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The title chiral photochromic Schiff base compound, C15H14BrNO, was synthesized from (R)-1-phenyl­ethyl­amine and 5-bromo­salicylaldehyde. The mol­ecule is the phenol–imine tautomer, the C=N and N—C bond distances being 1.261 (7) and 1.482 (7) Å, respectively. There is an intra­molecular O—H...N hydrogen bond with an O...N distance of 2.593 (7) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034891/ob2054sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034891/ob2054Isup2.hkl
Contains datablock I

CCDC reference: 624941

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.046
  • wR factor = 0.128
  • Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.113 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level G 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 27.56 From the CIF: _reflns_number_total 1743 Count of symmetry unique reflns 1753 Completeness (_total/calc) 99.43% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R
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 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(R)-4-bromo-2-[(1-phenylethyl)iminomethyl]phenol top
Crystal data top
C15H14BrNOF(000) = 616
Mr = 304.18Dx = 1.467 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 24 reflections
a = 20.955 (8) Åθ = 10.0–13.8°
b = 5.795 (3) ŵ = 2.97 mm1
c = 14.611 (7) ÅT = 297 K
β = 129.07 (3)°Prism, green
V = 1377.5 (13) Å30.30 × 0.30 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
1425 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode generatorRint = 0.113
Graphite monochromatorθmax = 27.6°, θmin = 2.5°
ω–2θ scansh = 1026
Absorption correction: ψ scan
(North et al., 1968)
k = 07
Tmin = 0.396, Tmax = 0.552l = 1814
1907 measured reflections3 standard reflections every 150 reflections
1743 independent reflections intensity decay: 1.4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.0737P)2 + 0.6987P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1743 reflectionsΔρmax = 0.73 e Å3
164 parametersΔρmin = 0.49 e Å3
1 restraintAbsolute structure: Flack (1983), no Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (2)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.41682 (3)0.53391 (18)0.26315 (5)0.0735 (3)
O10.0909 (2)0.0538 (10)0.0179 (4)0.0722 (11)
H1A0.05340.13390.03590.087*
N10.0233 (3)0.4037 (8)0.1245 (4)0.0537 (10)
C10.1626 (4)0.1602 (10)0.0688 (5)0.0546 (11)
C20.2339 (4)0.0600 (15)0.1653 (6)0.0665 (15)
H2A0.23110.08200.19230.079*
C30.3094 (4)0.1662 (11)0.2228 (5)0.0628 (13)
H3A0.35700.09670.28790.076*
C40.3134 (3)0.3775 (11)0.1822 (5)0.0545 (12)
C50.2436 (3)0.4829 (9)0.0853 (4)0.0525 (13)
H5A0.24730.62400.05850.060*
C60.1675 (3)0.3757 (10)0.0278 (4)0.0491 (10)
C70.0935 (3)0.4913 (9)0.0721 (4)0.0525 (13)
H7A0.09830.63250.09760.060*
C80.0494 (3)0.5287 (15)0.2258 (4)0.0565 (10)
H8A0.03090.66860.24080.066*
C90.1028 (4)0.5971 (13)0.1937 (6)0.0722 (19)
H9A0.07120.68870.12320.088*
H9B0.12210.46080.18060.088*
H9C0.14890.68510.25690.088*
C100.0915 (3)0.3713 (11)0.3323 (5)0.0567 (12)
C110.0850 (5)0.4105 (15)0.4202 (6)0.0746 (17)
H11A0.05650.53960.41500.092*
C120.1192 (6)0.265 (2)0.5129 (7)0.100 (3)
H12A0.11450.29690.57080.121*
C130.1609 (6)0.071 (2)0.5222 (6)0.099 (3)
H13A0.18270.03180.58450.115*
C140.1696 (4)0.031 (2)0.4378 (6)0.0879 (18)
H14A0.19990.09520.44500.106*
