3-(Hydroxy­diphenyl­meth­yl)-2-(methoxy­meth­oxy)benzaldehyde

The title compound, C₂₂H₂₀O₄, was obtained from methoxy­methyl phenyl ether by ortho-lithia­tion and electrophilic quenching. The mol­ecular packing in the crystal structure is stabilized by an intra­molecular hydrogen bond and van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.144
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and ViewerPro (Accelrys, 2001); software used to prepare material for publication: SHELXL97.

3-(Hydroxydiphenylmethyl)-2-(methoxymethoxy)benzaldehyde

Crystal data

C22H20O4	F(000) = 1472
Mr = 348.38	Dx = 1.334 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7316 reflections
a = 8.6967 (16) Å	θ = 2.2–28.2°
b = 14.557 (3) Å	µ = 0.09 mm^−1
c = 27.408 (5) Å	T = 273 K
V = 3469.7 (11) Å^3	Chunk, colorless
Z = 8	0.14 × 0.05 × 0.03 mm

Data collection

Bruker APEX area-detector diffractometer	3591 independent reflections
Radiation source: fine-focus sealed tube	2916 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 26.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.987, Tmax = 0.997	k = −18→16
18443 measured reflections	l = −27→34

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0793P)^2 + 0.6714P] where P = (Fo^2 + 2Fc^2)/3
3591 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.21 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
C1	0.0626 (2)	0.79013 (13)	0.20113 (6)	0.0536 (4)
O1	0.0892 (2)	0.93638 (12)	0.23690 (6)	0.0969 (6)
O2	−0.11886 (13)	0.77828 (8)	0.13596 (4)	0.0509 (3)
C2	−0.00426 (17)	0.73984 (11)	0.16359 (5)	0.0445 (4)
O3	−0.08100 (16)	0.82420 (9)	0.05671 (4)	0.0626 (4)
C3	0.04002 (17)	0.64910 (11)	0.15443 (5)	0.0435 (4)
O4	0.04116 (14)	0.64123 (8)	0.06778 (4)	0.0511 (3)
H4B	0.0050	0.6930	0.0652	0.077*
C4	0.15251 (19)	0.61205 (13)	0.18406 (6)	0.0539 (4)
H4A	0.1832	0.5516	0.1789	0.065*
C5	0.2208 (2)	0.66176 (15)	0.22101 (6)	0.0638 (5)
H5A	0.2970	0.6351	0.2401	0.077*
C6	0.1763 (2)	0.74981 (15)	0.22942 (6)	0.0631 (5)
H6A	0.2225	0.7833	0.2543	0.076*
C7	0.0153 (3)	0.88514 (14)	0.21188 (7)	0.0684 (5)
H7A	−0.0764	0.9065	0.1986	0.082*
C8	−0.0807 (2)	0.85286 (12)	0.10448 (6)	0.0554 (4)
H8A	−0.1548	0.9021	0.1087	0.066*
H8B	0.0202	0.8764	0.1129	0.066*
C9	−0.2304 (3)	0.82358 (15)	0.03538 (8)	0.0772 (6)
H9A	−0.2234	0.8030	0.0022	0.116*
H9B	−0.2725	0.8845	0.0362	0.116*
H9C	−0.2959	0.7828	0.0534	0.116*
C10	−0.02145 (18)	0.59768 (10)	0.10975 (5)	0.0417 (4)
C11	−0.19650 (18)	0.59526 (10)	0.10694 (5)	0.0433 (4)
C12	−0.2662 (2)	0.58410 (11)	0.06225 (6)	0.0558 (4)
H12A	−0.2060	0.5799	0.0343	0.067*
C13	−0.4238 (3)	0.57903 (13)	0.05847 (9)	0.0736 (6)
H13A	−0.4696	0.5726	0.0280	0.088*
