N,N′-Bis(4-bromo­phenyl)­urea

The crystal structure of the title compound, C₁₃H₁₀Br₂N₂O, has been determined by X-ray analysis. The mol­ecule has a twofold axis coincident with the C=O bond. In the crystal structure, the mol­ecules are linked into columns along the b axis by bifurcated intermolecular N—H...O hydrogen bonds and π–π interactions. The columns are connected by strong intermolecular π–π interactions, forming T-shaped dimers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.042
• wR factor = 0.110
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.35
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.36
PLAT334_ALERT_2_C Small Average Benzene C-C Dist.  C2     -C7            1.36 Ang.
PLAT747_ALERT_1_C D...A   Calc    2.850(5), Rep     2.84900 ......    Missing su
              N1   -O1      1.555   1.565

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.355
            Tmax scaled      0.355 Tmin scaled      0.175

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

N,N'-Bis(4-bromophenyl)urea

Crystal data

C13H10Br2N2O	F(000) = 720
Mr = 370.05	Dx = 1.968 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.701 (12) Å	Cell parameters from 624 reflections
b = 4.551 (2) Å	θ = 3.0–25.9°
c = 9.953 (4) Å	µ = 6.48 mm^−1
β = 95.418 (7)°	T = 293 K
V = 1249.1 (9) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1272 independent reflections
Radiation source: fine-focus sealed tube	892 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 26.3°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −34→34
Tmin = 0.175, Tmax = 0.355	k = −4→5
3676 measured reflections	l = −11→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 0.7328P] where P = (Fo^2 + 2Fc^2)/3
1272 reflections	(Δ/σ)max = 0.001
83 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

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
Br1	0.205713 (17)	0.51905 (12)	0.66083 (5)	0.0592 (3)
O1	0.0000	0.5817 (8)	0.2500	0.0363 (11)
N1	0.03510 (12)	1.0067 (7)	0.3174 (4)	0.0328 (8)
H1	0.0333	1.1950	0.3116	0.039*
C1	0.0000	0.8470 (12)	0.2500	0.0273 (13)
C2	0.07466 (13)	0.8838 (9)	0.3972 (4)	0.0253 (9)
C3	0.06833 (14)	0.6812 (9)	0.4936 (4)	0.0334 (10)
H3	0.0372	0.6184	0.5069	0.040*
C4	0.10700 (16)	0.5687 (10)	0.5710 (4)	0.0375 (11)
H4	0.1026	0.4274	0.6363	0.045*
C5	0.15237 (14)	0.6667 (10)	0.5513 (4)	0.0343 (10)
C6	0.15920 (15)	0.8698 (11)	0.4585 (5)	0.0416 (11)
H6	0.1903	0.9368	0.4475	0.050*
C7	0.12032 (16)	0.9791 (9)	0.3795 (5)	0.0403 (11)
H7	0.1250	1.1185	0.3137	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0324 (3)	0.0736 (5)	0.0671 (4)	0.0065 (3)	−0.0193 (2)	0.0090 (3)
O1	0.034 (2)	0.014 (2)	0.056 (3)	0.000	−0.017 (2)	0.000
N1	0.0250 (17)	0.0170 (16)	0.054 (2)	−0.0015 (13)	−0.0114 (15)	−0.0009 (16)
C1	0.020 (3)	0.028 (3)	0.032 (3)	0.000	−0.005 (2)	0.000
C2	0.021 (2)	0.0194 (19)	0.034 (2)	0.0014 (15)	−0.0042 (16)	−0.0047 (17)
C3	0.020 (2)	0.037 (3)	0.042 (2)	−0.0038 (17)	−0.0038 (17)	−0.001 (2)
C4	0.033 (2)	0.040 (3)	0.038 (2)	−0.0056 (19)	−0.0042 (19)	0.0069 (19)
C5	0.022 (2)	0.041 (3)	0.037 (2)	0.0035 (18)	−0.0120 (18)	−0.004 (2)
C6	0.020 (2)	0.056 (3)	0.049 (3)	−0.009 (2)	0.0003 (19)	0.003 (2)
C7	0.034 (2)	0.042 (3)	0.044 (3)	−0.007 (2)	0.0001 (19)	0.012 (2)

Geometric parameters (Å, º)

Br1—C5	1.876 (4)	C3—C4	1.360 (6)
O1—C1	1.207 (7)	C3—H3	0.9300
N1—C1	1.342 (4)	C4—C5	1.365 (6)
N1—C2	1.407 (5)	C4—H4	0.9300
N1—H1	0.8600	C5—C6	1.333 (6)
C1—N1^i	1.342 (4)	C6—C7	1.366 (6)
C2—C3	1.354 (6)	C6—H6	0.9300
C2—C7	1.364 (6)	C7—H7	0.9300
C1—N1—C2	123.7 (3)	C3—C4—C5	118.8 (4)
C1—N1—H1	118.1	C3—C4—H4	120.6
C2—N1—H1	118.1	C5—C4—H4	120.6
O1—C1—N1^i	122.8 (2)	C6—C5—C4	121.3 (4)
O1—C1—N1	122.8 (2)	C6—C5—Br1	119.7 (3)
N1^i—C1—N1	114.4 (5)	C4—C5—Br1	119.0 (3)
C3—C2—C7	119.4 (4)	C5—C6—C7	119.7 (4)
C3—C2—N1	121.6 (4)	C5—C6—H6	120.2
C7—C2—N1	118.9 (4)	C7—C6—H6	120.2
C2—C3—C4	120.7 (4)	C2—C7—C6	120.0 (4)
C2—C3—H3	119.7	C2—C7—H7	120.0
C4—C3—H3	119.7	C6—C7—H7	120.0
C2—N1—C1—O1	−1.6 (5)	C3—C4—C5—C6	0.3 (7)
C2—N1—C1—N1^i	178.4 (5)	C3—C4—C5—Br1	178.5 (3)
C1—N1—C2—C3	−51.4 (6)	C4—C5—C6—C7	−1.2 (7)
C1—N1—C2—C7	130.9 (4)	Br1—C5—C6—C7	−179.4 (4)
C7—C2—C3—C4	−1.2 (6)	C3—C2—C7—C6	0.2 (7)
N1—C2—C3—C4	−178.9 (4)	N1—C2—C7—C6	178.0 (4)
C2—C3—C4—C5	0.9 (7)	C5—C6—C7—C2	1.0 (7)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^ii	0.86	2.05	2.849	154

Symmetry code: (ii) x, y+1, z.