4,4'-Bis­[2,2-bis(4-methoxy­phenyl)­ethenyl]­bi­phenyl

The mol­ecule of 4,4'-bis­[2,2-bis(4-methoxy­phenyl)­ethenyl]­bi­phenyl, C₄₄H₃₈O₄, has a crystallographic center of symmetry at the midpoint of the bi­phenyl single bond, resulting in an asymmetric unit of one half-mol­ecule. The geometry of the structure is as expected.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
Some non-H atoms missing
• R factor = 0.038
• wR factor = 0.102
• Data-to-parameter ratio = 10.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



TYPE_017  Alert A _chemical_formula_weight is not data type numb.

TYPE_027  Alert A _exptl_crystal_density_diffrn is not of type numb.

TYPE_036  Alert A _exptl_absorpt_coefficient_mu is not of type numb.

ABSMU_01  Alert A The ratio of given/expected absorption coefficient lies
          outside the range 0.90 <> 1.10
          Calculated value of mu =     0.039
          Value of mu given      =     0.079

CHEMW_01  Alert A The ratio of given/expected molecular weight as calculated
          from the _chemical_formula_sum lies outside
          the range 0.90 <> 1.10
          Calculated formula weight =   315.3909
          Formula weight given      =   630.7400


 Alert Level C:



CHEMW_01  Alert C The difference between the given and expected weight for
          compound is greater 1 mass unit. Check that all hydrogen
          atoms have been taken into account.

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and _chemical_formula_moiety. This is
          usually due to the moiety formula being in the wrong format.
          Atom count from _chemical_formula_sum:   C22 H19 O2
          Atom count from _chemical_formula_moiety:C44 H38 O4

FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C22 H19 O2
          Atom count from the _atom_site data:  C44 H38 O4

CELLZ_01
         From the CIF: _cell_formula_units_Z    1
         From the CIF: _chemical_formula_sum  C22 H19 O2
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C         22.00     44.00  -22.00
         H         19.00     38.00  -19.00
         O          2.00      4.00   -2.00
          Difference between formula and atom_site contents detected.
          ALERT: Large difference may be due to a
          symmetry error - see SYMMG tests


 5 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: CAD-4 Software (Enraf Nonius, 1994); cell refinement: CAD-4 Software; data reduction: CAD-4 Software and WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97.

4,4'bis[2,2bis(4-methoxyphenyl)ethenyl]biphenyl

Crystal data

C44H38O4	Z = 1
Mr = 630.74	F(000) = 334
Triclinic, P1	Dx = 1.249 Mg m^−3
Hall symbol: -P 1	Melting point: 210-212° K
a = 7.748 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.792 (3) Å	Cell parameters from 25 reflections
c = 12.410 (5) Å	θ = 10–17°
α = 92.51 (3)°	µ = 0.08 mm^−1
β = 90.13 (3)°	T = 293 K
γ = 96.91 (3)°	Prism, light yellow–green
V = 838.4 (5) Å^3	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.021
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.6°
Graphite monochromator	h = −9→9
ω/2θ scans	k = −10→10
5886 measured reflections	l = −14→14
2943 independent reflections	3 standard reflections every 7200 min
2138 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	All H-atom parameters refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.1052P] where P = (Fo^2 + 2Fc^2)/3
2943 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. To determine the structure of the title compound we measured reflective intensities on our CAD4 diffractometer. A stationary anode served as X-ray source. The incident X-ray beam was monochromated with a pyrrolithic graphite crystal. Reflection intensities were measured in an ω/2θ scan mode with a scan angle of (1.30 + 0.70 t g θ). Intensities were measured with an aperture of (2.70 + 0.4 t gθ) Backgrounds were obtained from analysis of the scan profile (Blessing et al., 1974)

