The inclination of the two aryl rings (ring twists) in a series of benzophenone molecules has been examined. For each structure the dihedral angle (between the planes of the two sets of six aromatic C atoms) relates to both the steric considerations of the single molecule and the packing forces related to the crystal structure. Six new benzophenone structures are incorporated into the study including 2,2'-dihydroxy-4,4'-dimethoxybenzophenone (I), C15H14O5, that appears to have the smallest reported twist angle, 37.85 (5)°, of any substituted benzophenone reported to date. Three further benzophenones, 4,4'-bis(diethylamino)benzophenone (II), C21H28N2O, 3,4-dihydroxybenzophenone (III), C13H10O3, and 3-hydroxybenzophenone (IV), C13H10O2, have similar ring twists [49.83 (5), 49.84 (5) and 51.61 (5)°, respectively] that are comparable with the value of 54° found for the orthorhombic form of unsubstituted benzophenone. 4-Chloro-4'-hydroxybenzophenone (V), C13H9ClO2, has a ring twist of 64.66 (8)° that is close to the value of 65° found in the metastable monoclinic form of unsubstituted benzophenone and 2-amino-2',5-dichlorobenzophenone (VI), C13H9Cl2NO2, has a large ring twist of 83.72 (6)°. Comparisons with a further 98 substituted benzophenone molecules from the Cambridge Structural Database (CSD) have been made.
Supporting information
CCDC references: 685148; 685149; 685150; 685151; 685152; 685153
For all compounds, data collection: DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek,2002); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Crystal data top
C15H14O5 | F(000) = 576 |
Mr = 274.26 | Dx = 1.452 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8466 (1) Å | Cell parameters from 5660 reflections |
b = 25.1521 (12) Å | θ = 2.9–27.5° |
c = 12.9802 (6) Å | µ = 0.11 mm−1 |
β = 92.545 (3)° | T = 120 K |
V = 1254.60 (9) Å3 | Rod, yellow |
Z = 4 | 0.52 × 0.08 × 0.06 mm |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 1759 reflections with I > 2σ(I) |
ϕ and ω scans to fill Ewald sphere | Rint = 0.083 |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | θmax = 27.5°, θmin = 3.1° |
Tmin = 0.727, Tmax = 0.994 | h = −4→4 |
13532 measured reflections | k = −32→32 |
2798 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0601P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max < 0.001 |
S = 0.99 | Δρmax = 0.23 e Å−3 |
2798 reflections | Δρmin = −0.30 e Å−3 |
189 parameters | |
Crystal data top
C15H14O5 | V = 1254.60 (9) Å3 |
Mr = 274.26 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.8466 (1) Å | µ = 0.11 mm−1 |
b = 25.1521 (12) Å | T = 120 K |
c = 12.9802 (6) Å | 0.52 × 0.08 × 0.06 mm |
β = 92.545 (3)° | |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 2798 independent reflections |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | 1759 reflections with I > 2σ(I) |
Tmin = 0.727, Tmax = 0.994 | Rint = 0.083 |
13532 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.23 e Å−3 |
2798 reflections | Δρmin = −0.30 e Å−3 |
