2-Phenyl­quinoline 1-oxide

The title compound, C₁₅H₁₁NO, is not planar, as seen in the dihedral angle of 41.92 (12)° formed between the quinoline and phenyl residues. This conformation allows the crystal structure to be stabilized by C—H...O inter­actions. Zigzag chains along the a direction, mediated by C—H...O inter­actions, may be discerned in the crystal structure and these stack along the c direction, again via C—H...O inter­actions. Inter­actions of the type C—H...π serve to stabilize the zigzag chains and to provide links between them.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.115
• Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



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           27.50
           From the CIF: _reflns_number_total               1486
           Count of symmetry unique reflns         1487
           Completeness (_total/calc)             99.93%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); 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) and DIAMOND (Crystal Impact, 2006); software used to prepare material for publication: TEXSAN for Windows.

2-Phenylquinoline 1-oxide

Crystal data

C15H11NO	F(000) = 464
Mr = 221.25	Dx = 1.339 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 20 reflections
a = 7.754 (3) Å	θ = 12.6–17.5°
b = 21.436 (6) Å	µ = 0.08 mm^−1
c = 6.603 (2) Å	T = 293 K
V = 1097.5 (6) Å^3	Plate, pale yellow
Z = 4	0.50 × 0.30 × 0.20 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.011
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.8°
Graphite monochromator	h = −4→10
ω scans	k = 0→27
1772 measured reflections	l = −3→8
1486 independent reflections	3 standard reflections every 150 reflections
996 reflections with I > 2σ(I)	intensity decay: 1.5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 0.0354P] where P = (Fo^2 + 2Fc^2)/3
1486 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0122 (3)	−0.09998 (8)	0.2629 (3)	0.0605 (6)
N1	−0.0182 (3)	−0.05924 (9)	0.4045 (3)	0.0422 (5)
C2	−0.0881 (3)	−0.07611 (12)	0.5839 (4)	0.0406 (6)
C3	−0.1137 (3)	−0.03024 (11)	0.7336 (4)	0.0456 (6)
H3	−0.1606	−0.0419	0.8576	0.055*
C4	−0.0719 (4)	0.03061 (12)	0.7022 (4)	0.0488 (7)
H4	−0.0916	0.0600	0.8031	0.059*
C5	0.0470 (4)	0.11098 (12)	0.4721 (5)	0.0549 (7)
H5	0.0295	0.1421	0.5681	0.066*
C6	0.1170 (4)	0.12592 (14)	0.2890 (5)	0.0626 (8)
H6	0.1454	0.1671	0.2603	0.075*
C7	0.1465 (3)	0.07943 (14)	0.1437 (5)	0.0567 (8)
H7	0.1957	0.0901	0.0200	0.068*
C8	0.1040 (3)	0.01858 (13)	0.1814 (4)	0.0490 (7)
H8	0.1242	−0.0121	0.0846	0.059*
C9	0.0296 (3)	0.00324 (11)	0.3679 (4)	0.0405 (6)
C10	0.0006 (3)	0.04867 (11)	0.5177 (4)	0.0436 (6)
C21	−0.1413 (3)	−0.14144 (11)	0.6221 (4)	0.0452 (6)
C22	−0.2288 (3)	−0.17687 (11)	0.4803 (5)	0.0529 (7)
H22	−0.2435	−0.1617	0.3494	0.063*
C23	−0.2949 (4)	−0.23499 (13)	0.5320 (6)	0.0637 (8)
H23	−0.3558	−0.2581	0.4366	0.076*
C24	−0.2709 (5)	−0.25842 (13)	0.7229 (6)	0.0714 (10)
H24	−0.3155	−0.2973	0.7571	0.086*
C25	−0.1810 (5)	−0.22443 (13)	0.8631 (5)	0.0691 (9)
H25	−0.1622	−0.2409	0.9915	0.083*
C26	−0.1177 (4)	−0.16572 (12)	0.8158 (4)	0.0550 (7)
H26	−0.0594	−0.1426	0.9133	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0855 (14)	0.0496 (10)	0.0465 (10)	0.0038 (10)	0.0096 (11)	−0.0164 (9)
N1	0.0451 (11)	0.0403 (11)	0.0413 (11)	0.0051 (9)	−0.0006 (11)	−0.0073 (9)
C2	0.0395 (12)	0.0416 (13)	0.0407 (14)	0.0023 (11)	0.0014 (12)	−0.0059 (11)
C3	0.0495 (15)	0.0449 (14)	0.0426 (14)	0.0006 (11)	0.0071 (13)	−0.0059 (12)
C4	0.0544 (15)	0.0447 (14)	0.0473 (14)	0.0009 (12)	0.0042 (14)	−0.0114 (13)
C5	0.0556 (16)	0.0423 (14)	0.0668 (18)	−0.0045 (12)	0.0011 (16)	−0.0090 (14)
C6	0.0583 (18)	0.0485 (16)	0.081 (2)	−0.0055 (13)	0.0023 (18)	0.0090 (17)
C7	0.0464 (15)	0.0697 (18)	0.0540 (17)	0.0005 (14)	0.0051 (15)	0.0145 (16)
C8	0.0458 (14)	0.0544 (15)	0.0468 (15)	0.0038 (13)	0.0021 (14)	0.0005 (13)
C9	0.0367 (12)	0.0424 (13)	0.0423 (12)	0.0032 (11)	−0.0044 (12)	−0.0002 (11)
C10	0.0389 (13)	0.0413 (12)	0.0506 (14)	0.0019 (10)	−0.0028 (13)	−0.0046 (12)
C21	0.0441 (14)	0.0379 (13)	0.0537 (15)	0.0038 (11)	0.0020 (14)	−0.0070 (12)
C22	0.0518 (15)	0.0447 (14)	0.0621 (17)	0.0031 (12)	−0.0064 (15)	−0.0089 (14)
C23	0.0556 (16)	0.0454 (16)	0.090 (2)	−0.0001 (13)	−0.0062 (19)	−0.0163 (17)
C24	0.074 (2)	0.0397 (15)	0.100 (3)	−0.0020 (15)	0.013 (2)	0.0024 (18)
C25	0.090 (2)	0.0481 (16)	0.070 (2)	0.0009 (16)	0.011 (2)	0.0051 (16)
C26	0.0635 (18)	0.0466 (15)	0.0551 (17)	−0.0001 (13)	0.0016 (15)	0.0021 (14)

