(E)-2-Phenyl­benz­aldehyde oxime forms hydrogen-bonded C22(6) chains

Glidewell, C.; Low, J.N.; Skakle, J.M.S.; Wardell, J.L.

doi:10.1107/S1600536804003575

(E)-2-Phenylbenzaldehyde oxime forms hydrogen-bonded C₂²(6) chains

C. Glidewell, J. N. Low, J. M. S. Skakle and J. L. Wardell

The title compound, C₁₃H₁₁NO, crystallizes in space group Pca2₁ with Z′ = 2. The molecules are linked by two N—H

O hydrogen bonds [H

O = 1.96 and 1.97 Å, N

O = 2.789 (4) and 2.799 (4) Å, and N—H

O both 171°] into C²₂(6) chains.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003575/lh6171sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003575/lh6171Isup2.hkl Contains datablock I

CCDC reference: 236098

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.007 Å
R factor = 0.045
wR factor = 0.111
Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               2356
           Count of symmetry unique reflns         2367
           Completeness (_total/calc)             99.54%
           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           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

2-Phenylbenzaldehydeoxime top

Crystal data top

C₁₃H₁₁NO	F(000) = 832
M_r = 197.23	D_x = 1.291 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2356 reflections
a = 14.3555 (4) Å	θ = 2.9–27.5°
b = 4.4969 (1) Å	µ = 0.08 mm⁻¹
c = 31.4473 (10) Å	T = 120 K
V = 2030.09 (10) Å³	Needle, colourless
Z = 8	0.30 × 0.08 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	2356 independent reflections
Radiation source: rotating anode	1764 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SORTAV; Blessing 1995, 1997)	h = −18→18
T_min = 0.967, T_max = 0.994	k = −5→5
15601 measured reflections	l = −40→40