C14	−0.5132 (2)	0.58342 (13)	0.09949 (11)	0.0776 (7)
H14A	−0.6197	0.5804	0.0970	0.093*
C15	−0.4457 (2)	0.59228 (13)	0.14377 (9)	0.0694 (6)
H15A	−0.5061	0.5946	0.1717	0.083*
C16	−0.2877 (2)	0.59784 (12)	0.14761 (7)	0.0541 (4)
H16A	−0.2427	0.6034	0.1782	0.065*
C17	0.03335 (18)	0.49810 (11)	0.10824 (5)	0.0434 (4)
C18	0.12716 (19)	0.46686 (12)	0.07161 (6)	0.0500 (4)
H18A	0.1577	0.5067	0.0469	0.060*
C19	0.1766 (2)	0.37680 (13)	0.07118 (7)	0.0616 (5)
H19A	0.2415	0.3568	0.0464	0.074*
C20	0.1316 (2)	0.31668 (13)	0.10657 (8)	0.0649 (5)
H20A	0.1655	0.2561	0.1061	0.078*
C21	0.0360 (2)	0.34687 (13)	0.14284 (8)	0.0661 (5)
H21A	0.0039	0.3064	0.1670	0.079*
C22	−0.0127 (2)	0.43659 (13)	0.14374 (7)	0.0582 (5)
H22A	−0.0775	0.4562	0.1686	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0523 (10)	0.0636 (11)	0.0449 (8)	−0.0146 (8)	0.0059 (7)	−0.0048 (7)
O1	0.1349 (15)	0.0794 (10)	0.0765 (10)	−0.0322 (10)	−0.0054 (10)	−0.0271 (8)
O2	0.0469 (6)	0.0468 (6)	0.0592 (7)	−0.0055 (5)	−0.0039 (5)	0.0034 (5)
C2	0.0396 (8)	0.0511 (9)	0.0427 (8)	−0.0077 (6)	0.0035 (6)	0.0016 (7)
O3	0.0717 (8)	0.0613 (8)	0.0548 (7)	0.0042 (6)	0.0015 (6)	0.0025 (6)
C3	0.0381 (8)	0.0524 (9)	0.0398 (8)	−0.0058 (6)	0.0044 (6)	0.0028 (6)
O4	0.0614 (7)	0.0487 (6)	0.0433 (6)	0.0040 (5)	0.0136 (5)	0.0067 (5)
C4	0.0471 (9)	0.0680 (11)	0.0467 (9)	0.0027 (8)	0.0001 (7)	0.0032 (8)
C5	0.0521 (10)	0.0935 (15)	0.0458 (9)	0.0013 (9)	−0.0064 (8)	0.0027 (9)
C6	0.0572 (10)	0.0884 (14)	0.0437 (9)	−0.0171 (10)	−0.0024 (8)	−0.0080 (9)
C7	0.0859 (14)	0.0620 (11)	0.0573 (11)	−0.0169 (10)	0.0072 (10)	−0.0108 (9)
C8	0.0615 (10)	0.0435 (9)	0.0611 (10)	−0.0041 (7)	−0.0026 (8)	0.0034 (7)
C9	0.0944 (16)	0.0639 (12)	0.0733 (13)	0.0006 (11)	−0.0246 (12)	0.0027 (10)
C10	0.0436 (8)	0.0452 (8)	0.0363 (7)	0.0003 (6)	0.0031 (6)	0.0029 (6)
C11	0.0456 (8)	0.0380 (7)	0.0463 (8)	0.0018 (6)	−0.0025 (6)	−0.0030 (6)
C12	0.0666 (11)	0.0461 (9)	0.0546 (9)	0.0017 (8)	−0.0135 (8)	−0.0019 (7)
C13	0.0739 (14)	0.0521 (10)	0.0947 (16)	0.0013 (9)	−0.0406 (13)	−0.0062 (10)
C14	0.0449 (10)	0.0505 (11)	0.137 (2)	−0.0020 (8)	−0.0164 (13)	−0.0121 (12)
C15	0.0474 (10)	0.0569 (11)	0.1039 (16)	−0.0058 (8)	0.0154 (11)	−0.0168 (11)
C16	0.0473 (9)	0.0575 (10)	0.0574 (10)	−0.0045 (8)	0.0044 (7)	−0.0099 (8)
C17	0.0415 (8)	0.0462 (8)	0.0425 (8)	−0.0006 (6)	−0.0017 (6)	0.0007 (6)
C18	0.0527 (9)	0.0511 (9)	0.0463 (9)	−0.0007 (7)	0.0028 (7)	−0.0012 (7)
C19	0.0661 (11)	0.0567 (10)	0.0619 (11)	0.0086 (9)	0.0032 (9)	−0.0097 (8)
C20	0.0646 (11)	0.0465 (9)	0.0835 (13)	0.0069 (8)	−0.0104 (10)	0.0008 (9)
C21	0.0668 (12)	0.0559 (11)	0.0756 (13)	0.0020 (9)	0.0008 (10)	0.0212 (9)
C22	0.0565 (10)	0.0583 (10)	0.0597 (10)	0.0065 (8)	0.0093 (8)	0.0139 (8)

