6,7-Dihydro-3H-1,4-diazepino[1,2,3,4-lmn][1,10]phenanthroline-3,9(5H)-dione.

In the title compound, C(15)H(12)N(2)O(2), the seven-membered ring bearing the three methyl-ene C atoms displays a puckered conformation, with the methyl-ene C atoms deviating from the plane of the benzene ring by 0.05 (1), 0.98 (1) and 1.04 (1) Å. The phenanthroline unit is not planar; the dihedral angles between this benzene ring and the other pyridyl rings are 9.62 (4) and 9.31 (4)°. The crystal packing is stabilized by π-π inter-actions between two phenanthroline ring systems, forming a centrosymmetric dimer with a centroid-centroid distance of 3.656 (1) Å.

Related literature

For background to π–π inter­actions in supra­molecular chemistry, see: Sisson et al. (2006 ▶). For a related structure, see: Nadeem et al. (2009 ▶).

Experimental

Crystal data

C15H12N2O2

M = 252.27

Monoclinic,

a = 9.1853 (18) Å

b = 13.931 (3) Å

c = 9.4956 (19) Å

β = 111.14 (3)°

V = 1133.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 158 K

0.50 × 0.46 × 0.38 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.952, T max = 0.963

8367 measured reflections

2309 independent reflections

2115 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 1.06

2309 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024761/ng2793sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024761/ng2793Isup2.hkl

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

C15H12N2O2	F(000) = 528
Mr = 252.27	Dx = 1.478 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.1853 (18) Å	Cell parameters from 3526 reflections
b = 13.931 (3) Å	θ = 2.7–26.4°
c = 9.4956 (19) Å	µ = 0.10 mm−1
β = 111.14 (3)°	T = 158 K
V = 1133.3 (4) Å3	Chip, yellow
Z = 4	0.50 × 0.46 × 0.38 mm

Rigaku Mercury CCD diffractometer	2309 independent reflections
Radiation source: Sealed Tube	2115 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.016
Detector resolution: 14.6306 pixels mm-1	θmax = 26.4°, θmin = 2.7°
ω scans	h = −11→9
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −17→17
Tmin = 0.952, Tmax = 0.963	l = −10→11
8367 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.3698P] where P = (Fo2 + 2Fc2)/3
2309 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	1.02892 (11)	0.14451 (7)	0.36246 (11)	0.0183 (2)
N2	0.79115 (11)	0.11065 (7)	0.06165 (11)	0.0186 (2)
O1	1.09796 (11)	0.14573 (7)	0.61843 (10)	0.0313 (2)
O2	0.53670 (10)	0.10333 (7)	−0.09893 (10)	0.0285 (2)
C1	1.13585 (14)	0.13175 (9)	0.50775 (13)	0.0219 (3)
C2	1.29358 (14)	0.10579 (9)	0.52135 (13)	0.0239 (3)
H2	1.3694	0.0911	0.6190	0.029*
C3	1.33514 (14)	0.10204 (9)	0.39944 (14)	0.0234 (3)
H3	1.4423	0.0905	0.4128	0.028*
C3A	1.22264 (13)	0.11496 (8)	0.24970 (13)	0.0193 (3)
C4	1.26651 (14)	0.11749 (8)	0.12166 (14)	0.0228 (3)
H4	1.3735	0.1075	0.1328	0.027*
C5	1.15645 (14)	0.13419 (9)	−0.01825 (13)	0.0223 (3)
H5	1.1879	0.1443	−0.1032	0.027*
C5A	0.99677 (14)	0.13661 (8)	−0.03786 (13)	0.0197 (3)
C6	0.87822 (15)	0.14730 (9)	−0.18533 (13)	0.0238 (3)
H6	0.9079	0.1576	−0.2713	0.029*
C7	0.72644 (15)	0.14297 (9)	−0.20391 (13)	0.0250 (3)
H7	0.6497	0.1561	−0.3018	0.030*
C8	0.67481 (14)	0.11909 (8)	−0.08064 (14)	0.0216 (3)
C8A	0.94915 (13)	0.12578 (8)	0.08617 (13)	0.0171 (3)
C8B	1.06584 (13)	0.12776 (8)	0.23397 (13)	0.0170 (2)
C9	0.74874 (13)	0.06207 (8)	0.17982 (13)	0.0216 (3)
H9A	0.8241	0.0129	0.2259	0.026*
H9B	0.6488	0.0318	0.1341	0.026*
C10	0.74195 (14)	0.13128 (9)	0.30056 (14)	0.0239 (3)
H10A	0.7405	0.0961	0.3869	0.029*
H10B	0.6483	0.1689	0.2625	0.029*
C11	0.88345 (13)	0.19676 (8)	0.34603 (13)	0.0209 (3)
H11A	0.8667	0.2460	0.2712	0.025*
H11B	0.8950	0.2273	0.4401	0.025*

