Semiquinone (p-benzosemiquinone), a transient organic radical, was detected in the solid state by EPR spectroscopy revealing four symmetrically equivalent protons. A variable-temperature X-ray diffraction analysis (293 and 90 K) and EPR data support a dynamical disorder of the proton. A low-barrier O—H···O hydrogen bond stabilizes the radical. The C—O bond length is 1.297 (4) Å, corresponding to a bond order of ca 1.5. The geometry of the radical implies an electron delocalization throughout the benzenoid ring. Two polymorphs of semiquinone, monoclinic and triclinic, were observed and their structures determined. Their crystal packings were compared with those of quinhydrone polymorphs.
Supporting information
CCDC references: 629800; 629801; 629802; 629803
(type here to add preparation details)
(type here to add refinement details)
For all compounds, data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for sqt90k, sqm293k, sqt293k; SHELXS86 (Sheldrick, 1986) for sqm90k. For all compounds, 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 publication routines (Farrugia, 1999).
Crystal data top
C6H5O2 | Z = 1 |
Mr = 109.1 | F(000) = 51 |
Triclinic, P1 | Dx = 1.532 Mg m−3 |
a = 3.7615 (6) Å | Cu Kα radiation, λ = 1.54179 Å |
b = 5.6996 (12) Å | Cell parameters from 25 reflections |
c = 5.9065 (8) Å | θ = 8.3–30° |
α = 110.800 (15)° | µ = 0.97 mm−1 |
β = 91.164 (12)° | T = 90 K |
γ = 91.443 (15)° | Rod, red |
V = 118.28 (4) Å3 | 0.29 × 0.14 × 0.1 mm |
Data collection top
Enraf Nonius CAD4 diffractometer | θmax = 76.4°, θmin = 8.0° |
non–profiled ω/2θ scans | h = −4→4 |
1075 measured reflections | k = −7→7 |
499 independent reflections | l = −7→7 |
422 reflections with I > 2σ(I) | 3 standard reflections every 120 min |
Rint = 0.056 | intensity decay: 2% |
Refinement top
Refinement on F2 | All H-atom parameters refined |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.0384P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.036 | (Δ/σ)max < 0.001 |
wR(F2) = 0.106 | Δρmax = 0.35 e Å−3 |
S = 1.09 | Δρmin = −0.2 e Å−3 |
499 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
50 parameters | Extinction coefficient: 0.054 (15) |
0 restraints | |
Crystal data top
C6H5O2 | γ = 91.443 (15)° |
Mr = 109.1 | V = 118.28 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 3.7615 (6) Å | Cu Kα radiation |
b = 5.6996 (12) Å | µ = 0.97 mm−1 |
c = 5.9065 (8) Å | T = 90 K |
α = 110.800 (15)° | 0.29 × 0.14 × 0.1 mm |
β = 91.164 (12)° | |
Data collection top
Enraf Nonius CAD4 diffractometer | Rint = 0.056 |
1075 measured reflections | 3 standard reflections every 120 min |
499 independent reflections | intensity decay: 2% |
422 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.106 | All H-atom parameters refined |
S = 1.09 | Δρmax = 0.35 e Å−3 |
499 reflections | Δρmin = −0.2 e Å−3 |
50 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
H1 | 0.275 (4) | 0.076 (3) | 0.359 (3) | 0.016 (4)* | |
