2′-[(5-Bromo-1H-indol-3-yl)methyl­ene]-2-(1H-indol-3-yl)acetohydrazide ethyl acetate solvate

Ali, H.M.; Nazzatush Shimar, J.; Ng, S.W.

doi:10.1107/S1600536807019824

2'-[(5-Bromo-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide ethyl acetate solvate

H. M. Ali, J. Nazzatush Shimar and S. W. Ng

The constituent molecules of the title compound, C₁₉H₁₅BrN₄O·C₄H₈O₂, are linked by hydrogen bonds into a linear chain, with the acetohydrazide O atom serving as acceptor to the amide group as well as to the amino group of the bromoindole group. The ethyl acetate solvent molecule is also hydrogen bonded to the chain.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019824/hb2384sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019824/hb2384Isup2.hkl Contains datablock I

CCDC reference: 647710

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.031
wR factor = 0.097
Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.723     0.911
            Tmin and Tmax expected:      0.564     0.910
            RR =      1.281
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.29

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

2'-[(5-Chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide adopts a three-dimensional hydrogen-bonded network structure in the solid state (Ali et al., 2007). Replacing the chlorine atom by the heavier bromine atom furnishes the analogous molecule, but the compound crystallizes from ethyl acetate as the monosolvate (I) (Fig. 1). The Schff base adopts a chain structure arising from hydrogen bonds (Table 1); the solvent molecules are also hydrogen bonded to the chains.

Related literature top

For a related structure and background literature, see: Ali et al. (2007).

Experimental top

Indole-3-acetylhydrazine (0.3 g, 2 mmol) and 5-bromoindole-3-carboxaldehyde (0.4 g, 2 mmol) were dissolved in ethanol (100 ml). The reactants were heated under reflux for 1 h. The solvent was removed to give the Schiff base, which was purified by recrystallization from ethyl acetate to yield the title compound, (I), as a solvate.

Structure description top

For a related structure and background literature, see: Ali et al. (2007).

Computing details top

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 70% probability level (H atoms are shown as spheres of arbitrary radius).

2'-[(5-Bromo-1H-indol-3-yl)methylene]-2-(1H-indol-\3-yl)acetohydrazide ethyl acetate solvate top

Crystal data top

C₁₉H₁₅N₄OBr·C₄H₈O₂	F(000) = 992
M_r = 483.36	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5068 reflections
a = 11.9285 (2) Å	θ = 2.8–28.3°
b = 12.8010 (2) Å	µ = 1.89 mm⁻¹
c = 15.5177 (3) Å	T = 173 K
β = 110.665 (1)°	Plate, colourless
V = 2217.05 (7) Å³	0.45 × 0.26 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5100 independent reflections
Radiation source: medium-focus sealed tube	4019 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
φ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.723, T_max = 0.911	k = −16→16
34026 measured reflections	l = −20→20

