(E)-4-Iodo-2-[(phenyl­imino)­meth­yl]phenol

The title compound, C₁₃H₁₀INO, is not planar as the dihedral angle between the planes of the two aryl rings is 44.5 (9)°. The configuration about the central C=N bond is E, and there is an intra­molecular O—H...N hydrogen bond which generates an S(6) ring. The mol­ecular packing is stabilized by weak C—H...π inter­actions. The structure was refined as a two-component inversion twin.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.026 Å
• R factor = 0.080
• wR factor = 0.223
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT342_ALERT_3_B Low Bond Precision on  C-C Bonds ...............    0.02615 Ang.
PLAT971_ALERT_2_B Check Calcd Resid. Dens.  1.04A   From I1              2.79 eA-3

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.530
           From the CIF: _refine_ls_abs_structure_Flack_su    0.130
PLAT090_ALERT_3_C Poor Data / Parameter Ratio (Zmax > 18) ........       7.84 Note
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.37 Report
PLAT213_ALERT_2_C Atom C5              has ADP max/min Ratio .....        3.9 oblate
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT411_ALERT_2_C Short Inter H...H Contact  H10      ..H11      .       2.11 Ang.
                                             1-x,2-y,-1/2+z  =      2_674 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.951 Check
PLAT907_ALERT_2_C Flack x > 0.5, Structure Needs to be Inverted? .       0.53 Check
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          4 Check
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.88A   From I1              2.30 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         12 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          8 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.13 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      10.53 Why ?
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          2 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        148 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        99% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
  10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  13 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   8 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: APEX3 and SAINT (Bruker, 2016); data reduction: SAINT and XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2018); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-4-Iodo-2-[(phenylimino)methyl]phenol

Crystal data

C13H10INO	Dx = 1.830 Mg m^−3
Mr = 323.12	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 9900 reflections
a = 7.0848 (8) Å	θ = 2.9–30.8°
b = 26.422 (3) Å	µ = 2.71 mm^−1
c = 6.2664 (7) Å	T = 296 K
V = 1173.1 (2) Å^3	Plate, orange
Z = 4	0.30 × 0.25 × 0.15 mm
F(000) = 624

Data collection

Bruker Kappa APEX3 CMOS diffractometer	2057 independent reflections
Radiation source: fine-focus sealed tube	2043 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ω and φ scan	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −8→8
Tmin = 0.287, Tmax = 0.746	k = −31→31
13051 measured reflections	l = −7→7

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.080	w = 1/[σ^2(Fo^2) + (0.1256P)^2 + 10.5304P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.223	(Δ/σ)max < 0.001
S = 1.18	Δρmax = 2.90 e Å^−3
2057 reflections	Δρmin = −1.22 e Å^−3
146 parameters	Absolute structure: Refined as an inversion twin.
148 restraints	Absolute structure parameter: 0.53 (13)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a two-component inversion twin. C-bound H atoms were placed in geometrically idealized positions with C—H = 0.93 Å. The OH H1 atom was placed geometrically with O—H = 0.82 Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.528 (2)	0.7086 (7)	0.466 (3)	0.036 (3)
C2	0.557 (2)	0.6640 (6)	0.586 (3)	0.031 (3)
H2	0.598694	0.666661	0.725680	0.038*
C3	0.526 (2)	0.6174 (6)	0.503 (2)	0.027 (3)
C4	0.461 (2)	0.6133 (7)	0.289 (3)	0.035 (4)
H4	0.439214	0.581274	0.232509	0.042*
C5	0.429 (2)	0.6565 (6)	0.1556 (19)	0.034 (4)
H5	0.388597	0.653661	0.015024	0.040*
C6	0.465 (2)	0.7045 (7)	0.255 (2)	0.035 (3)
C7	0.551 (2)	0.7588 (8)	0.554 (4)	0.044 (4)
H7	0.595451	0.760351	0.693338	0.053*
N1	0.5206 (18)	0.7982 (6)	0.470 (3)	0.038 (3)
O1	0.445 (2)	0.7439 (6)	0.126 (3)	0.063 (5)
H1	0.478128	0.769632	0.188944	0.095*
C8	0.516 (2)	0.8464 (8)	0.565 (3)	0.043 (4)
C9	0.582 (3)	0.8877 (6)	0.444 (4)	0.052 (5)
H9	0.627478	0.883081	0.305929	0.062*
C10	0.577 (4)	0.9366 (9)	0.538 (5)	0.069 (7)
H10	0.628761	0.964479	0.468623	0.083*
C11	0.491 (3)	0.9414 (7)	0.738 (4)	0.063 (6)
H11	0.482026	0.973329	0.799836	0.076*
C12	0.420 (4)	0.9000 (8)	0.847 (5)	0.077 (7)
H12	0.363078	0.904559	0.979138	0.092*
C13	0.431 (2)	0.8520 (7)	0.760 (3)	0.049 (5)
H13	0.382080	0.824147	0.831719	0.059*
I1	0.54634 (16)	0.55120 (4)	0.6950 (5)	0.0477 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.036 (8)	0.039 (6)	0.034 (7)	−0.001 (5)	−0.011 (6)	0.005 (5)
C2	0.033 (8)	0.034 (6)	0.028 (7)	−0.005 (5)	−0.009 (6)	0.000 (5)
C3	0.026 (7)	0.034 (6)	0.021 (6)	−0.007 (5)	−0.008 (5)	−0.001 (5)
C4	0.038 (9)	0.043 (8)	0.024 (6)	−0.004 (6)	−0.009 (6)	−0.001 (6)
C5	0.044 (8)	0.052 (7)	0.004 (8)	0.000 (6)	−0.005 (5)	−0.001 (5)
C6	0.027 (7)	0.045 (7)	0.032 (7)	0.002 (6)	−0.008 (5)	0.000 (5)
C7	0.038 (10)	0.047 (6)	0.047 (10)	−0.003 (6)	−0.010 (7)	−0.006 (5)
N1	0.019 (6)	0.051 (7)	0.044 (8)	−0.002 (6)	−0.008 (6)	−0.001 (6)
O1	0.074 (11)	0.034 (8)	0.082 (14)	0.002 (7)	−0.015 (8)	0.005 (7)
C8	0.019 (7)	0.054 (9)	0.056 (10)	0.004 (7)	−0.009 (7)	0.015 (7)
C9	0.043 (10)	0.039 (7)	0.074 (13)	0.008 (7)	0.028 (9)	−0.002 (7)
C10	0.045 (11)	0.052 (9)	0.111 (17)	0.002 (10)	0.009 (12)	−0.027 (10)
C11	0.044 (9)	0.039 (8)	0.106 (18)	0.008 (7)	0.003 (12)	−0.031 (9)
C12	0.052 (12)	0.058 (9)	0.120 (18)	0.009 (9)	0.009 (12)	−0.012 (10)
C13	0.020 (7)	0.052 (8)	0.074 (13)	−0.009 (7)	0.014 (7)	0.003 (7)
I1	0.0529 (8)	0.0357 (7)	0.0545 (8)	0.0010 (4)	−0.0052 (8)	0.0067 (8)