H2 | 0.641 (4) | 0.216 (3) | 0.101 (3) | 0.018 (4)* | |
H3 | 0.046 (14) | 0.459 (11) | 0.931 (8) | 0.050 (14)* | 0.5 |
C1 | 0.3718 (3) | 0.2476 (2) | 0.4109 (2) | 0.0136 (4) | |
O1 | 0.0852 (3) | 0.32797 (18) | 0.78144 (16) | 0.0180 (4) | |
C3 | 0.2827 (3) | 0.4133 (2) | 0.6480 (2) | 0.0126 (4) | |
C2 | 0.5838 (3) | 0.3307 (2) | 0.2693 (2) | 0.0133 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0130 (7) | 0.0126 (6) | 0.0150 (7) | −0.0012 (5) | −0.0016 (5) | 0.0050 (5) |
O1 | 0.0238 (6) | 0.0169 (6) | 0.0139 (6) | −0.0017 (4) | 0.0038 (4) | 0.0062 (4) |
C3 | 0.0113 (7) | 0.0153 (7) | 0.0126 (7) | −0.0010 (5) | 0.0003 (5) | 0.0065 (5) |
C2 | 0.0130 (7) | 0.0143 (7) | 0.0115 (7) | 0.0000 (5) | 0.0004 (5) | 0.0031 (5) |
Geometric parameters (Å, º) top
C1—C2 | 1.3599 (18) | O1—H3 | 0.95 (5) |
C1—C3 | 1.4357 (19) | C3—C2i | 1.4378 (17) |
C1—H1 | 0.972 (18) | C2—C3i | 1.4378 (17) |
O1—C3 | 1.2988 (16) | C2—H2 | 1.007 (18) |
| | | |
C2—C1—C3 | 120.45 (11) | O1—C3—C2i | 121.98 (11) |
C2—C1—H1 | 122.5 (10) | C1—C3—C2i | 118.78 (12) |
C3—C1—H1 | 117.0 (10) | C1—C2—C3i | 120.76 (12) |
C3—O1—H3 | 110 (4) | C1—C2—H2 | 120.4 (10) |
O1—C3—C1 | 119.24 (11) | C3i—C2—H2 | 118.8 (10) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Crystal data top
C6H5O2 | F(000) = 114 |
Mr = 109.1 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54179 Å |
a = 3.8362 (2) Å | Cell parameters from 25 reflections |
b = 5.9980 (3) Å | θ = 8.1–28.8° |
c = 11.5007 (6) Å | µ = 0.92 mm−1 |
β = 108.790 (1)° | T = 293 K |
V = 250.52 (2) Å3 | Plate, green |
Z = 2 | 0.25 × 0.15 × 0.1 mm |
Data collection top
Enraf Nonius CAD4 diffractometer | θmax = 76.0°, θmin = 8.1° |
non–profiled ω/2θ scans | h = 0→4 |
601 measured reflections | k = 0→7 |
523 independent reflections | l = −14→13 |
412 reflections with I > 2σ(I) | 3 standard reflections every 120 min |
Rint = 0.066 | intensity decay: 3% |
Refinement top
Refinement on F2 | All H-atom parameters refined |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.0735P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.039 | (Δ/σ)max < 0.001 |
wR(F2) = 0.106 | Δρmax = 0.22 e Å−3 |
S = 1.04 | Δρmin = −0.15 e Å−3 |
523 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
50 parameters | Extinction coefficient: 0.025 (7) |
0 restraints | |
Crystal data top
C6H5O2 | V = 250.52 (2) Å3 |
Mr = 109.1 | Z = 2 |
Monoclinic, P21/c | Cu Kα radiation |
a = 3.8362 (2) Å | µ = 0.92 mm−1 |
b = 5.9980 (3) Å | T = 293 K |
c = 11.5007 (6) Å | 0.25 × 0.15 × 0.1 mm |
β = 108.790 (1)° | |
Data collection top
Enraf Nonius CAD4 diffractometer | Rint = 0.066 |
601 measured reflections | 3 standard reflections every 120 min |
523 independent reflections | intensity decay: 3% |
412 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.106 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.22 e Å−3 |
523 reflections | Δρmin = −0.15 e Å−3 |
50 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