Geometric parameters (Å, º)

C1—C6	1.387 (3)	C10—C11	1.525 (2)
C1—C2	1.390 (2)	C10—C17	1.526 (2)
C1—C7	1.473 (3)	C11—C16	1.369 (2)
O1—C7	1.200 (2)	C11—C12	1.376 (2)
O2—C2	1.3710 (19)	C12—C13	1.377 (3)
O2—C8	1.426 (2)	C12—H12A	0.9300
C2—C3	1.399 (2)	C13—C14	1.368 (3)
O3—C8	1.374 (2)	C13—H13A	0.9300
O3—C9	1.424 (3)	C14—C15	1.355 (3)
C3—C4	1.381 (2)	C14—H14A	0.9300
C3—C10	1.531 (2)	C15—C16	1.380 (3)
O4—C10	1.4219 (17)	C15—H15A	0.9300
O4—H4B	0.8200	C16—H16A	0.9300
C4—C5	1.379 (3)	C17—C18	1.371 (2)
C4—H4A	0.9300	C17—C22	1.382 (2)
C5—C6	1.358 (3)	C18—C19	1.380 (3)
C5—H5A	0.9300	C18—H18A	0.9300
C6—H6A	0.9300	C19—C20	1.364 (3)
C7—H7A	0.9300	C19—H19A	0.9300
C8—H8A	0.9700	C20—C21	1.368 (3)
C8—H8B	0.9700	C20—H20A	0.9300
C9—H9A	0.9600	C21—C22	1.373 (3)
C9—H9B	0.9600	C21—H21A	0.9300
C9—H9C	0.9600	C22—H22A	0.9300
C6—C1—C2	119.29 (17)	O4—C10—C3	107.18 (12)
C6—C1—C7	119.00 (17)	C11—C10—C3	113.59 (12)
C2—C1—C7	121.71 (17)	C17—C10—C3	112.14 (12)
C2—O2—C8	118.41 (13)	C16—C11—C12	118.22 (16)
O2—C2—C1	119.86 (15)	C16—C11—C10	122.48 (14)
O2—C2—C3	119.11 (13)	C12—C11—C10	119.16 (14)
C1—C2—C3	120.99 (15)	C11—C12—C13	120.77 (19)
C8—O3—C9	113.25 (16)	C11—C12—H12A	119.6
C4—C3—C2	117.28 (15)	C13—C12—H12A	119.6
C4—C3—C10	121.77 (15)	C14—C13—C12	120.10 (19)
C2—C3—C10	120.60 (14)	C14—C13—H13A	120.0
C10—O4—H4B	109.5	C12—C13—H13A	120.0
C3—C4—C5	122.14 (18)	C15—C14—C13	119.62 (19)
C3—C4—H4A	118.9	C15—C14—H14A	120.2
C5—C4—H4A	118.9	C13—C14—H14A	120.2
C6—C5—C4	119.81 (18)	C14—C15—C16	120.4 (2)
C6—C5—H5A	120.1	C14—C15—H15A	119.8
C4—C5—H5A	120.1	C16—C15—H15A	119.8
C5—C6—C1	120.49 (17)	C11—C16—C15	120.89 (18)
C5—C6—H6A	119.8	C11—C16—H16A	119.6
C1—C6—H6A	119.8	C15—C16—H16A	119.6
O1—C7—C1	123.3 (2)	C18—C17—C22	118.23 (16)
O1—C7—H7A	118.4	C18—C17—C10	121.38 (13)
C1—C7—H7A	118.4	C22—C17—C10	120.39 (14)
O3—C8—O2	110.18 (14)	C17—C18—C19	120.45 (16)
