N-(4-Bromo­benzyl­idene)-4-ethoxy­aniline

Ma, R.; Ma, R.; Hou, Y.; Yong, X.; Bao, F.

doi:10.1107/S1600536807049094

N-(4-Bromobenzylidene)-4-ethoxyaniline

R. Ma, R. Ma, Y. Hou, X. Yong and F. Bao

In the title compound, C₁₅H₁₄BrNO, there are two molecules in the asymmetric unit with different conformations, as illustrated by the dihedral angles between the aromatic ring planes of 17.4 (5) and 9.7 (5)°.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049094/hb2572sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049094/hb2572Isup2.hkl Contains datablock I

CCDC reference: 667351

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.015 Å
R factor = 0.059
wR factor = 0.222
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         86 PerFi

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.91
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         15

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      0.912
            Tmax scaled      0.833 Tmin scaled      0.783
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           28.23
           From the CIF: _reflns_number_total               4908
           Count of symmetry unique reflns         3319
           Completeness (_total/calc)            147.88%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1589
           Fraction of Friedel pairs measured     0.479
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

   2 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
   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

Comment top

As part of our onging studies of Schiff bases (Ma et al., 2007) we now report the synthesis and structure of the title compound, (I), arising from the condensation of p-bromobenzaldehyde with 4-ethoxyaniline.

There are two molecules in the asymmetric unit of (I) (Fig. 1) with different conformations, as quantified by the dihedral angles between the armoatic ring planes of 17.4 (5)° and 9.7 (5)° for the C1 and C16 molecules, respectively.

Related literature top

For related literature, see: Ma et al. (2007).

Experimental top

p-Ethoxyaniline (2.50 g, 18.2 mmol) and p-bromobenzaldehyde (3.33 g, 18.0 mmol) were dissolved in ethanol (35 ml) along with 1 ml of formic acid. The solution was refluxed for 8 h. Removal of the solvent followed by recrystallization from a 1:1 v/v ethanol/dichloromethane mixture (35 ml) gave the title compound in about 70% yield. Colourless blocks of (I) were grown from ethanol. Elemental analysis calculated for C₁₅H₁₄Br₁N₁O₁: C 59.23, H 4.64, N 4.60%; found: C 58.98, H 4.61, N 4.72%.

Structure description top

For related literature, see: Ma et al. (2007).

Computing details top

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

Figures top

Fig. 1. Vew of the molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level (H atoms are drawn as spheres of arbitrary radius).

N-(4-Bromobenzylidene)-4-ethoxyaniline top

Crystal data top

C₁₅H₁₄BrNO	Z = 2
M_r = 304.17	F(000) = 308
Triclinic, P1	D_x = 1.506 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0793 (10) Å	Cell parameters from 2326 reflections
b = 8.5700 (11) Å	θ = 2.5–24.4°
c = 10.3148 (13) Å	µ = 3.05 mm⁻¹
α = 88.390 (2)°	T = 293 K
β = 85.615 (2)°	Block, colourless
γ = 70.393 (2)°	0.10 × 0.10 × 0.06 mm
V = 670.81 (15) Å³

Data collection top

Bruker SMART CCD diffractometer	4908 independent reflections
Radiation source: fine-focus sealed tube	2957 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ω scans	θ_max = 28.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
T_min = 0.858, T_max = 0.913	k = −11→11
7771 measured reflections	l = −13→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.222	w = 1/[σ²(F_o²) + (0.1355P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4908 reflections	Δρ_max = 0.67 e Å⁻³
325 parameters	Δρ_min = −0.38 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1589 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.125 (19)

Crystal data top

C₁₅H₁₄BrNO	γ = 70.393 (2)°
M_r = 304.17	V = 670.81 (15) Å³
Triclinic, P1	Z = 2
a = 8.0793 (10) Å	Mo Kα radiation
b = 8.5700 (11) Å	µ = 3.05 mm⁻¹
c = 10.3148 (13) Å	T = 293 K
α = 88.390 (2)°	0.10 × 0.10 × 0.06 mm
β = 85.615 (2)°