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0523P)² + 0.4764P] where P = (F_o² + 2F_c²)/3
5100 reflections	(Δ/σ)_max = 0.001
294 parameters	Δρ_max = 0.40 e Å⁻³
3 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₁₅N₄OBr·C₄H₈O₂	V = 2217.05 (7) Å³
M_r = 483.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9285 (2) Å	µ = 1.89 mm⁻¹
b = 12.8010 (2) Å	T = 173 K
c = 15.5177 (3) Å	0.45 × 0.26 × 0.05 mm
β = 110.665 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5100 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4019 reflections with I > 2σ(I)
T_min = 0.723, T_max = 0.911	R_int = 0.044
34026 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	3 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.40 e Å⁻³
5100 reflections	Δρ_min = −0.35 e Å⁻³
294 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Br1	0.53417 (2)	0.232631 (19)	0.007875 (16)	0.03778 (10)
O1	0.82825 (13)	0.26073 (11)	0.42514 (9)	0.0248 (3)
O2	0.74889 (16)	0.55175 (13)	0.59819 (11)	0.0402 (4)
O3	0.78688 (14)	0.69909 (12)	0.68053 (10)	0.0311 (3)
N1	0.81936 (16)	0.20488 (15)	0.74199 (12)	0.0276 (4)
H1N	0.802 (2)	0.2053 (19)	0.7925 (11)	0.032 (6)*
N2	0.75052 (16)	0.41498 (13)	0.45022 (11)	0.0246 (4)
H2N	0.748 (2)	0.4622 (16)	0.4908 (14)	0.040 (7)*
N3	0.66752 (15)	0.42048 (13)	0.36088 (11)	0.0234 (4)
N4	0.35354 (17)	0.60494 (14)	0.15338 (13)	0.0309 (4)
H4N	0.3000 (18)	0.6535 (15)	0.1284 (17)	0.041 (7)*
C1	0.86676 (17)	0.12097 (16)	0.71193 (13)	0.0248 (4)
C2	0.87260 (19)	0.01600 (18)	0.73682 (15)	0.0321 (5)
H2	0.8393	−0.0081	0.7805	0.038*
C3	0.9284 (2)	−0.05150 (18)	0.69585 (16)	0.0367 (5)
H3	0.9332	−0.1236	0.7113	0.044*
C4	0.9783 (2)	−0.01653 (19)	0.63202 (16)	0.0361 (5)
H4	1.0183	−0.0648	0.6064	0.043*
C5	0.97030 (19)	0.08725 (17)	0.60547 (14)	0.0287 (5)
H5	1.0030	0.1101	0.5610	0.034*
C6	0.91329 (17)	0.15802 (16)	0.64522 (13)	0.0234 (4)
C7	0.88997 (18)	0.26799 (16)	0.63640 (13)	0.0226 (4)
C8	0.83429 (18)	0.29301 (17)	0.69700 (14)	0.0258 (4)
H8	0.8096	0.3613	0.7065	0.031*
C9	0.91793 (18)	0.34332 (16)	0.57291 (13)	0.0250 (4)
H9A	0.9991	0.3286	0.5722	0.030*
H9B	0.9178	0.4153	0.5961	0.030*
C10	0.82755 (17)	0.33558 (15)	0.47573 (13)	0.0218 (4)
C11	0.59448 (18)	0.49753 (15)	0.34742 (14)	0.0254 (4)
H11	0.5992	0.5412	0.3981	0.030*
C12	0.50573 (18)	0.52070 (15)	0.25894 (14)	0.0243 (4)
C13	0.4270 (2)	0.60308 (16)	0.24278 (15)	0.0304 (5)
H13	0.4245	0.6520	0.2881	0.036*
C14	0.47885 (17)	0.46777 (15)	0.17171 (14)	0.0224 (4)
C15	0.52562 (18)	0.38021 (15)	0.14205 (14)	0.0235 (4)
H15	0.5907	0.3419	0.1833	0.028*
C16	0.47385 (18)	0.35159 (16)	0.05091 (14)	0.0256 (4)
C17	0.37850 (19)	0.40635 (17)	−0.01250 (14)	0.0291 (5)
H17	0.3455	0.3835	−0.0747	0.035*
C18	0.33265 (19)	0.49350 (17)	0.01566 (15)	0.0300 (5)
H18	0.2687	0.5322	−0.0265	0.036*
C19	0.38279 (18)	0.52286 (16)	0.10744 (15)	0.0259 (4)
