2-[(3-Bromo­phen­yl)imino­meth­yl]phenol

The title compound, C₁₃H₁₀BrNO, was prepared by reaction of 3-bromo­aniline with 2-hydroxy­benzaldehyde at 377 K. The mol­ecular structure and packing are stabilized by an intra­molecular O—H...N hydrogen-bond inter­action.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.019 Å
• R factor = 0.083
• wR factor = 0.229
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         19

Alert level C
ABSTM02_ALERT_3_C  The ratio of Tmax/Tmin expected RT(exp) is > 1.10
            Absorption corrections should be applied.
            Tmin and Tmax expected:      0.646     0.770
            RT(exp) =      1.192
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.19
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT180_ALERT_4_C Check Cell Rounding: # of Values Ending with 0 =          4

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           24.99
           From the CIF: _reflns_number_total               1822
           Count of symmetry unique reflns         1025
           Completeness (_total/calc)            177.76%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       797
           Fraction of Friedel pairs measured     0.778
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The recent growing interest in Schiff bases is also due to their ability to form intramolecular hydrogen bonds by electron coupling between acid–base centers (Rozwadowski et al., 1999). The part of our research is to find Schiff base with higher biological activity, we synthesized the title compound (I) and report its crystal structure here.

In the crystal structure of compound (I) (Fig. 1), the dihedral angle between the benzene rings (C1–C6) and (C7–C12) was 4.6 (2)°. The C═N bond length [1.273 (1) Å] is in agreement with that observed before (Jian et al., 2006). There are intramolecular O—H···N hydrogen-bond interactions to stabilize the crystal structure (Table 1, Fig. 2).

Related literature

For related literature, see: Jian et al. (2006); Rozwadowski et al. (1999).

S2. Experimental

A mixture of 2-nitrobenzaldehyde (0.02 mol) and 4-methoxyaniline (0.02 mol) was stirred with ethanol (50 mL) at 377 K for 5 h, affording the title compound (4.33 g, yield 84.5%). Single crystals suitable for X-ray measurements were obtained by recrystallization from acetone at room temperature.

S3. Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with O—H and C—H distances of 0.82 and 0.93 Å, respectively, and with U_iso(H) = 1.2 or 1.5U_eq of the parent atoms.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the packing and the intramolecular hydrogen bonding (dashed lines) of (I) in the unitcell.

2-[(3-Bromophenyl)iminomethyl]phenol

Crystal data

C13H10BrNO	F(000) = 276.0
Mr = 276.13	Dx = 1.676 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1666 reflections
a = 3.9700 (8) Å	θ = 1.6–25.0°
b = 10.540 (2) Å	µ = 3.73 mm^−1
c = 13.200 (3) Å	T = 293 K
β = 98.00 (3)°	Bar, yellow
V = 546.96 (19) Å^3	0.12 × 0.10 × 0.07 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1666 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 1.6°
φ and ω scans	h = −4→4
2736 measured reflections	k = −12→12
1822 independent reflections	l = −12→15

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)] = 0.082	H-atom parameters constrained
wR(F^2) = 0.229	w = 1/[σ^2(Fo^2) + (0.1154P)^2 + 2.8393P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
1822 reflections	Δρmax = 1.43 e Å^−3
145 parameters	Δρmin = −1.17 e Å^−3
1 restraint	Absolute structure: Flack (1983), 787 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (4)

