2-[(4-Chloro­phen­yl)imino]-1,2-di­phenyl­ethanone

The title Schiff base, C₂₀H₁₄ClNO, obtained from the reaction of 4-chloro aniline with benzil, has an approximate T shape. The dihedral angle between the phenyl rings of the benzil unit is 74.14 (15)°. The extended structure features C—H...O hydrogen bonds.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 94%
• R factor = 0.062
• wR factor = 0.186
• Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT043_ALERT_1_C Calculated and Reported Mol. Weight Differ by ..       1.01 Check
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...     Please Check

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C20 H15 Cl1 N1 O1
            Atom count from _chemical_formula_moiety:C20 H14 Cl1 N1 O1
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C20 H15 Cl1 N1 O1
            Atom count from the _atom_site data:  C20 H14 Cl1 N1 O1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C20 H15 Cl N O
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         80.00     80.00    0.00
           H         60.00     56.00    4.00
           Cl         4.00      4.00    0.00
           N          4.00      4.00    0.00
           O          4.00      4.00    0.00
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3       ..O1       .       2.67 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H9       ..O1       .       2.64 Ang.
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        556 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.4 Low
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
   0 ALERT level B = A potentially serious problem, consider carefully
   3 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

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

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-[(4-Chlorophenyl)imino]-1,2-diphenylethanone

Crystal data

C20H14ClNO	F(000) = 668
Mr = 320.78	Dx = 1.337 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0982 (12) Å	Cell parameters from 3987 reflections
b = 8.2447 (11) Å	θ = 4.3–29.1°
c = 19.365 (3) Å	µ = 0.24 mm^−1
β = 98.592 (12)°	T = 293 K
V = 1594.2 (4) Å^3	Block, clear pinkish yellow
Z = 4	0.20 × 0.17 × 0.12 mm

Data collection

Xcalibur, Atlas, Gemini ultra diffractometer	2805 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	Rint = 0.045
ω scans	θmax = 29.9°, θmin = 2.7°
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2018)	h = −13→14
Tmin = 0.968, Tmax = 0.974	k = −11→11
13558 measured reflections	l = −23→26
4026 independent reflections

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)] = 0.062	w = 1/[σ^2(Fo^2) + (0.0695P)^2 + 1.2547P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.186	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.38 e Å^−3
4026 reflections	Δρmin = −0.58 e Å^−3
209 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0115 (19)

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. H-atom treatment: Fixed U_iso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)