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0652P)²] where P = (F_o² + 2F_c²)/3
2356 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.27 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C11	0.7517 (3)	0.4288 (9)	0.33826 (13)	0.0204 (8)
C12	0.7584 (2)	0.5864 (9)	0.37654 (12)	0.0218 (7)
C13	0.8345 (2)	0.7762 (8)	0.38242 (11)	0.0260 (7)
C14	0.9017 (2)	0.8108 (8)	0.35128 (11)	0.0285 (8)
C15	0.8941 (2)	0.6566 (8)	0.31341 (13)	0.0279 (8)
C16	0.8208 (4)	0.4677 (8)	0.3070 (2)	0.0244 (12)
C17	0.6778 (2)	0.2061 (7)	0.33201 (11)	0.0206 (7)
N17	0.6569 (2)	0.1075 (7)	0.29523 (9)	0.0221 (6)
O17	0.58706 (17)	−0.1110 (6)	0.29799 (7)	0.0236 (5)
C21	0.6879 (3)	0.5642 (9)	0.41035 (16)	0.0227 (9)
C22	0.5921 (2)	0.5997 (9)	0.40172 (11)	0.0240 (7)
C23	0.5270 (3)	0.5976 (10)	0.43404 (12)	0.0305 (8)
C24	0.5537 (5)	0.5526 (11)	0.4761 (2)	0.0333 (12)
C25	0.6486 (6)	0.5143 (8)	0.4854 (2)	0.0333 (16)
C26	0.7136 (6)	0.5203 (8)	0.4537 (2)	0.0274 (14)
C31	0.4999 (3)	0.9255 (9)	0.17603 (13)	0.0203 (7)
C32	0.4924 (2)	1.0781 (9)	0.13732 (12)	0.0202 (7)
C33	0.4167 (2)	1.2694 (8)	0.13112 (11)	0.0253 (7)
C34	0.3507 (2)	1.3106 (8)	0.16229 (12)	0.0294 (8)
C35	0.3581 (2)	1.1612 (8)	0.20038 (13)	0.0278 (8)
C36	0.4328 (4)	0.9694 (8)	0.2074 (2)	0.0233 (12)
C37	0.5735 (2)	0.7037 (7)	0.18216 (11)	0.0195 (7)
N37	0.5944 (2)	0.6053 (7)	0.21885 (9)	0.0208 (6)
O37	0.66503 (17)	0.3880 (5)	0.21622 (7)	0.0249 (5)
C41	0.5644 (4)	1.0487 (8)	0.10287 (17)	0.0213 (9)
C42	0.6583 (2)	1.0950 (9)	0.11154 (12)	0.0241 (7)
C43	0.7231 (3)	1.0772 (10)	0.07915 (13)	0.0288 (8)
C44	0.6950 (5)	1.0156 (8)	0.0380 (2)	0.0324 (14)
C45	0.6038 (6)	0.9708 (9)	0.0294 (2)	0.0334 (16)
C46	0.5375 (5)	0.9891 (8)	0.0624 (2)	0.0294 (15)
H13	0.8402	0.8835	0.4083	0.031*
H14	0.9530	0.9403	0.3559	0.034*
H15	0.9397	0.6819	0.2918	0.033*
H16	0.8165	0.3608	0.2810	0.029*
H17	0.6448	0.1339	0.3561	0.025*
H17A	0.5829	−0.2010	0.2747	0.035*
H22	0.5721	0.6254	0.3732	0.029*
H23	0.4631	0.6272	0.4275	0.037*
H24	0.5085	0.5479	0.4982	0.040*
H25	0.6678	0.4839	0.5140	0.040*
H26	0.7775	0.4945	0.4607	0.033*
H33	0.4108	1.3728	0.1049	0.030*
H34	0.2999	1.4421	0.1575	0.035*
H35	0.3124	1.1889	0.2219	0.033*
H36	0.4379	0.8676	0.2337	0.028*
H37	0.6065	0.6316	0.1581	0.023*
H37A	0.6657	0.2871	0.2387	0.037*
H42	0.6779	1.1388	0.1397	0.029*
H43	0.7873	1.1075	0.0852	0.035*
H44	0.7398	1.0048	0.0158	0.039*
H45	0.5844	0.9269	0.0012	0.040*
H46	0.4733	0.9596	0.0562	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0186 (18)	0.0219 (16)	0.0207 (19)	0.0027 (17)	0.0003 (14)	0.0038 (19)
C12	0.0224 (19)	0.0210 (17)	0.0219 (18)	0.0045 (16)	−0.0049 (14)	0.0048 (19)
C13	0.0253 (18)	0.0273 (18)	0.0256 (16)	0.0003 (13)	−0.0083 (15)	0.0004 (14)
C14	0.0216 (17)	0.0273 (19)	0.0365 (19)	−0.0026 (14)	−0.0030 (15)	0.0086 (16)
C15	0.0210 (16)	0.032 (2)	0.0308 (18)	0.0035 (14)	0.0048 (15)	0.0084 (16)
C16	0.025 (3)	0.026 (2)	0.021 (3)	0.0066 (15)	0.003 (2)	0.0032 (15)
C17	0.0221 (16)	0.0212 (17)	0.0186 (15)	0.0037 (13)	0.0025 (13)	0.0009 (13)
N17	0.0247 (16)	0.0182 (16)	0.0233 (15)	0.0008 (13)	0.0009 (12)	0.0012 (13)
O17	0.0285 (14)	0.0244 (14)	0.0179 (13)	−0.0045 (11)	0.0014 (10)	−0.0046 (11)
C21	0.026 (2)	0.0207 (16)	0.021 (2)	−0.0049 (18)	−0.0030 (16)	0.001 (2)
C22	0.0254 (18)	0.0243 (18)	0.0222 (19)	−0.0028 (15)	0.0006 (13)	−0.0050 (17)
C23	0.031 (2)	0.030 (2)	0.031 (2)	−0.0012 (19)	0.0020 (16)	−0.006 (2)
C24	0.042 (3)	0.033 (2)	0.025 (3)	−0.004 (2)	0.011 (2)	−0.0063 (19)
C25	0.042 (4)	0.038 (3)	0.020 (3)	−0.0025 (16)	−0.002 (3)	0.0002 (14)
C26	0.036 (4)	0.035 (3)	0.011 (3)	0.0013 (15)	−0.011 (3)	−0.0005 (14)
C31	0.0206 (19)	0.0192 (16)	0.0209 (18)	−0.0031 (17)	−0.0016 (14)	−0.0020 (19)
C32	0.0168 (18)	0.0243 (17)	0.0194 (17)	−0.0005 (16)	−0.0022 (13)	−0.0036 (19)
C33	0.0266 (18)	0.0239 (18)	0.0255 (17)	−0.0002 (14)	−0.0034 (14)	−0.0003 (14)
C34	0.0207 (17)	0.0287 (19)	0.039 (2)	0.0054 (14)	−0.0050 (16)	−0.0053 (16)
C35	0.0230 (17)	0.032 (2)	0.0282 (17)	0.0001 (14)	0.0026 (15)	−0.0074 (15)
C36	0.022 (3)	0.027 (2)	0.021 (3)	0.0002 (15)	0.000 (2)	−0.0012 (15)
C37	0.0213 (16)	0.0189 (16)	0.0184 (15)	−0.0038 (13)	0.0016 (13)	−0.0008 (13)
N37	0.0184 (15)	0.0220 (16)	0.0221 (15)	0.0013 (12)	0.0003 (11)	0.0010 (14)
O37	0.0286 (14)	0.0244 (14)	0.0217 (14)	0.0051 (11)	0.0014 (10)	0.0038 (12)
C41	0.023 (2)	0.0224 (17)	0.018 (2)	−0.0036 (17)	0.0022 (16)	0.0041 (18)
C42	0.0271 (19)	0.0223 (19)	0.0231 (19)	0.0018 (16)	−0.0009 (13)	−0.0009 (17)
C43	0.023 (2)	0.0363 (19)	0.027 (2)	0.0048 (18)	0.0025 (15)	0.000 (2)
C44	0.040 (3)	0.031 (2)	0.027 (3)	0.0038 (15)	0.010 (2)	0.0016 (15)
C45	0.047 (4)	0.036 (3)	0.016 (3)	0.0009 (18)	0.005 (3)	0.0008 (16)
C46	0.026 (3)	0.031 (3)	0.031 (4)	−0.0023 (13)	0.003 (3)	0.0041 (14)