H3 | −0.028 (5) | 0.486 (3) | 0.2924 (18) | 0.041 (5)* | |
H2 | 0.305 (6) | 0.216 (4) | 0.639 (2) | 0.052 (5)* | |
H1 | 0.421 (16) | 0.067 (10) | 0.474 (6) | 0.09 (2)* | 0.5 |
O1 | 0.3177 (4) | 0.1598 (2) | 0.41739 (13) | 0.0512 (5) | |
C1 | 0.1673 (4) | 0.3216 (3) | 0.45904 (15) | 0.0337 (4) | |
C3 | −0.0196 (4) | 0.4930 (3) | 0.37616 (15) | 0.0354 (4) | |
C2 | 0.1830 (4) | 0.3351 (3) | 0.58420 (15) | 0.0354 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0616 (9) | 0.0377 (8) | 0.0502 (9) | 0.0145 (7) | 0.0124 (6) | −0.0086 (6) |
C1 | 0.0360 (8) | 0.0289 (8) | 0.0373 (8) | 0.0034 (7) | 0.0135 (6) | −0.0033 (7) |
C3 | 0.0400 (8) | 0.0375 (9) | 0.0296 (8) | 0.0034 (7) | 0.0127 (6) | 0.0012 (7) |
C2 | 0.0373 (8) | 0.0306 (8) | 0.0371 (9) | 0.0049 (7) | 0.0105 (6) | 0.0057 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.297 (2) | C3—C2i | 1.359 (2) |
O1—H1 | 0.85 (6) | C3—H3 | 0.955 (19) |
C1—C2 | 1.424 (2) | C2—C3i | 1.359 (2) |
C1—C3 | 1.428 (2) | C2—H2 | 0.97 (2) |
| | | |
C1—O1—H1 | 111 (4) | C2i—C3—H3 | 120.1 (12) |
O1—C1—C2 | 122.51 (16) | C1—C3—H3 | 119.3 (12) |
O1—C1—C3 | 118.65 (15) | C3i—C2—C1 | 120.58 (15) |
C2—C1—C3 | 118.83 (14) | C3i—C2—H2 | 121.1 (13) |
C2i—C3—C1 | 120.58 (14) | C1—C2—H2 | 118.2 (13) |
Symmetry code: (i) −x, −y+1, −z+1. |
Crystal data top
C6H5O2 | F(000) = 114 |
Mr = 109.1 | Dx = 1.492 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 3.770 (3) Å | Cell parameters from 16 reflections |
b = 5.980 (3) Å | θ = 8.2–25.8° |
c = 11.458 (14) Å | µ = 0.95 mm−1 |
β = 109.99 (8)° | T = 90 K |
V = 242.8 (4) Å3 | Plate, red |
Z = 2 | 0.18 × 0.07 × 0.05 mm |
Data collection top
Enraf Nonius CAD4 diffractometer | θmax = 75.8°, θmin = 8.2° |
non–profiled ω/2θ scans | h = −4→4 |
531 measured reflections | k = −7→0 |
507 independent reflections | l = −4→14 |
382 reflections with I > 2σ(I) | 3 standard reflections every 120 min |
Rint = 0.102 | intensity decay: 2% |
Refinement top
Refinement on F2 | All H-atom parameters refined |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0849P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.047 | (Δ/σ)max < 0.001 |
wR(F2) = 0.131 | Δρmax = 0.33 e Å−3 |
S = 1.09 | Δρmin = −0.42 e Å−3 |
507 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
50 parameters | Extinction coefficient: 0.053 (13) |
0 restraints | |
Crystal data top
C6H5O2 | V = 242.8 (4) Å3 |
Mr = 109.1 | Z = 2 |
Monoclinic, P21/c | Cu Kα radiation |
a = 3.770 (3) Å | µ = 0.95 mm−1 |
b = 5.980 (3) Å | T = 90 K |
c = 11.458 (14) Å | 0.18 × 0.07 × 0.05 mm |
β = 109.99 (8)° | |
Data collection top
Enraf Nonius CAD4 diffractometer | Rint = 0.102 |
531 measured reflections | 3 standard reflections every 120 min |
507 independent reflections | intensity decay: 2% |
382 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.131 | All H-atom parameters refined |
S = 1.09 | Δρmax = 0.33 e Å−3 |
507 reflections | Δρmin = −0.42 e Å−3 |
