(E)-3-[(Di-methyl-amino)-methyl-idene]-4-phenyl-1-(prop-2-yn-yl)-1H-1,5-benzodiazepin-2(3H)-one.

The title compound, C21H19N3O, exhibits an E configuration with respect to the C=C bond between the benzodiazepine and tri-methyl-amine groups. The seven-membered diazepine ring displays a boat conformation. In the crystal, mol-ecules are linked by a C-H⋯O hydrogen bond, forming a chain along [110].

Related literature

For benzodiazepine derivatives, see: Di Braccio et al. (2001 ▶); Pevarello et al. (1993 ▶). For related structures, see: Loughzail et al. (2011 ▶); Boudina et al. (2006 ▶).

Experimental

Crystal data

C21H19N3O

M = 329.39

Monoclinic,

a = 12.8122 (10) Å

b = 13.9317 (12) Å

c = 19.7795 (14) Å

β = 94.647 (3)°

V = 3519.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 300 K

0.13 × 0.10 × 0.08 mm

Data collection

Bruker X8 KappaCCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.990, T max = 0.994

21544 measured reflections

3220 independent reflections

2555 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.099

S = 1.02

3220 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, HasRB. DOI: 10.1107/S1600536813032960/is5319sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032960/is5319Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032960/is5319Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H19N3O	F(000) = 1392
Mr = 329.39	Dx = 1.243 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 12.8122 (10) Å	θ = 10–15°
b = 13.9317 (12) Å	µ = 0.08 mm−1
c = 19.7795 (14) Å	T = 300 K
β = 94.647 (3)°	Block, yellow
V = 3519.0 (5) Å3	0.13 × 0.10 × 0.08 mm
Z = 8

Bruker X8 KappaCCD APEXII diffractometer	3220 independent reflections
Radiation source: fine-focus sealed tube	2555 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scans	θmax = 25.4°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.990, Tmax = 0.994	k = −16→13
21544 measured reflections	l = −23→23

