	0.75177 (12)	0.65404 (14)	0.9454 (2)	0.0298 (5)
C1	0.31443 (15)	0.37280 (14)	0.6847 (3)	0.0251 (5)
C2	0.29827 (17)	0.38043 (16)	0.8365 (3)	0.0318 (6)
H2	0.3393	0.3670	0.9099	0.038*
C3	0.22235 (19)	0.40758 (17)	0.8778 (3)	0.0382 (6)
H3	0.2124	0.4121	0.9786	0.046*
C4	0.16095 (18)	0.42805 (17)	0.7692 (3)	0.0384 (6)
H4	0.1091	0.4449	0.7969	0.046*
C5	0.17692 (16)	0.42341 (15)	0.6190 (3)	0.0308 (5)
H5	0.1359	0.4385	0.5467	0.037*
C6	0.25334 (15)	0.39661 (13)	0.5746 (3)	0.0240 (5)
C7	0.33523 (15)	0.41709 (14)	0.3543 (3)	0.0242 (5)
C8	0.40776 (14)	0.44186 (14)	0.4628 (2)	0.0232 (5)
H8	0.3882	0.4782	0.5375	0.028*
C9	0.43852 (14)	0.36629 (14)	0.5383 (3)	0.0250 (5)
C10	0.19504 (16)	0.36807 (17)	0.3156 (3)	0.0329 (6)
H10A	0.2141	0.3334	0.2408	0.049*
H10B	0.1711	0.4139	0.2682	0.049*
H10C	0.1537	0.3421	0.3704	0.049*
C11	0.47672 (15)	0.48013 (16)	0.3774 (3)	0.0295 (5)
H11A	0.4954	0.4434	0.3040	0.035*
H11B	0.4540	0.5255	0.3239	0.035*
C12	0.54896 (16)	0.50462 (16)	0.4769 (3)	0.0324 (5)
C13	0.60798 (19)	0.5229 (2)	0.5539 (4)	0.0446 (7)
H13	0.6549 (15)	0.537 (2)	0.614 (4)	0.062 (11)*
C14	0.42070 (18)	0.26755 (16)	0.7274 (3)	0.0373 (6)
H14A	0.4325	0.2277	0.6563	0.056*
H14B	0.3784	0.2493	0.7898	0.056*
H14C	0.4704	0.2794	0.7884	0.056*
C15	0.83776 (15)	0.68259 (15)	1.1784 (3)	0.0279 (5)
C16	0.84147 (18)	0.69589 (16)	1.3331 (3)	0.0343 (6)
H16	0.8919	0.7095	1.3829	0.041*
C17	0.7709 (2)	0.68902 (17)	1.4124 (3)	0.0404 (7)
H17	0.7745	0.6968	1.5154	0.049*
C18	0.6949 (2)	0.67062 (18)	1.3391 (3)	0.0429 (7)
H18	0.6477	0.6658	1.3932	0.052*
C19	0.68919 (17)	0.65948 (16)	1.1858 (3)	0.0357 (6)
H19	0.6378	0.6481	1.1369	0.043*
C20	0.75997 (16)	0.66527 (14)	1.1039 (3)	0.0278 (5)
C21	0.79742 (15)	0.60039 (16)	0.8740 (3)	0.0281 (5)
C22	0.87014 (15)	0.56424 (15)	0.9697 (3)	0.0274 (5)
H22	0.8497	0.5453	1.0640	0.033*
C23	0.93407 (15)	0.62914 (15)	1.0034 (3)	0.0272 (5)
C24	0.67961 (17)	0.68895 (18)	0.8601 (3)	0.0386 (6)
H24A	0.6957	0.7049	0.7634	0.058*
H24B	0.6605	0.7336	0.9131	0.058*
H24C	0.6356	0.6511	0.8484	0.058*
C25	0.90761 (17)	0.49596 (16)	0.8873 (3)	0.0330 (6)
H25A	0.8631	0.4621	0.8477	0.040*