189 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 | |
O1 | 0.2426 (4) | 0.33006 (5) | 0.61210 (10) | 0.0338 (4) | |
O2 | 0.4075 (3) | 0.42282 (5) | 0.55737 (10) | 0.0276 (3) | |
H2 | 0.381 (5) | 0.3930 (8) | 0.5979 (16) | 0.036* | |
O3 | −0.0324 (4) | 0.24312 (5) | 0.67400 (10) | 0.0317 (4) | |
H3 | 0.070 (6) | 0.2763 (9) | 0.6786 (17) | 0.041* | |
O4 | 0.0095 (3) | 0.48074 (5) | 0.22432 (9) | 0.0239 (3) | |
O5 | −0.1132 (3) | 0.10187 (4) | 0.43090 (10) | 0.0260 (3) | |
C1 | 0.1229 (5) | 0.35934 (7) | 0.44219 (14) | 0.0196 (4) | |
C2 | 0.2486 (5) | 0.41104 (7) | 0.46524 (14) | 0.0214 (4) | |
C3 | 0.2200 (4) | 0.45220 (7) | 0.39415 (14) | 0.0213 (4) | |
H3A | 0.3132 | 0.4863 | 0.4106 | 0.026* | |
C4 | 0.0548 (4) | 0.44305 (7) | 0.29931 (14) | 0.0195 (4) | |
C5 | −0.0861 (4) | 0.39294 (7) | 0.27505 (14) | 0.0216 (4) | |
H5 | −0.2036 | 0.3871 | 0.2101 | 0.026* | |
C6 | −0.0537 (5) | 0.35252 (7) | 0.34528 (14) | 0.0201 (4) | |
H6 | −0.1527 | 0.3189 | 0.3284 | 0.024* | |
C7 | 0.1609 (5) | 0.31745 (7) | 0.51936 (14) | 0.0226 (4) | |
C8 | 0.0985 (4) | 0.26080 (7) | 0.49646 (14) | 0.0204 (4) | |
C9 | −0.0052 (5) | 0.22660 (7) | 0.57542 (13) | 0.0214 (4) | |
C10 | −0.0920 (4) | 0.17398 (7) | 0.55475 (14) | 0.0210 (4) | |
H10 | −0.1814 | 0.1522 | 0.6072 | 0.025* | |
C11 | −0.0477 (4) | 0.15351 (7) | 0.45766 (14) | 0.0206 (4) | |
C12 | 0.0805 (5) | 0.18543 (7) | 0.37953 (14) | 0.0224 (4) | |
H12 | 0.1201 | 0.1708 | 0.3136 | 0.027* | |
C13 | 0.1481 (4) | 0.23805 (7) | 0.39920 (14) | 0.0204 (4) | |
H13 | 0.2309 | 0.2598 | 0.3456 | 0.024* | |
C14 | 0.1601 (5) | 0.53209 (7) | 0.24568 (15) | 0.0268 (5) | |
H14A | 0.4127 | 0.5285 | 0.2567 | 0.032* | |
H14B | 0.0613 | 0.5469 | 0.3077 | 0.032* | |
H14C | 0.1091 | 0.5559 | 0.1871 | 0.032* | |
C15 | −0.2433 (5) | 0.06766 (7) | 0.50848 (16) | 0.0294 (5) | |
H15A | −0.4637 | 0.0818 | 0.5319 | 0.035* | |
H15B | −0.0737 | 0.0657 | 0.567 | 0.035* | |
H15C | −0.2816 | 0.032 | 0.4797 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0563 (10) | 0.0266 (7) | 0.0184 (7) | −0.0064 (7) | −0.0016 (7) | −0.0016 (6) |
O2 | 0.0406 (8) | 0.0223 (7) | 0.0194 (7) | −0.0049 (6) | −0.0034 (6) | 0.0001 (6) |
O3 | 0.0506 (9) | 0.0258 (7) | 0.0192 (7) | −0.0043 (7) | 0.0088 (7) | 0.0000 (6) |
O4 | 0.0298 (7) | 0.0190 (6) | 0.0227 (7) | −0.0003 (6) | −0.0025 (6) | 0.0017 (5) |
O5 | 0.0340 (8) | 0.0168 (7) | 0.0275 (8) | −0.0036 (5) | 0.0026 (6) | 0.0012 (5) |
C1 | 0.0198 (9) | 0.0188 (9) | 0.0207 (10) | 0.0000 (7) | 0.0055 (8) | −0.0017 (7) |
C2 | 0.0201 (10) | 0.0242 (10) | 0.0198 (10) | 0.0001 (8) | 0.0017 (8) | −0.0047 (8) |
C3 | 0.0209 (10) | 0.0181 (9) | 0.0251 (10) | −0.0012 (8) | 0.0033 (8) | −0.0022 (8) |
C4 | 0.0190 (9) | 0.0196 (9) | 0.0202 (10) | 0.0016 (7) | 0.0039 (8) | 0.0009 (8) |
C5 | 0.0208 (10) | 0.0230 (10) | 0.0208 (10) | −0.0004 (8) | −0.0004 (8) | −0.0040 (8) |
C6 | 0.0179 (9) | 0.0173 (9) | 0.0254 (10) | −0.0008 (7) | 0.0038 (8) | −0.0031 (8) |
C7 | 0.0243 (10) | 0.0219 (9) | 0.0219 (10) | −0.0013 (8) | 0.0051 (8) | −0.0028 (8) |