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: difference Fourier map
wR(F2) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0423P)2 + 1.6343P] where P = (Fo2 + 2Fc2)/3
3220 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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	0.23744 (12)	−0.00078 (11)	0.47258 (7)	0.0493 (4)
H1A	0.1759	−0.0412	0.4656	0.059*
H1B	0.2886	−0.0345	0.5026	0.059*
C2	0.20897 (11)	0.08866 (12)	0.50454 (8)	0.0500 (4)
C3	0.18446 (14)	0.15873 (15)	0.53145 (9)	0.0687 (5)
H3	0.1649	0.2146	0.5529	0.082*
C4	0.27086 (11)	−0.06084 (10)	0.36193 (7)	0.0418 (3)
C5	0.30050 (10)	−0.04291 (10)	0.29321 (7)	0.0387 (3)
C6	0.27571 (10)	0.05269 (10)	0.26392 (7)	0.0396 (3)
C7	0.19842 (11)	0.05802 (11)	0.20333 (7)	0.0449 (4)
C8	0.20304 (13)	0.13347 (11)	0.15770 (8)	0.0545 (4)
H8	0.2563	0.1788	0.1638	0.065*
C9	0.12883 (16)	0.14127 (14)	0.10342 (9)	0.0710 (5)
H9	0.1331	0.1913	0.0726	0.085*
C10	0.04882 (16)	0.07593 (18)	0.09453 (10)	0.0811 (6)
H10	−0.0017	0.0823	0.0583	0.097*
C11	0.04357 (15)	0.00075 (17)	0.13950 (11)	0.0806 (6)
H11	−0.0107	−0.0436	0.1336	0.097*
C12	0.11855 (13)	−0.00900 (13)	0.19330 (9)	0.0603 (4)
H12	0.1155	−0.0606	0.2229	0.072*
C13	0.37939 (11)	0.13592 (10)	0.34662 (7)	0.0418 (3)
C14	0.46264 (12)	0.20107 (11)	0.34809 (9)	0.0555 (4)
H14	0.4713	0.2385	0.3100	0.067*
C15	0.53236 (12)	0.21109 (13)	0.40479 (10)	0.0630 (5)
H15	0.5886	0.2532	0.4043	0.076*
C16	0.51758 (12)	0.15823 (13)	0.46185 (9)	0.0598 (4)
H16	0.5634	0.1653	0.5005	0.072*
C17	0.43540 (11)	0.09509 (11)	0.46209 (8)	0.0497 (4)
H17	0.4257	0.0605	0.5013	0.060*
C18	0.36619 (10)	0.08181 (10)	0.40482 (7)	0.0396 (3)
C19	0.33035 (10)	−0.12223 (10)	0.25861 (7)	0.0418 (3)
H19	0.3208	−0.1804	0.2803	0.050*
C20	0.40194 (12)	−0.04771 (12)	0.16008 (8)	0.0537 (4)
H20A	0.4630	−0.0639	0.1374	0.064*
H20B	0.4175	0.0056	0.1900	0.064*
H20C	0.3460	−0.0306	0.1271	0.064*
C21	0.39525 (14)	−0.22348 (12)	0.17186 (9)	0.0653 (5)
H21A	0.4697	−0.2296	0.1706	0.078*
H21B	0.3620	−0.2300	0.1268	0.078*
H21C	0.3701	−0.2727	0.2004	0.078*
