2-Methyl-2,4-di-4-pyridyl-2,3-dihydro-1H-1,5-benzodiazepine acetic acid solvate

Wang, S.-C.; Hou, Q.-F.; Jiang, S.-M.

doi:10.1107/S1600536809049836

organic compounds

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Volume 65| Part 12| December 2009| Page o3213

doi:10.1107/S1600536809049836

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2-Methyl-2,4-di-4-pyridyl-2,3-dihydro-1H-1,5-benzodiazepine acetic acid solvate

Shi-Chao Wang,^a Qiu-Fei Hou ^a and Shi-Mei Jiang ^a ^*

^aState Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, People's Republic of China
^*Correspondence e-mail: smjiang@jlu.edu.cn

(Received 18 November 2009; accepted 20 November 2009; online 25 November 2009)

In the title compound, C₂₀H₁₈N₄·CH₃COOH, the benzene ring forms dihedral angles of 81.34 (11) and 54.32 (11)° with the two pyridine rings. In the crystal, intermolecular O—H⋯N hydrogen bonding links one 1,5-benzodiazepine molecule and one acetic acid solvent molecule into a dimer. These dimers, related by translation along the b axis, are further linked into chains via weak intermolecular N—H⋯N hydrogen bonds.

Related literature

For details of the synthesis and a related compound, see Hou et al. (2007 ).

Experimental

Crystal data

C₂₀H₁₈N₄·C₂H₄O₂
M_r = 374.44
Triclinic, $[P \overline 1]$
a = 8.925 (6) Å
b = 10.172 (8) Å
c = 12.283 (9) Å
α = 68.56 (3)°
β = 75.41 (3)°
γ = 88.52 (3)°
V = 1001.8 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 K
0.11 × 0.10 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.991, T_max = 0.993
9946 measured reflections
4547 independent reflections
2400 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.211
S = 1.04
4547 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.24 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
N2—H2A⋯N4ⁱ	0.86	2.23	3.079 (4)	172
O2—H2B⋯N3ⁱⁱ	0.82	1.83	2.640 (4)	168
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z.

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/S1600536809049836/cv2662sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049836/cv2662Isup2.hkl

checkCIF report

Comment top

The title compound (I) was unexpectedly obtained during our study of the Schiff base bis-pyridine complex (Hou et al., 2007). In this paper, we report its crystal structure.

In (I) (Fig.1), the dihedral angles between benzene ring and two pyridine rings are 81.34 (11) ° and 54.32 (11) °, respectively. In the crystal structure, the intramolecular O—H···N and intermolecule N—H···N hydrogen bonds (Table 1) are observed.

Related literature top

For details of the synthesis and a related compound, see Hou et al. (2007).

Experimental top

The title compound and its single crystals suitable for the X-ray diffraction were prepared by slow evaporation of the ethanol solution which contains o-phenylenediamine, 4-acetylpyridine and a small amount of acetic acid at room temperatue.

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 asymmetric unit of the title compound showing the atomic numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probability level.

2-Methyl-2,4-di-4-pyridyl-2,3-dihydro-1H-1,5-benzodiazepine acetic acid solvate top

Crystal data top

C₂₀H₁₈N₄·C₂H₄O₂	Z = 2
M_r = 374.44	F(000) = 396
Triclinic, P1	D_x = 1.241 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.925 (6) Å	Cell parameters from 6051 reflections
b = 10.172 (8) Å	θ = 3.1–27.5°
c = 12.283 (9) Å	µ = 0.08 mm⁻¹
α = 68.56 (3)°	T = 290 K
β = 75.41 (3)°	Block, colourless
γ = 88.52 (3)°	0.11 × 0.10 × 0.09 mm
V = 1001.8 (12) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4547 independent reflections
Radiation source: fine-focus sealed tube	2400 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
T_min = 0.991, T_max = 0.993	k = −13→13
9946 measured reflections	l = −15→15

