2,2′-[2,3-Bis(1-formyl-2-naphthyloxymethyl)but-2-ene-1,4-diyldioxy]bis(naphthalene-1-carbaldehyde)

The mol­ecule of the title compound, C₅₀H₃₆O₈, lies on an inversion centre. Inter­molecular C—H...O hydrogen bonds result in the formation of an intricate three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.046
• wR factor = 0.065
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         33 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C17    -   C18     ..       7.55 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C24    -   C25     ..       7.81 su

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.762
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.114
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 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, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C50H36O8	F(000) = 800
Mr = 764.79	Dx = 1.396 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1046 reflections
a = 7.598 (2) Å	θ = 2.0–25.0°
b = 19.448 (5) Å	µ = 0.09 mm^−1
c = 12.541 (3) Å	T = 173 K
β = 100.896 (6)°	Prism, colorless
V = 1819.7 (8) Å^3	0.45 × 0.35 × 0.25 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1046 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.114
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −9→7
9367 measured reflections	k = −23→20
3190 independent reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H-atom parameters constrained
S = 0.76	w = 1/[σ^2(Fo^2) + (0.0042P)^2] where P = (Fo^2 + 2Fc^2)/3
3190 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.16 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
O3	0.2307 (3)	−0.00234 (10)	0.70255 (16)	0.0557 (6)
O2	−0.1370 (3)	0.12673 (11)	0.54371 (16)	0.0653 (7)
O4	0.7292 (3)	0.04863 (12)	0.79148 (17)	0.0733 (7)
O1	−0.6319 (3)	0.07826 (13)	0.4297 (2)	0.0946 (9)
C23	0.5866 (4)	−0.06138 (15)	0.9215 (2)	0.0416 (8)
C8	−0.3666 (4)	0.23894 (17)	0.2711 (3)	0.0513 (9)
C24	0.4916 (4)	−0.02386 (15)	0.8296 (2)	0.0365 (8)
C15	0.3103 (4)	−0.03642 (15)	0.7936 (2)	0.0408 (8)
C18	0.4914 (4)	−0.10888 (16)	0.9742 (3)	0.0429 (9)
C2	−0.3869 (4)	0.14881 (16)	0.4047 (3)	0.0454 (8)
C11	−0.2084 (5)	0.16110 (16)	0.4502 (3)	0.0470 (9)
C16	0.2163 (4)	−0.08291 (15)	0.8477 (2)	0.0498 (9)
H16	0.0941	−0.0899	0.8239	0.060*
C19	0.5804 (5)	−0.14616 (16)	1.0647 (2)	0.0583 (10)
H19	0.5162	−0.1767	1.0998	0.070*
C10	−0.1085 (4)	0.21114 (16)	0.4084 (2)	0.0593 (10)
H10	0.0099	0.2191	0.4415	0.071*
C22	0.7722 (4)	−0.05430 (15)	0.9618 (2)	0.0509 (9)
H22	0.8387	−0.0236	0.9286	0.061*
C6	−0.6193 (6)	0.27144 (19)	0.1346 (3)	0.0775 (12)
H6	−0.6702	0.2983	0.0754	0.093*
C7	−0.4428 (5)	0.27938 (16)	0.1802 (3)	0.0653 (11)
H7	−0.3728	0.3112	0.1517	0.078*
C3	−0.4704 (4)	0.18975 (16)	0.3133 (2)	0.0457 (9)
C9	−0.1841 (4)	0.24849 (15)	0.3188 (3)	0.0589 (10)
H9	−0.1152	0.2802	0.2893	0.071*
C17	0.3065 (5)	−0.11778 (15)	0.9356 (3)	0.0537 (9)