H25B	0.9365	0.5159	0.8034	0.040*
C26	0.96610 (17)	0.45014 (16)	0.9847 (3)	0.0326 (6)
C27	1.01106 (19)	0.41189 (19)	1.0637 (4)	0.0445 (7)
H27	1.043 (2)	0.3804 (19)	1.130 (4)	0.070 (12)*
C28	0.97458 (18)	0.74656 (18)	1.1443 (4)	0.0426 (7)
H28A	1.0095	0.7556	1.0630	0.064*
H28B	1.0082	0.7291	1.2305	0.064*
H28C	0.9468	0.7942	1.1679	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.0256 (9)	0.0397 (10)	0.0365 (11)	0.0051 (8)	0.0020 (7)	−0.0001 (8)
O2	0.0345 (9)	0.0472 (11)	0.0175 (9)	−0.0022 (8)	−0.0014 (7)	0.0014 (8)
O3	0.0284 (10)	0.0455 (11)	0.0350 (11)	−0.0010 (8)	0.0007 (8)	−0.0021 (9)
O4	0.0363 (10)	0.0558 (13)	0.0210 (10)	−0.0022 (9)	−0.0054 (8)	−0.0026 (8)
N1	0.0276 (10)	0.0311 (10)	0.0210 (10)	0.0018 (8)	−0.0029 (8)	0.0052 (9)
N2	0.0234 (10)	0.0323 (11)	0.0197 (10)	−0.0023 (8)	−0.0022 (8)	−0.0003 (8)
N3	0.0267 (10)	0.0350 (12)	0.0254 (11)	−0.0037 (8)	−0.0038 (8)	−0.0050 (9)
N4	0.0256 (10)	0.0398 (12)	0.0233 (11)	−0.0010 (8)	−0.0030 (8)	0.0021 (9)
C1	0.0275 (12)	0.0277 (12)	0.0202 (11)	−0.0040 (9)	0.0019 (9)	0.0009 (10)
C2	0.0372 (13)	0.0376 (14)	0.0204 (12)	−0.0069 (11)	0.0008 (10)	0.0013 (10)
C3	0.0507 (16)	0.0403 (15)	0.0249 (13)	−0.0065 (12)	0.0139 (12)	−0.0015 (12)
C4	0.0376 (15)	0.0383 (15)	0.0411 (16)	−0.0005 (12)	0.0161 (12)	−0.0007 (13)
C5	0.0272 (12)	0.0342 (13)	0.0312 (13)	−0.0017 (10)	0.0034 (10)	0.0002 (11)
C6	0.0256 (11)	0.0261 (11)	0.0202 (11)	−0.0039 (9)	0.0015 (9)	0.0003 (9)
C7	0.0244 (11)	0.0288 (12)	0.0194 (11)	0.0038 (9)	−0.0003 (8)	0.0019 (9)
C8	0.0243 (11)	0.0293 (12)	0.0162 (10)	−0.0010 (9)	0.0022 (8)	−0.0013 (9)
C9	0.0230 (11)	0.0309 (12)	0.0202 (11)	−0.0016 (9)	−0.0056 (9)	−0.0008 (9)
C10	0.0276 (13)	0.0400 (15)	0.0295 (14)	−0.0048 (11)	−0.0102 (10)	−0.0004 (11)
C11	0.0279 (12)	0.0380 (14)	0.0227 (12)	−0.0040 (10)	0.0017 (9)	0.0037 (10)
C12	0.0308 (13)	0.0374 (13)	0.0296 (13)	−0.0036 (11)	0.0060 (11)	0.0054 (11)
C13	0.0379 (15)	0.0542 (19)	0.0412 (17)	−0.0145 (14)	−0.0016 (13)	0.0030 (14)
C14	0.0414 (15)	0.0365 (15)	0.0335 (14)	0.0051 (12)	−0.0019 (11)	0.0121 (12)
C15	0.0316 (13)	0.0288 (13)	0.0231 (12)	0.0016 (10)	−0.0010 (10)	−0.0013 (10)
