3-(4-Bromo­phen­yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Elkady, M.; Keck, P.R.W.E.F.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536812046752

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3397

doi:10.1107/S1600536812046752

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3-(4-Bromophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Mahmoud Elkady,^a Peter R. W. E. F. Keck,^a Dieter Schollmeyer ^b and Stefan Laufer ^a ^*

^aEberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^bUniversity Mainz, Institut of Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 12 November 2012; accepted 13 November 2012; online 24 November 2012)

The asymmetric unit of the title compound, C₁₆H₁₁BrN₂O, contains two independent molecules with slightly different geometries. The 4-bromobenzene ring forms dihedral angles of 26.0 (2) and 39.9 (7)° with the pyrazole ring in the two molecules while the phenyl ring is oriented at 19.7 (5) and 7.3 (0)° with respect to the pyrazole ring.

Related literature

For the biological activity of inhibitors for the microsomal prostaglandin E₂ synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO), see: Elkady et al. (2012 ). For details of the synthesis, see: Rathelot et al. (2002 ).

Experimental

Crystal data

C₁₆H₁₁BrN₂O
M_r = 327.18
Triclinic, $[P \overline 1]$
a = 9.6716 (8) Å
b = 11.4617 (9) Å
c = 13.8257 (10) Å
α = 113.497 (5)°
β = 92.753 (6)°
γ = 93.753 (6)°
V = 1397.91 (19) Å³
Z = 4
Mo Kα radiation
μ = 2.94 mm⁻¹
T = 298 K
0.34 × 0.18 × 0.06 mm

Data collection

Stoe IPDS 2T diffractometer
Absorption correction: multi-scan (MULABS; Blessing, 1995 ) T_min = 0.477, T_max = 0.660
14312 measured reflections
6740 independent reflections
2856 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.158
S = 0.92
6740 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2010 ); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812046752/bt6856sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046752/bt6856Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812046752/bt6856Isup3.cml

checkCIF report

Comment top

We synthesized and evaluated inhibitors for the microsomal prostaglandin E₂ synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO) (Elkady et al., 2012). The title compound was synthesized to obtain a template which leads to series of different derivates of the pyrazole scaffold (Rathelot et al., 2002) the asymmetric unit of the crystal structure contains two slightly different molecules.

The 4-Bromobenzene ring is oriented with dihedral angles of 26.0 (2)°, 39.9 (7)° (first and second molecule) with the pyrazole ring. The phenyl ring is oriented with dihedral angles of 19.7 (5)°, 7.3 (0)° with the pyrazole ring.

Related literature top

For the biological activity of inhibitors for the microsomal prostaglandin E₂ synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO), see: Elkady et al. (2012). For details of the synthesis, see: Rathelot et al. (2002).

Experimental top

The compound was prepared by a Vilsmeyer–Haack reaction. Phosphoryl chloride (4.16 ml, 44.7 mmol) was added dropwise to ice-cooled solution of 7 ml dimethylformamide. The mixture was left stirring for 30 min at 273 K. 4.3 g (14.9 mmol) of (E)-1-(1-(4-bromophenyl)ethylidene)-2-phenylhydrazine were dissolved in 10 ml dimethylformamide, and then slowly added to the mixture. The mixture was heated to 343 K and left for stirring for 4 h. The mixture was cooled to 273 K, quenched by water and adjusted to pH 12 with aqueous saturated sodium carbonate solution. The product was extracted with ethyl acetate three times, dried over anhydrous sodium sulfate and finally concentrated under vacuum. The product was purified by washing with methanol. Crystals of the title compound were obtained by slow evaporation of methanol at room temperature.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2010); cell refinement: X-AREA (Stoe & Cie, 2010); data reduction: X-RED (Stoe & Cie, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. View of compound I. Displacement ellipsoids are drawn at the 50% probability level.

