3-(4-Bromo­anilino)isobenzofuran-1(3H)-one

Crystals of the title compound, C₁₄H₁₀BrNO₂, contain N—H...O hydrogen bond inter­actions that generate C(6) chains; these chains are linked by C—H...O hydrogen bonds, generating an R₄³(21) ring motif.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.035
• wR factor = 0.079
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.77 mm
PLAT245_ALERT_2_C U(iso) H1      Smaller than U(eq) N1      by ...       0.01 AngSq
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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           26.00
           From the CIF: _reflns_number_total               2452
           Count of symmetry unique reflns         1363
           Completeness (_total/calc)            179.90%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1089
           Fraction of Friedel pairs measured     0.799
           Are heavy atom types Z>Si present        yes
PLAT792_ALERT_1_G Check the Absolute Configuration of C8     = ...          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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, 1990); 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).

3-(4-bromoanilino)isobenzofuran-1(3H)-one

Crystal data

C14H10BrNO2	F(000) = 608
Mr = 304.14	Dx = 1.602 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c-2n	Cell parameters from 9319 reflections
a = 8.1158 (8) Å	θ = 1.5–26.0°
b = 27.3737 (18) Å	µ = 3.25 mm^−1
c = 5.6775 (4) Å	T = 296 K
V = 1261.31 (17) Å^3	Plate, colorless
Z = 4	0.77 × 0.31 × 0.07 mm

Data collection

Stoe IPDS-2 diffractometer	2452 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1446 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.081
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.5°
ω scans	h = −9→10
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −33→33
Tmin = 0.298, Tmax = 0.810	l = −6→7
11941 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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0347P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max = 0.002
2452 reflections	Δρmax = 0.21 e Å^−3
168 parameters	Δρmin = −0.29 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1089 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (15)

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	0.6677 (5)	0.33614 (12)	0.2659 (11)	0.0549 (9)
C2	0.5734 (5)	0.30529 (15)	0.4317 (8)	0.0527 (11)
C3	0.5539 (7)	0.25487 (16)	0.4308 (10)	0.0678 (13)
H3	0.5996	0.2355	0.3132	0.081*
C4	0.4638 (7)	0.23514 (18)	0.6118 (12)	0.0771 (15)
H4	0.4481	0.2015	0.6168	0.093*
C5	0.3971 (6)	0.26330 (17)	0.7836 (16)	0.0780 (13)
H5	0.3378	0.2484	0.9040	0.094*
C6	0.4149 (5)	0.31387 (15)	0.7846 (14)	0.0683 (11)
H6	0.3685	0.3332	0.9018	0.082*
C7	0.5053 (6)	0.33382 (14)	0.6020 (8)	0.0537 (10)
C8	0.5545 (5)	0.38607 (15)	0.5609 (8)	0.0539 (10)
H8	0.4555	0.4057	0.5316	0.065*
C9	0.6985 (5)	0.45492 (12)	0.7475 (10)	0.0494 (9)
C10	0.7964 (6)	0.47086 (16)	0.9303 (8)	0.0562 (11)
H10	0.8265	0.4492	1.0490	0.067*
C11	0.8498 (5)	0.51863 (17)	0.9385 (9)	0.0595 (12)
H11	0.9167	0.5290	1.0617	0.071*
C12	0.8048 (5)	0.55067 (13)	0.7665 (12)	0.0584 (9)
C13	0.7083 (6)	0.53591 (14)	0.5822 (9)	0.0626 (12)
H13	0.6787	0.5580	0.4651	0.075*
C14	0.6551 (5)	0.48792 (14)	0.5710 (8)	0.0542 (11)
H14	0.5902	0.4777	0.4454	0.065*
N1	0.6427 (5)	0.40664 (12)	0.7450 (9)	0.0559 (10)
O1	0.7447 (4)	0.32583 (11)	0.0939 (6)	0.0711 (9)
O2	0.6535 (4)	0.38300 (10)	0.3399 (4)	0.0566 (8)
Br1	0.88224 (7)	0.616096 (15)	0.77553 (17)	0.0923 (2)
H1	0.696 (5)	0.3888 (13)	0.821 (7)	0.041 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.064 (3)	0.0445 (19)	0.056 (2)	0.0028 (16)	−0.009 (4)	0.004 (3)
C2	0.056 (3)	0.046 (2)	0.056 (2)	−0.004 (2)	−0.008 (2)	0.005 (2)
C3	0.073 (3)	0.046 (2)	0.084 (3)	−0.005 (2)	−0.011 (3)	−0.003 (3)
C4	0.080 (4)	0.054 (3)	0.097 (4)	−0.020 (3)	−0.014 (3)	0.012 (3)
C5	0.072 (3)	0.076 (3)	0.087 (3)	−0.030 (3)	−0.014 (4)	0.021 (5)
C6	0.059 (3)	0.070 (2)	0.076 (3)	−0.0106 (19)	0.001 (4)	0.005 (4)
C7	0.053 (3)	0.050 (2)	0.058 (3)	−0.004 (2)	−0.006 (2)	0.005 (2)
C8	0.057 (2)	0.050 (2)	0.055 (3)	0.002 (2)	−0.001 (2)	−0.002 (2)
C9	0.053 (2)	0.0458 (18)	0.049 (2)	0.0001 (17)	0.006 (3)	−0.002 (3)
C10	0.065 (3)	0.052 (2)	0.052 (3)	0.000 (2)	−0.005 (3)	0.000 (2)
C11	0.049 (3)	0.067 (3)	0.062 (3)	−0.009 (2)	−0.012 (2)	−0.010 (3)
C12	0.055 (2)	0.0486 (19)	0.072 (3)	0.0019 (17)	0.005 (4)	0.001 (3)
C13	0.075 (3)	0.043 (2)	0.071 (3)	0.006 (2)	0.002 (3)	0.009 (2)
C14	0.066 (3)	0.046 (2)	0.051 (3)	−0.001 (2)	−0.008 (2)	0.002 (2)
N1	0.071 (2)	0.0417 (16)	0.055 (3)	0.0015 (17)	−0.007 (3)	0.008 (2)
O1	0.089 (3)	0.0617 (19)	0.063 (2)	0.0043 (18)	0.0107 (19)	−0.0078 (17)
O2	0.077 (2)	0.0456 (13)	0.047 (2)	−0.0043 (15)	0.0071 (14)	0.0041 (13)
Br1	0.0826 (3)	0.0507 (2)	0.1436 (5)	−0.0105 (3)	−0.0030 (5)	−0.0080 (5)