H17	0.2437	−0.1485	0.9712	0.064*
C5	−0.7234 (5)	0.2232 (2)	0.1767 (3)	0.0757 (13)
H5	−0.8433	0.2180	0.1443	0.091*
C4	−0.6541 (4)	0.18308 (18)	0.2645 (3)	0.0650 (11)
H4	−0.7268	0.1518	0.2919	0.078*
C21	0.8560 (4)	−0.09208 (17)	1.0492 (3)	0.0598 (10)
H21	0.9786	−0.0870	1.0741	0.072*
C20	0.7594 (5)	−0.13795 (18)	1.1011 (3)	0.0669 (11)
H20	0.8173	−0.1630	1.1607	0.080*
C13	0.0161 (4)	0.01804 (17)	0.5461 (2)	0.0463 (9)
C14	0.0442 (4)	−0.01548 (15)	0.6570 (2)	0.0541 (9)
H14A	−0.0334	0.0049	0.7015	0.065*
H14B	0.0207	−0.0645	0.6507	0.065*
C12	0.0364 (4)	0.09585 (16)	0.5510 (2)	0.0574 (9)
H12A	0.1134	0.1091	0.6187	0.069*
H12B	0.0911	0.1117	0.4916	0.069*
C25	0.5753 (4)	0.02883 (16)	0.7731 (2)	0.0557 (10)
H25	0.5005	0.0501	0.7152	0.067*
C1	−0.4752 (5)	0.09216 (17)	0.4496 (3)	0.0645 (11)
H1	−0.4024	0.0638	0.4990	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0441 (15)	0.0649 (17)	0.0509 (15)	−0.0067 (11)	−0.0096 (13)	0.0141 (12)
O2	0.0626 (17)	0.0771 (19)	0.0547 (16)	0.0223 (13)	0.0070 (14)	0.0113 (14)
O4	0.0480 (16)	0.093 (2)	0.0741 (18)	−0.0142 (14)	−0.0017 (14)	0.0230 (14)
O1	0.0617 (18)	0.095 (2)	0.131 (2)	−0.0146 (15)	0.0281 (19)	0.0172 (17)
C23	0.045 (2)	0.040 (2)	0.038 (2)	0.0052 (18)	0.0066 (19)	−0.0055 (17)
C8	0.054 (3)	0.047 (3)	0.052 (3)	0.007 (2)	0.007 (2)	−0.0025 (19)
C24	0.034 (2)	0.042 (2)	0.035 (2)	0.0007 (16)	0.0098 (18)	0.0017 (17)
C15	0.044 (2)	0.043 (2)	0.036 (2)	0.0051 (17)	0.008 (2)	0.0012 (17)
C18	0.043 (2)	0.042 (2)	0.043 (2)	0.0059 (17)	0.006 (2)	−0.0001 (17)
C2	0.044 (2)	0.044 (2)	0.051 (2)	−0.0021 (18)	0.014 (2)	−0.0059 (19)
C11	0.054 (3)	0.043 (2)	0.044 (2)	0.0035 (18)	0.010 (2)	0.0044 (18)
C16	0.043 (2)	0.057 (2)	0.049 (2)	−0.0070 (18)	0.0062 (19)	0.0000 (19)
C19	0.068 (3)	0.050 (2)	0.057 (3)	0.009 (2)	0.011 (2)	0.013 (2)
C10	0.054 (2)	0.059 (3)	0.060 (3)	−0.006 (2)	−0.004 (2)	−0.001 (2)
C22	0.053 (2)	0.050 (2)	0.047 (2)	0.0019 (18)	0.002 (2)	0.0021 (19)
C6	0.088 (3)	0.073 (3)	0.064 (3)	0.029 (3)	−0.003 (3)	−0.002 (2)
C7	0.078 (3)	0.054 (3)	0.061 (3)	0.017 (2)	0.007 (2)	0.000 (2)
C3	0.044 (2)	0.043 (2)	0.048 (2)	0.0053 (18)	0.004 (2)	−0.0137 (19)
C9	0.056 (3)	0.055 (3)	0.066 (3)	−0.0092 (19)	0.014 (2)	0.006 (2)
C17	0.068 (3)	0.042 (2)	0.055 (3)	−0.0028 (18)	0.019 (2)	0.0043 (18)
C5	0.061 (3)	0.079 (3)	0.076 (3)	0.021 (2)	−0.014 (3)	−0.016 (2)
C4	0.053 (3)	0.061 (3)	0.080 (3)	0.003 (2)	0.008 (2)	−0.015 (2)
C21	0.049 (2)	0.066 (3)	0.059 (3)	0.007 (2)	−0.005 (2)	0.001 (2)
C20	0.074 (3)	0.066 (3)	0.057 (3)	0.022 (2)	0.001 (2)	0.013 (2)
C13	0.0291 (18)	0.056 (3)	0.051 (3)	0.0020 (16)	−0.0015 (19)	−0.0035 (18)
C14	0.040 (2)	0.063 (2)	0.055 (2)	0.0008 (17)	−0.0022 (19)	−0.0013 (19)
C12	0.047 (2)	0.056 (3)	0.061 (2)	−0.0008 (18)	−0.0109 (19)	−0.0035 (19)
C25	0.045 (2)	0.071 (3)	0.046 (2)	−0.001 (2)	−0.003 (2)	0.0062 (19)
C1	0.063 (3)	0.056 (3)	0.080 (3)	0.001 (2)	0.026 (3)	−0.001 (2)

Geometric parameters (Å, º)