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1067P)² + 0.0338P] where P = (F_o² + 2F_c²)/3
4547 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₀H₁₈N₄·C₂H₄O₂	γ = 88.52 (3)°
M_r = 374.44	V = 1001.8 (12) Å³
Triclinic, P1	Z = 2
a = 8.925 (6) Å	Mo Kα radiation
b = 10.172 (8) Å	µ = 0.08 mm⁻¹
c = 12.283 (9) Å	T = 290 K
α = 68.56 (3)°	0.11 × 0.10 × 0.09 mm
β = 75.41 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4547 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2400 reflections with I > 2σ(I)
T_min = 0.991, T_max = 0.993	R_int = 0.039
9946 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 1.04	Δρ_max = 0.24 e Å⁻³
4547 reflections	Δρ_min = −0.36 e Å⁻³
256 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	0.2037 (3)	0.2500 (2)	1.0826 (2)	0.0436 (6)
C2	0.1293 (3)	0.2017 (3)	1.2065 (3)	0.0533 (7)
H2	0.0990	0.2679	1.2422	0.064*
C3	0.0993 (3)	0.0601 (3)	1.2775 (3)	0.0603 (7)
H3	0.0519	0.0310	1.3600	0.072*
C4	0.1407 (3)	−0.0376 (3)	1.2242 (3)	0.0598 (8)
H4	0.1206	−0.1338	1.2707	0.072*
C5	0.2111 (3)	0.0060 (2)	1.1037 (3)	0.0545 (7)
H5	0.2379	−0.0623	1.0698	0.065*
C6	0.2455 (3)	0.1504 (2)	1.0273 (2)	0.0448 (6)
C7	0.3831 (3)	0.3117 (2)	0.8120 (2)	0.0456 (6)
C8	0.5137 (3)	0.2748 (3)	0.7236 (3)	0.0616 (8)
H8A	0.5878	0.2247	0.7652	0.092*
H8B	0.5639	0.3603	0.6590	0.092*
H8C	0.4717	0.2163	0.6907	0.092*
C9	0.2688 (3)	0.3983 (2)	0.7451 (2)	0.0476 (6)
C10	0.1148 (4)	0.3542 (3)	0.7753 (3)	0.0701 (9)
H10	0.0750	0.2681	0.8374	0.084*
C11	0.0187 (4)	0.4432 (4)	0.7092 (4)	0.0911 (12)
H11	−0.0858	0.4136	0.7294	0.109*
C12	0.2161 (5)	0.6063 (4)	0.5942 (3)	0.0795 (10)
H12	0.2526	0.6934	0.5325	0.095*
C13	0.3180 (4)	0.5278 (3)	0.6521 (3)	0.0652 (8)
H13	0.4216	0.5614	0.6290	0.078*
C14	0.4524 (3)	0.4008 (2)	0.8686 (2)	0.0458 (6)
H14A	0.5078	0.3404	0.9244	0.055*
H14B	0.5263	0.4741	0.8050	0.055*
C15	0.3307 (3)	0.4680 (2)	0.9343 (2)	0.0400 (5)
C16	0.3302 (3)	0.6249 (2)	0.8930 (2)	0.0409 (5)
C17	0.4648 (3)	0.7133 (2)	0.8320 (2)	0.0468 (6)
H17	0.5584	0.6766	0.8080	0.056*
C18	0.4577 (3)	0.8567 (2)	0.8072 (3)	0.0533 (7)
H18	0.5499	0.9139	0.7690	0.064*
C19	0.1991 (3)	0.8327 (3)	0.8883 (3)	0.0587 (7)
H19	0.1058	0.8733	0.9053	0.070*
C20	0.1949 (3)	0.6889 (3)	0.9202 (3)	0.0534 (7)
H20	0.1013	0.6344	0.9601	0.064*
C21	0.6804 (5)	0.8687 (5)	0.4824 (4)	0.1079 (15)
H21A	0.5708	0.8432	0.5084	0.162*
H21B	0.7133	0.9067	0.3955	0.162*
H21C	0.7025	0.9387	0.5126	0.162*
C22	0.7639 (4)	0.7424 (4)	0.5294 (3)	0.0768 (10)
N1	0.2212 (2)	0.39891 (19)	1.02797 (19)	0.0445 (5)
N2	0.3101 (3)	0.1793 (2)	0.9066 (2)	0.0551 (6)
H2A	0.3069	0.1093	0.8836	0.066*
N3	0.0682 (4)	0.5654 (3)	0.6210 (3)	0.0836 (9)
N4	0.3286 (3)	0.9185 (2)	0.8342 (2)	0.0556 (6)
O1	0.7070 (3)	0.6287 (3)	0.6004 (3)	0.1032 (9)
O2	0.9124 (3)	0.7674 (3)	0.5022 (3)	0.1017 (9)
H2B	0.9495	0.7015	0.5469	0.153*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0418 (12)	0.0344 (12)	0.0494 (14)	−0.0018 (10)	−0.0064 (11)	−0.0128 (10)
C2	0.0505 (14)	0.0459 (14)	0.0580 (17)	−0.0008 (11)	−0.0022 (13)	−0.0207 (12)
C3	0.0594 (16)	0.0541 (16)	0.0506 (16)	−0.0054 (13)	−0.0016 (13)	−0.0082 (13)
C4	0.0639 (17)	0.0381 (13)	0.0614 (18)	−0.0055 (12)	−0.0059 (15)	−0.0063 (12)
C5	0.0593 (16)	0.0318 (12)	0.0657 (18)	0.0025 (11)	−0.0113 (14)	−0.0136 (12)
C6	0.0443 (13)	0.0330 (11)	0.0535 (15)	0.0023 (10)	−0.0088 (12)	−0.0145 (10)
C7	0.0493 (13)	0.0320 (11)	0.0527 (14)	0.0030 (10)	−0.0068 (12)	−0.0167 (10)
C8	0.0634 (17)	0.0520 (15)	0.0663 (18)	0.0084 (13)	−0.0006 (15)	−0.0295 (14)
C9	0.0530 (15)	0.0407 (12)	0.0531 (15)	0.0034 (11)	−0.0099 (12)	−0.0247 (11)
C10	0.0612 (18)	0.0599 (17)	0.089 (2)	0.0034 (14)	−0.0206 (17)	−0.0266 (16)
C11	0.065 (2)	0.099 (3)	0.125 (3)	0.009 (2)	−0.034 (2)	−0.053 (3)
C12	0.089 (3)	0.074 (2)	0.073 (2)	0.0165 (19)	−0.028 (2)	−0.0203 (17)
C13	0.0704 (19)	0.0555 (16)	0.0571 (17)	0.0060 (14)	−0.0128 (15)	−0.0090 (13)
C14	0.0445 (13)	0.0332 (11)	0.0576 (15)	0.0035 (10)	−0.0088 (12)	−0.0175 (11)
C15	0.0426 (12)	0.0310 (11)	0.0477 (13)	0.0001 (9)	−0.0107 (11)	−0.0166 (10)
C16	0.0439 (12)	0.0337 (11)	0.0467 (13)	0.0007 (9)	−0.0102 (11)	−0.0178 (10)
C17	0.0439 (13)	0.0386 (12)	0.0554 (15)	−0.0006 (10)	−0.0055 (12)	−0.0193 (11)
C18	0.0523 (15)	0.0373 (13)	0.0640 (17)	−0.0072 (11)	−0.0067 (13)	−0.0167 (12)
C19	0.0472 (14)	0.0398 (13)	0.090 (2)	0.0043 (11)	−0.0119 (14)	−0.0291 (14)
C20	0.0448 (13)	0.0366 (12)	0.0772 (19)	−0.0015 (10)	−0.0091 (13)	−0.0235 (12)
C21	0.094 (3)	0.110 (3)	0.105 (3)	0.022 (2)	−0.039 (3)	−0.015 (3)
C22	0.0560 (18)	0.089 (2)	0.081 (2)	−0.0001 (17)	−0.0146 (17)	−0.028 (2)
N1	0.0446 (11)	0.0336 (10)	0.0524 (12)	0.0004 (8)	−0.0069 (10)	−0.0163 (9)
N2	0.0783 (15)	0.0291 (10)	0.0525 (13)	−0.0022 (10)	−0.0052 (12)	−0.0163 (9)
N3	0.104 (2)	0.0753 (19)	0.083 (2)	0.0293 (17)	−0.0411 (19)	−0.0328 (16)
N4	0.0589 (13)	0.0346 (10)	0.0743 (16)	0.0030 (10)	−0.0151 (12)	−0.0228 (10)
O1	0.0889 (18)	0.0776 (17)	0.108 (2)	−0.0144 (14)	0.0036 (16)	−0.0122 (16)
O2	0.0828 (17)	0.097 (2)	0.094 (2)	−0.0047 (14)	−0.0226 (15)	0.0014 (15)