	U11	U22	U33	U12	U13	U23
N1	0.0176 (5)	0.0208 (5)	0.0166 (5)	0.0005 (4)	0.0063 (4)	0.0000 (4)
N2	0.0164 (5)	0.0197 (5)	0.0181 (5)	−0.0012 (4)	0.0044 (4)	0.0005 (4)
O1	0.0303 (5)	0.0472 (6)	0.0171 (4)	0.0023 (4)	0.0094 (4)	0.0011 (4)
O2	0.0179 (4)	0.0298 (5)	0.0316 (5)	−0.0017 (3)	0.0015 (4)	0.0023 (4)
C1	0.0220 (6)	0.0245 (6)	0.0178 (5)	−0.0021 (4)	0.0055 (4)	0.0008 (4)
C2	0.0206 (6)	0.0270 (6)	0.0194 (5)	−0.0007 (5)	0.0016 (4)	0.0024 (4)
C3	0.0165 (5)	0.0260 (6)	0.0250 (6)	0.0013 (4)	0.0040 (5)	0.0009 (5)
C3A	0.0183 (6)	0.0187 (5)	0.0204 (6)	−0.0006 (4)	0.0065 (4)	−0.0011 (4)
C4	0.0201 (6)	0.0238 (6)	0.0267 (6)	−0.0010 (4)	0.0112 (5)	−0.0032 (5)
C5	0.0255 (6)	0.0229 (6)	0.0220 (6)	−0.0029 (5)	0.0130 (5)	−0.0027 (4)
C5A	0.0228 (6)	0.0174 (5)	0.0189 (5)	−0.0016 (4)	0.0077 (5)	−0.0009 (4)
C6	0.0296 (6)	0.0231 (6)	0.0177 (6)	−0.0016 (5)	0.0073 (5)	−0.0001 (4)
C7	0.0264 (6)	0.0248 (6)	0.0180 (5)	0.0000 (5)	0.0011 (5)	0.0005 (4)
C8	0.0202 (6)	0.0172 (5)	0.0231 (6)	−0.0003 (4)	0.0026 (5)	−0.0009 (4)
C8A	0.0174 (5)	0.0151 (5)	0.0189 (6)	−0.0007 (4)	0.0065 (4)	−0.0005 (4)
C8B	0.0177 (6)	0.0157 (5)	0.0176 (5)	−0.0007 (4)	0.0063 (4)	0.0001 (4)
C9	0.0188 (5)	0.0225 (6)	0.0236 (6)	−0.0034 (4)	0.0077 (4)	0.0019 (4)
C10	0.0195 (6)	0.0290 (6)	0.0254 (6)	−0.0010 (5)	0.0107 (5)	0.0003 (5)
C11	0.0190 (5)	0.0226 (6)	0.0216 (5)	0.0019 (4)	0.0081 (4)	−0.0011 (4)

