Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049094/hb2572sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049094/hb2572Isup2.hkl |
CCDC reference: 667351
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
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%.
The H atoms were placed in calculated positions (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
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.
For related literature, see: Ma et al. (2007).
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).
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). |
C15H14BrNO | Z = 2 |
Mr = 304.17 | F(000) = 308 |
Triclinic, P1 | Dx = 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 |
Bruker SMART CCD diffractometer | 4908 independent reflections |
Radiation source: fine-focus sealed tube | 2957 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
ω scans | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −10→10 |
Tmin = 0.858, Tmax = 0.913 | k = −11→11 |
7771 measured reflections | l = −13→12 |
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(Fo2) + (0.1355P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4908 reflections | Δρmax = 0.67 e Å−3 |
325 parameters | Δρmin = −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) |
C15H14BrNO | γ = 70.393 (2)° |
Mr = 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)° |
Bruker SMART CCD diffractometer | 4908 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 2957 reflections with I > 2σ(I) |
Tmin = 0.858, Tmax = 0.913 | Rint = 0.058 |
7771 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.222 | Δρmax = 0.67 e Å−3 |
S = 1.03 | Δρmin = −0.38 e Å−3 |
4908 reflections | Absolute structure: Flack (1983), 1589 Friedel pairs |
325 parameters | Absolute structure parameter: −0.125 (19) |
3 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.858, 0.913 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7771, 4908, 2957 |
Rint | 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 |
Δρmax, Δρmin (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).
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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.