Geometric parameters (Å, º) top

C11—C12	1.400 (5)	C31—C36	1.393 (7)
C11—C16	1.407 (8)	C31—C32	1.402 (5)
C11—C17	1.472 (5)	C31—C37	1.466 (5)
C12—C13	1.399 (5)	C32—C33	1.399 (5)
C12—C21	1.471 (6)	C32—C41	1.503 (6)
C13—C14	1.383 (5)	C33—C34	1.376 (5)
C13—H13	0.95	C33—H33	0.95
C14—C15	1.382 (5)	C34—C35	1.377 (5)
C14—H14	0.95	C34—H34	0.95
C15—C16	1.367 (7)	C35—C36	1.393 (7)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—N17	1.275 (4)	C37—N37	1.272 (4)
C17—H17	0.95	C37—H37	0.95
N17—O17	1.407 (4)	N37—O37	1.410 (4)
O17—H17A	0.84	O37—H37A	0.84
C21—C22	1.410 (6)	C41—C46	1.358 (8)
C21—C26	1.425 (7)	C41—C42	1.392 (6)
C22—C23	1.381 (5)	C42—C43	1.382 (5)
C22—H22	0.95	C42—H42	0.95
C23—C24	1.393 (8)	C43—C44	1.384 (8)
C23—H23	0.95	C43—H43	0.95
C24—C25	1.403 (11)	C44—C45	1.353 (11)
C24—H24	0.95	C44—H44	0.95
C25—C26	1.366 (11)	C45—C46	1.409 (10)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95

C12—C11—C16	119.3 (4)	C36—C31—C32	119.4 (4)
C12—C11—C17	120.5 (3)	C36—C31—C37	120.2 (4)
C16—C11—C17	120.0 (4)	C32—C31—C37	120.2 (3)
C13—C12—C11	118.4 (3)	C33—C32—C31	118.8 (3)
C13—C12—C21	118.9 (4)	C33—C32—C41	119.2 (4)
C11—C12—C21	122.7 (4)	C31—C32—C41	122.0 (4)
C14—C13—C12	121.3 (3)	C34—C33—C32	121.2 (3)
C14—C13—H13	119.3	C34—C33—H33	119.4
C12—C13—H13	119.3	C32—C33—H33	119.4
C15—C14—C13	119.9 (3)	C33—C34—C35	120.0 (3)
C15—C14—H14	120.1	C33—C34—H34	120.0
C13—C14—H14	120.1	C35—C34—H34	120.0
C16—C15—C14	120.0 (4)	C34—C35—C36	119.9 (4)
C16—C15—H15	120.0	C34—C35—H35	120.0
C14—C15—H15	120.0	C36—C35—H35	120.0
C15—C16—C11	121.2 (5)	C35—C36—C31	120.6 (5)
C15—C16—H16	119.4	C35—C36—H36	119.7
C11—C16—H16	119.4	C31—C36—H36	119.7
C11—C17—N17	121.8 (3)	C31—C37—N37	121.8 (3)
N17—C17—H17	119.1	N37—C37—H37	119.1
C11—C17—H17	119.1	C31—C37—H37	119.1
C17—N17—O17	110.8 (3)	C37—N37—O37	111.0 (3)
N17—O17—H17A	109.5	N37—O37—H37A	109.5
C22—C21—C26	116.9 (5)	C46—C41—C42	119.3 (5)
C22—C21—C12	121.6 (4)	C46—C41—C32	119.9 (5)
C26—C21—C12	121.5 (5)	C42—C41—C32	120.8 (4)
C23—C22—C21	121.2 (4)	C43—C42—C41	120.0 (4)
C23—C22—H22	119.4	C43—C42—H42	120.0
C21—C22—H22	119.4	C41—C42—H42	120.0
C22—C23—C24	120.9 (4)	C42—C43—C44	120.3 (4)
C22—C23—H23	119.6	C42—C43—H43	119.8
C24—C23—H23	119.6	C44—C43—H43	119.8
C23—C24—C25	118.9 (6)	C45—C44—C43	119.8 (6)
C23—C24—H24	120.6	C45—C44—H44	120.1
C25—C24—H24	120.6	C43—C44—H44	120.1
C26—C25—C24	120.6 (7)	C44—C45—C46	120.0 (7)
C26—C25—H25	119.7	C44—C45—H45	120.0
C24—C25—H25	119.7	C46—C45—H45	120.0
C25—C26—C21	121.6 (7)	C41—C46—C45	120.6 (7)
C25—C26—H26	119.2	C41—C46—H46	119.7
C21—C26—H26	119.2	C45—C46—H46	119.7