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

	x	y	z	Uiso*/Ueq
C1	0.8370 (2)	0.8256 (3)	0.40271 (13)	0.0317 (5)
C2	0.7484 (3)	0.9348 (3)	0.42442 (13)	0.0329 (5)
H2	0.773837	0.997474	0.464122	0.040*
C3	0.6214 (3)	0.9505 (3)	0.38673 (13)	0.0318 (5)
H3	0.561128	1.023849	0.401135	0.038*
C4	0.5837 (2)	0.8566 (3)	0.32725 (12)	0.0291 (5)
C5	0.6759 (2)	0.7494 (3)	0.30579 (13)	0.0335 (6)
H5	0.652069	0.688099	0.265528	0.040*
C6	0.8023 (2)	0.7329 (3)	0.34361 (13)	0.0330 (5)
H6	0.863287	0.660176	0.329374	0.040*
C7	0.3486 (2)	0.8532 (3)	0.30665 (13)	0.0289 (5)
C8	0.2203 (2)	0.8607 (3)	0.25828 (13)	0.0322 (5)
C9	0.1038 (3)	0.9201 (4)	0.27901 (15)	0.0402 (6)
H9	0.104682	0.955946	0.324621	0.048*
C10	−0.0139 (3)	0.9263 (4)	0.23202 (17)	0.0480 (8)
H10	−0.091026	0.969215	0.245795	0.058*
C11	−0.0170 (3)	0.8691 (4)	0.16500 (17)	0.0521 (8)
H11	−0.096307	0.872138	0.133672	0.062*
C12	0.0979 (3)	0.8075 (4)	0.14449 (18)	0.0547 (8)
H12	0.095682	0.767683	0.099394	0.066*
C13	0.2163 (3)	0.8044 (4)	0.19061 (15)	0.0458 (7)
H13	0.293727	0.764354	0.176137	0.055*
C14	0.3371 (2)	0.8150 (3)	0.38222 (12)	0.0292 (5)
C15	0.3471 (2)	0.6436 (3)	0.40449 (12)	0.0268 (5)
C16	0.3846 (2)	0.5223 (3)	0.36134 (12)	0.0306 (5)
H16	0.403267	0.548117	0.317048	0.037*
C17	0.3940 (3)	0.3635 (3)	0.38435 (14)	0.0359 (6)
H17	0.420029	0.282786	0.355635	0.043*
C18	0.3652 (3)	0.3243 (3)	0.44943 (14)	0.0377 (6)
H18	0.370854	0.216977	0.464414	0.045*
C19	0.3277 (3)	0.4438 (3)	0.49268 (14)	0.0363 (6)
H19	0.308420	0.416916	0.536746	0.044*
C20	0.3191 (2)	0.6030 (3)	0.47047 (12)	0.0311 (5)
H20	0.294378	0.683342	0.499741	0.037*
Cl1	0.99595 (7)	0.80122 (10)	0.45011 (4)	0.0468 (3)
N1	0.4585 (2)	0.8715 (3)	0.28342 (10)	0.0312 (5)
O1	0.31698 (19)	0.9261 (2)	0.42112 (10)	0.0386 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0287 (12)	0.0394 (13)	0.0268 (12)	−0.0027 (10)	0.0034 (9)	0.0037 (10)
C2	0.0341 (13)	0.0343 (13)	0.0306 (12)	−0.0052 (11)	0.0054 (10)	−0.0028 (10)
C3	0.0315 (12)	0.0310 (12)	0.0339 (13)	0.0012 (10)	0.0081 (10)	−0.0001 (10)
C4	0.0277 (12)	0.0333 (12)	0.0261 (11)	−0.0009 (10)	0.0036 (9)	0.0052 (9)
C5	0.0303 (12)	0.0443 (14)	0.0262 (12)	0.0002 (11)	0.0047 (10)	−0.0041 (10)
C6	0.0273 (12)	0.0423 (14)	0.0299 (12)	0.0022 (11)	0.0063 (10)	−0.0026 (10)
C7	0.0305 (12)	0.0253 (11)	0.0310 (12)	0.0026 (10)	0.0051 (10)	0.0018 (9)
C8	0.0312 (12)	0.0317 (12)	0.0329 (13)	−0.0005 (10)	0.0019 (10)	0.0048 (10)
C9	0.0323 (13)	0.0520 (16)	0.0369 (14)	0.0013 (12)	0.0077 (11)	0.0126 (12)
C10	0.0293 (13)	0.0615 (19)	0.0535 (18)	0.0031 (13)	0.0069 (13)	0.0206 (15)
C11	0.0379 (16)	0.0588 (19)	0.0537 (19)	−0.0061 (14)	−0.0123 (14)	0.0087 (15)
C12	0.0476 (18)	0.064 (2)	0.0466 (18)	0.0059 (15)	−0.0120 (14)	−0.0122 (15)
C13	0.0417 (16)	0.0536 (17)	0.0396 (16)	0.0099 (13)	−0.0026 (12)	−0.0083 (13)
C14	0.0240 (11)	0.0337 (12)	0.0298 (12)	0.0020 (10)	0.0040 (9)	−0.0024 (9)
C15	0.0231 (11)	0.0344 (12)	0.0222 (11)	−0.0005 (9)	0.0007 (8)	−0.0010 (9)
C16	0.0338 (13)	0.0320 (12)	0.0253 (11)	−0.0010 (10)	0.0022 (9)	0.0002 (9)
C17	0.0425 (15)	0.0315 (12)	0.0318 (13)	0.0036 (11)	−0.0007 (11)	−0.0031 (10)
C18	0.0384 (14)	0.0354 (13)	0.0372 (14)	−0.0040 (11)	−0.0010 (11)	0.0063 (11)
C19	0.0353 (13)	0.0434 (15)	0.0296 (13)	−0.0062 (11)	0.0036 (10)	0.0081 (10)
C20	0.0302 (12)	0.0364 (13)	0.0274 (12)	−0.0008 (10)	0.0060 (10)	−0.0010 (9)
Cl1	0.0312 (4)	0.0681 (5)	0.0381 (4)	0.0023 (3)	−0.0047 (3)	−0.0040 (3)
N1	0.0274 (10)	0.0365 (11)	0.0290 (10)	0.0012 (9)	0.0022 (8)	0.0043 (8)
O1	0.0460 (11)	0.0336 (9)	0.0378 (10)	0.0018 (8)	0.0115 (8)	−0.0051 (8)