Data collection top

Bruker SMART CCD diffractometer	4908 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2957 reflections with I > 2σ(I)
T_min = 0.858, T_max = 0.913	R_int = 0.058
7771 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.222	Δρ_max = 0.67 e Å⁻³
S = 1.03	Δρ_min = −0.38 e Å⁻³
4908 reflections	Absolute structure: Flack (1983), 1589 Friedel pairs
325 parameters	Absolute structure parameter: −0.125 (19)
3 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	−0.22363 (11)	−0.10639 (12)	0.46304 (9)	0.0755 (5)
Br2	0.24929 (11)	0.45540 (12)	0.45854 (9)	0.0746 (5)
C7	0.2988 (14)	0.1021 (14)	0.7530 (13)	0.051 (3)
H7A	0.4005	0.1089	0.7082	0.061*
C2	0.0784 (14)	−0.0185 (13)	0.4837 (10)	0.058 (3)
H2A	0.0932	−0.0340	0.3942	0.070*
C22	0.8171 (15)	0.5733 (14)	0.7634 (10)	0.044 (3)
H22A	0.9347	0.5187	0.7372	0.053*
C9	0.5246 (13)	0.2394 (11)	0.8860 (9)	0.046 (2)
H9A	0.5330	0.2558	0.7966	0.055*
C8	0.4014 (12)	0.1767 (12)	0.9370 (10)	0.044 (2)
C24	1.0866 (13)	0.5919 (12)	0.9241 (11)	0.050 (2)
H24A	1.1293	0.5046	0.8655	0.060*
N2	0.7844 (11)	0.6655 (10)	0.8580 (8)	0.0442 (18)
C21	0.3703 (14)	0.6083 (11)	0.6459 (9)	0.047 (2)
H21A	0.2520	0.6685	0.6654	0.056*
O1	1.2500 (11)	0.7989 (10)	1.1729 (8)	0.051 (2)
C28	0.8533 (12)	0.8233 (11)	1.0187 (9)	0.044 (2)
H28A	0.7351	0.8890	1.0263	0.053*
C17	0.5989 (12)	0.4026 (12)	0.5183 (10)	0.053 (2)
H17A	0.6299	0.3270	0.4503	0.064*
C6	−0.0879 (12)	−0.0166 (12)	0.6807 (9)	0.047 (2)
H6A	−0.1858	−0.0312	0.7259	0.057*
O2	0.7400 (10)	0.2858 (10)	1.1812 (7)	0.048 (2)
C10	0.6409 (13)	0.2811 (11)	0.9618 (10)	0.048 (2)
H10A	0.7214	0.3268	0.9223	0.058*
C25	1.1941 (15)	0.6240 (13)	1.0027 (12)	0.058 (3)
H25A	1.3106	0.5540	1.0005	0.070*
C13	0.3944 (13)	0.1517 (10)	1.0740 (8)	0.042 (2)
H13A	0.3115	0.1082	1.1126	0.051*
C4	0.1760 (13)	0.0553 (12)	0.6805 (11)	0.048 (2)
C23	0.9093 (15)	0.6902 (12)	0.9303 (11)	0.046 (3)
C27	0.9710 (12)	0.8582 (10)	1.0945 (8)	0.043 (2)
H27A	0.9325	0.9502	1.1488	0.052*
C26	1.1393 (15)	0.7604 (12)	1.0900 (10)	0.042 (2)
N1	0.2768 (12)	0.1336 (10)	0.8706 (8)	0.0482 (19)
C11	0.6364 (15)	0.2543 (11)	1.0960 (10)	0.041 (2)
C15	0.9732 (15)	0.3761 (15)	1.2359 (10)	0.058 (3)
H15A	1.0599	0.4229	1.2012	0.088*
H15B	1.0309	0.2702	1.2742	0.088*
H15C	0.8965	0.4487	1.3009	0.088*
C30	1.5091 (16)	0.7643 (12)	1.2688 (9)	0.054 (3)
H30A	1.6314	0.6997	1.2725	0.082*
H30B	1.4484	0.7624	1.3523	0.082*
H30C	1.4980	0.8765	1.2459	0.082*
C3	0.1990 (14)	0.0285 (13)	0.5487 (10)	0.057 (2)
H3A	0.2965	0.0420	0.5021	0.068*
C14	0.8666 (13)	0.3548 (12)	1.1279 (9)	0.051 (2)
H14A	0.8084	0.4612	1.0882	0.061*
H14B	0.9433	0.2821	1.0615	0.061*
C19	0.6839 (15)	0.5442 (12)	0.6899 (9)	0.044 (2)
C20	0.5079 (13)	0.6343 (12)	0.7134 (10)	0.046 (2)
H20A	0.4764	0.7165	0.7766	0.056*
C29	1.4326 (13)	0.6951 (14)	1.1719 (10)	0.052 (2)
H29A	1.4922	0.6965	1.0868	0.062*