50 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.5021 (4) | 0.3395 (2) | 0.41682 (13) | 0.0242 (5) | |
C1 | 1.0156 (5) | −0.1659 (3) | 0.41428 (16) | 0.0169 (5) | |
C2 | 0.7654 (5) | 0.0050 (3) | 0.37502 (17) | 0.0166 (5) | |
C3 | 0.7420 (5) | 0.1783 (3) | 0.45841 (17) | 0.0162 (5) | |
H2 | 0.610 (6) | 0.015 (4) | 0.294 (2) | 0.019 (5)* | |
H1 | 1.025 (7) | −0.283 (5) | 0.357 (3) | 0.029 (6)* | |
H3 | 0.498 (14) | 0.429 (7) | 0.478 (4) | 0.018 (12)* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0334 (9) | 0.0161 (8) | 0.0254 (8) | 0.0090 (6) | 0.0132 (6) | 0.0041 (6) |
C1 | 0.0185 (9) | 0.0141 (9) | 0.0197 (9) | −0.0012 (7) | 0.0086 (7) | −0.0015 (7) |
C2 | 0.0158 (8) | 0.0175 (9) | 0.0161 (8) | −0.0014 (7) | 0.0051 (6) | −0.0021 (8) |
C3 | 0.0144 (8) | 0.0136 (8) | 0.0206 (9) | 0.0009 (7) | 0.0061 (6) | 0.0013 (7) |
Geometric parameters (Å, º) top
O1—C3 | 1.296 (2) | C1—H1 | 0.97 (3) |
O1—H3 | 0.88 (4) | C2—C3 | 1.433 (3) |
C1—C2 | 1.359 (3) | C2—H2 | 0.92 (2) |
C1—C3i | 1.434 (3) | C3—C1i | 1.434 (3) |
| | | |
C3—O1—H3 | 111 (3) | C1—C2—H2 | 121.1 (15) |
C2—C1—C3i | 120.29 (17) | C3—C2—H2 | 117.8 (16) |
C2—C1—H1 | 120.1 (16) | O1—C3—C2 | 119.16 (18) |
C3i—C1—H1 | 119.6 (16) | O1—C3—C1i | 122.30 (18) |
C1—C2—C3 | 121.15 (18) | C2—C3—C1i | 118.54 (18) |
Symmetry code: (i) −x+2, −y, −z+1. |
Crystal data top
C6H5O2 | Z = 1 |
Mr = 109.1 | F(000) = 51 |
Triclinic, P1 | Dx = 1.476 Mg m−3 |
a = 3.8291 (2) Å | Cu Kα radiation, λ = 1.54179 Å |
b = 5.7546 (3) Å | Cell parameters from 25 reflections |
c = 5.9771 (2) Å | θ = 11.6–27.4° |
α = 111.121 (3)° | µ = 0.94 mm−1 |
β = 89.936 (4)° | T = 293 K |
γ = 92.453 (4)° | Rod, red |
V = 122.73 (1) Å3 | 0.28 × 0.14 × 0.1 mm |
Data collection top
Enraf Nonius CAD4 diffractometer | θmax = 76.2°, θmin = 8.0° |
non–profiled ω/2θ scans | h = −4→4 |
654 measured reflections | k = −6→7 |
513 independent reflections | l = −7→0 |
409 reflections with I > 2σ(I) | 3 standard reflections every 120 min |
Rint = 0.062 | intensity decay: 10% |
Refinement top
Refinement on F2 | All H-atom parameters refined |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0702P)2 + 0.0343P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.043 | (Δ/σ)max < 0.001 |
wR(F2) = 0.124 | Δρmax = 0.24 e Å−3 |
S = 1.04 | Δρmin = −0.25 e Å−3 |
513 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
50 parameters | Extinction coefficient: 0.06 (2) |
0 restraints | |
Crystal data top
C6H5O2 | γ = 92.453 (4)° |
Mr = 109.1 | V = 122.73 (1) Å3 |
Triclinic, P1 | Z = 1 |
a = 3.8291 (2) Å | Cu Kα radiation |
b = 5.7546 (3) Å | µ = 0.94 mm−1 |
c = 5.9771 (2) Å | T = 293 K |
α = 111.121 (3)° | 0.28 × 0.14 × 0.1 mm |
β = 89.936 (4)° | |
Data collection top
Enraf Nonius CAD4 diffractometer | Rint = 0.062 |
654 measured reflections | 3 standard reflections every 120 min |
513 independent reflections | intensity decay: 10% |
409 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.124 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.24 e Å−3 |