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	0.40049 (16)	−0.18029 (12)	0.26682 (10)	0.0590 (3)
C1	0.95731 (19)	0.92495 (16)	0.01648 (12)	0.0397 (3)
C8	0.6903 (2)	0.42967 (17)	0.21031 (12)	0.0428 (4)
C9	0.60446 (19)	0.27249 (17)	0.22458 (12)	0.0426 (4)
C13	0.5712 (2)	0.04317 (18)	0.32676 (14)	0.0492 (4)
H13	0.600 (2)	−0.011 (2)	0.3893 (14)	0.059*
C12	0.4622 (2)	−0.03157 (17)	0.24853 (13)	0.0458 (4)
C15	0.7614 (2)	0.52010 (17)	0.30800 (12)	0.0432 (4)
C6	0.8630 (2)	0.91000 (18)	0.11132 (13)	0.0468 (4)
H6	0.848 (2)	0.999 (2)	0.1569 (13)	0.056*
C4	0.7957 (2)	0.63693 (17)	0.08225 (12)	0.0434 (4)
C2	0.9643 (2)	0.79104 (18)	−0.04618 (13)	0.0511 (4)
H2	1.027 (2)	0.793 (2)	−0.1137 (14)	0.061*
C7	0.7162 (2)	0.48489 (18)	0.11187 (13)	0.0473 (4)
H7	0.680 (2)	0.4137 (19)	0.0496 (14)	0.057*
C3	0.8834 (2)	0.65243 (19)	−0.01497 (13)	0.0510 (4)
H3	0.891 (2)	0.562 (2)	−0.0621 (14)	0.061*
C14	0.6406 (2)	0.19342 (18)	0.31555 (13)	0.0468 (4)
H14	0.719 (2)	0.2442 (19)	0.3710 (14)	0.056*
C11	0.4214 (2)	0.0448 (2)	0.15928 (14)	0.0525 (4)
H11	0.346 (2)	−0.005 (2)	0.1034 (14)	0.063*
C5	0.7863 (2)	0.77102 (18)	0.14410 (13)	0.0487 (4)
H5	0.724 (2)	0.7675 (19)	0.2108 (14)	0.058*
C10	0.4915 (2)	0.1951 (2)	0.14863 (14)	0.0510 (4)
H10	0.459 (2)	0.247 (2)	0.0843 (14)	0.061*
C20	0.6562 (2)	0.57786 (19)	0.38532 (13)	0.0501 (4)
H20	0.529 (2)	0.5513 (19)	0.3796 (13)	0.060*
O2	0.98523 (18)	0.80877 (17)	0.55581 (11)	0.0779 (4)
C19	0.7256 (2)	0.6744 (2)	0.46991 (13)	0.0530 (4)
H19	0.648 (2)	0.716 (2)	0.5208 (15)	0.064*
C17	1.0100 (2)	0.6498 (2)	0.40436 (15)	0.0584 (5)
H17	1.136 (3)	0.676 (2)	0.4126 (15)	0.070*
C16	0.9396 (2)	0.5551 (2)	0.32123 (14)	0.0520 (4)
H16	1.015 (2)	0.5128 (19)	0.2677 (14)	0.062*
C18	0.9024 (2)	0.71183 (19)	0.47807 (13)	0.0537 (4)
C21	0.3170 (3)	−0.2696 (3)	0.1797 (2)	0.0733 (6)
H21A	0.197 (4)	−0.242 (3)	0.161 (2)	0.110*
H21B	0.302 (3)	−0.376 (3)	0.2054 (19)	0.110*
H21C	0.394 (3)	−0.261 (3)	0.112 (2)	0.110*
C22	0.8802 (4)	0.8879 (4)	0.6278 (2)	0.0968 (9)
H22A	0.790 (4)	0.948 (3)	0.583 (2)	0.145*
H22B	0.964 (4)	0.952 (4)	0.672 (2)	0.145*
H22C	0.814 (4)	0.800 (4)	0.672 (2)	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0668 (8)	0.0397 (6)	0.0674 (8)	−0.0076 (6)	0.0030 (6)	0.0047 (5)
C1	0.0428 (8)	0.0376 (8)	0.0399 (8)	0.0093 (6)	0.0005 (6)	0.0047 (6)
C8	0.0447 (9)	0.0368 (8)	0.0467 (9)	0.0044 (7)	0.0043 (7)	0.0018 (7)
C9	0.0433 (8)	0.0393 (8)	0.0450 (9)	0.0036 (7)	0.0032 (7)	0.0031 (7)
C13	0.0578 (10)	0.0421 (9)	0.0478 (9)	0.0040 (8)	−0.0005 (8)	0.0071 (7)
C12	0.0455 (9)	0.0376 (8)	0.0531 (9)	0.0001 (7)	0.0063 (7)	0.0024 (7)
C15	0.0497 (9)	0.0347 (8)	0.0447 (9)	0.0013 (7)	0.0031 (7)	0.0052 (7)
C6	0.0572 (10)	0.0354 (8)	0.0479 (9)	0.0070 (7)	0.0113 (7)	−0.0002 (7)
C4	0.0494 (9)	0.0374 (8)	0.0434 (9)	0.0046 (7)	−0.0004 (7)	0.0051 (7)
C2	0.0724 (12)	0.0404 (9)	0.0406 (9)	0.0068 (8)	0.0133 (8)	0.0035 (7)
C7	0.0565 (10)	0.0380 (9)	0.0464 (9)	0.0021 (7)	0.0018 (7)	0.0000 (7)
C3	0.0720 (11)	0.0382 (9)	0.0418 (9)	0.0042 (8)	0.0063 (8)	−0.0015 (7)
C14	0.0522 (10)	0.0419 (9)	0.0450 (9)	0.0012 (7)	−0.0030 (7)	0.0009 (7)
C11	0.0504 (10)	0.0509 (10)	0.0529 (10)	−0.0069 (8)	−0.0061 (8)	0.0004 (8)
C5	0.0588 (10)	0.0401 (9)	0.0474 (9)	0.0057 (7)	0.0154 (8)	0.0037 (7)
C10	0.0528 (10)	0.0506 (10)	0.0485 (10)	−0.0009 (8)	−0.0060 (8)	0.0089 (8)
C20	0.0475 (10)	0.0497 (10)	0.0519 (10)	0.0010 (8)	0.0058 (8)	0.0016 (8)
O2	0.0716 (9)	0.0890 (10)	0.0707 (9)	0.0123 (8)	−0.0162 (7)	−0.0294 (8)
C19	0.0576 (11)	0.0541 (10)	0.0476 (10)	0.0092 (8)	0.0080 (8)	−0.0016 (8)
C17	0.0465 (10)	0.0636 (11)	0.0642 (11)	0.0059 (9)	−0.0036 (9)	−0.0054 (9)
C16	0.0485 (10)	0.0539 (10)	0.0533 (10)	0.0062 (8)	0.0051 (8)	−0.0035 (8)
C18	0.0599 (11)	0.0516 (10)	0.0488 (10)	0.0063 (8)	−0.0072 (8)	−0.0039 (8)
C21	0.0753 (14)	0.0532 (12)	0.0839 (15)	−0.0198 (11)	−0.0041 (12)	−0.0040 (11)
C22	0.1007 (19)	0.109 (2)	0.0778 (17)	0.0183 (16)	−0.0105 (14)	−0.0472 (15)