Geometric parameters (Å, º)

C1—C6	1.377 (4)	C10—H10	0.9300
C1—C2	1.379 (4)	C11—C12	1.378 (5)
C1—Cl1	1.737 (3)	C11—H11	0.9300
C2—C3	1.384 (3)	C12—C13	1.382 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.393 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—O1	1.222 (3)
C4—C5	1.392 (4)	C14—C15	1.477 (3)
C4—N1	1.419 (3)	C15—C20	1.390 (3)
C5—C6	1.380 (3)	C15—C16	1.391 (3)
C5—H5	0.9300	C16—C17	1.382 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—N1	1.268 (3)	C17—C18	1.374 (4)
C7—C8	1.482 (3)	C17—H17	0.9300
C7—C14	1.518 (3)	C18—C19	1.382 (4)
C8—C13	1.385 (4)	C18—H18	0.9300
C8—C9	1.388 (4)	C19—C20	1.380 (4)
C9—C10	1.385 (4)	C19—H19	0.9300
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.377 (5)
C6—C1—C2	121.3 (2)	C10—C11—H11	120.1
C6—C1—Cl1	118.4 (2)	C12—C11—H11	120.1
C2—C1—Cl1	120.3 (2)	C11—C12—C13	120.3 (3)
C1—C2—C3	119.5 (2)	C11—C12—H12	119.8
C1—C2—H2	120.2	C13—C12—H12	119.8
C3—C2—H2	120.2	C12—C13—C8	120.4 (3)
C2—C3—C4	120.1 (2)	C12—C13—H13	119.8
C2—C3—H3	120.0	C8—C13—H13	119.8
C4—C3—H3	120.0	O1—C14—C15	123.2 (2)
C5—C4—C3	119.2 (2)	O1—C14—C7	118.9 (2)
C5—C4—N1	116.9 (2)	C15—C14—C7	117.9 (2)
C3—C4—N1	123.7 (2)	C20—C15—C16	119.3 (2)
C6—C5—C4	120.7 (2)	C20—C15—C14	119.0 (2)
C6—C5—H5	119.6	C16—C15—C14	121.7 (2)
C4—C5—H5	119.6	C17—C16—C15	119.9 (2)
C1—C6—C5	119.1 (2)	C17—C16—H16	120.0
C1—C6—H6	120.4	C15—C16—H16	120.0
C5—C6—H6	120.4	C18—C17—C16	120.3 (2)
N1—C7—C8	120.0 (2)	C18—C17—H17	119.8
N1—C7—C14	124.3 (2)	C16—C17—H17	119.8
C8—C7—C14	115.6 (2)	C17—C18—C19	120.2 (2)
C13—C8—C9	119.1 (2)	C17—C18—H18	119.9
C13—C8—C7	118.9 (2)	C19—C18—H18	119.9
C9—C8—C7	122.0 (2)	C20—C19—C18	120.0 (2)
C10—C9—C8	120.3 (3)	C20—C19—H19	120.0
C10—C9—H9	119.9	C18—C19—H19	120.0
C8—C9—H9	119.9	C19—C20—C15	120.2 (2)
C11—C10—C9	120.2 (3)	C19—C20—H20	119.9
C11—C10—H10	119.9	C15—C20—H20	119.9
C9—C10—H10	119.9	C7—N1—C4	121.8 (2)
C10—C11—C12	119.8 (3)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.93	2.67	3.247 (3)	120
C9—H9···O1	0.93	2.64	3.231 (3)	122
C2—H2···O1^i	0.93	2.60	3.360 (3)	139
C19—H19···Cg1^ii	0.93	2.88	3.689 (3)	146

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