513 reflections | Δρmin = −0.25 e Å−3 |
50 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
H2 | 0.283 (5) | 0.081 (4) | 0.367 (4) | 0.039 (5)* | |
H3 | 0.636 (6) | 0.221 (4) | 0.104 (4) | 0.047 (6)* | |
H1 | 0.057 (13) | 0.458 (10) | 0.926 (8) | 0.051 (13)* | 0.5 |
C2 | 0.3722 (4) | 0.2500 (3) | 0.4123 (3) | 0.0326 (5) | |
O1 | 0.0890 (4) | 0.3286 (2) | 0.7807 (2) | 0.0443 (5) | |
C1 | 0.2853 (4) | 0.4142 (3) | 0.6475 (3) | 0.0303 (5) | |
C3 | 0.5823 (4) | 0.3332 (3) | 0.2716 (3) | 0.0332 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0360 (9) | 0.0285 (8) | 0.0311 (9) | −0.0050 (6) | 0.0030 (6) | 0.0089 (7) |
O1 | 0.0562 (9) | 0.0428 (8) | 0.0340 (8) | −0.0080 (6) | 0.0146 (6) | 0.0153 (6) |
C1 | 0.0306 (8) | 0.0337 (9) | 0.0279 (8) | −0.0023 (6) | 0.0061 (6) | 0.0129 (7) |
C3 | 0.0368 (9) | 0.0335 (9) | 0.0266 (8) | −0.0016 (7) | 0.0069 (7) | 0.0078 (7) |
Geometric parameters (Å, º) top
C2—C3 | 1.356 (2) | O1—H1 | 0.93 (5) |
C2—C1 | 1.431 (2) | C1—C3i | 1.426 (2) |
C2—H2 | 0.96 (2) | C3—C1i | 1.426 (2) |
O1—C1 | 1.3004 (19) | C3—H3 | 1.00 (2) |
| | | |
C3—C2—C1 | 120.25 (15) | O1—C1—C2 | 119.06 (14) |
C3—C2—H2 | 123.6 (13) | C3i—C1—C2 | 118.84 (14) |
C1—C2—H2 | 116.0 (13) | C2—C3—C1i | 120.90 (14) |
C1—O1—H1 | 108 (3) | C2—C3—H3 | 120.8 (13) |
O1—C1—C3i | 122.10 (14) | C1i—C3—H3 | 118.2 (12) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
| (sqt90k) | (sqm293k) | (sqm90k) | (sqt293k) |
Crystal data |
Chemical formula | C6H5O2 | C6H5O2 | C6H5O2 | C6H5O2 |
Mr | 109.1 | 109.1 | 109.1 | 109.1 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 90 | 293 | 90 | 293 |
a, b, c (Å) | 3.7615 (6), 5.6996 (12), 5.9065 (8) | 3.8362 (2), 5.9980 (3), 11.5007 (6) | 3.770 (3), 5.980 (3), 11.458 (14) | 3.8291 (2), 5.7546 (3), 5.9771 (2) |
α, β, γ (°) | 110.800 (15), 91.164 (12), 91.443 (15) | 90, 108.790 (1), 90 | 90, 109.99 (8), 90 | 111.121 (3), 89.936 (4), 92.453 (4) |
V (Å3) | 118.28 (4) | 250.52 (2) | 242.8 (4) | 122.73 (1) |
Z | 1 | 2 | 2 | 1 |
Radiation type | Cu Kα | Cu Kα | Cu Kα | Cu Kα |
µ (mm−1) | 0.97 | 0.92 | 0.95 | 0.94 |
Crystal size (mm) | 0.29 × 0.14 × 0.1 | 0.25 × 0.15 × 0.1 | 0.18 × 0.07 × 0.05 | 0.28 × 0.14 × 0.1 |
|
Data collection |
Diffractometer | Enraf Nonius CAD4 diffractometer | Enraf Nonius CAD4 diffractometer | Enraf Nonius CAD4 diffractometer | Enraf Nonius CAD4 diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1075, 499, 422 | 601, 523, 412 | 531, 507, 382 | 654, 513, 409 |
Rint | 0.056 | 0.066 | 0.102 | 0.062 |
(sin θ/λ)max (Å−1) | 0.630 | 0.629 | 0.629 | 0.630 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.106, 1.09 | 0.039, 0.106, 1.04 | 0.047, 0.131, 1.09 | 0.043, 0.124, 1.04 |
No. of reflections | 499 | 523 | 507 | 513 |
No. of parameters | 50 | 50 | 50 | 50 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.35, −0.2 | 0.22, −0.15 | 0.33, −0.42 | 0.24, −0.25 |
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