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In the molecular structure of the title Schiff base, C
13H
10ClNO, the chlorophenyl ring and formimidoyl moiety are almost coplanar, and the dihedral angle between the planes of the phenol and chlorophenyl ring is 34.57 (9)°. The crystal structure is stabilized by intermolecular O—H
N hydrogen bonds, forming an infinite one-dimensional chain extending in the
b direction, with an O
N distance of 2.846 (2) Å.
Supporting information
CCDC reference: 234900
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.063
- wR factor = 0.193
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractomer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractomer Control Software; data reduction: TEXSAN (Molecular Structure Corporation,1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
4-[(4-chlorobenzylidene)-amino]-phenol
top
Crystal data top
C13H10ClNO | Dx = 1.380 Mg m−3 |
Mr = 231.67 | Mo Kα radiation, λ = 0.71069 Å |
Orthorhombic, Pbca | Cell parameters from 25 reflections |
a = 16.866 (3) Å | θ = 20.6–24.2° |
b = 12.704 (5) Å | µ = 0.32 mm−1 |
c = 10.410 (2) Å | T = 293 K |
V = 2230.6 (10) Å3 | Prismatic, yellow |
Z = 8 | 0.40 × 0.38 × 0.30 mm |
F(000) = 960 | |
Data collection top
Rigaku AFC-7S diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 2.4° |
Graphite monochromator | h = 0→23 |
ω/2θ scans | k = 0→17 |
3250 measured reflections | l = 0→14 |
3250 independent reflections | 3 standard reflections every 150 reflections |
2209 reflections with I > 2σ(I) | intensity decay: 0.5% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.193 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0975P)2 + 0.6308P] where P = (Fo2 + 2Fc2)/3 |
3250 reflections | (Δ/σ)max = 0.005 |
185 parameters | Δρmax = 0.76 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
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 | Uiso*/Ueq | |
Cl1 | 0.38455 (4) | 0.93228 (5) | 0.16354 (8) | 0.0780 (3) | |
N1 | 0.63405 (9) | 0.58122 (11) | −0.11516 (15) | 0.0412 (3) | |
O1 | 0.80338 (10) | 0.23262 (11) | −0.28930 (14) | 0.0549 (4) | |
C1 | 0.76179 (10) | 0.31491 (12) | −0.23989 (18) | 0.0421 (4) | |
C2 | 0.72864 (12) | 0.38553 (14) | −0.32672 (16) | 0.0440 (4) | |
C3 | 0.68722 (12) | 0.47236 (13) | −0.28280 (17) | 0.0435 (4) | |
C4 | 0.67652 (10) | 0.48927 (12) | −0.15165 (16) | 0.0391 (4) | |
C5 | 0.70966 (11) | 0.41764 (13) | −0.06484 (17) | 0.0418 (4) | |