Geometric parameters (Å, º)

C1—O1	1.193 (6)	C8—O2	1.493 (5)
C1—O2	1.354 (4)	C8—H8	0.9800
C1—C2	1.478 (7)	C9—C10	1.378 (6)
C2—C7	1.360 (6)	C9—C14	1.394 (6)
C2—C3	1.389 (6)	C9—N1	1.397 (5)
C3—C4	1.372 (7)	C10—C11	1.379 (6)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.356 (9)	C11—C12	1.363 (7)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.392 (5)	C12—C13	1.368 (7)
C5—H5	0.9300	C12—Br1	1.899 (4)
C6—C7	1.383 (7)	C13—C14	1.384 (5)
C6—H6	0.9300	C13—H13	0.9300
C7—C8	1.503 (5)	C14—H14	0.9300
C8—N1	1.386 (6)	N1—H1	0.78 (4)
O1—C1—O2	121.5 (4)	O2—C8—H8	109.2
O1—C1—C2	131.1 (4)	C7—C8—H8	109.2
O2—C1—C2	107.4 (4)	C10—C9—C14	118.8 (4)
C7—C2—C3	121.8 (5)	C10—C9—N1	119.6 (4)
C7—C2—C1	109.6 (4)	C14—C9—N1	121.6 (5)
C3—C2—C1	128.6 (5)	C9—C10—C11	120.5 (4)
C4—C3—C2	116.7 (5)	C9—C10—H10	119.8
C4—C3—H3	121.7	C11—C10—H10	119.8
C2—C3—H3	121.7	C12—C11—C10	120.1 (4)
C5—C4—C3	121.9 (5)	C12—C11—H11	119.9
C5—C4—H4	119.1	C10—C11—H11	119.9
C3—C4—H4	119.1	C11—C12—C13	120.8 (4)
C4—C5—C6	121.8 (6)	C11—C12—Br1	119.9 (4)
C4—C5—H5	119.1	C13—C12—Br1	119.3 (4)
C6—C5—H5	119.1	C12—C13—C14	119.6 (4)
C7—C6—C5	116.4 (6)	C12—C13—H13	120.2
C7—C6—H6	121.8	C14—C13—H13	120.2
C5—C6—H6	121.8	C13—C14—C9	120.2 (4)
C2—C7—C6	121.5 (4)	C13—C14—H14	119.9
C2—C7—C8	109.2 (4)	C9—C14—H14	119.9
C6—C7—C8	129.3 (4)	C8—N1—C9	124.0 (5)
N1—C8—O2	112.2 (3)	C8—N1—H1	117 (3)
N1—C8—C7	114.0 (4)	C9—N1—H1	114 (3)
O2—C8—C7	102.7 (3)	C1—O2—C8	111.1 (3)
N1—C8—H8	109.2
O1—C1—C2—C7	−179.7 (5)	C14—C9—C10—C11	0.2 (7)
O2—C1—C2—C7	−0.3 (5)	N1—C9—C10—C11	−178.6 (4)
O1—C1—C2—C3	1.6 (8)	C9—C10—C11—C12	0.7 (7)
O2—C1—C2—C3	−178.9 (4)	C10—C11—C12—C13	−0.9 (7)
C7—C2—C3—C4	−0.7 (7)	C10—C11—C12—Br1	−178.8 (3)
C1—C2—C3—C4	177.8 (5)	C11—C12—C13—C14	0.4 (7)
C2—C3—C4—C5	−0.1 (8)	Br1—C12—C13—C14	178.2 (3)
C3—C4—C5—C6	0.6 (9)	C12—C13—C14—C9	0.5 (7)
C4—C5—C6—C7	−0.5 (8)	C10—C9—C14—C13	−0.7 (7)
C3—C2—C7—C6	0.9 (7)	N1—C9—C14—C13	178.0 (4)
C1—C2—C7—C6	−177.8 (4)	O2—C8—N1—C9	65.0 (5)
C3—C2—C7—C8	177.5 (4)	C7—C8—N1—C9	−178.8 (4)
C1—C2—C7—C8	−1.2 (5)	C10—C9—N1—C8	−174.9 (4)
C5—C6—C7—C2	−0.3 (7)	C14—C9—N1—C8	6.3 (7)
C5—C6—C7—C8	−176.1 (5)	O1—C1—O2—C8	−178.8 (4)
C2—C7—C8—N1	−119.5 (4)	C2—C1—O2—C8	1.7 (4)
C6—C7—C8—N1	56.7 (6)	N1—C8—O2—C1	120.5 (4)
C2—C7—C8—O2	2.1 (4)	C7—C8—O2—C1	−2.4 (4)
C6—C7—C8—O2	178.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.78 (4)	2.35 (4)	3.083 (5)	156 (4)
C5—H5···O1^ii	0.93	2.42	3.254 (7)	149

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