N1—C1	1.3866 (16)	C5—C5A	1.4107 (17)
N1—C8B	1.3987 (15)	C5—H5	0.9600
N1—C11	1.4795 (14)	C5A—C8A	1.4044 (16)
N2—C8	1.3929 (16)	C5A—C6	1.4385 (17)
N2—C8A	1.4005 (15)	C6—C7	1.3420 (18)
N2—C9	1.4779 (14)	C6—H6	0.9600
O1—C1	1.2358 (15)	C7—C8	1.4512 (18)
O2—C8	1.2364 (15)	C7—H7	0.9600
C1—C2	1.4531 (17)	C8A—C8B	1.4264 (17)
C2—C3	1.3443 (17)	C9—C10	1.5165 (17)
C2—H2	0.9600	C9—H9A	0.9600
C3—C3A	1.4361 (17)	C9—H9B	0.9600
C3—H3	0.9600	C10—C11	1.5176 (16)
C3A—C8B	1.4048 (16)	C10—H10A	0.9600
C3A—C4	1.4124 (17)	C10—H10B	0.9600
C4—C5	1.3684 (18)	C11—H11A	0.9600
C4—H4	0.9600	C11—H11B	0.9600
C1—N1—C8B	122.61 (10)	C6—C7—C8	122.03 (11)
C1—N1—C11	117.18 (10)	C6—C7—H7	119.0
C8B—N1—C11	118.94 (9)	C8—C7—H7	119.0
C8—N2—C8A	122.35 (10)	O2—C8—N2	120.71 (11)
C8—N2—C9	117.07 (9)	O2—C8—C7	123.00 (11)
C8A—N2—C9	118.93 (9)	N2—C8—C7	116.25 (11)
O1—C1—N1	120.68 (11)	N2—C8A—C5A	119.61 (10)
O1—C1—C2	122.76 (11)	N2—C8A—C8B	122.17 (10)
N1—C1—C2	116.50 (10)	C5A—C8A—C8B	118.19 (11)
C3—C2—C1	121.12 (11)	N1—C8B—C3A	119.36 (10)
C3—C2—H2	119.4	N1—C8B—C8A	121.94 (10)
C1—C2—H2	119.4	C3A—C8B—C8A	118.68 (11)
C2—C3—C3A	121.42 (11)	N2—C9—C10	112.13 (10)
C2—C3—H3	119.3	N2—C9—H9A	109.2
C3A—C3—H3	119.3	C10—C9—H9A	109.2
C8B—C3A—C4	120.34 (11)	N2—C9—H9B	109.2
C8B—C3A—C3	117.73 (11)	C10—C9—H9B	109.2
C4—C3A—C3	121.91 (11)	H9A—C9—H9B	107.9
C5—C4—C3A	119.98 (11)	C9—C10—C11	109.44 (9)
C5—C4—H4	120.0	C9—C10—H10A	109.8
C3A—C4—H4	120.0	C11—C10—H10A	109.8
C4—C5—C5A	120.08 (11)	C9—C10—H10B	109.8
C4—C5—H5	120.0	C11—C10—H10B	109.8
C5A—C5—H5	120.0	H10A—C10—H10B	108.2
C8A—C5A—C5	120.67 (11)	N1—C11—C10	112.49 (10)
C8A—C5A—C6	118.17 (11)	N1—C11—H11A	109.1
C5—C5A—C6	121.14 (11)	C10—C11—H11A	109.1
C7—C6—C5A	120.61 (11)	N1—C11—H11B	109.1
C7—C6—H6	119.7	C10—C11—H11B	109.1
C5A—C6—H6	119.7	H11A—C11—H11B	107.8
C8B—N1—C1—O1	−178.75 (11)	C8—N2—C8A—C8B	172.78 (10)
C11—N1—C1—O1	14.27 (16)	C9—N2—C8A—C8B	−22.26 (15)
C8B—N1—C1—C2	3.94 (16)	C5—C5A—C8A—N2	−168.25 (11)
C11—N1—C1—C2	−163.05 (10)	C6—C5A—C8A—N2	9.93 (15)
O1—C1—C2—C3	−172.18 (12)	C5—C5A—C8A—C8B	9.86 (16)
N1—C1—C2—C3	5.07 (17)	C6—C5A—C8A—C8B	−171.97 (10)
C1—C2—C3—C3A	−5.67 (19)	C1—N1—C8B—C3A	−12.22 (16)
C2—C3—C3A—C8B	−2.60 (17)	C11—N1—C8B—C3A	154.55 (10)
C2—C3—C3A—C4	175.74 (11)	C1—N1—C8B—C8A	169.50 (10)
C8B—C3A—C4—C5	1.19 (17)	C11—N1—C8B—C8A	−23.73 (15)
C3—C3A—C4—C5	−177.11 (11)	C4—C3A—C8B—N1	−167.08 (10)
C3A—C4—C5—C5A	−8.16 (17)	C3—C3A—C8B—N1	11.29 (16)
C4—C5—C5A—C8A	2.53 (17)	C4—C3A—C8B—C8A	11.25 (16)
C4—C5—C5A—C6	−175.58 (11)	C3—C3A—C8B—C8A	−170.38 (10)
C8A—C5A—C6—C7	−2.72 (17)	N2—C8A—C8B—N1	−20.18 (16)
C5—C5A—C6—C7	175.44 (11)	C5A—C8A—C8B—N1	161.76 (10)
C5A—C6—C7—C8	−5.58 (18)	N2—C8A—C8B—C3A	161.53 (11)
C8A—N2—C8—O2	178.52 (10)	C5A—C8A—C8B—C3A	−16.53 (15)
C9—N2—C8—O2	13.30 (16)	C8—N2—C9—C10	−109.99 (11)
C8A—N2—C8—C7	1.04 (16)	C8A—N2—C9—C10	84.27 (12)
C9—N2—C8—C7	−164.18 (10)	N2—C9—C10—C11	−44.99 (13)
C6—C7—C8—O2	−170.97 (12)	C1—N1—C11—C10	−108.30 (11)
C6—C7—C8—N2	6.44 (17)	C8B—N1—C11—C10	84.22 (12)
C8—N2—C8A—C5A	−9.19 (16)	C9—C10—C11—N1	−42.52 (13)
C9—N2—C8A—C5A	155.77 (10)