Geometric parameters (Å, º)

O1—N1	1.301 (3)	C7—H7	0.9300
N1—C2	1.352 (3)	C8—C9	1.399 (3)
N1—C9	1.411 (3)	C8—H8	0.9300
C2—C3	1.409 (3)	C9—C10	1.406 (3)
C2—C21	1.482 (3)	C21—C22	1.383 (3)
C3—C4	1.360 (4)	C21—C26	1.393 (4)
C3—H3	0.9300	C22—C23	1.390 (4)
C4—C10	1.396 (3)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.369 (5)
C5—C6	1.363 (4)	C23—H23	0.9300
C5—C10	1.416 (4)	C24—C25	1.369 (5)
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.402 (4)	C25—C26	1.387 (4)
C6—H6	0.9300	C25—H25	0.9300
C7—C8	1.368 (4)	C26—H26	0.9300
O1—N1—C2	121.5 (2)	C8—C9—C10	121.5 (2)
O1—N1—C9	117.8 (2)	C8—C9—N1	118.8 (2)
C2—N1—C9	120.6 (2)	C10—C9—N1	119.7 (2)
N1—C2—C3	119.0 (2)	C4—C10—C9	119.1 (2)
N1—C2—C21	120.9 (2)	C4—C10—C5	123.3 (2)
C3—C2—C21	120.1 (2)	C9—C10—C5	117.6 (3)
C4—C3—C2	121.9 (3)	C22—C21—C26	118.8 (3)
C4—C3—H3	119.0	C22—C21—C2	122.7 (3)
C2—C3—H3	119.0	C26—C21—C2	118.2 (2)
C3—C4—C10	119.7 (2)	C21—C22—C23	120.4 (3)
C3—C4—H4	120.2	C21—C22—H22	119.8
C10—C4—H4	120.2	C23—C22—H22	119.8
C6—C5—C10	120.8 (3)	C24—C23—C22	120.3 (3)
C6—C5—H5	119.6	C24—C23—H23	119.8
C10—C5—H5	119.6	C22—C23—H23	119.8
C5—C6—C7	120.3 (3)	C23—C24—C25	119.8 (3)
C5—C6—H6	119.8	C23—C24—H24	120.1
C7—C6—H6	119.8	C25—C24—H24	120.1
C8—C7—C6	120.9 (3)	C26—C25—C24	120.7 (3)
C8—C7—H7	119.5	C26—C25—H25	119.6
C6—C7—H7	119.5	C24—C25—H25	119.6
C7—C8—C9	118.9 (3)	C25—C26—C21	119.9 (3)
C7—C8—H8	120.5	C25—C26—H26	120.0
C9—C8—H8	120.5	C21—C26—H26	120.0
O1—N1—C2—C3	178.2 (2)	C8—C9—C10—C4	−179.2 (2)
C9—N1—C2—C3	0.5 (4)	N1—C9—C10—C4	1.4 (4)
O1—N1—C2—C21	−3.3 (4)	C8—C9—C10—C5	0.9 (4)
C9—N1—C2—C21	179.0 (2)	N1—C9—C10—C5	−178.5 (2)
N1—C2—C3—C4	0.7 (4)	C6—C5—C10—C4	−179.8 (3)
C21—C2—C3—C4	−177.8 (3)	C6—C5—C10—C9	0.1 (4)
C2—C3—C4—C10	−0.8 (4)	N1—C2—C21—C22	−43.1 (4)
C10—C5—C6—C7	−0.9 (4)	C3—C2—C21—C22	135.4 (3)
C5—C6—C7—C8	0.8 (4)	N1—C2—C21—C26	143.6 (2)
C6—C7—C8—C9	0.2 (4)	C3—C2—C21—C26	−37.9 (4)
C7—C8—C9—C10	−1.1 (4)	C26—C21—C22—C23	1.4 (4)
C7—C8—C9—N1	178.4 (2)	C2—C21—C22—C23	−171.8 (3)
O1—N1—C9—C8	1.2 (3)	C21—C22—C23—C24	−1.4 (4)
C2—N1—C9—C8	179.0 (2)	C22—C23—C24—C25	−0.1 (5)
O1—N1—C9—C10	−179.4 (2)	C23—C24—C25—C26	1.7 (5)
C2—N1—C9—C10	−1.5 (3)	C24—C25—C26—C21	−1.7 (5)
C3—C4—C10—C9	−0.2 (4)	C22—C21—C26—C25	0.2 (4)
C3—C4—C10—C5	179.6 (3)	C2—C21—C26—C25	173.7 (3)