C20	0.8670 (3)	0.6856 (2)	0.56376 (19)	0.0478 (6)
H20A	0.8618	0.6422	0.5104	0.072*
H20B	0.9509	0.6907	0.6048	0.072*
H20C	0.8361	0.7556	0.5428	0.072*
C21	0.7946 (2)	0.63731 (18)	0.61433 (15)	0.0309 (5)
C22	0.7207 (2)	0.65917 (18)	0.73583 (15)	0.0327 (5)
H22A	0.7569	0.5933	0.7666	0.039*
H22B	0.6363	0.6454	0.6968	0.039*
C23	0.7271 (3)	0.7415 (2)	0.8057 (2)	0.0445 (6)
H23A	0.6880	0.7161	0.8476	0.067*
H23B	0.6864	0.8047	0.7744	0.067*
H23C	0.8112	0.7576	0.8409	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04173 (16)	0.03789 (15)	0.03209 (14)	0.00672 (10)	0.01101 (10)	−0.00710 (9)
O1	0.0280 (8)	0.0282 (7)	0.0178 (7)	−0.0006 (6)	0.0074 (6)	−0.0008 (5)
O2	0.0530 (11)	0.0346 (9)	0.0346 (9)	−0.0034 (8)	0.0173 (8)	−0.0096 (7)
O3	0.0379 (9)	0.0315 (8)	0.0284 (8)	−0.0070 (7)	0.0172 (7)	−0.0053 (6)
N1	0.0278 (9)	0.0394 (10)	0.0174 (9)	−0.0011 (8)	0.0104 (7)	0.0004 (7)
N2	0.0292 (9)	0.0278 (9)	0.0147 (8)	−0.0018 (7)	0.0053 (7)	−0.0031 (7)
N3	0.0260 (9)	0.0274 (9)	0.0148 (8)	−0.0022 (7)	0.0049 (7)	0.0002 (6)
N4	0.0299 (10)	0.0277 (9)	0.0328 (10)	0.0088 (8)	0.0084 (8)	0.0046 (8)
C1	0.0193 (10)	0.0351 (11)	0.0163 (9)	−0.0011 (8)	0.0019 (8)	0.0019 (8)
C2	0.0283 (11)	0.0408 (12)	0.0221 (11)	0.0001 (10)	0.0028 (9)	0.0087 (9)
C3	0.0360 (13)	0.0322 (12)	0.0314 (12)	0.0041 (10)	−0.0012 (10)	0.0074 (9)
C4	0.0309 (12)	0.0392 (13)	0.0321 (12)	0.0087 (10)	0.0036 (10)	−0.0041 (10)
C5	0.0248 (10)	0.0381 (12)	0.0229 (10)	−0.0004 (9)	0.0080 (8)	−0.0042 (9)
C6	0.0192 (9)	0.0325 (10)	0.0151 (9)	−0.0012 (8)	0.0019 (7)	−0.0003 (8)
C7	0.0194 (9)	0.0306 (10)	0.0147 (9)	−0.0041 (8)	0.0020 (7)	−0.0025 (8)
C8	0.0233 (10)	0.0324 (11)	0.0191 (10)	−0.0009 (8)	0.0042 (8)	−0.0032 (8)
C9	0.0233 (10)	0.0316 (11)	0.0178 (9)	−0.0057 (8)	0.0044 (8)	−0.0007 (8)
C10	0.0240 (10)	0.0273 (10)	0.0157 (9)	−0.0071 (8)	0.0089 (8)	−0.0003 (7)
C11	0.0268 (10)	0.0279 (11)	0.0215 (10)	−0.0031 (8)	0.0087 (8)	−0.0024 (8)
C12	0.0237 (10)	0.0252 (9)	0.0242 (10)	−0.0015 (8)	0.0086 (8)	0.0006 (8)
C13	0.0332 (12)	0.0263 (10)	0.0323 (12)	0.0017 (9)	0.0124 (10)	−0.0003 (9)
C14	0.0205 (9)	0.0227 (9)	0.0232 (10)	−0.0022 (8)	0.0067 (8)	0.0036 (8)
C15	0.0198 (9)	0.0247 (10)	0.0244 (10)	0.0006 (8)	0.0059 (8)	0.0052 (8)
C16	0.0240 (10)	0.0273 (10)	0.0259 (10)	−0.0019 (8)	0.0092 (8)	−0.0005 (8)
C17	0.0249 (10)	0.0372 (12)	0.0216 (10)	−0.0025 (9)	0.0039 (8)	0.0006 (8)
C18	0.0231 (10)	0.0355 (12)	0.0263 (11)	0.0046 (9)	0.0024 (9)	0.0079 (9)
C19	0.0218 (10)	0.0275 (10)	0.0280 (11)	0.0020 (8)	0.0083 (8)	0.0056 (8)
C20	0.0534 (16)	0.0572 (17)	0.0437 (15)	−0.0050 (14)	0.0307 (13)	−0.0049 (13)
C21	0.0319 (11)	0.0349 (12)	0.0253 (11)	0.0036 (10)	0.0094 (9)	−0.0009 (9)
C22	0.0377 (12)	0.0347 (12)	0.0289 (11)	−0.0077 (10)	0.0157 (10)	−0.0023 (9)
C23	0.0434 (15)	0.0535 (16)	0.0462 (15)	−0.0113 (12)	0.0277 (13)	−0.0197 (12)