N1	0.28111 (9)	0.01576 (8)	0.40710 (6)	0.0415 (3)
N2	0.30977 (9)	0.13373 (8)	0.28823 (6)	0.0446 (3)
N3	0.37076 (9)	−0.12945 (9)	0.19895 (6)	0.0462 (3)
O1	0.23521 (10)	−0.13715 (8)	0.38040 (6)	0.0660 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0566 (9)	0.0513 (9)	0.0418 (8)	−0.0016 (7)	0.0155 (7)	0.0015 (7)
C2	0.0463 (8)	0.0615 (10)	0.0434 (8)	0.0012 (7)	0.0107 (6)	−0.0030 (8)
C3	0.0633 (10)	0.0749 (13)	0.0700 (12)	0.0078 (9)	0.0182 (9)	−0.0209 (10)
C4	0.0450 (7)	0.0363 (8)	0.0452 (8)	−0.0025 (6)	0.0109 (6)	0.0006 (6)
C5	0.0420 (7)	0.0362 (7)	0.0384 (7)	−0.0030 (6)	0.0065 (6)	−0.0013 (6)
C6	0.0440 (7)	0.0383 (8)	0.0377 (7)	−0.0002 (6)	0.0114 (6)	−0.0005 (6)
C7	0.0484 (8)	0.0449 (8)	0.0421 (8)	0.0077 (7)	0.0078 (6)	−0.0031 (6)
C8	0.0659 (10)	0.0487 (9)	0.0493 (9)	0.0135 (8)	0.0064 (7)	0.0002 (7)
C9	0.0899 (14)	0.0705 (12)	0.0518 (10)	0.0326 (11)	0.0009 (9)	0.0031 (9)
C10	0.0723 (13)	0.1024 (17)	0.0650 (12)	0.0292 (12)	−0.0170 (10)	−0.0110 (12)
C11	0.0597 (11)	0.0990 (17)	0.0804 (14)	−0.0018 (11)	−0.0105 (10)	−0.0117 (13)
C12	0.0547 (9)	0.0672 (11)	0.0585 (10)	−0.0035 (8)	0.0013 (8)	−0.0025 (8)
C13	0.0461 (8)	0.0360 (8)	0.0448 (8)	−0.0011 (6)	0.0122 (6)	−0.0075 (6)
C14	0.0625 (9)	0.0452 (9)	0.0621 (10)	−0.0125 (7)	0.0257 (8)	−0.0110 (8)
C15	0.0442 (8)	0.0583 (11)	0.0880 (13)	−0.0119 (8)	0.0155 (8)	−0.0270 (10)
C16	0.0444 (8)	0.0629 (11)	0.0711 (11)	0.0035 (8)	−0.0023 (8)	−0.0188 (9)
C17	0.0486 (8)	0.0495 (9)	0.0508 (9)	0.0080 (7)	0.0017 (7)	−0.0060 (7)
C18	0.0390 (7)	0.0369 (7)	0.0440 (8)	0.0019 (6)	0.0098 (6)	−0.0055 (6)
C19	0.0438 (7)	0.0373 (8)	0.0449 (8)	−0.0043 (6)	0.0078 (6)	−0.0009 (6)
C20	0.0531 (9)	0.0621 (10)	0.0480 (9)	−0.0015 (7)	0.0166 (7)	0.0018 (8)
C21	0.0720 (11)	0.0573 (11)	0.0690 (11)	−0.0003 (9)	0.0213 (9)	−0.0224 (9)
N1	0.0481 (6)	0.0402 (7)	0.0375 (6)	−0.0046 (5)	0.0121 (5)	−0.0020 (5)
N2	0.0569 (7)	0.0367 (7)	0.0415 (7)	−0.0019 (5)	0.0111 (5)	0.0003 (5)
N3	0.0501 (7)	0.0442 (7)	0.0458 (7)	−0.0024 (5)	0.0138 (6)	−0.0082 (6)
O1	0.0993 (9)	0.0428 (6)	0.0605 (7)	−0.0180 (6)	0.0342 (6)	−0.0033 (5)

