(E)-5-(4-Bromo­phenyl­diazen­yl)salicylaldehyde

The molecule of the title compound, C₁₃H₉BrN₂O₂, is approximately planar and displays a trans configuration with respect to the N=N double bond. The dihedral angle between the two aromatic rings is 3.65 (16)°. The mol­ecules are linked by inter­molecular O—H...O hydrogen bonds, forming a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.080
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.00
           From the CIF: _reflns_number_total               2744
           Count of symmetry unique reflns         1532
           Completeness (_total/calc)            179.11%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1212
           Fraction of Friedel pairs measured     0.791
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-5-(4-Bromophenyldiazenyl)salicylaldehyde

Crystal data

C13H9BrN2O2	F(000) = 304
Mr = 305.13	Dx = 1.744 Mg m^−3
Monoclinic, P21	Melting point = 489–491 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 3.8914 (6) Å	Cell parameters from 9332 reflections
b = 5.8043 (5) Å	θ = 1.6–28.0°
c = 25.745 (4) Å	µ = 3.53 mm^−1
β = 92.101 (12)°	T = 296 K
V = 581.11 (13) Å^3	Plate, orange
Z = 2	0.50 × 0.29 × 0.04 mm

Data collection

Stoe IPDS-2 diffractometer	2744 independent reflections
Radiation source: fine-focus sealed tube	2547 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
Detector resolution: 6.67 pixels mm^-1	θmax = 28.0°, θmin = 1.6°
ω scans	h = −5→5
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
Tmin = 0.258, Tmax = 0.854	l = −33→33
9332 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0352P)^2 + 0.0931P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2744 reflections	Δρmax = 0.31 e Å^−3
167 parameters	Δρmin = −0.99 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1213 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.140 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2505 (9)	0.8568 (5)	0.89216 (12)	0.0443 (7)
C2	0.1045 (7)	1.0694 (8)	0.87838 (11)	0.0438 (6)
C3	0.0843 (9)	1.1366 (5)	0.82646 (13)	0.0440 (7)
H3	−0.0126	1.2779	0.8172	0.053*
C4	0.2073 (9)	0.9942 (5)	0.78895 (12)	0.0415 (7)
H4	0.1943	1.0412	0.7544	0.050*
C5	0.3516 (9)	0.7804 (5)	0.80146 (12)	0.0386 (6)
C6	0.3731 (9)	0.7142 (5)	0.85316 (13)	0.0431 (7)
H6	0.4705	0.5727	0.8621	0.052*
C7	0.2690 (14)	0.7782 (7)	0.94562 (14)	0.0612 (10)
H7	0.3716	0.6363	0.9527	0.073*
C8	0.5550 (8)	0.5340 (5)	0.68011 (11)	0.0365 (6)
C9	0.5068 (9)	0.6044 (5)	0.62879 (12)	0.0415 (7)
H9	0.4031	0.7457	0.6215	0.050*
C10	0.6113 (9)	0.4666 (5)	0.58846 (13)	0.0430 (7)
H10	0.5791	0.5128	0.5540	0.052*
C11	0.7658 (8)	0.2571 (5)	0.60090 (12)	0.0391 (6)
C12	0.8148 (9)	0.1843 (5)	0.65164 (13)	0.0414 (6)
H12	0.9174	0.0426	0.6589	0.050*
C13	0.7105 (9)	0.3233 (5)	0.69149 (13)	0.0413 (6)
H13	0.7438	0.2764	0.7258	0.050*
Br1	0.91129 (7)	0.06559 (6)	0.545937 (11)	0.04836 (11)
N1	0.4795 (7)	0.6226 (4)	0.76440 (11)	0.0410 (6)
N2	0.4343 (8)	0.6899 (5)	0.71817 (10)	0.0416 (6)
O1	0.1574 (12)	0.8874 (6)	0.98215 (11)	0.0834 (11)
O2	−0.0211 (9)	1.2197 (5)	0.91331 (11)	0.0606 (7)
H2	0.024 (15)	1.172 (10)	0.944 (2)	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.057 (2)	0.0443 (15)	0.0312 (15)	−0.0085 (14)	0.0013 (14)	0.0001 (12)
C2	0.0536 (14)	0.0436 (12)	0.0348 (13)	−0.005 (2)	0.0079 (11)	−0.0085 (17)
C3	0.0518 (17)	0.0405 (14)	0.0397 (17)	0.0026 (11)	0.0022 (14)	−0.0019 (11)
C4	0.0505 (17)	0.0441 (15)	0.0300 (14)	0.0015 (11)	0.0043 (13)	−0.0006 (10)
C5	0.0445 (16)	0.0415 (14)	0.0299 (14)	−0.0011 (12)	0.0032 (12)	−0.0046 (11)
C6	0.0548 (18)	0.0397 (14)	0.0351 (16)	−0.0005 (13)	0.0035 (14)	0.0003 (12)
C7	0.094 (3)	0.0537 (19)	0.0363 (18)	−0.0030 (19)	0.002 (2)	−0.0015 (15)
C8	0.0432 (13)	0.0317 (16)	0.0346 (14)	0.0002 (11)	0.0005 (11)	−0.0037 (11)
C9	0.0479 (15)	0.038 (2)	0.0387 (15)	0.0035 (12)	0.0025 (12)	0.0013 (11)
C10	0.0530 (18)	0.0440 (13)	0.0323 (14)	0.0009 (13)	0.0047 (13)	0.0025 (12)
C11	0.0378 (15)	0.0441 (14)	0.0354 (15)	−0.0026 (12)	0.0019 (12)	−0.0023 (12)
C12	0.0461 (16)	0.0418 (14)	0.0363 (16)	0.0058 (12)	0.0024 (13)	−0.0021 (12)
C13	0.0474 (17)	0.0450 (15)	0.0317 (15)	0.0053 (13)	0.0027 (13)	0.0026 (12)
Br1	0.05167 (16)	0.05427 (16)	0.03971 (17)	0.0018 (2)	0.00924 (11)	−0.01062 (16)
N1	0.0494 (14)	0.0410 (15)	0.0330 (13)	0.0017 (9)	0.0060 (11)	−0.0028 (9)
N2	0.0508 (15)	0.0436 (13)	0.0307 (13)	0.0048 (11)	0.0047 (11)	−0.0038 (10)
O1	0.141 (3)	0.0753 (19)	0.0347 (15)	0.006 (2)	0.0179 (17)	−0.0027 (14)
O2	0.086 (2)	0.0554 (13)	0.0413 (14)	0.0045 (13)	0.0152 (14)	−0.0104 (11)