Geometric parameters (Å, º) top

Br1—C16	1.903 (2)	C8—H8	0.9500
O1—C10	1.241 (2)	C9—C10	1.516 (3)
O2—C21	1.210 (3)	C9—H9A	0.9900
O3—C21	1.325 (3)	C9—H9B	0.9900
O3—C22	1.449 (3)	C11—C12	1.438 (3)
N1—C1	1.370 (3)	C11—H11	0.9500
N1—C8	1.371 (3)	C12—C13	1.375 (3)
N1—H1N	0.876 (10)	C12—C14	1.445 (3)
N2—C10	1.333 (3)	C13—H13	0.9500
N2—N3	1.392 (2)	C14—C15	1.400 (3)
N2—H2N	0.880 (10)	C14—C19	1.414 (3)
N3—C11	1.283 (3)	C15—C16	1.378 (3)
N4—C13	1.355 (3)	C15—H15	0.9500
N4—C19	1.382 (3)	C16—C17	1.401 (3)
N4—H4N	0.878 (10)	C17—C18	1.379 (3)
C1—C2	1.393 (3)	C17—H17	0.9500
C1—C6	1.418 (3)	C18—C19	1.388 (3)
C2—C3	1.376 (3)	C18—H18	0.9500
C2—H2	0.9500	C20—C21	1.491 (3)
C3—C4	1.397 (4)	C20—H20A	0.9800
C3—H3	0.9500	C20—H20B	0.9800
C4—C5	1.384 (3)	C20—H20C	0.9800
C4—H4	0.9500	C22—C23	1.494 (3)
C5—C6	1.400 (3)	C22—H22A	0.9900
C5—H5	0.9500	C22—H22B	0.9900
C6—C7	1.432 (3)	C23—H23A	0.9800
C7—C8	1.367 (3)	C23—H23B	0.9800
C7—C9	1.498 (3)	C23—H23C	0.9800

C21—O3—C22	116.75 (17)	C12—C11—H11	118.6
C1—N1—C8	109.18 (17)	C13—C12—C11	123.89 (19)
C1—N1—H1N	124.2 (16)	C13—C12—C14	106.10 (18)
C8—N1—H1N	124.3 (16)	C11—C12—C14	130.01 (18)
C10—N2—N3	120.51 (16)	N4—C13—C12	110.71 (19)
C10—N2—H2N	120.2 (17)	N4—C13—H13	124.6
N3—N2—H2N	119.2 (17)	C12—C13—H13	124.6
C11—N3—N2	113.85 (17)	C15—C14—C19	119.02 (19)
C13—N4—C19	108.97 (17)	C15—C14—C12	134.50 (18)
C13—N4—H4N	124.9 (17)	C19—C14—C12	106.48 (18)
C19—N4—H4N	126.0 (17)	C16—C15—C14	117.64 (18)
N1—C1—C2	130.4 (2)	C16—C15—H15	121.2
N1—C1—C6	107.53 (18)	C14—C15—H15	121.2
C2—C1—C6	122.1 (2)	C15—C16—C17	123.1 (2)
C3—C2—C1	117.6 (2)	C15—C16—Br1	119.00 (15)
C3—C2—H2	121.2	C17—C16—Br1	117.88 (16)
C1—C2—H2	121.2	C18—C17—C16	119.76 (19)
C2—C3—C4	121.5 (2)	C18—C17—H17	120.1
C2—C3—H3	119.2	C16—C17—H17	120.1
C4—C3—H3	119.2	C17—C18—C19	117.94 (19)
C5—C4—C3	121.1 (2)	C17—C18—H18	121.0
C5—C4—H4	119.4	C19—C18—H18	121.0
C3—C4—H4	119.4	N4—C19—C18	129.75 (19)
C4—C5—C6	118.9 (2)	N4—C19—C14	107.74 (18)
C4—C5—H5	120.6	C18—C19—C14	122.5 (2)
C6—C5—H5	120.6	C21—C20—H20A	109.5
C5—C6—C1	118.78 (19)	C21—C20—H20B	109.5
C5—C6—C7	134.60 (19)	H20A—C20—H20B	109.5
C1—C6—C7	106.60 (18)	C21—C20—H20C	109.5
C8—C7—C6	106.84 (18)	H20A—C20—H20C	109.5
C8—C7—C9	125.21 (19)	H20B—C20—H20C	109.5
C6—C7—C9	127.94 (18)	O2—C21—O3	123.5 (2)
C7—C8—N1	109.84 (19)	O2—C21—C20	124.7 (2)
C7—C8—H8	125.1	O3—C21—C20	111.9 (2)
N1—C8—H8	125.1	O3—C22—C23	106.35 (18)
C7—C9—C10	111.52 (16)	O3—C22—H22A	110.5
C7—C9—H9A	109.3	C23—C22—H22A	110.5
C10—C9—H9A	109.3	O3—C22—H22B	110.5
C7—C9—H9B	109.3	C23—C22—H22B	110.5
C10—C9—H9B	109.3	H22A—C22—H22B	108.6
H9A—C9—H9B	108.0	C22—C23—H23A	109.5
O1—C10—N2	123.97 (18)	C22—C23—H23B	109.5
O1—C10—C9	121.24 (18)	H23A—C23—H23B	109.5
N2—C10—C9	114.78 (17)	C22—C23—H23C	109.5
N3—C11—C12	122.86 (19)	H23A—C23—H23C	109.5
N3—C11—H11	118.6	H23B—C23—H23C	109.5