Geometric parameters (Å, º) top

C1—C2	1.400 (4)	C12—C13	1.358 (4)
C1—C6	1.408 (4)	C12—H12	0.9300
C1—N1	1.409 (3)	C13—H13	0.9300
C2—C3	1.375 (4)	C14—C15	1.491 (3)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.373 (4)	C14—H14B	0.9700
C3—H3	0.9300	C15—N1	1.284 (3)
C4—C5	1.360 (4)	C15—C16	1.488 (3)
C4—H4	0.9300	C16—C20	1.381 (4)
C5—C6	1.415 (3)	C16—C17	1.387 (3)
C5—H5	0.9300	C17—C18	1.380 (3)
C6—N2	1.370 (4)	C17—H17	0.9300
C7—N2	1.452 (3)	C18—N4	1.325 (3)
C7—C8	1.522 (4)	C18—H18	0.9300
C7—C9	1.529 (3)	C19—N4	1.334 (3)
C7—C14	1.546 (4)	C19—C20	1.368 (4)
C8—H8A	0.9600	C19—H19	0.9300
C8—H8B	0.9600	C20—H20	0.9300
C8—H8C	0.9600	C21—C22	1.471 (5)
C9—C10	1.371 (4)	C21—H21A	0.9600
C9—C13	1.382 (4)	C21—H21B	0.9600
C10—C11	1.410 (5)	C21—H21C	0.9600
C10—H10	0.9300	C22—O1	1.194 (4)
C11—N3	1.309 (5)	C22—O2	1.290 (4)
C11—H11	0.9300	N2—H2A	0.8600
C12—N3	1.317 (5)	O2—H2B	0.8200