C16—C11—C12—C13	−0.5 (5)	C36—C31—C32—C33	−0.5 (6)
C17—C11—C12—C13	174.4 (3)	C37—C31—C32—C33	174.6 (3)
C16—C11—C12—C21	178.4 (4)	C36—C31—C32—C41	177.8 (4)
C17—C11—C12—C21	−6.7 (6)	C37—C31—C32—C41	−7.2 (5)
C11—C12—C13—C14	0.5 (5)	C31—C32—C33—C34	0.4 (5)
C21—C12—C13—C14	−178.5 (4)	C41—C32—C33—C34	−177.9 (4)
C12—C13—C14—C15	0.2 (5)	C32—C33—C34—C35	−0.3 (5)
C13—C14—C15—C16	−0.8 (6)	C33—C34—C35—C36	0.3 (5)
C14—C15—C16—C11	0.7 (6)	C34—C35—C36—C31	−0.4 (6)
C12—C11—C16—C15	−0.1 (6)	C32—C31—C36—C35	0.5 (6)
C17—C11—C16—C15	−175.0 (4)	C37—C31—C36—C35	−174.6 (4)
C12—C11—C17—N17	164.3 (3)	C36—C31—C37—N37	−19.3 (6)
C16—C11—C17—N17	−20.9 (6)	C32—C31—C37—N37	165.6 (3)
C11—C17—N17—O17	177.6 (3)	C31—C37—N37—O37	178.1 (3)
C13—C12—C21—C22	128.6 (4)	C33—C32—C41—C46	−51.4 (5)
C11—C12—C21—C22	−50.3 (6)	C31—C32—C41—C46	130.4 (4)
C13—C12—C21—C26	−48.3 (5)	C33—C32—C41—C42	125.7 (4)
C11—C12—C21—C26	132.7 (4)	C31—C32—C41—C42	−52.5 (5)
C26—C21—C22—C23	1.3 (6)	C46—C41—C42—C43	−0.6 (6)
C12—C21—C22—C23	−175.8 (4)	C32—C41—C42—C43	−177.7 (4)
C21—C22—C23—C24	−1.7 (7)	C41—C42—C43—C44	0.5 (6)
C22—C23—C24—C25	1.1 (7)	C42—C43—C44—C45	−0.4 (7)
C23—C24—C25—C26	−0.2 (7)	C43—C44—C45—C46	0.5 (6)
C24—C25—C26—C21	−0.2 (6)	C42—C41—C46—C45	0.7 (6)
C22—C21—C26—C25	−0.3 (6)	C32—C41—C46—C45	177.9 (4)
C12—C21—C26—C25	176.7 (4)	C44—C45—C46—C41	−0.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O17—H17A···N37ⁱ	0.84	1.97	2.799 (3)	171
O37—H37A···N17	0.84	1.96	2.789 (4)	171

Symmetry code: (i) x, y−1, z.

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(E)-2-Phenyl­benz­aldehyde oxime forms hydrogen-bonded C22(6) chains

Supporting information

Key indicators

checkCIF/PLATON results

(E)-2-Phenylbenzaldehyde oxime forms hydrogen-bonded C₂²(6) chains