C16	0.0438 (15)	0.0345 (14)	0.0238 (13)	0.0031 (11)	−0.0047 (11)	−0.0013 (11)
C17	0.0598 (18)	0.0374 (15)	0.0244 (13)	0.0026 (13)	0.0047 (13)	0.0006 (12)
C18	0.0497 (17)	0.0412 (17)	0.0401 (17)	−0.0037 (13)	0.0199 (14)	0.0010 (13)
C19	0.0337 (14)	0.0384 (15)	0.0356 (15)	−0.0055 (11)	0.0056 (12)	−0.0004 (12)
C20	0.0317 (12)	0.0284 (12)	0.0233 (12)	−0.0028 (10)	0.0011 (10)	0.0004 (10)
C21	0.0254 (11)	0.0374 (13)	0.0210 (12)	−0.0078 (10)	−0.0016 (9)	0.0018 (10)
C22	0.0312 (12)	0.0335 (13)	0.0170 (11)	−0.0003 (10)	−0.0016 (9)	0.0007 (10)
C23	0.0250 (11)	0.0353 (13)	0.0202 (12)	0.0019 (9)	−0.0056 (9)	0.0023 (10)
C24	0.0291 (13)	0.0506 (17)	0.0351 (15)	0.0009 (12)	−0.0066 (11)	0.0030 (13)
C25	0.0422 (14)	0.0367 (14)	0.0197 (12)	−0.0012 (11)	−0.0007 (11)	−0.0029 (10)
C26	0.0341 (13)	0.0362 (14)	0.0279 (13)	−0.0034 (11)	0.0051 (10)	−0.0044 (11)
C27	0.0344 (15)	0.0495 (18)	0.0488 (19)	−0.0012 (13)	−0.0036 (13)	0.0078 (14)
C28	0.0351 (14)	0.0497 (17)	0.0423 (17)	−0.0121 (13)	−0.0030 (12)	−0.0113 (14)

O1—C9	1.226 (3)	C11—C12	1.478 (4)
O2—C7	1.226 (3)	C11—H11A	0.97
O3—C23	1.223 (3)	C11—H11B	0.97
O4—C21	1.222 (3)	C12—C13	1.179 (4)
N1—C9	1.361 (3)	C13—H13	0.93 (3)
N1—C1	1.427 (3)	C14—H14A	0.96
N1—C14	1.472 (3)	C14—H14B	0.96
N2—C7	1.367 (3)	C14—H14C	0.96
N2—C6	1.424 (3)	C15—C16	1.401 (3)
N2—C10	1.470 (3)	C15—C20	1.411 (3)
N3—C23	1.371 (3)	C16—C17	1.381 (4)
N3—C15	1.421 (3)	C16—H16	0.93
N3—C28	1.476 (3)	C17—C18	1.385 (4)
N4—C21	1.360 (3)	C17—H17	0.93
N4—C20	1.430 (3)	C18—C19	1.383 (4)
N4—C24	1.473 (3)	C18—H18	0.93
C1—C6	1.406 (3)	C19—C20	1.397 (4)
C1—C2	1.406 (4)	C19—H19	0.93
C2—C3	1.379 (4)	C21—C22	1.535 (3)
C2—H2	0.93	C22—C25	1.526 (4)
C3—C4	1.385 (4)	C22—C23	1.530 (3)
C3—H3	0.93	C22—H22	0.98
C4—C5	1.388 (4)	C24—H24A	0.96
C4—H4	0.93	C24—H24B	0.96
C5—C6	1.393 (4)	C24—H24C	0.96
C5—H5	0.93	C25—C26	1.468 (4)
C7—C8	1.528 (3)	C25—H25A	0.97
C8—C9	1.526 (3)	C25—H25B	0.97
C8—C11	1.534 (3)	C26—C27	1.177 (4)
C8—H8	0.98	C27—H27	0.93 (3)
C10—H10A	0.96	C28—H28A	0.96
C10—H10B	0.96	C28—H28B	0.96
C10—H10C	0.96	C28—H28C	0.96
C9—N1—C1	123.77 (19)	N1—C14—H14A	109.5