3-(4-Bromophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde top

Crystal data top

C₁₆H₁₁BrN₂O	Z = 4
M_r = 327.18	F(000) = 656
Triclinic, P1	D_x = 1.555 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6716 (8) Å	Cell parameters from 5561 reflections
b = 11.4617 (9) Å	θ = 2.7–28.0°
c = 13.8257 (10) Å	µ = 2.94 mm⁻¹
α = 113.497 (5)°	T = 298 K
β = 92.753 (6)°	Block, colourless
γ = 93.753 (6)°	0.34 × 0.18 × 0.06 mm
V = 1397.91 (19) Å³

Data collection top

Stoe IPDS 2T diffractometer	6740 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2856 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
Detector resolution: 6.67 pixels mm^-1	θ_max = 28.0°, θ_min = 2.6°
rotation method scans	h = −12→11
Absorption correction: multi-scan (MULABS; Blessing, 1995)	k = −15→15
T_min = 0.477, T_max = 0.660	l = −18→18
14312 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.0707P)²] where P = (F_o² + 2F_c²)/3
6740 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₁₆H₁₁BrN₂O	γ = 93.753 (6)°
M_r = 327.18	V = 1397.91 (19) Å³
Triclinic, P1	Z = 4
a = 9.6716 (8) Å	Mo Kα radiation
b = 11.4617 (9) Å	µ = 2.94 mm⁻¹
c = 13.8257 (10) Å	T = 298 K
α = 113.497 (5)°	0.34 × 0.18 × 0.06 mm
β = 92.753 (6)°

Data collection top

Stoe IPDS 2T diffractometer	6740 independent reflections
Absorption correction: multi-scan (MULABS; Blessing, 1995)	2856 reflections with I > 2σ(I)
T_min = 0.477, T_max = 0.660	R_int = 0.063
14312 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 0.92	Δρ_max = 0.52 e Å⁻³
6740 reflections	Δρ_min = −0.73 e Å⁻³
361 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.