C150.1339 (4)0.1760 (13)0.3433 (6)0.0720 (16)
H15A0.13810.14250.28510.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0591 (3)0.0747 (4)0.0810 (4)0.0109 (4)0.0415 (3)0.0138 (4)
O10.064 (2)0.053 (2)0.082 (2)0.005 (2)0.0376 (19)0.018 (3)
N10.060 (2)0.044 (2)0.056 (2)0.000 (2)0.036 (2)0.002 (2)
C10.062 (3)0.042 (3)0.060 (3)0.001 (2)0.038 (2)0.004 (2)
C20.074 (3)0.043 (3)0.078 (3)0.004 (3)0.046 (3)0.002 (3)
C30.058 (3)0.054 (3)0.062 (3)0.007 (3)0.031 (3)0.006 (3)
C40.057 (3)0.054 (3)0.053 (3)0.001 (2)0.035 (2)0.007 (2)
C50.064 (3)0.042 (3)0.060 (3)0.001 (2)0.043 (2)0.002 (2)
C60.059 (3)0.042 (2)0.053 (3)0.000 (2)0.038 (2)0.002 (2)
C70.063 (3)0.047 (4)0.054 (2)0.001 (2)0.040 (2)0.004 (2)
C80.063 (2)0.045 (2)0.057 (2)0.000 (4)0.036 (2)0.008 (3)
C90.074 (3)0.076 (5)0.067 (3)0.011 (3)0.045 (3)0.001 (3)
C100.059 (3)0.054 (3)0.051 (3)0.012 (3)0.032 (2)0.010 (2)
C110.085 (4)0.076 (4)0.069 (3)0.021 (4)0.052 (3)0.014 (3)
C120.132 (7)0.104 (7)0.068 (4)0.049 (6)0.065 (5)0.025 (5)
C130.103 (5)0.092 (8)0.056 (3)0.035 (6)0.029 (3)0.001 (4)
C140.085 (4)0.062 (3)0.078 (4)0.000 (5)0.033 (3)0.000 (5)
C150.074 (4)0.062 (4)0.068 (3)0.006 (3)0.039 (3)0.004 (3)
Geometric parameters (Å, º) top
Br1—C41.921 (6)C8—C101.517 (9)
O1—C11.335 (7)C8—H8A0.9800
O1—H1A0.8199C9—H9A0.9600
N1—C71.261 (7)C9—H9B0.9600
N1—C81.482 (7)C9—H9C0.9600
C1—C21.379 (9)C10—C151.384 (10)
C1—C61.416 (8)C10—C111.392 (9)
C2—C31.384 (10)C11—C121.355 (13)
C2—H2A0.9300C11—H11A0.9300
C3—C41.385 (9)C12—C131.379 (16)
C3—H3A0.9300C12—H12A0.9300
C4—C51.381 (8)C13—C141.376 (14)
C5—C61.395 (7)C13—H13A0.9300
C5—H5A0.9300C14—C151.367 (12)
C6—C71.459 (7)C14—H14A0.9300
C7—H7A0.9300C15—H15A0.9300
C8—C91.514 (9)
C1—O1—H1A109.5C9—C8—H8A109.0
C7—N1—C8118.8 (5)C10—C8—H8A109.0
O1—C1—C2119.2 (5)C8—C9—H9A109.5
O1—C1—C6121.9 (5)C8—C9—H9B109.5
C2—C1—C6118.9 (6)H9A—C9—H9B109.5
C1—C2—C3121.4 (7)C8—C9—H9C109.5
C1—C2—H2A119.3H9A—C9—H9C109.5
C3—C2—H2A119.3H9B—C9—H9C109.5
C4—C3—C2119.1 (6)C15—C10—C11117.1 (6)
C4—C3—H3A120.4C15—C10—C8121.8 (5)
C2—C3—H3A120.4C11—C10—C8121.0 (6)
C5—C4—C3121.3 (5)C12—C11—C10121.5 (8)
C5—C4—Br1118.5 (4)C12—C11—H11A119.2
C3—C4—Br1120.1 (5)C10—C11—H11A119.2
C4—C5—C6119.3 (5)C11—C12—C13120.7 (8)
C4—C5—H5A120.3C11—C12—H12A119.7
C6—C5—H5A120.3C13—C12—H12A119.7
C5—C6—C1119.9 (5)C14—C13—C12118.8 (9)
C5—C6—C7119.2 (5)C14—C13—H13A120.6
C1—C6—C7120.9 (5)C12—C13—H13A120.6
N1—C7—C6121.3 (5)C15—C14—C13120.4 (10)
N1—C7—H7A119.3C15—C14—H14A119.8
C6—C7—H7A119.3C13—C14—H14A119.8
N1—C8—C9108.2 (4)C14—C15—C10121.5 (7)
N1—C8—C10107.4 (6)C14—C15—H15A119.3
C9—C8—C10114.2 (5)C10—C15—H15A119.3
N1—C8—H8A109.0
O1—C1—C2—C3178.4 (6)C1—C6—C7—N10.3 (7)
C6—C1—C2—C30.4 (9)C7—N1—C8—C9115.9 (6)
C1—C2—C3—C40.1 (10)C7—N1—C8—C10120.4 (5)
C2—C3—C4—C50.4 (9)N1—C8—C10—C1571.2 (7)
C2—C3—C4—Br1178.0 (5)C9—C8—C10—C1548.7 (8)
C3—C4—C5—C60.7 (7)N1—C8—C10—C11105.0 (6)
Br1—C4—C5—C6177.8 (4)C9—C8—C10—C11135.1 (7)
C4—C5—C6—C10.4 (7)C15—C10—C11—C120.6 (10)
C4—C5—C6—C7177.9 (5)C8—C10—C11—C12176.9 (7)
O1—C1—C6—C5178.7 (5)C10—C11—C12—C130.9 (12)
C2—C1—C6—C50.1 (8)C11—C12—C13—C142.2 (13)
O1—C1—C6—C70.4 (8)C12—C13—C14—C153.3 (14)
C2—C1—C6—C7178.4 (6)C13—C14—C15—C103.1 (13)
C8—N1—C7—C6179.6 (5)C11—C10—C15—C141.6 (10)
C5—C6—C7—N1178.0 (5)C8—C10—C15—C14178.0 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.811.882.593 (7)146
 

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