C10—N2—N3—C11	176.08 (18)	N3—C11—C12—C13	−179.6 (2)
C8—N1—C1—C2	−179.7 (2)	N3—C11—C12—C14	0.4 (3)
C8—N1—C1—C6	0.0 (2)	C19—N4—C13—C12	−0.3 (3)
N1—C1—C2—C3	−178.7 (2)	C11—C12—C13—N4	−179.56 (19)
C6—C1—C2—C3	1.6 (3)	C14—C12—C13—N4	0.4 (2)
C1—C2—C3—C4	0.4 (3)	C13—C12—C14—C15	179.9 (2)
C2—C3—C4—C5	−1.9 (3)	C11—C12—C14—C15	−0.1 (4)
C3—C4—C5—C6	1.4 (3)	C13—C12—C14—C19	−0.4 (2)
C4—C5—C6—C1	0.6 (3)	C11—C12—C14—C19	179.6 (2)
C4—C5—C6—C7	179.0 (2)	C19—C14—C15—C16	−0.7 (3)
N1—C1—C6—C5	178.16 (17)	C12—C14—C15—C16	179.0 (2)
C2—C1—C6—C5	−2.1 (3)	C14—C15—C16—C17	0.6 (3)
N1—C1—C6—C7	−0.6 (2)	C14—C15—C16—Br1	−179.69 (14)
C2—C1—C6—C7	179.09 (18)	C15—C16—C17—C18	0.2 (3)
C5—C6—C7—C8	−177.4 (2)	Br1—C16—C17—C18	−179.52 (16)
C1—C6—C7—C8	1.1 (2)	C16—C17—C18—C19	−0.8 (3)
C5—C6—C7—C9	3.5 (4)	C13—N4—C19—C18	−180.0 (2)
C1—C6—C7—C9	−178.03 (18)	C13—N4—C19—C14	0.1 (2)
C6—C7—C8—N1	−1.1 (2)	C17—C18—C19—N4	−179.2 (2)
C9—C7—C8—N1	178.00 (18)	C17—C18—C19—C14	0.8 (3)
C1—N1—C8—C7	0.7 (2)	C15—C14—C19—N4	180.00 (18)
C8—C7—C9—C10	−100.6 (2)	C12—C14—C19—N4	0.2 (2)
C6—C7—C9—C10	78.3 (3)	C15—C14—C19—C18	0.0 (3)
N3—N2—C10—O1	−3.1 (3)	C12—C14—C19—C18	−179.76 (19)
N3—N2—C10—C9	176.19 (16)	C22—O3—C21—O2	0.7 (3)
C7—C9—C10—O1	−74.1 (2)	C22—O3—C21—C20	−178.6 (2)
C7—C9—C10—N2	106.7 (2)	C21—O3—C22—C23	178.9 (2)
N2—N3—C11—C12	176.69 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1ⁱ	0.88 (1)	2.02 (1)	2.841 (2)	156 (2)
N2—H2n···O2	0.88 (1)	2.02 (1)	2.893 (2)	171 (2)
N4—H4n···O1ⁱⁱ	0.88 (1)	2.00 (1)	2.881 (2)	177 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₄OBr·C₄H₈O₂
M_r	483.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.9285 (2), 12.8010 (2), 15.5177 (3)
β (°)	110.665 (1)
V (Å³)	2217.05 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.45 × 0.26 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.723, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	34026, 5100, 4019
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.097, 1.08
No. of reflections	5100
No. of parameters	294
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.35

Computer programs: APEXII (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).