2-(4-Chloro­benz­yloxy)benzaldehyde

In the title compound, C₁₄H₁₁ClO₂, the salicylaldehyde group makes a dihedral angle of 56.32 (7)° with the benzene ring.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.084
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C7      ..       5.87 su

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           25.02
           From the CIF: _reflns_number_total               2090
           Count of symmetry unique reflns         1276
           Completeness (_total/calc)            163.79%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       814
           Fraction of Friedel pairs measured     0.638
           Are heavy atom types Z>Si present        yes

   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
   1 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: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2-(4-Chlorobenzyloxy)benzaldehyde

Crystal data

C14H11ClO2	F(000) = 512
Mr = 246.68	Dx = 1.373 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1962 reflections
a = 4.0635 (11) Å	θ = 2.9–21.9°
b = 14.894 (4) Å	µ = 0.31 mm^−1
c = 19.715 (5) Å	T = 294 K
V = 1193.2 (5) Å^3	Block, colorless
Z = 4	0.20 × 0.16 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2090 independent reflections
Radiation source: fine-focus sealed tube	1496 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.926, Tmax = 0.982	k = −17→17
6035 measured reflections	l = −15→23

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0351P)^2 + 0.063P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.007
2090 reflections	Δρmax = 0.11 e Å^−3
154 parameters	Δρmin = −0.10 e Å^−3
0 restraints	Absolute structure: Flack (1983), 817 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (9)

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 > 2σ(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
Cl1	0.8073 (2)	0.57136 (5)	1.11020 (4)	0.0908 (3)
O1	0.8994 (4)	0.66909 (10)	0.78416 (8)	0.0646 (5)
O2	0.5618 (5)	0.90579 (12)	0.72731 (10)	0.0861 (6)
C1	0.9607 (6)	0.68961 (16)	0.71798 (13)	0.0551 (6)
C2	1.1272 (7)	0.63429 (17)	0.67372 (14)	0.0668 (7)
H2	1.2059	0.5788	0.6881	0.080*
C3	1.1752 (8)	0.6624 (2)	0.60799 (15)	0.0813 (8)
H3	1.2898	0.6255	0.5781	0.098*
C4	1.0579 (8)	0.7437 (2)	0.58531 (15)	0.0843 (10)
H4	1.0910	0.7616	0.5406	0.101*
C5	0.8914 (7)	0.79778 (19)	0.62977 (14)	0.0708 (8)
H5	0.8101	0.8526	0.6147	0.085*
C6	0.8416 (6)	0.77294 (15)	0.69617 (12)	0.0555 (6)
C7	0.6685 (7)	0.83306 (18)	0.74226 (13)	0.0687 (7)
H7	0.6382	0.8137	0.7867	0.082*
C8	1.0320 (6)	0.58681 (15)	0.81037 (12)	0.0632 (7)
H8A	1.2671	0.5841	0.8021	0.076*
H8B	0.9291	0.5359	0.7882	0.076*
C9	0.9654 (6)	0.58427 (14)	0.88453 (13)	0.0554 (6)
C10	1.0830 (6)	0.65084 (15)	0.92731 (14)	0.0636 (7)
H10	1.1966	0.6992	0.9088	0.076*
C11	1.0363 (7)	0.64716 (15)	0.99600 (13)	0.0629 (7)
H11	1.1174	0.6925	1.0238	0.075*
C12	0.8685 (6)	0.57587 (16)	1.02329 (13)	0.0617 (7)
C13	0.7494 (7)	0.50885 (16)	0.98266 (13)	0.0678 (7)
H13	0.6382	0.4603	1.0015	0.081*
C14	0.7961 (7)	0.51419 (15)	0.91375 (13)	0.0635 (7)
H14	0.7110	0.4692	0.8861	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1048 (6)	0.0868 (5)	0.0808 (5)	−0.0094 (5)	0.0026 (5)	0.0059 (4)
O1	0.0767 (12)	0.0485 (9)	0.0686 (11)	0.0131 (9)	0.0031 (9)	0.0036 (8)
O2	0.1051 (16)	0.0514 (11)	0.1018 (15)	0.0119 (11)	−0.0129 (12)	0.0127 (10)
C1	0.0512 (15)	0.0511 (14)	0.0632 (15)	−0.0099 (12)	−0.0049 (13)	−0.0040 (12)
C2	0.0605 (18)	0.0628 (16)	0.0770 (18)	−0.0043 (14)	−0.0003 (16)	−0.0141 (14)
C3	0.0641 (17)	0.100 (2)	0.080 (2)	−0.0136 (19)	0.0022 (19)	−0.0265 (19)
C4	0.068 (2)	0.116 (3)	0.0686 (19)	−0.027 (2)	−0.0027 (16)	0.0022 (19)
C5	0.0615 (18)	0.0790 (19)	0.0718 (19)	−0.0168 (16)	−0.0120 (15)	0.0066 (16)
C6	0.0533 (15)	0.0515 (13)	0.0616 (15)	−0.0096 (13)	−0.0083 (13)	0.0005 (12)
C7	0.0803 (18)	0.0543 (16)	0.0716 (16)	0.0017 (16)	−0.0128 (16)	0.0079 (14)
C8	0.0625 (16)	0.0441 (13)	0.0829 (19)	0.0110 (13)	−0.0075 (14)	0.0006 (12)
C9	0.0515 (14)	0.0372 (13)	0.0776 (16)	0.0053 (12)	−0.0080 (14)	0.0031 (13)
C10	0.0621 (18)	0.0395 (13)	0.0891 (19)	−0.0030 (13)	−0.0001 (15)	0.0051 (13)
C11	0.0650 (17)	0.0422 (13)	0.0815 (19)	0.0003 (14)	−0.0083 (15)	−0.0023 (13)
C12	0.0579 (16)	0.0461 (13)	0.0811 (17)	0.0063 (14)	−0.0063 (14)	0.0054 (13)
C13	0.0690 (18)	0.0446 (14)	0.0899 (19)	−0.0077 (14)	−0.0055 (16)	0.0097 (14)
C14	0.0610 (16)	0.0400 (13)	0.0896 (19)	−0.0033 (13)	−0.0153 (15)	−0.0006 (13)