H29B	1.4422	0.5817	1.1938	0.062*
C18	0.7266 (13)	0.4298 (12)	0.5881 (11)	0.057 (3)
H18A	0.8445	0.3701	0.5665	0.068*
C1	−0.0611 (15)	−0.0413 (13)	0.5533 (11)	0.057 (3)
C12	0.5048 (12)	0.1892 (11)	1.1491 (9)	0.043 (2)
H12A	0.4949	0.1722	1.2384	0.051*
C5	0.0303 (13)	0.0308 (12)	0.7459 (11)	0.049 (2)
H5A	0.0119	0.0466	0.8354	0.059*
C16	0.4229 (14)	0.4914 (12)	0.5527 (9)	0.048 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0730 (10)	0.0956 (11)	0.0752 (9)	−0.0457 (10)	−0.0265 (8)	−0.0109 (9)
Br2	0.0686 (10)	0.0923 (11)	0.0770 (9)	−0.0416 (9)	−0.0176 (7)	−0.0163 (9)
C7	0.029 (5)	0.053 (6)	0.070 (8)	−0.008 (4)	−0.021 (5)	−0.025 (5)
C2	0.060 (6)	0.074 (7)	0.048 (6)	−0.031 (5)	0.002 (5)	−0.020 (5)
C22	0.043 (6)	0.062 (6)	0.031 (6)	−0.020 (5)	−0.007 (5)	−0.002 (5)
C9	0.047 (6)	0.043 (5)	0.042 (6)	−0.008 (4)	−0.005 (5)	−0.001 (4)
C8	0.033 (5)	0.042 (5)	0.048 (6)	0.002 (4)	−0.007 (4)	−0.014 (4)
C24	0.038 (5)	0.040 (5)	0.068 (7)	−0.005 (4)	−0.008 (5)	−0.020 (5)
N2	0.040 (4)	0.044 (4)	0.051 (5)	−0.016 (4)	−0.005 (4)	−0.004 (4)
C21	0.054 (6)	0.048 (5)	0.039 (5)	−0.018 (4)	−0.003 (4)	0.008 (4)
O1	0.053 (5)	0.057 (4)	0.048 (4)	−0.023 (4)	−0.008 (4)	−0.017 (3)
C28	0.037 (5)	0.035 (5)	0.048 (5)	0.006 (4)	−0.006 (4)	−0.004 (4)
C17	0.041 (5)	0.055 (6)	0.065 (7)	−0.015 (4)	−0.010 (5)	−0.021 (5)
C6	0.032 (5)	0.068 (6)	0.048 (6)	−0.026 (4)	0.003 (4)	−0.012 (4)
O2	0.053 (5)	0.063 (4)	0.036 (4)	−0.028 (4)	−0.008 (3)	−0.008 (3)
C10	0.053 (6)	0.036 (5)	0.057 (6)	−0.015 (4)	−0.005 (5)	0.003 (4)
C25	0.045 (6)	0.037 (5)	0.082 (8)	0.005 (5)	−0.016 (6)	−0.019 (5)
C13	0.054 (6)	0.043 (5)	0.033 (5)	−0.022 (4)	−0.002 (4)	−0.002 (4)
C4	0.041 (5)	0.046 (5)	0.058 (6)	−0.013 (4)	−0.003 (5)	−0.014 (4)
C23	0.040 (6)	0.035 (5)	0.055 (7)	−0.004 (4)	−0.007 (5)	−0.004 (4)
C27	0.048 (5)	0.036 (4)	0.040 (5)	−0.007 (4)	0.000 (4)	−0.007 (4)
C26	0.042 (5)	0.041 (5)	0.040 (5)	−0.007 (4)	−0.008 (4)	−0.007 (4)
N1	0.053 (5)	0.050 (5)	0.042 (5)	−0.017 (4)	−0.003 (4)	−0.014 (4)
C11	0.052 (5)	0.028 (4)	0.037 (5)	−0.004 (4)	−0.003 (4)	0.000 (3)
C15	0.061 (7)	0.083 (8)	0.044 (6)	−0.040 (6)	−0.009 (5)	−0.002 (5)
C30	0.086 (8)	0.051 (6)	0.030 (5)	−0.025 (6)	−0.019 (5)	0.006 (4)
C3	0.059 (6)	0.068 (6)	0.053 (6)	−0.031 (5)	−0.003 (5)	−0.015 (5)
C14	0.048 (6)	0.060 (6)	0.049 (6)	−0.026 (5)	0.003 (5)	−0.002 (5)
C19	0.063 (7)	0.044 (5)	0.031 (5)	−0.024 (5)	0.000 (5)	−0.002 (4)
C20	0.043 (6)	0.048 (5)	0.047 (6)	−0.013 (4)	0.001 (5)	−0.018 (4)
C29	0.045 (6)	0.070 (7)	0.042 (6)	−0.020 (5)	−0.011 (5)	0.003 (5)
C18	0.043 (5)	0.052 (5)	0.075 (7)	−0.012 (4)	−0.005 (5)	−0.023 (5)
C1	0.054 (6)	0.053 (6)	0.065 (7)	−0.015 (5)	−0.025 (5)	−0.010 (5)
C12	0.046 (5)	0.049 (5)	0.031 (5)	−0.013 (4)	−0.001 (4)	−0.007 (4)
C5	0.043 (5)	0.057 (6)	0.052 (6)	−0.019 (4)	−0.005 (5)	−0.020 (5)
C16	0.062 (7)	0.054 (6)	0.041 (5)	−0.034 (5)	−0.018 (5)	0.007 (4)