Geometric parameters (Å, º)

C1—C6	1.402 (18)	N1—C8	1.41 (3)
C1—C2	1.412 (19)	O1—H1	0.8200
C1—C7	1.44 (3)	C8—C13	1.37 (2)
C2—C3	1.353 (19)	C8—C9	1.41 (2)
C2—H2	0.9300	C9—C10	1.42 (2)
C3—C4	1.421 (19)	C9—H9	0.9300
C3—I1	2.130 (16)	C10—C11	1.40 (2)
C4—C5	1.431 (19)	C10—H10	0.9300
C4—H4	0.9300	C11—C12	1.38 (2)
C5—C6	1.433 (19)	C11—H11	0.9300
C5—H5	0.9300	C12—C13	1.38 (2)
C6—O1	1.32 (2)	C12—H12	0.9300
C7—N1	1.19 (3)	C13—H13	0.9300
C7—H7	0.9300
C6—C1—C2	118.9 (17)	C7—N1—C8	127.6 (19)
C6—C1—C7	117.9 (17)	C6—O1—H1	109.5
C2—C1—C7	123.2 (16)	C13—C8—N1	119.1 (17)
C3—C2—C1	122.1 (15)	C13—C8—C9	123 (2)
C3—C2—H2	119.0	N1—C8—C9	117.5 (17)
C1—C2—H2	119.0	C8—C9—C10	118 (2)
C2—C3—C4	119.0 (15)	C8—C9—H9	120.9
C2—C3—I1	121.2 (11)	C10—C9—H9	120.9
C4—C3—I1	119.6 (12)	C11—C10—C9	118 (2)
C3—C4—C5	122.7 (15)	C11—C10—H10	121.1
C3—C4—H4	118.7	C9—C10—H10	121.1
C5—C4—H4	118.7	C12—C11—C10	122 (2)
C4—C5—C6	115.2 (13)	C12—C11—H11	119.1
C4—C5—H5	122.4	C10—C11—H11	119.1
C6—C5—H5	122.4	C13—C12—C11	121 (2)
O1—C6—C1	123.1 (17)	C13—C12—H12	119.7
O1—C6—C5	114.5 (14)	C11—C12—H12	119.7
C1—C6—C5	122.2 (16)	C8—C13—C12	118 (2)
N1—C7—C1	128 (2)	C8—C13—H13	120.8
N1—C7—H7	116.0	C12—C13—H13	120.8
C1—C7—H7	116.0
C6—C1—C2—C3	0 (3)	C6—C1—C7—N1	1 (3)
C7—C1—C2—C3	176.9 (17)	C2—C1—C7—N1	−175.8 (19)
C1—C2—C3—C4	0 (2)	C1—C7—N1—C8	169.5 (17)
C1—C2—C3—I1	−174.3 (13)	C7—N1—C8—C13	−42 (3)
C2—C3—C4—C5	0 (2)	C7—N1—C8—C9	145 (2)
I1—C3—C4—C5	174.8 (13)	C13—C8—C9—C10	7 (3)
C3—C4—C5—C6	−1 (2)	N1—C8—C9—C10	180 (2)
C2—C1—C6—O1	−175.6 (16)	C8—C9—C10—C11	−6 (4)
C7—C1—C6—O1	7 (3)	C9—C10—C11—C12	2 (4)
C2—C1—C6—C5	0 (3)	C10—C11—C12—C13	0 (4)
C7—C1—C6—C5	−177.3 (16)	N1—C8—C13—C12	−177 (2)
C4—C5—C6—O1	176.3 (16)	C9—C8—C13—C12	−4 (3)
C4—C5—C6—C1	1 (2)	C11—C12—C13—C8	1 (4)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C1–C6 benzene ring and the C8–C13 phenyl ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.94	2.64 (2)	143
C5—H5···Cg1^i	0.93	2.86	3.476 (15)	125
C9—H9···Cg2^ii	0.93	2.81	3.48 (2)	129
C12—H12···Cg2^iii	0.93	2.82	3.55 (3)	136

Symmetry codes: (i) x+1/2, −y, z−1; (ii) x+3/2, −y, z−1; (iii) x+1/2, −y, z.