O3—C15	1.359 (3)	C10—H10	0.9300
O3—C14	1.447 (3)	C22—C21	1.373 (3)
O2—C11	1.369 (3)	C22—H22	0.9300
O2—C12	1.435 (3)	C6—C7	1.363 (4)
O4—C25	1.211 (3)	C6—C5	1.394 (4)
O1—C1	1.200 (3)	C6—H6	0.9300
C23—C18	1.412 (4)	C7—H7	0.9300
C23—C22	1.412 (3)	C3—C4	1.420 (4)
C23—C24	1.438 (3)	C9—H9	0.9300
C8—C3	1.405 (4)	C17—H17	0.9300
C8—C9	1.415 (4)	C5—C4	1.371 (4)
C8—C7	1.416 (4)	C5—H5	0.9300
C24—C15	1.388 (3)	C4—H4	0.9300
C24—C25	1.458 (4)	C21—C20	1.393 (4)
C15—C16	1.404 (3)	C21—H21	0.9300
C18—C19	1.407 (4)	C20—H20	0.9300
C18—C17	1.407 (4)	C13—C13^i	1.335 (5)
C2—C11	1.389 (4)	C13—C14	1.514 (4)
C2—C3	1.440 (4)	C13—C12	1.521 (4)
C2—C1	1.458 (4)	C14—H14A	0.9700
C11—C10	1.396 (4)	C14—H14B	0.9700
C16—C17	1.363 (3)	C12—H12A	0.9700
C16—H16	0.9300	C12—H12B	0.9700
C19—C20	1.360 (4)	C25—H25	0.9300
C19—H19	0.9300	C1—H1	0.9300
C10—C9	1.369 (4)
C15—O3—C14	119.5 (2)	C8—C3—C2	118.8 (3)
C11—O2—C12	118.0 (2)	C4—C3—C2	122.8 (3)
C18—C23—C22	117.5 (3)	C10—C9—C8	120.2 (3)
C18—C23—C24	118.9 (3)	C10—C9—H9	119.9
C22—C23—C24	123.6 (3)	C8—C9—H9	119.9
C3—C8—C9	120.4 (3)	C16—C17—C18	122.2 (3)
C3—C8—C7	120.5 (3)	C16—C17—H17	118.9
C9—C8—C7	119.1 (4)	C18—C17—H17	118.9
C15—C24—C23	119.2 (3)	C4—C5—C6	121.8 (4)
C15—C24—C25	117.6 (3)	C4—C5—H5	119.1
C23—C24—C25	123.2 (3)	C6—C5—H5	119.1
O3—C15—C24	116.4 (3)	C5—C4—C3	119.4 (3)
O3—C15—C16	122.3 (3)	C5—C4—H4	120.3
C24—C15—C16	121.3 (3)	C3—C4—H4	120.3
C19—C18—C17	120.7 (3)	C22—C21—C20	120.7 (3)
C19—C18—C23	120.3 (3)	C22—C21—H21	119.7
C17—C18—C23	119.1 (3)	C20—C21—H21	119.7
C11—C2—C3	118.8 (3)	C19—C20—C21	120.0 (3)
C11—C2—C1	117.1 (3)	C19—C20—H20	120.0
C3—C2—C1	124.0 (3)	C21—C20—H20	120.0
O2—C11—C2	117.8 (3)	C13^i—C13—C14	122.7 (4)
O2—C11—C10	120.5 (3)	C13^i—C13—C12	124.0 (4)
C2—C11—C10	121.5 (3)	C14—C13—C12	113.3 (2)
C17—C16—C15	119.2 (3)	O3—C14—C13	104.2 (2)
C17—C16—H16	120.4	O3—C14—H14A	110.9
C15—C16—H16	120.4	C13—C14—H14A	110.9
C20—C19—C18	120.5 (3)	O3—C14—H14B	110.9
C20—C19—H19	119.7	C13—C14—H14B	110.9
C18—C19—H19	119.7	H14A—C14—H14B	108.9
C9—C10—C11	120.3 (3)	O2—C12—C13	109.2 (2)
C9—C10—H10	119.8	O2—C12—H12A	109.8
C11—C10—H10	119.8	C13—C12—H12A	109.8
C21—C22—C23	121.0 (3)	O2—C12—H12B	109.8
C21—C22—H22	119.5	C13—C12—H12B	109.8
C23—C22—H22	119.5	H12A—C12—H12B	108.3
C7—C6—C5	120.1 (4)	O4—C25—C24	128.7 (3)
C7—C6—H6	120.0	O4—C25—H25	115.7
C5—C6—H6	120.0	C24—C25—H25	115.7
C6—C7—C8	119.6 (4)	O1—C1—C2	126.9 (4)
C6—C7—H7	120.2	O1—C1—H1	116.5
C8—C7—H7	120.2	C2—C1—H1	116.5
C8—C3—C4	118.4 (3)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O4^ii	0.97	2.45	3.414 (4)	171
C12—H12B···O1^iii	0.97	2.46	3.199 (4)	132

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