Geometric parameters (Å, º) top

Br1—C1	1.900 (10)	C6—H6A	0.9300
Br2—C16	1.877 (9)	O2—C11	1.350 (12)
C7—N1	1.237 (14)	O2—C14	1.415 (12)
C7—C4	1.449 (13)	C10—C11	1.397 (14)
C7—H7A	0.9300	C10—H10A	0.9300
C2—C1	1.356 (16)	C25—C26	1.423 (14)
C2—C3	1.392 (13)	C25—H25A	0.9300
C2—H2A	0.9300	C13—C12	1.346 (12)
C22—N2	1.228 (13)	C13—H13A	0.9300
C22—C19	1.453 (14)	C4—C3	1.374 (15)
C22—H22A	0.9300	C4—C5	1.386 (14)
C9—C8	1.349 (15)	C27—C26	1.335 (14)
C9—C10	1.405 (13)	C27—H27A	0.9300
C9—H9A	0.9300	C11—C12	1.426 (14)
C8—N1	1.410 (12)	C15—C14	1.509 (13)
C8—C13	1.423 (13)	C15—H15A	0.9600
C24—C25	1.329 (15)	C15—H15B	0.9600
C24—C23	1.395 (14)	C15—H15C	0.9600
C24—H24A	0.9300	C30—C29	1.451 (13)
N2—C23	1.373 (13)	C30—H30A	0.9600
C21—C16	1.347 (14)	C30—H30B	0.9600
C21—C20	1.437 (14)	C30—H30C	0.9600
C21—H21A	0.9300	C3—H3A	0.9300
O1—C26	1.404 (12)	C14—H14A	0.9700
O1—C29	1.444 (13)	C14—H14B	0.9700
C28—C27	1.387 (12)	C19—C20	1.378 (14)
C28—C23	1.410 (14)	C19—C18	1.400 (14)
C28—H28A	0.9300	C20—H20A	0.9300
C17—C18	1.386 (13)	C29—H29A	0.9700
C17—C16	1.392 (14)	C29—H29B	0.9700
C17—H17A	0.9300	C18—H18A	0.9300
C6—C1	1.327 (14)	C12—H12A	0.9300
C6—C5	1.379 (13)	C5—H5A	0.9300