C6 | 0.75225 (10) | 0.33153 (13) | −0.10876 (17) | 0.0416 (4) | |
C7 | 0.59178 (11) | 0.57966 (14) | −0.01360 (19) | 0.0432 (4) | |
C8 | 0.54422 (10) | 0.66934 (13) | 0.03053 (17) | 0.0407 (4) | |
C9 | 0.54219 (12) | 0.76471 (16) | −0.0355 (2) | 0.0516 (4) | |
C10 | 0.49398 (15) | 0.84590 (18) | 0.0060 (2) | 0.0604 (5) | |
C11 | 0.44741 (11) | 0.83150 (16) | 0.1139 (2) | 0.0504 (4) | |
C12 | 0.44841 (12) | 0.73825 (19) | 0.1809 (2) | 0.0545 (5) | |
C13 | 0.49705 (12) | 0.65748 (16) | 0.13874 (19) | 0.0501 (4) | |
H1 | 0.820 (2) | 0.195 (3) | −0.230 (3) | 0.089 (10)* | |
H2 | 0.7347 (12) | 0.3741 (18) | −0.416 (2) | 0.045 (5)* | |
H3 | 0.6622 (14) | 0.5227 (18) | −0.344 (2) | 0.045 (6)* | |
H5 | 0.7055 (13) | 0.4309 (16) | 0.025 (2) | 0.046 (6)* | |
H6 | 0.7796 (14) | 0.2840 (19) | −0.047 (2) | 0.059 (6)* | |
H7 | 0.5882 (15) | 0.521 (2) | 0.038 (2) | 0.054 (6)* | |
H9 | 0.5708 (18) | 0.775 (2) | −0.110 (3) | 0.081 (8)* | |
H10 | 0.4900 (18) | 0.911 (2) | −0.043 (3) | 0.072 (8)* | |
H12 | 0.4162 (15) | 0.7293 (19) | 0.250 (2) | 0.058 (6)* | |
H13 | 0.4987 (17) | 0.591 (2) | 0.186 (2) | 0.062 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0740 (4) | 0.0685 (4) | 0.0915 (5) | 0.0255 (3) | 0.0163 (3) | −0.0143 (3) |
N1 | 0.0440 (7) | 0.0330 (6) | 0.0467 (8) | 0.0002 (5) | 0.0003 (6) | −0.0022 (5) |
O1 | 0.0730 (10) | 0.0423 (7) | 0.0494 (7) | 0.0158 (6) | 0.0072 (6) | 0.0009 (6) |
C1 | 0.0475 (8) | 0.0327 (7) | 0.0460 (8) | 0.0006 (6) | 0.0032 (7) | −0.0004 (6) |
C2 | 0.0572 (10) | 0.0368 (8) | 0.0379 (8) | 0.0029 (7) | 0.0055 (7) | 0.0027 (6) |
C3 | 0.0527 (9) | 0.0360 (8) | 0.0417 (8) | 0.0026 (7) | 0.0008 (7) | 0.0053 (6) |
C4 | 0.0419 (8) | 0.0309 (7) | 0.0445 (8) | −0.0008 (6) | 0.0019 (6) | 0.0001 (6) |
C5 | 0.0468 (9) | 0.0391 (8) | 0.0395 (8) | −0.0005 (6) | −0.0018 (6) | −0.0007 (6) |
C6 | 0.0453 (8) | 0.0357 (7) | 0.0439 (8) | 0.0012 (6) | −0.0016 (7) | 0.0049 (6) |
C7 | 0.0417 (8) | 0.0375 (8) | 0.0505 (9) | −0.0005 (6) | −0.0004 (7) | −0.0002 (7) |
C8 | 0.0387 (8) | 0.0394 (8) | 0.0440 (8) | −0.0006 (6) | −0.0008 (6) | −0.0058 (6) |
C9 | 0.0556 (10) | 0.0462 (10) | 0.0529 (10) | 0.0081 (8) | 0.0087 (8) | 0.0035 (8) |
C10 | 0.0676 (13) | 0.0478 (10) | 0.0660 (12) | 0.0127 (9) | 0.0108 (10) | 0.0042 (9) |
C11 | 0.0449 (9) | 0.0502 (10) | 0.0562 (10) | 0.0074 (7) | 0.0005 (8) | −0.0121 (8) |
C12 | 0.0449 (9) | 0.0639 (12) | 0.0547 (10) | 0.0009 (9) | 0.0109 (8) | −0.0018 (9) |