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
Br1	0.32448 (7)	0.17418 (5)	−0.10411 (4)	0.0974 (3)
N1	0.2200 (3)	0.6242 (3)	0.3849 (2)	0.0482 (8)
N2	0.2418 (3)	0.7380 (3)	0.4705 (2)	0.0456 (7)
C3	0.3427 (4)	0.8149 (3)	0.4591 (3)	0.0468 (9)
H3	0.3743	0.8967	0.5078	0.056*
C4	0.3921 (4)	0.7507 (3)	0.3612 (3)	0.0456 (9)
C5	0.3115 (4)	0.6312 (3)	0.3181 (3)	0.0457 (9)
C6	0.1618 (4)	0.7599 (3)	0.5587 (3)	0.0450 (9)
C7	0.1515 (4)	0.8810 (4)	0.6313 (3)	0.0570 (10)
H7	0.1947	0.9507	0.6226	0.068*
C8	0.0763 (5)	0.8990 (4)	0.7178 (3)	0.0660 (12)
H8	0.0710	0.9814	0.7683	0.079*
C9	0.0099 (5)	0.7980 (4)	0.7302 (4)	0.0692 (12)
H9	−0.0417	0.8110	0.7881	0.083*
C10	0.0202 (5)	0.6772 (4)	0.6565 (4)	0.0703 (13)
H10	−0.0256	0.6078	0.6641	0.084*
C11	0.0976 (4)	0.6567 (4)	0.5708 (3)	0.0579 (11)
H11	0.1061	0.5741	0.5219	0.070*
C12	0.5114 (4)	0.7921 (4)	0.3201 (3)	0.0537 (10)
H12	0.5384	0.7351	0.2559	0.064*
O13	0.5781 (3)	0.8928 (3)	0.3614 (2)	0.0668 (8)
C14	0.3153 (4)	0.5230 (4)	0.2171 (3)	0.0456 (9)
C15	0.3337 (4)	0.5387 (4)	0.1243 (3)	0.0556 (10)
H15	0.3454	0.6209	0.1264	0.067*
C16	0.3352 (4)	0.4363 (4)	0.0292 (3)	0.0626 (11)
H16	0.3460	0.4488	−0.0326	0.075*
C17	0.3207 (4)	0.3157 (4)	0.0265 (3)	0.0610 (11)
C18	0.3015 (4)	0.2953 (4)	0.1167 (3)	0.0583 (11)
H18	0.2904	0.2128	0.1139	0.070*
C19	0.2991 (4)	0.3994 (4)	0.2112 (3)	0.0524 (10)
H19	0.2863	0.3863	0.2725	0.063*
Br2	0.83318 (7)	0.15393 (6)	−0.08996 (5)	0.1091 (3)
N21	0.7249 (3)	0.6207 (3)	0.3891 (2)	0.0473 (8)
N22	0.7455 (3)	0.7353 (3)	0.4734 (2)	0.0453 (7)
C23	0.8472 (4)	0.8114 (3)	0.4605 (3)	0.0487 (9)
H23	0.8795	0.8934	0.5084	0.058*
C24	0.8949 (4)	0.7456 (3)	0.3631 (3)	0.0478 (9)
C25	0.8145 (4)	0.6255 (3)	0.3209 (3)	0.0457 (9)
C26	0.6588 (4)	0.7623 (4)	0.5591 (3)	0.0484 (9)
C27	0.6652 (5)	0.8807 (4)	0.6382 (3)	0.0638 (12)
H27	0.7294	0.9451	0.6390	0.077*
C28	0.5759 (5)	0.9050 (4)	0.7174 (4)	0.0692 (12)
H28	0.5813	0.9858	0.7721	0.083*
C29	0.4796 (5)	0.8119 (4)	0.7167 (3)	0.0623 (11)
H29	0.4192	0.8288	0.7700	0.075*
C30	0.4738 (4)	0.6930 (4)	0.6357 (4)	0.0620 (11)
H30	0.4084	0.6289	0.6342	0.074*
C31	0.5632 (4)	0.6669 (4)	0.5567 (3)	0.0553 (10)
H31	0.5589	0.5858	0.5024	0.066*
C32	0.9995 (4)	0.7970 (4)	0.3158 (3)	0.0593 (11)
H32	1.0124	0.7504	0.2449	0.071*
O33	1.0705 (3)	0.8950 (3)	0.3615 (3)	0.0702 (9)
C34	0.8187 (4)	0.5151 (3)	0.2220 (3)	0.0477 (9)
C35	0.9388 (4)	0.4886 (4)	0.1687 (3)	0.0595 (11)
H35	1.0188	0.5443	0.1966	0.071*
C36	0.9428 (4)	0.3834 (4)	0.0769 (4)	0.0657 (12)
H36	1.0239	0.3691	0.0420	0.079*
C37	0.8276 (5)	0.2994 (4)	0.0365 (3)	0.0630 (11)
C38	0.7060 (5)	0.3220 (4)	0.0872 (3)	0.0623 (11)
H38	0.6271	0.2647	0.0595	0.075*
C39	0.7026 (4)	0.4291 (4)	0.1782 (3)	0.0543 (10)
H39	0.6202	0.4446	0.2114	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1105 (5)	0.0877 (4)	0.0613 (3)	−0.0126 (3)	0.0273 (3)	−0.0034 (3)