C1—C2	1.457 (2)	C12—H12	0.9300
C1—N1	1.4700 (18)	C13—C18	1.398 (2)
C1—H1A	0.9700	C13—C14	1.399 (2)
C1—H1B	0.9700	C13—N2	1.4012 (18)
C2—C3	1.167 (2)	C14—C15	1.383 (2)
C3—H3	0.9300	C14—H14	0.9300
C4—O1	1.2244 (16)	C15—C16	1.373 (3)
C4—N1	1.3911 (18)	C15—H15	0.9300
C4—C5	1.4622 (19)	C16—C17	1.372 (2)
C5—C19	1.3705 (19)	C16—H16	0.9300
C5—C6	1.4767 (19)	C17—C18	1.393 (2)
C6—N2	1.2893 (17)	C17—H17	0.9300
C6—C7	1.493 (2)	C18—N1	1.4301 (17)
C7—C12	1.388 (2)	C19—N3	1.3303 (18)
C7—C8	1.390 (2)	C19—H19	0.9300
C8—C9	1.380 (2)	C20—N3	1.4482 (19)
C8—H8	0.9300	C20—H20A	0.9600
C9—C10	1.372 (3)	C20—H20B	0.9600
C9—H9	0.9300	C20—H20C	0.9600
C10—C11	1.379 (3)	C21—N3	1.4590 (19)
C10—H10	0.9300	C21—H21A	0.9600
C11—C12	1.381 (2)	C21—H21B	0.9600
C11—H11	0.9300	C21—H21C	0.9600
C2—C1—N1	112.02 (12)	C15—C14—C13	121.58 (16)
C2—C1—H1A	109.2	C15—C14—H14	119.2
N1—C1—H1A	109.2	C13—C14—H14	119.2
C2—C1—H1B	109.2	C16—C15—C14	119.29 (15)
N1—C1—H1B	109.2	C16—C15—H15	120.4
H1A—C1—H1B	107.9	C14—C15—H15	120.4
C3—C2—C1	177.97 (17)	C17—C16—C15	120.23 (15)
C2—C3—H3	180.0	C17—C16—H16	119.9
O1—C4—N1	119.51 (13)	C15—C16—H16	119.9
O1—C4—C5	123.84 (13)	C16—C17—C18	121.35 (15)
N1—C4—C5	116.61 (12)	C16—C17—H17	119.3
C19—C5—C4	115.50 (12)	C18—C17—H17	119.3
C19—C5—C6	126.24 (12)	C17—C18—C13	119.11 (13)
C4—C5—C6	117.07 (11)	C17—C18—N1	119.76 (13)
N2—C6—C5	126.02 (12)	C13—C18—N1	121.10 (12)
N2—C6—C7	115.98 (12)	N3—C19—C5	130.42 (13)
C5—C6—C7	117.85 (12)	N3—C19—H19	114.8
C12—C7—C8	119.06 (14)	C5—C19—H19	114.8
C12—C7—C6	120.98 (13)	N3—C20—H20A	109.5
C8—C7—C6	119.89 (14)	N3—C20—H20B	109.5
C9—C8—C7	120.13 (17)	H20A—C20—H20B	109.5
C9—C8—H8	119.9	N3—C20—H20C	109.5
C7—C8—H8	119.9	H20A—C20—H20C	109.5
C10—C9—C8	120.55 (18)	H20B—C20—H20C	109.5
C10—C9—H9	119.7	N3—C21—H21A	109.5
C8—C9—H9	119.7	N3—C21—H21B	109.5
C9—C10—C11	119.76 (18)	H21A—C21—H21B	109.5
C9—C10—H10	120.1	N3—C21—H21C	109.5
C11—C10—H10	120.1	H21A—C21—H21C	109.5
C10—C11—C12	120.28 (19)	H21B—C21—H21C	109.5
C10—C11—H11	119.9	C4—N1—C18	120.39 (11)
C12—C11—H11	119.9	C4—N1—C1	115.01 (11)
C11—C12—C7	120.19 (18)	C18—N1—C1	118.30 (11)
C11—C12—H12	119.9	C6—N2—C13	120.00 (12)
C7—C12—H12	119.9	C19—N3—C20	123.73 (12)
C18—C13—C14	118.40 (14)	C19—N3—C21	120.29 (13)
C18—C13—N2	123.75 (12)	C20—N3—C21	115.74 (12)
C14—C13—N2	117.69 (13)
O1—C4—C5—C19	−27.5 (2)	C16—C17—C18—C13	−1.7 (2)
N1—C4—C5—C19	154.90 (12)	C16—C17—C18—N1	−179.66 (13)
O1—C4—C5—C6	140.80 (15)	C14—C13—C18—C17	0.53 (19)
N1—C4—C5—C6	−36.78 (17)	N2—C13—C18—C17	−174.84 (12)
C19—C5—C6—N2	−133.01 (15)	C14—C13—C18—N1	178.43 (12)
C4—C5—C6—N2	60.09 (18)	N2—C13—C18—N1	3.1 (2)
C19—C5—C6—C7	51.59 (19)	C4—C5—C19—N3	−172.74 (14)
C4—C5—C6—C7	−115.32 (14)	C6—C5—C19—N3	20.2 (2)
N2—C6—C7—C12	−146.20 (14)	O1—C4—N1—C18	146.04 (14)
C5—C6—C7—C12	29.67 (19)	C5—C4—N1—C18	−36.26 (18)
N2—C6—C7—C8	30.81 (19)	O1—C4—N1—C1	−5.6 (2)
C5—C6—C7—C8	−153.32 (13)	C5—C4—N1—C1	172.08 (12)
C12—C7—C8—C9	0.2 (2)	C17—C18—N1—C4	−121.72 (14)
C6—C7—C8—C9	−176.90 (14)	C13—C18—N1—C4	60.39 (18)
C7—C8—C9—C10	1.2 (3)	C17—C18—N1—C1	29.02 (18)
C8—C9—C10—C11	−1.2 (3)	C13—C18—N1—C1	−148.87 (13)
C9—C10—C11—C12	−0.1 (3)	C2—C1—N1—C4	−155.14 (13)
C10—C11—C12—C7	1.4 (3)	C2—C1—N1—C18	52.58 (17)
C8—C7—C12—C11	−1.5 (2)	C5—C6—N2—C13	2.0 (2)
C6—C7—C12—C11	175.58 (15)	C7—C6—N2—C13	177.51 (11)
C18—C13—C14—C15	1.4 (2)	C18—C13—N2—C6	−45.70 (19)
N2—C13—C14—C15	177.09 (14)	C14—C13—N2—C6	138.91 (14)
C13—C14—C15—C16	−2.2 (2)	C5—C19—N3—C20	6.6 (2)
C14—C15—C16—C17	1.0 (2)	C5—C19—N3—C21	−179.16 (15)
C15—C16—C17—C18	1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.93	2.50	3.415 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.93	2.50	3.415 (2)	170

Symmetry code: (i) .