Geometric parameters (Å, º)

Cl1—C12	1.733 (3)	C7—H7	0.9300
O1—C1	1.363 (3)	C8—C9	1.488 (3)
O1—C8	1.435 (3)	C8—H8A	0.9700
O2—C7	1.203 (3)	C8—H8B	0.9700
C1—C2	1.378 (3)	C9—C14	1.377 (3)
C1—C6	1.400 (3)	C9—C10	1.387 (3)
C2—C3	1.376 (4)	C10—C11	1.369 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.376 (4)	C11—C12	1.372 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.369 (4)	C12—C13	1.368 (3)
C4—H4	0.9300	C13—C14	1.374 (3)
C5—C6	1.375 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.457 (3)
C1—O1—C8	117.88 (18)	O1—C8—H8A	110.1
O1—C1—C2	124.2 (2)	C9—C8—H8A	110.1
O1—C1—C6	115.4 (2)	O1—C8—H8B	110.1
C2—C1—C6	120.4 (3)	C9—C8—H8B	110.1
C3—C2—C1	119.0 (3)	H8A—C8—H8B	108.4
C3—C2—H2	120.5	C14—C9—C10	117.4 (2)
C1—C2—H2	120.5	C14—C9—C8	121.4 (2)
C2—C3—C4	121.7 (3)	C10—C9—C8	121.1 (2)
C2—C3—H3	119.2	C11—C10—C9	121.7 (2)
C4—C3—H3	119.2	C11—C10—H10	119.2
C5—C4—C3	118.7 (3)	C9—C10—H10	119.2
C5—C4—H4	120.6	C10—C11—C12	119.2 (2)
C3—C4—H4	120.6	C10—C11—H11	120.4
C4—C5—C6	121.6 (3)	C12—C11—H11	120.4
C4—C5—H5	119.2	C13—C12—C11	120.7 (2)
C6—C5—H5	119.2	C13—C12—Cl1	120.0 (2)
C5—C6—C1	118.7 (2)	C11—C12—Cl1	119.3 (2)
C5—C6—C7	120.0 (2)	C12—C13—C14	119.2 (2)
C1—C6—C7	121.4 (2)	C12—C13—H13	120.4
O2—C7—C6	125.1 (2)	C14—C13—H13	120.4
O2—C7—H7	117.5	C13—C14—C9	121.8 (2)
C6—C7—H7	117.5	C13—C14—H14	119.1
O1—C8—C9	107.90 (18)	C9—C14—H14	119.1
C8—O1—C1—C2	3.5 (3)	C1—C6—C7—O2	179.4 (3)
C8—O1—C1—C6	−176.5 (2)	C1—O1—C8—C9	173.8 (2)
O1—C1—C2—C3	−179.8 (2)	O1—C8—C9—C14	123.7 (2)
C6—C1—C2—C3	0.2 (4)	O1—C8—C9—C10	−58.9 (3)
C1—C2—C3—C4	−0.8 (4)	C14—C9—C10—C11	0.6 (4)
C2—C3—C4—C5	0.4 (4)	C8—C9—C10—C11	−177.0 (2)
C3—C4—C5—C6	0.5 (4)	C9—C10—C11—C12	−0.1 (4)
C4—C5—C6—C1	−1.0 (4)	C10—C11—C12—C13	0.2 (4)
C4—C5—C6—C7	178.9 (3)	C10—C11—C12—Cl1	−179.7 (2)
O1—C1—C6—C5	−179.4 (2)	C11—C12—C13—C14	−0.8 (4)
C2—C1—C6—C5	0.6 (3)	Cl1—C12—C13—C14	179.1 (2)
O1—C1—C6—C7	0.8 (3)	C12—C13—C14—C9	1.3 (4)
C2—C1—C6—C7	−179.2 (2)	C10—C9—C14—C13	−1.2 (4)
C5—C6—C7—O2	−0.5 (4)	C8—C9—C14—C13	176.3 (2)