N1	0.0435 (19)	0.0514 (17)	0.0455 (17)	−0.0017 (14)	0.0070 (14)	0.0157 (15)
N2	0.0432 (19)	0.0482 (17)	0.0444 (17)	−0.0026 (14)	0.0089 (14)	0.0180 (15)
C3	0.045 (2)	0.0484 (19)	0.047 (2)	−0.0034 (17)	0.0084 (17)	0.0208 (18)
C4	0.040 (2)	0.051 (2)	0.046 (2)	−0.0008 (16)	0.0083 (17)	0.0208 (18)
C5	0.038 (2)	0.055 (2)	0.045 (2)	0.0029 (17)	0.0066 (17)	0.0212 (18)
C6	0.041 (2)	0.055 (2)	0.041 (2)	0.0006 (17)	0.0086 (16)	0.0219 (18)
C7	0.059 (3)	0.054 (2)	0.057 (2)	−0.0005 (19)	0.015 (2)	0.021 (2)
C8	0.065 (3)	0.063 (3)	0.058 (3)	0.004 (2)	0.018 (2)	0.010 (2)
C9	0.068 (3)	0.080 (3)	0.054 (3)	−0.002 (2)	0.023 (2)	0.021 (2)
C10	0.076 (3)	0.073 (3)	0.066 (3)	−0.007 (2)	0.024 (2)	0.033 (3)
C11	0.062 (3)	0.055 (2)	0.054 (2)	0.002 (2)	0.015 (2)	0.018 (2)
C12	0.053 (3)	0.062 (2)	0.052 (2)	0.003 (2)	0.0122 (19)	0.028 (2)
O13	0.0653 (19)	0.0557 (16)	0.075 (2)	−0.0154 (14)	0.0153 (16)	0.0234 (15)
C14	0.034 (2)	0.060 (2)	0.043 (2)	0.0019 (17)	0.0079 (16)	0.0206 (18)
C15	0.057 (3)	0.059 (2)	0.053 (2)	−0.0051 (19)	0.0065 (19)	0.026 (2)
C16	0.062 (3)	0.077 (3)	0.046 (2)	−0.011 (2)	0.006 (2)	0.024 (2)
C17	0.053 (3)	0.068 (3)	0.047 (2)	−0.006 (2)	0.0162 (19)	0.007 (2)
C18	0.055 (3)	0.050 (2)	0.064 (3)	0.0037 (18)	0.016 (2)	0.016 (2)
C19	0.052 (2)	0.056 (2)	0.051 (2)	0.0059 (18)	0.0121 (18)	0.0232 (19)
Br2	0.1057 (5)	0.0904 (4)	0.0834 (4)	−0.0047 (3)	0.0324 (4)	−0.0156 (3)
N21	0.0460 (19)	0.0457 (16)	0.0471 (18)	−0.0029 (14)	0.0079 (15)	0.0162 (15)
N22	0.0445 (19)	0.0414 (15)	0.0457 (17)	−0.0028 (13)	0.0053 (14)	0.0138 (14)
C23	0.046 (2)	0.0447 (19)	0.052 (2)	−0.0031 (17)	0.0096 (18)	0.0164 (18)
C24	0.043 (2)	0.049 (2)	0.051 (2)	−0.0016 (17)	0.0074 (18)	0.0198 (18)
C25	0.040 (2)	0.049 (2)	0.046 (2)	−0.0013 (16)	0.0015 (17)	0.0177 (18)
C26	0.047 (2)	0.052 (2)	0.048 (2)	0.0028 (17)	0.0075 (18)	0.0221 (19)
C27	0.063 (3)	0.055 (2)	0.061 (3)	−0.007 (2)	0.012 (2)	0.012 (2)
C28	0.069 (3)	0.067 (3)	0.059 (3)	0.006 (2)	0.017 (2)	0.010 (2)
C29	0.056 (3)	0.082 (3)	0.055 (3)	0.011 (2)	0.017 (2)	0.031 (2)
C30	0.058 (3)	0.066 (3)	0.066 (3)	−0.004 (2)	0.013 (2)	0.031 (2)
C31	0.056 (3)	0.052 (2)	0.055 (2)	−0.0034 (19)	0.011 (2)	0.0189 (19)
C32	0.064 (3)	0.053 (2)	0.062 (3)	0.001 (2)	0.020 (2)	0.023 (2)
O33	0.0640 (19)	0.0537 (16)	0.088 (2)	−0.0133 (14)	0.0199 (16)	0.0247 (16)
C34	0.041 (2)	0.055 (2)	0.049 (2)	0.0007 (17)	0.0062 (17)	0.0231 (19)
C35	0.040 (2)	0.063 (2)	0.062 (3)	−0.0044 (18)	0.0065 (19)	0.012 (2)
C36	0.043 (2)	0.072 (3)	0.070 (3)	0.004 (2)	0.020 (2)	0.015 (2)
C37	0.066 (3)	0.060 (2)	0.052 (2)	0.004 (2)	0.018 (2)	0.009 (2)
C38	0.053 (3)	0.064 (2)	0.057 (3)	−0.011 (2)	0.006 (2)	0.013 (2)
C39	0.043 (2)	0.062 (2)	0.052 (2)	−0.0064 (18)	0.0100 (18)	0.018 (2)