Geometric parameters (Å, º)

O1—C12	1.3660 (19)	C7—H7	0.990 (17)
O1—C21	1.415 (2)	C3—H3	0.970 (18)
C1—C2	1.389 (2)	C14—H14	0.973 (17)
C1—C6	1.390 (2)	C11—C10	1.379 (2)
C1—C1^i	1.478 (3)	C11—H11	0.964 (18)
C8—C7	1.341 (2)	C5—H5	0.959 (17)
C8—C9	1.478 (2)	C10—H10	0.983 (18)
C8—C15	1.487 (2)	C20—C19	1.386 (2)
C9—C10	1.383 (2)	C20—H20	0.986 (18)
C9—C14	1.397 (2)	O2—C18	1.365 (2)
C13—C12	1.376 (2)	O2—C22	1.425 (3)
C13—C14	1.378 (2)	C19—C18	1.372 (3)
C13—H13	0.969 (18)	C19—H19	0.962 (18)
C12—C11	1.376 (2)	C17—C16	1.367 (2)
C15—C20	1.380 (2)	C17—C18	1.377 (3)
C15—C16	1.386 (2)	C17—H17	0.98 (2)
C6—C5	1.372 (2)	C16—H16	0.977 (17)
C6—H6	0.965 (17)	C21—H21A	1.01 (3)
C4—C5	1.388 (2)	C21—H21B	1.00 (3)
C4—C3	1.390 (2)	C21—H21C	1.03 (2)
C4—C7	1.465 (2)	C22—H22A	1.09 (3)
C2—C3	1.374 (2)	C22—H22B	0.96 (3)
C2—H2	0.971 (18)	C22—H22C	1.05 (3)
C12—O1—C21	117.36 (15)	C12—C11—C10	119.63 (16)
C2—C1—C6	116.06 (14)	C12—C11—H11	121.2 (11)
C2—C1—C1^i	122.06 (17)	C10—C11—H11	119.1 (11)
C6—C1—C1^i	121.87 (17)	C6—C5—C4	121.33 (15)
C7—C8—C9	121.25 (14)	C6—C5—H5	118.9 (10)
C7—C8—C15	120.70 (14)	C4—C5—H5	119.8 (10)
C9—C8—C15	117.83 (13)	C11—C10—C9	122.14 (16)
C10—C9—C14	117.04 (15)	C11—C10—H10	117.7 (10)
C10—C9—C8	122.64 (14)	C9—C10—H10	120.1 (10)
C14—C9—C8	120.27 (14)	C15—C20—C19	121.25 (16)
C12—C13—C14	120.32 (16)	C15—C20—H20	119.3 (10)
C12—C13—H13	119.3 (10)	C19—C20—H20	119.4 (10)
C14—C13—H13	120.4 (10)	C18—O2—C22	117.58 (17)
O1—C12—C11	124.35 (15)	C18—C19—C20	119.56 (16)
O1—C12—C13	115.94 (15)	C18—C19—H19	121.2 (11)
C11—C12—C13	119.70 (15)	C20—C19—H19	119.2 (11)
C20—C15—C16	117.58 (15)	C16—C17—C18	119.74 (17)
C20—C15—C8	122.52 (15)	C16—C17—H17	121.5 (11)
C16—C15—C8	119.84 (14)	C18—C17—H17	118.7 (11)
C5—C6—C1	122.51 (15)	C17—C16—C15	121.76 (16)
C5—C6—H6	117.0 (10)	C17—C16—H16	120.1 (10)
C1—C6—H6	120.5 (10)	C15—C16—H16	118.1 (10)
C5—C4—C3	116.28 (15)	O2—C18—C19	124.84 (16)