C8 | 0.0200 (10) | 0.0193 (9) | 0.0219 (10) | 0.0003 (7) | 0.0019 (8) | 0.0004 (8) |
C9 | 0.0214 (9) | 0.0242 (10) | 0.0188 (10) | 0.0029 (8) | 0.0035 (8) | −0.0006 (8) |
C10 | 0.0207 (10) | 0.0212 (9) | 0.0214 (10) | 0.0011 (7) | 0.0026 (8) | 0.0050 (8) |
C11 | 0.0181 (9) | 0.0166 (9) | 0.0269 (10) | 0.0003 (7) | −0.0014 (8) | 0.0006 (8) |
C12 | 0.0257 (10) | 0.0223 (9) | 0.0196 (10) | 0.0004 (8) | 0.0036 (8) | −0.0006 (8) |
C13 | 0.0212 (9) | 0.0204 (9) | 0.0199 (10) | 0.0013 (7) | 0.0041 (8) | 0.0030 (8) |
C14 | 0.0305 (11) | 0.0210 (10) | 0.0289 (11) | −0.0042 (8) | −0.0006 (9) | 0.0030 (8) |
C15 | 0.0314 (11) | 0.0215 (10) | 0.0351 (12) | −0.0070 (8) | −0.0001 (10) | 0.0051 (9) |
Geometric parameters (Å, º) top
O1—C7 | 1.271 (2) | C6—H6 | 0.95 |
O2—C2 | 1.352 (2) | C7—C8 | 1.473 (2) |
O2—H2 | 0.92 (2) | C8—C13 | 1.407 (2) |
O3—C9 | 1.354 (2) | C8—C9 | 1.409 (2) |
O3—H3 | 0.92 (2) | C9—C10 | 1.388 (2) |
O4—C4 | 1.364 (2) | C10—C11 | 1.379 (2) |
O4—C14 | 1.438 (2) | C10—H10 | 0.95 |
O5—C11 | 1.365 (2) | C11—C12 | 1.400 (2) |
O5—C15 | 1.432 (2) | C12—C13 | 1.370 (2) |
C1—C6 | 1.413 (2) | C12—H12 | 0.95 |
C1—C2 | 1.415 (2) | C13—H13 | 0.95 |
C1—C7 | 1.457 (2) | C14—H14A | 0.98 |
C2—C3 | 1.388 (2) | C14—H14B | 0.98 |
C3—C4 | 1.379 (2) | C14—H14C | 0.98 |
C3—H3A | 0.95 | C15—H15A | 0.98 |
C4—C5 | 1.402 (2) | C15—H15B | 0.98 |
C5—C6 | 1.368 (2) | C15—H15C | 0.98 |
C5—H5 | 0.95 | | |
| | | |
C2—O2—H2 | 105.6 (13) | O3—C9—C10 | 116.57 (16) |
C9—O3—H3 | 106.8 (14) | O3—C9—C8 | 122.43 (16) |
C4—O4—C14 | 116.68 (14) | C10—C9—C8 | 120.99 (16) |
C11—O5—C15 | 117.33 (14) | C11—C10—C9 | 119.62 (16) |
C6—C1—C2 | 116.50 (16) | C11—C10—H10 | 120.2 |
C6—C1—C7 | 123.63 (16) | C9—C10—H10 | 120.2 |
C2—C1—C7 | 119.77 (16) | O5—C11—C10 | 123.98 (16) |
O2—C2—C3 | 116.37 (16) | O5—C11—C12 | 115.36 (16) |
O2—C2—C1 | 121.71 (17) | C10—C11—C12 | 120.64 (16) |
C3—C2—C1 | 121.92 (17) | C13—C12—C11 | 119.26 (17) |
C4—C3—C2 | 119.25 (17) | C13—C12—H12 | 120.4 |
C4—C3—H3A | 120.4 | C11—C12—H12 | 120.4 |
C2—C3—H3A | 120.4 | C12—C13—C8 | 121.86 (16) |
O4—C4—C3 | 124.06 (15) | C12—C13—H13 | 119.1 |
O4—C4—C5 | 115.37 (16) | C8—C13—H13 | 119.1 |
C3—C4—C5 | 120.57 (16) | O4—C14—H14A | 109.5 |
C6—C5—C4 | 119.71 (17) | O4—C14—H14B | 109.5 |
C6—C5—H5 | 120.1 | H14A—C14—H14B | 109.5 |
C4—C5—H5 | 120.1 | O4—C14—H14C | 109.5 |
C5—C6—C1 | 121.94 (16) | H14A—C14—H14C | 109.5 |
C5—C6—H6 | 119 | H14B—C14—H14C | 109.5 |
C1—C6—H6 | 119 | O5—C15—H15A | 109.5 |
O1—C7—C1 | 118.94 (16) | O5—C15—H15B | 109.5 |
O1—C7—C8 | 117.64 (16) | H15A—C15—H15B | 109.5 |
C1—C7—C8 | 123.40 (16) | O5—C15—H15C | 109.5 |
C13—C8—C9 | 117.28 (16) | H15A—C15—H15C | 109.5 |
C13—C8—C7 | 123.18 (16) | H15B—C15—H15C | 109.5 |
C9—C8—C7 | 119.51 (16) | | |
| | | |
C6—C1—C2—O2 | 176.98 (15) | O1—C7—C8—C13 | −152.89 (17) |
C7—C1—C2—O2 | 0.6 (2) | C1—C7—C8—C13 | 29.1 (3) |
C6—C1—C2—C3 | −3.9 (2) | O1—C7—C8—C9 | 25.0 (3) |
C7—C1—C2—C3 | 179.70 (16) | C1—C7—C8—C9 | −153.03 (17) |
O2—C2—C3—C4 | −178.80 (15) | C13—C8—C9—O3 | 174.32 (16) |
C1—C2—C3—C4 | 2.0 (3) | C7—C8—C9—O3 | −3.7 (3) |