Geometric parameters (Å, º) top

Br1—C17	1.890 (4)	Br2—C37	1.880 (4)
N1—C5	1.330 (4)	N21—C25	1.326 (4)
N1—N2	1.363 (4)	N21—N22	1.358 (4)
N2—C3	1.330 (4)	N22—C23	1.337 (4)
N2—C6	1.421 (4)	N22—C26	1.428 (5)
C3—C4	1.383 (5)	C23—C24	1.375 (5)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.416 (5)	C24—C25	1.420 (5)
C4—C12	1.445 (5)	C24—C32	1.446 (5)
C5—C14	1.457 (5)	C25—C34	1.451 (5)
C6—C7	1.364 (5)	C26—C27	1.357 (6)
C6—C11	1.372 (5)	C26—C31	1.374 (5)
C7—C8	1.382 (6)	C27—C28	1.379 (6)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.362 (6)	C28—C29	1.366 (6)
C8—H8	0.9300	C28—H28	0.9300
C9—C10	1.367 (6)	C29—C30	1.371 (6)
C9—H9	0.9300	C29—H29	0.9300
C10—C11	1.381 (5)	C30—C31	1.377 (5)
C10—H10	0.9300	C30—H30	0.9300
C11—H11	0.9300	C31—H31	0.9300
C12—O13	1.190 (4)	C32—O33	1.193 (5)
C12—H12	0.9300	C32—H32	0.9300
C14—C15	1.383 (5)	C34—C39	1.383 (5)
C14—C19	1.384 (5)	C34—C35	1.391 (5)
C15—C16	1.371 (6)	C35—C36	1.363 (6)
C15—H15	0.9300	C35—H35	0.9300
C16—C17	1.365 (6)	C36—C37	1.361 (6)
C16—H16	0.9300	C36—H36	0.9300
C17—C18	1.377 (6)	C37—C38	1.384 (6)
C18—C19	1.376 (5)	C38—C39	1.368 (5)
C18—H18	0.9300	C38—H38	0.9300
C19—H19	0.9300	C39—H39	0.9300