C5—C4—C7	124.29 (15)	O2—C18—C17	115.17 (16)
C3—C4—C7	119.41 (14)	C19—C18—C17	119.99 (16)
C3—C2—C1	121.48 (15)	O1—C21—H21A	114.3 (14)
C3—C2—H2	118.1 (10)	O1—C21—H21B	104.4 (14)
C1—C2—H2	120.4 (10)	H21A—C21—H21B	107 (2)
C8—C7—C4	128.93 (15)	O1—C21—H21C	109.8 (14)
C8—C7—H7	116.7 (10)	H21A—C21—H21C	109 (2)
C4—C7—H7	114.3 (10)	H21B—C21—H21C	111.5 (19)
C2—C3—C4	122.24 (15)	O2—C22—H22A	110.7 (16)
C2—C3—H3	118.3 (10)	O2—C22—H22B	103.4 (18)
C4—C3—H3	119.5 (10)	H22A—C22—H22B	116 (2)
C13—C14—C9	121.13 (16)	O2—C22—H22C	103.5 (17)
C13—C14—H14	119.3 (10)	H22A—C22—H22C	112 (2)
C9—C14—H14	119.5 (10)	H22B—C22—H22C	111 (2)
C21—O1—C12—C11	12.6 (2)	C7—C8—C9—C10	−24.7 (2)
C21—O1—C12—C13	−167.84 (16)	C7—C8—C9—C14	152.94 (16)
C22—O2—C18—C17	173.99 (19)	C15—C8—C9—C10	160.69 (15)
C22—O2—C18—C19	−6.1 (3)	C9—C8—C15—C16	111.56 (17)
C6—C1—C1^i—C2^i	1.0 (2)	C9—C8—C15—C20	−71.5 (2)
C6—C1—C1^i—C6^i	−180.00 (15)	C8—C9—C10—C11	175.47 (15)
C6—C1—C2—C3	−0.5 (2)	C10—C9—C14—C13	2.2 (2)
C1^i—C1—C2—C3	−179.56 (15)	C14—C9—C10—C11	−2.2 (2)
C2—C1—C6—C5	2.4 (2)	C8—C9—C14—C13	−175.49 (15)
C1^i—C1—C6—C5	−178.54 (15)	C9—C10—C11—C12	0.8 (2)
C2—C1—C1^i—C2^i	180.00 (15)	C10—C11—C12—C13	0.6 (2)
C2—C1—C1^i—C6^i	−1.0 (2)	C10—C11—C12—O1	−179.81 (15)
C1—C2—C3—C4	−2.4 (2)	O1—C12—C13—C14	179.82 (15)
C2—C3—C4—C7	−178.38 (15)	C11—C12—C13—C14	−0.6 (2)
C2—C3—C4—C5	3.2 (2)	C12—C13—C14—C9	−0.9 (2)
C5—C4—C7—C8	−31.7 (3)	C8—C15—C20—C19	−173.49 (15)
C3—C4—C5—C6	−1.3 (2)	C20—C15—C16—C17	−3.4 (2)
C7—C4—C5—C6	−179.63 (15)	C8—C15—C16—C17	173.74 (16)
C3—C4—C7—C8	150.00 (17)	C16—C15—C20—C19	3.5 (2)
C4—C5—C6—C1	−1.5 (2)	C15—C16—C17—C18	0.6 (3)
C4—C7—C8—C9	178.97 (15)	C16—C17—C18—O2	−177.92 (16)
C4—C7—C8—C15	−6.5 (3)	C16—C17—C18—C19	2.2 (3)
C15—C8—C9—C14	−21.7 (2)	C17—C18—C19—C20	−2.0 (3)
C7—C8—C15—C16	−63.1 (2)	O2—C18—C19—C20	178.11 (16)
C7—C8—C15—C20	113.84 (19)	C18—C19—C20—C15	−0.9 (3)

Symmetry code: (i) −x+2, −y+2, −z.