C9—N1—C14	117.4 (2)	N1—C14—H14B	109.5
C1—N1—C14	118.8 (2)	H14A—C14—H14B	109.5
C7—N2—C6	124.09 (19)	N1—C14—H14C	109.5
C7—N2—C10	116.2 (2)	H14A—C14—H14C	109.5
C6—N2—C10	118.88 (19)	H14B—C14—H14C	109.5
C23—N3—C15	122.7 (2)	C16—C15—C20	118.8 (2)
C23—N3—C28	117.8 (2)	C16—C15—N3	119.6 (2)
C15—N3—C28	118.7 (2)	C20—C15—N3	121.6 (2)
C21—N4—C20	122.6 (2)	C17—C16—C15	120.7 (2)
C21—N4—C24	117.4 (2)	C17—C16—H16	119.7
C20—N4—C24	118.6 (2)	C15—C16—H16	119.7
C6—C1—C2	119.1 (2)	C16—C17—C18	120.3 (3)
C6—C1—N1	122.0 (2)	C16—C17—H17	119.9
C2—C1—N1	118.8 (2)	C18—C17—H17	119.9
C3—C2—C1	120.8 (2)	C17—C18—C19	120.1 (3)
C3—C2—H2	119.6	C17—C18—H18	120.0
C1—C2—H2	119.6	C19—C18—H18	120.0
C2—C3—C4	120.0 (3)	C18—C19—C20	120.5 (3)
C2—C3—H3	120.0	C18—C19—H19	119.8
C4—C3—H3	120.0	C20—C19—H19	119.8
C3—C4—C5	119.8 (3)	C19—C20—C15	119.6 (2)
C3—C4—H4	120.1	C19—C20—N4	119.1 (2)
C5—C4—H4	120.1	C15—C20—N4	121.3 (2)
C4—C5—C6	121.1 (3)	O4—C21—N4	122.7 (2)
C4—C5—H5	119.4	O4—C21—C22	122.1 (2)
C6—C5—H5	119.4	N4—C21—C22	115.1 (2)
C5—C6—C1	119.0 (2)	C25—C22—C23	111.7 (2)
C5—C6—N2	118.9 (2)	C25—C22—C21	110.40 (19)
C1—C6—N2	122.1 (2)	C23—C22—C21	107.2 (2)
O2—C7—N2	122.0 (2)	C25—C22—H22	109.2
O2—C7—C8	122.3 (2)	C23—C22—H22	109.2
N2—C7—C8	115.7 (2)	C21—C22—H22	109.2
C9—C8—C7	105.00 (19)	O3—C23—N3	121.9 (2)
C9—C8—C11	111.0 (2)	O3—C23—C22	121.6 (2)
C7—C8—C11	110.36 (19)	N3—C23—C22	116.4 (2)
C9—C8—H8	110.1	N4—C24—H24A	109.5
C7—C8—H8	110.1	N4—C24—H24B	109.5
C11—C8—H8	110.1	H24A—C24—H24B	109.5
O1—C9—N1	121.8 (2)	N4—C24—H24C	109.5
O1—C9—C8	122.4 (2)	H24A—C24—H24C	109.5
N1—C9—C8	115.7 (2)	H24B—C24—H24C	109.5
N2—C10—H10A	109.5	C26—C25—C22	112.3 (2)
N2—C10—H10B	109.5	C26—C25—H25A	109.1
H10A—C10—H10B	109.5	C22—C25—H25A	109.1
N2—C10—H10C	109.5	C26—C25—H25B	109.1
H10A—C10—H10C	109.5	C22—C25—H25B	109.1
H10B—C10—H10C	109.5	H25A—C25—H25B	107.9
C12—C11—C8	112.7 (2)	C27—C26—C25	178.0 (3)
C12—C11—H11A	109.1	C26—C27—H27	176 (3)
C8—C11—H11A	109.1	N3—C28—H28A	109.5
C12—C11—H11B	109.1	N3—C28—H28B	109.5
C8—C11—H11B	109.1	H28A—C28—H28B	109.5
H11A—C11—H11B	107.8	N3—C28—H28C	109.5
C13—C12—C11	178.1 (3)	H28A—C28—H28C	109.5