C13 | 0.0488 (9) | 0.0464 (9) | 0.0551 (10) | −0.0001 (8) | 0.0060 (8) | 0.0023 (8) |
Geometric parameters (Å, º) top
Cl1—C11 | 1.741 (2) | C6—H6 | 0.99 (3) |
N1—C7 | 1.275 (2) | C7—C8 | 1.467 (2) |
N1—C4 | 1.422 (2) | C7—H7 | 0.92 (3) |
O1—C1 | 1.360 (2) | C8—C13 | 1.387 (2) |
O1—H1 | 0.83 (4) | C8—C9 | 1.394 (3) |
C1—C6 | 1.391 (3) | C9—C10 | 1.382 (3) |
C1—C2 | 1.391 (2) | C9—H9 | 0.92 (3) |
C2—C3 | 1.383 (3) | C10—C11 | 1.383 (3) |
C2—H2 | 0.94 (2) | C10—H10 | 0.97 (3) |
C3—C4 | 1.394 (2) | C11—C12 | 1.375 (3) |
C3—H3 | 1.00 (2) | C12—C13 | 1.385 (3) |
C4—C5 | 1.399 (2) | C12—H12 | 0.91 (3) |
C5—C6 | 1.386 (2) | C13—H13 | 0.98 (3) |
C5—H5 | 0.95 (2) | | |
| | | |
C7—N1—C4 | 119.4 (2) | N1—C7—H7 | 122.1 (15) |
C1—O1—H1 | 110 (2) | C8—C7—H7 | 114.3 (15) |
O1—C1—C6 | 123.2 (2) | C13—C8—C9 | 118.74 (17) |
O1—C1—C2 | 117.2 (2) | C13—C8—C7 | 118.91 (17) |
C6—C1—C2 | 119.57 (15) | C9—C8—C7 | 122.3 (2) |
C3—C2—C1 | 120.17 (16) | C10—C9—C8 | 120.60 (19) |
C3—C2—H2 | 120.2 (14) | C10—C9—H9 | 117.6 (18) |
C1—C2—H2 | 119.7 (14) | C8—C9—H9 | 121.7 (18) |
C2—C3—C4 | 120.80 (16) | C11—C10—C9 | 119.3 (2) |
C2—C3—H3 | 121.0 (13) | C11—C10—H10 | 120.1 (17) |
C4—C3—H3 | 118.2 (13) | C9—C10—H10 | 120.5 (17) |
C3—C4—C5 | 118.73 (16) | C12—C11—C10 | 121.28 (18) |
C3—C4—N1 | 116.97 (15) | C12—C11—Cl1 | 119.4 (2) |
C5—C4—N1 | 124.3 (2) | C10—C11—Cl1 | 119.31 (17) |
C6—C5—C4 | 120.48 (16) | C11—C12—C13 | 119.01 (18) |
C6—C5—H5 | 120.1 (13) | C11—C12—H12 | 120.1 (16) |
C4—C5—H5 | 119.3 (13) | C13—C12—H12 | 120.8 (16) |
C5—C6—C1 | 120.23 (15) | C12—C13—C8 | 121.10 (19) |
C5—C6—H6 | 120.5 (14) | C12—C13—H13 | 119.6 (16) |
C1—C6—H6 | 119.2 (14) | C8—C13—H13 | 119.3 (16) |
N1—C7—C8 | 123.6 (2) | | |
| | | |
O1—C1—C2—C3 | −178.45 (17) | N1—C7—C8—C13 | 176.64 (18) |
C6—C1—C2—C3 | 0.7 (3) | N1—C7—C8—C9 | −0.6 (3) |
C1—C2—C3—C4 | −1.4 (3) | C13—C8—C9—C10 | −0.1 (3) |
C2—C3—C4—C5 | 1.1 (3) | C7—C8—C9—C10 | 177.17 (19) |
C2—C3—C4—N1 | 179.24 (16) | C8—C9—C10—C11 | −0.2 (4) |
C7—N1—C4—C3 | 148.14 (18) | C9—C10—C11—C12 | 0.2 (4) |
C7—N1—C4—C5 | −33.8 (3) | C9—C10—C11—Cl1 | −178.14 (18) |
C3—C4—C5—C6 | −0.1 (3) | C10—C11—C12—C13 | −0.1 (3) |
N1—C4—C5—C6 | −178.05 (16) | Cl1—C11—C12—C13 | 178.30 (16) |
C4—C5—C6—C1 | −0.6 (3) | C11—C12—C13—C8 | −0.1 (3) |
O1—C1—C6—C5 | 179.43 (16) | C9—C8—C13—C12 | 0.2 (3) |
C2—C1—C6—C5 | 0.3 (3) | C7—C8—C13—C12 | −177.11 (18) |
C4—N1—C7—C8 | −178.41 (16) | | |
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