Geometric parameters (Å, º)

C1—C6	1.399 (5)	C8—C9	1.389 (4)
C1—C2	1.399 (6)	C8—C13	1.391 (4)
C1—C7	1.449 (5)	C8—N2	1.426 (4)
C2—O2	1.357 (4)	C9—C10	1.384 (4)
C2—C3	1.392 (5)	C9—H9	0.9300
C3—C4	1.371 (4)	C10—C11	1.388 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.395 (4)	C11—C12	1.380 (4)
C4—H4	0.9300	C11—Br1	1.902 (3)
C5—C6	1.385 (4)	C12—C13	1.378 (4)
C5—N1	1.426 (4)	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—O1	1.227 (5)	N1—N2	1.259 (4)
C7—H7	0.9300	O2—H2	0.84 (6)
C6—C1—C2	119.1 (3)	C9—C8—C13	120.1 (3)
C6—C1—C7	119.3 (3)	C9—C8—N2	115.5 (3)
C2—C1—C7	121.6 (3)	C13—C8—N2	124.4 (3)
O2—C2—C3	116.6 (4)	C10—C9—C8	120.7 (3)
O2—C2—C1	123.5 (3)	C10—C9—H9	119.7
C3—C2—C1	119.9 (3)	C8—C9—H9	119.7
C4—C3—C2	119.9 (3)	C9—C10—C11	118.0 (3)
C4—C3—H3	120.0	C9—C10—H10	121.0
C2—C3—H3	120.0	C11—C10—H10	121.0
C3—C4—C5	121.5 (3)	C12—C11—C10	122.0 (3)
C3—C4—H4	119.3	C12—C11—Br1	119.4 (2)
C5—C4—H4	119.3	C10—C11—Br1	118.6 (2)
C6—C5—C4	118.6 (3)	C13—C12—C11	119.4 (3)
C6—C5—N1	117.0 (3)	C13—C12—H12	120.3
C4—C5—N1	124.4 (3)	C11—C12—H12	120.3
C5—C6—C1	121.0 (3)	C12—C13—C8	119.7 (3)
C5—C6—H6	119.5	C12—C13—H13	120.1
C1—C6—H6	119.5	C8—C13—H13	120.1
O1—C7—C1	123.9 (4)	N2—N1—C5	113.2 (2)
O1—C7—H7	118.0	N1—N2—C8	114.5 (3)
C1—C7—H7	118.0	C2—O2—H2	110 (4)
C6—C1—C2—O2	−179.9 (3)	C13—C8—C9—C10	0.1 (5)
C7—C1—C2—O2	1.8 (6)	N2—C8—C9—C10	−179.5 (3)
C6—C1—C2—C3	−0.3 (5)	C8—C9—C10—C11	−0.2 (5)
C7—C1—C2—C3	−178.5 (4)	C9—C10—C11—C12	0.3 (5)
O2—C2—C3—C4	179.7 (3)	C9—C10—C11—Br1	−180.0 (2)
C1—C2—C3—C4	0.0 (5)	C10—C11—C12—C13	−0.5 (5)
C2—C3—C4—C5	0.5 (5)	Br1—C11—C12—C13	179.8 (3)
C3—C4—C5—C6	−0.8 (5)	C11—C12—C13—C8	0.5 (5)
C3—C4—C5—N1	179.0 (3)	C9—C8—C13—C12	−0.3 (5)
C4—C5—C6—C1	0.6 (5)	N2—C8—C13—C12	179.3 (3)
N1—C5—C6—C1	−179.3 (3)	C6—C5—N1—N2	176.5 (3)
C2—C1—C6—C5	0.0 (5)	C4—C5—N1—N2	−3.3 (5)
C7—C1—C6—C5	178.3 (4)	C5—N1—N2—C8	−179.1 (3)
C6—C1—C7—O1	−177.4 (4)	C9—C8—N2—N1	179.8 (3)
C2—C1—C7—O1	0.9 (7)	C13—C8—N2—N1	0.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.84 (6)	1.99 (6)	2.693 (4)	141 (5)
O2—H2···O1^i	0.84 (6)	2.41 (6)	2.929 (4)	121 (5)

Symmetry code: (i) −x, y+1/2, −z+2.