N1—C7—C4	124.2 (12)	O1—C26—C25	124.5 (11)
N1—C7—H7A	117.9	C7—N1—C8	122.0 (10)
C4—C7—H7A	117.9	O2—C11—C10	127.5 (9)
C1—C2—C3	118.9 (9)	O2—C11—C12	116.5 (8)
C1—C2—H2A	120.6	C10—C11—C12	116.0 (9)
C3—C2—H2A	120.6	C14—C15—H15A	109.5
N2—C22—C19	124.2 (11)	C14—C15—H15B	109.5
N2—C22—H22A	117.9	H15A—C15—H15B	109.5
C19—C22—H22A	117.9	C14—C15—H15C	109.5
C8—C9—C10	123.0 (9)	H15A—C15—H15C	109.5
C8—C9—H9A	118.5	H15B—C15—H15C	109.5
C10—C9—H9A	118.5	C29—C30—H30A	109.5
C9—C8—N1	127.6 (9)	C29—C30—H30B	109.5
C9—C8—C13	116.7 (9)	H30A—C30—H30B	109.5
N1—C8—C13	115.7 (9)	C29—C30—H30C	109.5
C25—C24—C23	119.5 (11)	H30A—C30—H30C	109.5
C25—C24—H24A	120.3	H30B—C30—H30C	109.5
C23—C24—H24A	120.3	C4—C3—C2	120.9 (10)
C22—N2—C23	124.6 (11)	C4—C3—H3A	119.5
C16—C21—C20	115.9 (9)	C2—C3—H3A	119.5
C16—C21—H21A	122.0	O2—C14—C15	108.5 (8)
C20—C21—H21A	122.0	O2—C14—H14A	110.0
C26—O1—C29	119.2 (8)	C15—C14—H14A	110.0
C27—C28—C23	121.3 (9)	O2—C14—H14B	110.0
C27—C28—H28A	119.4	C15—C14—H14B	110.0
C23—C28—H28A	119.4	H14A—C14—H14B	108.4
C18—C17—C16	118.3 (8)	C20—C19—C18	116.3 (10)
C18—C17—H17A	120.8	C20—C19—C22	121.2 (10)
C16—C17—H17A	120.8	C18—C19—C22	122.4 (10)
C1—C6—C5	119.6 (9)	C19—C20—C21	123.6 (9)
C1—C6—H6A	120.2	C19—C20—H20A	118.2
C5—C6—H6A	120.2	C21—C20—H20A	118.2
C11—O2—C14	116.0 (8)	O1—C29—C30	105.8 (9)
C11—C10—C9	120.5 (9)	O1—C29—H29A	110.6
C11—C10—H10A	119.8	C30—C29—H29A	110.6
C9—C10—H10A	119.8	O1—C29—H29B	110.6
C24—C25—C26	123.1 (11)	C30—C29—H29B	110.6
C24—C25—H25A	118.4	H29A—C29—H29B	108.7
C26—C25—H25A	118.4	C17—C18—C19	122.1 (9)
C12—C13—C8	121.7 (9)	C17—C18—H18A	119.0
C12—C13—H13A	119.1	C19—C18—H18A	119.0
C8—C13—H13A	119.1	C6—C1—C2	121.9 (10)
C3—C4—C5	117.4 (10)	C6—C1—Br1	119.8 (9)
C3—C4—C7	123.1 (10)	C2—C1—Br1	118.2 (8)
C5—C4—C7	119.5 (10)	C13—C12—C11	122.0 (8)
N2—C23—C24	124.9 (10)	C13—C12—H12A	119.0
N2—C23—C28	117.5 (9)	C11—C12—H12A	119.0
C24—C23—C28	117.6 (11)	C6—C5—C4	121.2 (10)
C26—C27—C28	120.3 (8)	C6—C5—H5A	119.4
C26—C27—H27A	119.8	C4—C5—H5A	119.4
C28—C27—H27A	119.8	C21—C16—C17	123.5 (9)
C27—C26—O1	117.5 (9)	C21—C16—Br2	117.8 (8)
C27—C26—C25	118.0 (10)	C17—C16—Br2	118.5 (7)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄BrNO
M_r	304.17
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.0793 (10), 8.5700 (11), 10.3148 (13)
α, β, γ (°)	88.390 (2), 85.615 (2), 70.393 (2)
V (Å³)	670.81 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.05
Crystal size (mm)	0.10 × 0.10 × 0.06

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.858, 0.913
No. of measured, independent and observed [I > 2σ(I)] reflections	7771, 4908, 2957
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.222, 1.03
No. of reflections	4908
No. of parameters	325
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.38
Absolute structure	Flack (1983), 1589 Friedel pairs
Absolute structure parameter	−0.125 (19)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

N-(4-Bromo­benzyl­idene)-4-ethoxy­aniline

Supporting information

Key indicators

checkCIF/PLATON results

N-(4-Bromobenzylidene)-4-ethoxyaniline