C5—N1—N2	105.3 (3)	C25—N21—N22	106.1 (3)
C3—N2—N1	112.2 (3)	C23—N22—N21	111.8 (3)
C3—N2—C6	128.4 (3)	C23—N22—C26	128.6 (3)
N1—N2—C6	119.4 (3)	N21—N22—C26	119.6 (3)
N2—C3—C4	107.3 (3)	N22—C23—C24	107.1 (3)
N2—C3—H3	126.4	N22—C23—H23	126.5
C4—C3—H3	126.4	C24—C23—H23	126.5
C3—C4—C5	104.7 (3)	C23—C24—C25	105.3 (3)
C3—C4—C12	126.5 (3)	C23—C24—C32	124.8 (3)
C5—C4—C12	128.3 (3)	C25—C24—C32	129.8 (3)
N1—C5—C4	110.5 (3)	N21—C25—C24	109.7 (3)
N1—C5—C14	119.1 (3)	N21—C25—C34	119.2 (3)
C4—C5—C14	130.3 (3)	C24—C25—C34	131.1 (3)
C7—C6—C11	120.5 (3)	C27—C26—C31	120.5 (4)
C7—C6—N2	120.7 (3)	C27—C26—N22	121.2 (3)
C11—C6—N2	118.8 (3)	C31—C26—N22	118.2 (3)
C6—C7—C8	119.4 (4)	C26—C27—C28	119.7 (4)
C6—C7—H7	120.3	C26—C27—H27	120.2
C8—C7—H7	120.3	C28—C27—H27	120.2
C9—C8—C7	120.9 (4)	C29—C28—C27	120.9 (4)
C9—C8—H8	119.5	C29—C28—H28	119.5
C7—C8—H8	119.5	C27—C28—H28	119.5
C8—C9—C10	119.1 (4)	C28—C29—C30	118.7 (4)
C8—C9—H9	120.4	C28—C29—H29	120.6
C10—C9—H9	120.4	C30—C29—H29	120.6
C9—C10—C11	120.9 (4)	C29—C30—C31	121.0 (4)
C9—C10—H10	119.5	C29—C30—H30	119.5
C11—C10—H10	119.5	C31—C30—H30	119.5
C6—C11—C10	119.1 (4)	C26—C31—C30	119.1 (4)
C6—C11—H11	120.4	C26—C31—H31	120.4
C10—C11—H11	120.4	C30—C31—H31	120.4
O13—C12—C4	125.6 (4)	O33—C32—C24	124.6 (4)
O13—C12—H12	117.2	O33—C32—H32	117.7
C4—C12—H12	117.2	C24—C32—H32	117.7
C15—C14—C19	117.7 (4)	C39—C34—C35	117.1 (4)
C15—C14—C5	122.1 (3)	C39—C34—C25	120.7 (3)
C19—C14—C5	120.3 (3)	C35—C34—C25	122.2 (3)
C16—C15—C14	121.7 (4)	C36—C35—C34	122.0 (4)
C16—C15—H15	119.2	C36—C35—H35	119.0
C14—C15—H15	119.2	C34—C35—H35	119.0
C17—C16—C15	119.1 (4)	C37—C36—C35	119.7 (4)
C17—C16—H16	120.5	C37—C36—H36	120.2
C15—C16—H16	120.5	C35—C36—H36	120.2
C16—C17—C18	121.3 (4)	C36—C37—C38	120.2 (4)
C16—C17—Br1	119.3 (3)	C36—C37—Br2	119.7 (3)
C18—C17—Br1	119.4 (3)	C38—C37—Br2	120.1 (3)
C19—C18—C17	118.7 (4)	C39—C38—C37	119.5 (4)
C19—C18—H18	120.6	C39—C38—H38	120.2
C17—C18—H18	120.6	C37—C38—H38	120.2
C18—C19—C14	121.5 (4)	C38—C39—C34	121.5 (4)
C18—C19—H19	119.2	C38—C39—H39	119.2
C14—C19—H19	119.2	C34—C39—H39	119.2