C2—C1—C6	119.0 (2)	C12—C13—H13	119.8
C2—C1—N1	112.7 (2)	C9—C13—H13	119.8
C6—C1—N1	128.2 (2)	C15—C14—C7	112.2 (2)
C3—C2—C1	122.5 (3)	C15—C14—H14A	109.2
C3—C2—H2	118.7	C7—C14—H14A	109.2
C1—C2—H2	118.7	C15—C14—H14B	109.2
C4—C3—C2	118.7 (3)	C7—C14—H14B	109.2
C4—C3—H3	120.6	H14A—C14—H14B	107.9
C2—C3—H3	120.6	N1—C15—C16	115.3 (2)
C5—C4—C3	120.2 (2)	N1—C15—C14	124.3 (2)
C5—C4—H4	119.9	C16—C15—C14	120.4 (2)
C3—C4—H4	119.9	C20—C16—C17	116.8 (2)
C4—C5—C6	123.1 (3)	C20—C16—C15	120.8 (2)
C4—C5—H5	118.4	C17—C16—C15	122.3 (2)
C6—C5—H5	118.5	C18—C17—C16	119.0 (2)
N2—C6—C1	126.6 (2)	C18—C17—H17	120.5
N2—C6—C5	116.9 (2)	C16—C17—H17	120.5
C1—C6—C5	116.5 (2)	N4—C18—C17	124.4 (2)
N2—C7—C8	107.2 (2)	N4—C18—H18	117.8
N2—C7—C9	112.2 (2)	C17—C18—H18	117.8
C8—C7—C9	109.8 (2)	N4—C19—C20	124.1 (2)
N2—C7—C14	109.4 (2)	N4—C19—H19	117.9
C8—C7—C14	109.2 (2)	C20—C19—H19	117.9
C9—C7—C14	108.97 (19)	C19—C20—C16	119.8 (2)
C7—C8—H8A	109.5	C19—C20—H20	120.1
C7—C8—H8B	109.5	C16—C20—H20	120.1
H8A—C8—H8B	109.5	C22—C21—H21A	109.5
C7—C8—H8C	109.5	C22—C21—H21B	109.5
H8A—C8—H8C	109.5	H21A—C21—H21B	109.5
H8B—C8—H8C	109.5	C22—C21—H21C	109.5
C10—C9—C13	117.3 (3)	H21A—C21—H21C	109.5
C10—C9—C7	122.5 (2)	H21B—C21—H21C	109.5
C13—C9—C7	120.2 (2)	O1—C22—O2	118.9 (3)
C9—C10—C11	117.9 (3)	O1—C22—C21	126.4 (4)
C9—C10—H10	121.0	O2—C22—C21	113.9 (3)
C11—C10—H10	121.0	C15—N1—C1	123.9 (2)
N3—C11—C10	123.7 (3)	C6—N2—C7	129.0 (2)
N3—C11—H11	118.1	C6—N2—H2A	115.5
C10—C11—H11	118.1	C7—N2—H2A	115.5
N3—C12—C13	123.3 (3)	C11—N3—C12	117.4 (3)
N3—C12—H12	118.3	C18—N4—C19	115.8 (2)
C13—C12—H12	118.3	C22—O2—H2B	109.5
C12—C13—C9	120.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N4ⁱ	0.86	2.23	3.079 (4)	172
O2—H2B···N3ⁱⁱ	0.82	1.83	2.640 (4)	168

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₄·C₂H₄O₂
M_r	374.44
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	8.925 (6), 10.172 (8), 12.283 (9)
α, β, γ (°)	68.56 (3), 75.41 (3), 88.52 (3)
V (Å³)	1001.8 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.11 × 0.10 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.991, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	9946, 4547, 2400
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.211, 1.04
No. of reflections	4547
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −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
N2—H2A···N4ⁱ	0.86	2.23	3.079 (4)	171.8
O2—H2B···N3ⁱⁱ	0.82	1.83	2.640 (4)	168.3

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20874038) and the National Basic Research Program of China (grant No. 2007CB936402).

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Hou, Q.-F., Ye, L. & Jiang, S.-M. (2007). Acta Cryst. E63, o939–o940. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC & Rigaku Corporation (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Page o3213

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

2-Methyl-2,4-di-4-pyridyl-2,3-di­hydro-1H-1,5-benzodiazepine acetic acid solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Methyl-2,4-di-4-pyridyl-2,3-dihydro-1H-1,5-benzodiazepine acetic acid solvate