O3—C8—H8A	109.6	C17—C18—H18A	119.8
O2—C8—H8A	109.6	C19—C18—H18A	119.8
O3—C8—H8B	109.6	C20—C19—C18	120.96 (17)
O2—C8—H8B	109.6	C20—C19—H19A	119.5
H8A—C8—H8B	108.1	C18—C19—H19A	119.5
O3—C9—H9A	109.5	C19—C20—C21	118.99 (18)
O3—C9—H9B	109.5	C19—C20—H20A	120.5
H9A—C9—H9B	109.5	C21—C20—H20A	120.5
O3—C9—H9C	109.5	C20—C21—C22	120.40 (18)
H9A—C9—H9C	109.5	C20—C21—H21A	119.8
H9B—C9—H9C	109.5	C22—C21—H21A	119.8
O4—C10—C11	110.59 (12)	C21—C22—C17	120.95 (18)
O4—C10—C17	106.36 (12)	C21—C22—H22A	119.5
C11—C10—C17	106.76 (12)	C17—C22—H22A	119.5
C8—O2—C2—C1	67.88 (19)	C17—C10—C11—C16	95.29 (17)
C8—O2—C2—C3	−114.19 (16)	C3—C10—C11—C16	−28.8 (2)
C6—C1—C2—O2	178.76 (15)	O4—C10—C11—C12	34.90 (19)
C7—C1—C2—O2	−0.9 (2)	C17—C10—C11—C12	−80.41 (16)
C6—C1—C2—C3	0.9 (2)	C3—C10—C11—C12	155.46 (14)
C7—C1—C2—C3	−178.83 (15)	C16—C11—C12—C13	2.3 (2)
O2—C2—C3—C4	−178.04 (13)	C10—C11—C12—C13	178.18 (15)
C1—C2—C3—C4	−0.1 (2)	C11—C12—C13—C14	−1.2 (3)
O2—C2—C3—C10	8.7 (2)	C12—C13—C14—C15	−0.4 (3)
C1—C2—C3—C10	−173.42 (13)	C13—C14—C15—C16	0.7 (3)
C2—C3—C4—C5	−0.7 (2)	C12—C11—C16—C15	−2.0 (3)
C10—C3—C4—C5	172.55 (15)	C10—C11—C16—C15	−177.71 (15)
C3—C4—C5—C6	0.7 (3)	C14—C15—C16—C11	0.5 (3)
C4—C5—C6—C1	0.1 (3)	O4—C10—C17—C18	1.11 (19)
C2—C1—C6—C5	−0.8 (3)	C11—C10—C17—C18	119.23 (16)
C7—C1—C6—C5	178.86 (17)	C3—C10—C17—C18	−115.75 (15)
C6—C1—C7—O1	15.6 (3)	O4—C10—C17—C22	−178.01 (15)
C2—C1—C7—O1	−164.70 (18)	C11—C10—C17—C22	−59.89 (19)
C9—O3—C8—O2	83.02 (18)	C3—C10—C17—C22	65.1 (2)
C2—O2—C8—O3	106.87 (16)	C22—C17—C18—C19	−1.5 (2)
C4—C3—C10—O4	−105.94 (16)	C10—C17—C18—C19	179.38 (16)
C2—C3—C10—O4	67.05 (17)	C17—C18—C19—C20	1.0 (3)
C4—C3—C10—C11	131.60 (15)	C18—C19—C20—C21	0.0 (3)
C2—C3—C10—C11	−55.42 (18)	C19—C20—C21—C22	−0.6 (3)
C4—C3—C10—C17	10.4 (2)	C20—C21—C22—C17	0.1 (3)
C2—C3—C10—C17	−176.58 (13)	C18—C17—C22—C21	1.0 (3)
O4—C10—C11—C16	−149.40 (14)	C10—C17—C22—C21	−179.88 (17)