C5—N1—N2—C3	0.2 (4)	C25—N21—N22—C23	−0.8 (4)
C5—N1—N2—C6	−178.3 (3)	C25—N21—N22—C26	176.9 (3)
N1—N2—C3—C4	−0.0 (4)	N21—N22—C23—C24	0.8 (4)
C6—N2—C3—C4	178.3 (4)	C26—N22—C23—C24	−176.6 (4)
N2—C3—C4—C5	−0.1 (4)	N22—C23—C24—C25	−0.5 (4)
N2—C3—C4—C12	−173.0 (4)	N22—C23—C24—C32	176.1 (4)
N2—N1—C5—C4	−0.3 (4)	N22—N21—C25—C24	0.5 (4)
N2—N1—C5—C14	180.0 (3)	N22—N21—C25—C34	179.3 (3)
C3—C4—C5—N1	0.3 (4)	C23—C24—C25—N21	−0.0 (5)
C12—C4—C5—N1	172.9 (4)	C32—C24—C25—N21	−176.4 (4)
C3—C4—C5—C14	180.0 (4)	C23—C24—C25—C34	−178.6 (4)
C12—C4—C5—C14	−7.4 (7)	C32—C24—C25—C34	5.0 (7)
C3—N2—C6—C7	20.3 (6)	C23—N22—C26—C27	5.3 (6)
N1—N2—C6—C7	−161.4 (4)	N21—N22—C26—C27	−171.9 (4)
C3—N2—C6—C11	−158.2 (4)	C23—N22—C26—C31	−178.0 (4)
N1—N2—C6—C11	20.0 (5)	N21—N22—C26—C31	4.7 (5)
C11—C6—C7—C8	0.4 (7)	C31—C26—C27—C28	0.7 (7)
N2—C6—C7—C8	−178.1 (4)	N22—C26—C27—C28	177.3 (4)
C6—C7—C8—C9	−1.5 (7)	C26—C27—C28—C29	−0.9 (8)
C7—C8—C9—C10	1.0 (8)	C27—C28—C29—C30	0.4 (7)
C8—C9—C10—C11	0.6 (8)	C28—C29—C30—C31	0.3 (7)
C7—C6—C11—C10	1.1 (7)	C27—C26—C31—C30	−0.0 (7)
N2—C6—C11—C10	179.7 (4)	N22—C26—C31—C30	−176.7 (4)
C9—C10—C11—C6	−1.7 (7)	C29—C30—C31—C26	−0.5 (7)
C3—C4—C12—O13	−6.5 (7)	C23—C24—C32—O33	11.3 (7)
C5—C4—C12—O13	−177.6 (4)	C25—C24—C32—O33	−172.9 (4)
N1—C5—C14—C15	139.7 (4)	N21—C25—C34—C39	26.1 (6)
C4—C5—C14—C15	−40.0 (6)	C24—C25—C34—C39	−155.4 (4)
N1—C5—C14—C19	−39.7 (5)	N21—C25—C34—C35	−152.2 (4)
C4—C5—C14—C19	140.6 (4)	C24—C25—C34—C35	26.3 (7)
C19—C14—C15—C16	0.4 (6)	C39—C34—C35—C36	0.5 (6)
C5—C14—C15—C16	−179.0 (4)	C25—C34—C35—C36	178.8 (4)
C14—C15—C16—C17	−1.2 (7)	C34—C35—C36—C37	−1.6 (7)
C15—C16—C17—C18	1.5 (7)	C35—C36—C37—C38	1.4 (7)
C15—C16—C17—Br1	−179.4 (3)	C35—C36—C37—Br2	−179.8 (4)
C16—C17—C18—C19	−1.0 (7)	C36—C37—C38—C39	−0.2 (7)
Br1—C17—C18—C19	180.0 (3)	Br2—C37—C38—C39	−179.0 (3)
C17—C18—C19—C14	0.1 (6)	C37—C38—C39—C34	−1.0 (7)
C15—C14—C19—C18	0.2 (6)	C35—C34—C39—C38	0.8 (6)
C5—C14—C19—C18	179.6 (4)	C25—C34—C39—C38	−177.5 (4)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁BrN₂O
M_r	327.18
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.6716 (8), 11.4617 (9), 13.8257 (10)
α, β, γ (°)	113.497 (5), 92.753 (6), 93.753 (6)
V (Å³)	1397.91 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.94
Crystal size (mm)	0.34 × 0.18 × 0.06

Data collection
Diffractometer	Stoe IPDS 2T diffractometer
Absorption correction	Multi-scan (MULABS; Blessing, 1995)
T_min, T_max	0.477, 0.660
No. of measured, independent and observed [I > 2σ(I)] reflections	14312, 6740, 2856
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.158, 0.92
No. of reflections	6740
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.73

Computer programs: X-AREA (Stoe & Cie, 2010), X-RED (Stoe & Cie, 2010), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Acknowledgements

This research was supported financially by the Landesgraduiertenförderung program of the Ministry of Science, Research and Arts of the state of Baden-Württemberg, Germany.

References

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