2,5-Dibenzo­yl-1,4-phenyl­enediamine

The title compound, C₂₀H₁₆N₂O₂, was synthesized from the reaction of 2,5-dibenzoyl­terephthalamide and sodium hypochlorite solution. The asymmetric unit contains one half-mol­ecule, the molecule being centrosymmetric. Intra- and inter­molecular N—H...O hydrogen bonds are highly effective in forming a two-dimensional layer structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.054
• wR factor = 0.151
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       2.47 Sigma

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT128_ALERT_4_C Non-standard setting of Space group Pbca    ....    Pcab
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT420_ALERT_2_C D-H Without Acceptor       N      -   H3     ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  O       ..       2.61 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 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
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius,1989); cell refinement: CAD-4 Software; data reduction: XAD4 (Harms, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

2,5-dibenzoyl-1,4-phenylenediamine

Crystal data

C20H16N2O2	Dx = 1.355 Mg m^−3
Mr = 316.35	Melting point: 492 K
Orthorhombic, Pcab	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2bc 2ac	Cell parameters from 25 reflections
a = 7.4651 (15) Å	θ = 9–12°
b = 13.0034 (16) Å	µ = 0.09 mm^−1
c = 15.9759 (18) Å	T = 296 K
V = 1550.8 (4) Å^3	Prism, brown
Z = 4	0.3 × 0.3 × 0.1 mm
F(000) = 664

Data collection

Enraf–Nonius CAD-4 diffractometer	614 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 2.6°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (XPREP in SHELXTL; Bruker, 2000)	k = 0→16
Tmin = 0.974, Tmax = 0.991	l = 0→19
1519 measured reflections	3 standard reflections every 200 reflections
1519 independent reflections	intensity decay: none

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.0432P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
1519 reflections	Δρmax = 0.19 e Å^−3
118 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (19)

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
O	−0.1312 (4)	0.2506 (2)	0.08228 (16)	0.0549 (8)
N	0.3402 (5)	−0.0911 (3)	−0.0079 (2)	0.0490 (10)
H1	0.349 (5)	−0.154 (3)	−0.025 (2)	0.044 (12)*
H3	0.421 (7)	−0.066 (3)	0.034 (3)	0.097 (18)*
C1	0.1691 (5)	−0.0489 (3)	−0.0026 (2)	0.0341 (9)
C2	0.1372 (5)	0.0349 (3)	0.0494 (2)	0.0345 (9)
H2	0.2299	0.0592	0.0828	0.041*
C3	−0.0277 (5)	0.0833 (2)	0.0531 (2)	0.0344 (9)
C4	−0.0501 (5)	0.1747 (3)	0.1084 (2)	0.0378 (9)
C5	0.0523 (5)	0.2689 (3)	0.2348 (2)	0.0474 (11)
H5	0.0280	0.3302	0.2071	0.057*
C6	0.1164 (6)	0.2708 (3)	0.3154 (3)	0.0599 (13)
H6	0.1365	0.3337	0.3416	0.072*
C7	0.1508 (6)	0.1818 (4)	0.3577 (2)	0.0626 (13)
H7	0.1957	0.1841	0.4120	0.075*
C8	0.1191 (6)	0.0889 (4)	0.3199 (2)	0.0587 (13)
H8	0.1390	0.0281	0.3490	0.070*
C9	0.0576 (6)	0.0860 (3)	0.2386 (2)	0.0469 (11)
H9	0.0385	0.0227	0.2130	0.056*
C10	0.0236 (5)	0.1754 (3)	0.1943 (2)	0.0360 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O	0.074 (2)	0.0400 (14)	0.0510 (15)	0.0126 (16)	−0.0046 (14)	−0.0001 (15)
N	0.041 (2)	0.048 (2)	0.058 (2)	0.0097 (19)	−0.0022 (18)	−0.013 (2)
C1	0.037 (2)	0.0330 (19)	0.032 (2)	0.0019 (18)	0.0020 (18)	0.0028 (17)
C2	0.036 (2)	0.037 (2)	0.0307 (18)	−0.0040 (19)	−0.0048 (17)	−0.0003 (16)
C3	0.038 (2)	0.034 (2)	0.0310 (18)	−0.0031 (19)	0.0020 (17)	0.0000 (16)
C4	0.041 (2)	0.034 (2)	0.038 (2)	−0.004 (2)	0.0070 (19)	0.0033 (18)
C5	0.050 (2)	0.044 (3)	0.048 (2)	−0.001 (2)	−0.001 (2)	−0.011 (2)
C6	0.066 (3)	0.064 (3)	0.049 (3)	−0.012 (3)	0.004 (2)	−0.022 (2)
C7	0.055 (3)	0.102 (4)	0.031 (2)	−0.008 (3)	0.003 (2)	−0.012 (3)
C8	0.071 (3)	0.069 (3)	0.037 (2)	0.009 (3)	0.001 (2)	0.004 (2)
C9	0.058 (3)	0.045 (2)	0.038 (2)	−0.004 (2)	0.000 (2)	−0.0045 (19)
C10	0.036 (2)	0.041 (2)	0.0311 (19)	−0.0017 (19)	0.0065 (16)	−0.0010 (18)