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	0.4943 (3)	0.6144 (2)	0.53030 (8)	0.0544 (5)
N1	0.643 (3)	0.4449 (9)	0.9014 (8)	0.041 (2)
C4	0.538 (4)	0.5109 (12)	0.7289 (10)	0.046 (3)
H4A	0.6652	0.5830	0.7485	0.055*
C10	0.793 (3)	0.3864 (10)	1.0766 (9)	0.036 (3)
C3	0.402 (4)	0.4950 (13)	0.6277 (11)	0.049 (3)
C11	0.800 (4)	0.2937 (12)	1.1480 (10)	0.043 (3)
H11A	0.7186	0.2137	1.1274	0.052*
C5	0.487 (3)	0.4229 (12)	0.8000 (10)	0.043 (3)
C8	1.128 (4)	0.5145 (14)	1.2004 (12)	0.057 (4)
H8A	1.2470	0.5889	1.2187	0.068*
C12	0.918 (4)	0.3124 (13)	1.2476 (10)	0.052 (4)
H12A	0.8763	0.2550	1.2978	0.062*
C13	0.644 (4)	0.3630 (11)	0.9723 (11)	0.041 (3)
H13A	0.5431	0.2846	0.9561	0.050*
C9	0.978 (4)	0.4994 (12)	1.1041 (10)	0.045 (3)
C7	1.110 (4)	0.4238 (15)	1.2716 (13)	0.060 (4)
H7A	1.2254	0.4348	1.3373	0.072*
O1	0.995 (3)	0.5906 (16)	1.0355 (8)	0.081 (6)
H1	0.8925	0.5681	0.9801	0.121*
C6	0.304 (3)	0.3157 (12)	0.7675 (13)	0.050 (4)
H6A	0.2798	0.2530	0.8157	0.060*
C2	0.216 (4)	0.3883 (13)	0.5982 (12)	0.049 (3)
H2A	0.1275	0.3769	0.5298	0.059*
C1	0.157 (5)	0.2960 (13)	0.6708 (11)	0.054 (4)
H1B	0.0231	0.2250	0.6527	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0649 (8)	0.0635 (8)	0.0338 (6)	−0.0095 (9)	0.0028 (5)	0.0168 (7)
N1	0.053 (6)	0.034 (5)	0.034 (5)	−0.002 (4)	0.001 (5)	−0.001 (4)
C4	0.060 (8)	0.041 (7)	0.035 (7)	0.005 (6)	−0.002 (6)	0.001 (5)
C10	0.042 (7)	0.035 (6)	0.026 (6)	0.004 (5)	−0.009 (5)	−0.007 (5)
C3	0.053 (8)	0.053 (8)	0.040 (7)	0.006 (6)	0.000 (6)	−0.002 (6)
C11	0.052 (8)	0.045 (7)	0.035 (7)	0.015 (6)	0.009 (6)	0.002 (6)
C5	0.039 (7)	0.049 (7)	0.038 (7)	0.013 (6)	−0.002 (5)	−0.002 (5)
C8	0.061 (9)	0.043 (7)	0.060 (9)	−0.009 (6)	−0.015 (7)	−0.003 (6)
C12	0.073 (10)	0.045 (7)	0.034 (7)	0.001 (7)	−0.007 (6)	0.013 (6)
C13	0.060 (8)	0.028 (6)	0.034 (7)	0.004 (5)	0.000 (6)	0.000 (4)
C9	0.056 (8)	0.039 (6)	0.041 (7)	0.007 (6)	0.003 (6)	0.003 (6)
C7	0.052 (9)	0.066 (9)	0.060 (9)	0.002 (7)	−0.001 (7)	−0.005 (7)
O1	0.096 (8)	0.077 (16)	0.065 (7)	−0.043 (8)	−0.005 (6)	−0.004 (7)
C6	0.035 (7)	0.032 (6)	0.079 (10)	−0.009 (5)	−0.002 (7)	0.004 (6)
C2	0.039 (7)	0.059 (9)	0.049 (8)	0.003 (6)	0.006 (6)	−0.010 (7)
C1	0.084 (11)	0.043 (8)	0.037 (7)	−0.011 (7)	0.014 (7)	−0.013 (6)

Geometric parameters (Å, º)

Br1—C3	1.872 (15)	C8—C7	1.35 (2)
N1—C13	1.273 (17)	C8—H8A	0.9300
N1—C5	1.414 (16)	C12—C7	1.41 (2)
C4—C5	1.354 (19)	C12—H12A	0.9300
C4—C3	1.379 (19)	C13—H13A	0.9300
C4—H4A	0.9300	C9—O1	1.328 (19)
C10—C11	1.355 (18)	C7—H7A	0.9300
C10—C9	1.420 (18)	O1—H1	0.8200
C10—C13	1.443 (18)	C6—C1	1.34 (2)
C3—C2	1.37 (2)	C6—H6A	0.9300
C11—C12	1.348 (19)	C2—C1	1.41 (2)
C11—H11A	0.9300	C2—H2A	0.9300
C5—C6	1.381 (18)	C1—H1B	0.9300
C8—C9	1.34 (2)
C13—N1—C5	122.7 (11)	C7—C12—H12A	121.8
C5—C4—C3	120.8 (13)	N1—C13—C10	123.0 (11)
C5—C4—H4A	119.6	N1—C13—H13A	118.5
C3—C4—H4A	119.6	C10—C13—H13A	118.5
C11—C10—C9	117.9 (11)	O1—C9—C8	120.3 (13)
C11—C10—C13	120.4 (11)	O1—C9—C10	120.4 (11)
C9—C10—C13	121.1 (11)	C8—C9—C10	119.3 (12)
C2—C3—C4	119.8 (14)	C8—C7—C12	120.8 (14)
C2—C3—Br1	120.4 (11)	C8—C7—H7A	119.6
C4—C3—Br1	119.7 (11)	C12—C7—H7A	119.6
C12—C11—C10	122.9 (13)	C9—O1—H1	109.5
C12—C11—H11A	118.6	C1—C6—C5	124.1 (13)
C10—C11—H11A	118.6	C1—C6—H6A	117.9
C4—C5—C6	117.9 (13)	C5—C6—H6A	117.9
C4—C5—N1	117.2 (12)	C3—C2—C1	120.5 (14)
C6—C5—N1	124.8 (13)	C3—C2—H2A	119.8
C9—C8—C7	121.2 (14)	C1—C2—H2A	119.8
C9—C8—H8A	119.4	C6—C1—C2	116.7 (13)
C7—C8—H8A	119.4	C6—C1—H1B	121.6
C11—C12—C7	116.5 (14)	C2—C1—H1B	121.6
C11—C12—H12A	121.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.599 (17)	149