C12—C13—H13	180 (3)	H28B—C28—H28C	109.5
C9—N1—C1—C6	44.7 (3)	C23—N3—C15—C16	131.1 (3)
C14—N1—C1—C6	−133.7 (3)	C28—N3—C15—C16	−38.5 (3)
C9—N1—C1—C2	−137.7 (2)	C23—N3—C15—C20	−48.5 (3)
C14—N1—C1—C2	43.9 (3)	C28—N3—C15—C20	142.0 (3)
C6—C1—C2—C3	2.9 (4)	C20—C15—C16—C17	2.7 (4)
N1—C1—C2—C3	−174.9 (2)	N3—C15—C16—C17	−176.9 (3)
C1—C2—C3—C4	−0.3 (4)	C15—C16—C17—C18	−1.5 (4)
C2—C3—C4—C5	−1.9 (4)	C16—C17—C18—C19	−0.4 (4)
C3—C4—C5—C6	1.6 (4)	C17—C18—C19—C20	1.1 (4)
C4—C5—C6—C1	1.0 (4)	C18—C19—C20—C15	0.0 (4)
C4—C5—C6—N2	178.2 (2)	C18—C19—C20—N4	−179.5 (3)
C2—C1—C6—C5	−3.2 (3)	C16—C15—C20—C19	−1.9 (4)
N1—C1—C6—C5	174.4 (2)	N3—C15—C20—C19	177.7 (2)
C2—C1—C6—N2	179.8 (2)	C16—C15—C20—N4	177.6 (2)
N1—C1—C6—N2	−2.6 (3)	N3—C15—C20—N4	−2.8 (4)
C7—N2—C6—C5	133.8 (2)	C21—N4—C20—C19	−124.8 (3)
C10—N2—C6—C5	−35.1 (3)	C24—N4—C20—C19	41.7 (3)
C7—N2—C6—C1	−49.2 (3)	C21—N4—C20—C15	55.7 (3)
C10—N2—C6—C1	141.9 (2)	C24—N4—C20—C15	−137.8 (2)
C6—N2—C7—O2	−173.0 (2)	C20—N4—C21—O4	171.5 (2)
C10—N2—C7—O2	−3.8 (3)	C24—N4—C21—O4	4.8 (4)
C6—N2—C7—C8	9.9 (3)	C20—N4—C21—C22	−11.6 (3)
C10—N2—C7—C8	179.0 (2)	C24—N4—C21—C22	−178.2 (2)
O2—C7—C8—C9	−109.3 (3)	O4—C21—C22—C25	−12.3 (3)
N2—C7—C8—C9	67.9 (3)	N4—C21—C22—C25	170.7 (2)
O2—C7—C8—C11	10.4 (3)	O4—C21—C22—C23	109.5 (3)
N2—C7—C8—C11	−172.4 (2)	N4—C21—C22—C23	−67.4 (3)
C1—N1—C9—O1	−173.1 (2)	C15—N3—C23—O3	−177.0 (2)
C14—N1—C9—O1	5.3 (3)	C28—N3—C23—O3	−7.4 (4)
C1—N1—C9—C8	4.2 (3)	C15—N3—C23—C22	6.0 (3)
C14—N1—C9—C8	−177.4 (2)	C28—N3—C23—C22	175.6 (2)
C7—C8—C9—O1	100.1 (2)	C25—C22—C23—O3	14.7 (3)
C11—C8—C9—O1	−19.1 (3)	C21—C22—C23—O3	−106.3 (3)
C7—C8—C9—N1	−77.2 (2)	C25—C22—C23—N3	−168.3 (2)
C11—C8—C9—N1	163.55 (19)	C21—C22—C23—N3	70.7 (3)
C9—C8—C11—C12	−63.5 (3)	C23—C22—C25—C26	72.0 (3)
C7—C8—C11—C12	−179.5 (2)	C21—C22—C25—C26	−168.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O4	0.93 (3)	2.44 (3)	3.366 (3)	172 (3)
C8—H8···O2i	0.98	2.56	3.536 (3)	175
C19—H19···O1i	0.93	2.49	3.374 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O4	0.93 (3)	2.44 (3)	3.366 (3)	172 (3)
C8—H8⋯O2i	0.98	2.56	3.536 (3)	175
C19—H19⋯O1i	0.93	2.49	3.374 (3)	160

Symmetry code: (i) .