Geometric parameters (Å, º)

O—C4	1.231 (4)	C3—C1^i	1.402 (5)
C10—C9	1.384 (5)	C3—C4	1.491 (4)
C10—C5	1.394 (5)	C5—C6	1.375 (5)
C10—C4	1.478 (5)	C5—H5	0.9300
N—C1	1.393 (4)	C6—C7	1.364 (6)
N—H1	0.87 (4)	C6—H6	0.9300
N—H3	0.96 (5)	C7—C8	1.371 (6)
C1—C2	1.390 (4)	C7—H7	0.9300
C1—C3^i	1.402 (5)	C8—C9	1.378 (5)
C2—C3	1.384 (5)	C8—H8	0.9300
C2—H2	0.9300	C9—H9	0.9300
C9—C10—C5	117.8 (3)	C10—C4—C3	120.9 (3)
C9—C10—C4	122.6 (3)	C6—C5—C10	120.3 (4)
C5—C10—C4	119.5 (3)	C6—C5—H5	119.9
C1—N—H1	117 (3)	C10—C5—H5	119.9
C1—N—H3	114 (3)	C7—C6—C5	120.9 (4)
H1—N—H3	119 (4)	C7—C6—H6	119.5
C2—C1—C3^i	117.7 (3)	C5—C6—H6	119.5
C2—C1—N	120.1 (3)	C8—C7—C6	119.7 (4)
C3^i—C1—N	122.0 (3)	C8—C7—H7	120.1
C1—C2—C3	122.4 (3)	C6—C7—H7	120.1
C1—C2—H2	118.8	C7—C8—C9	119.8 (4)
C3—C2—H2	118.8	C7—C8—H8	120.1
C2—C3—C1^i	119.9 (3)	C9—C8—H8	120.1
C2—C3—C4	119.3 (3)	C10—C9—C8	121.3 (4)
C1^i—C3—C4	120.7 (3)	C10—C9—H9	119.3
O—C4—C10	119.6 (3)	C8—C9—H9	119.3
O—C4—C3	119.5 (3)
C3^i—C1—C2—C3	0.6 (5)	C2—C3—C4—C10	−43.9 (5)
N—C1—C2—C3	176.1 (3)	C1^i—C3—C4—C10	138.6 (4)
C1—C2—C3—C1^i	−0.7 (6)	C9—C10—C5—C6	1.5 (6)
C1—C2—C3—C4	−178.1 (3)	C4—C10—C5—C6	178.3 (3)
C9—C10—C4—O	156.3 (4)	C10—C5—C6—C7	−0.9 (6)
C5—C10—C4—O	−20.3 (5)	C5—C6—C7—C8	−0.9 (7)
C9—C10—C4—C3	−23.7 (5)	C6—C7—C8—C9	1.9 (6)
C5—C10—C4—C3	159.7 (3)	C5—C10—C9—C8	−0.5 (6)
C2—C3—C4—O	136.1 (4)	C4—C10—C9—C8	−177.2 (4)
C1^i—C3—C4—O	−41.3 (5)	C7—C8—C9—C10	−1.2 (6)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1···O^i	0.87 (4)	2.25 (4)	2.855 (5)	127 (3)
N—H1···O^ii	0.87 (4)	2.61 (4)	3.220 (5)	128 (3)

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