C14—O4—C4—C3 | 3.0 (2) | C13—C8—C9—C10 | −7.0 (3) |
C14—O4—C4—C5 | −178.19 (14) | C7—C8—C9—C10 | 174.99 (16) |
C2—C3—C4—O4 | 179.36 (16) | O3—C9—C10—C11 | −175.60 (16) |
C2—C3—C4—C5 | 0.6 (3) | C8—C9—C10—C11 | 5.7 (3) |
O4—C4—C5—C6 | 179.93 (15) | C15—O5—C11—C10 | 1.5 (3) |
C3—C4—C5—C6 | −1.2 (3) | C15—O5—C11—C12 | 179.74 (16) |
C4—C5—C6—C1 | −0.8 (3) | C9—C10—C11—O5 | 177.49 (16) |
C2—C1—C6—C5 | 3.3 (2) | C9—C10—C11—C12 | −0.7 (3) |
C7—C1—C6—C5 | 179.52 (16) | O5—C11—C12—C13 | 178.96 (16) |
C6—C1—C7—O1 | −162.36 (17) | C10—C11—C12—C13 | −2.7 (3) |
C2—C1—C7—O1 | 13.8 (2) | C11—C12—C13—C8 | 1.2 (3) |
C6—C1—C7—C8 | 15.6 (3) | C9—C8—C13—C12 | 3.6 (3) |
C2—C1—C7—C8 | −168.26 (17) | C7—C8—C13—C12 | −178.52 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.92 (2) | 1.68 (2) | 2.5278 (18) | 150.4 (19) |
O3—H3···O1 | 0.92 (2) | 1.75 (2) | 2.5733 (18) | 147 (2) |
Crystal data top
C21H28N2O | F(000) = 704 |
Mr = 324.45 | Dx = 1.148 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.8519 (6) Å | Cell parameters from 7747 reflections |
b = 8.0488 (3) Å | θ = 2.9–27.5° |
c = 14.3060 (5) Å | µ = 0.07 mm−1 |
β = 104.6390 (18)° | T = 120 K |
V = 1877.44 (12) Å3 | Block, yellow |
Z = 4 | 0.4 × 0.35 × 0.3 mm |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 2862 reflections with I > 2σ(I) |
ϕ and ω scans to fill Ewald sphere | Rint = 0.077 |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | θmax = 27.6°, θmin = 2.9° |
Tmin = 0.948, Tmax = 0.979 | h = −21→20 |
18012 measured reflections | k = −10→10 |
4315 independent reflections | l = −18→17 |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0604P)2 + 0.1446P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.047 | (Δ/σ)max < 0.001 |
wR(F2) = 0.122 | Δρmax = 0.21 e Å−3 |
S = 1.01 | Δρmin = −0.22 e Å−3 |
4315 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
288 parameters | Extinction coefficient: 0.022 (3) |
12 restraints | |
Crystal data top
C21H28N2O | V = 1877.44 (12) Å3 |
Mr = 324.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.8519 (6) Å | µ = 0.07 mm−1 |
b = 8.0488 (3) Å | T = 120 K |
c = 14.3060 (5) Å | 0.4 × 0.35 × 0.3 mm |
β = 104.6390 (18)° | |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 4315 independent reflections |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | 2862 reflections with I > 2σ(I) |
Tmin = 0.948, Tmax = 0.979 | Rint = 0.077 |
18012 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 12 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.21 e Å−3 |
4315 reflections | Δρmin = −0.22 e Å−3 |
288 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 | 0.21302 (6) | 0.37913 (13) | −0.03565 (6) | 0.0378 (3) | |
N1 | 0.04238 (6) | 0.46832 (13) | 0.30992 (8) | 0.0276 (3) | |
C1 | 0.19625 (8) | 0.41149 (15) | 0.12139 (9) | 0.0248 (3) | |
C2 | 0.11718 (8) | 0.47691 (16) | 0.08965 (9) | 0.0279 (3) | |
H2 | 0.0979 | 0.5087 | 0.0238 | 0.033* | |
C3 | 0.06650 (8) | 0.49685 (16) | 0.15005 (9) | 0.0283 (3) | |
H3 | 0.0133 | 0.5424 | 0.1255 | 0.034* | |
C4 | 0.09226 (7) | 0.45064 (15) | 0.24850 (9) | 0.0239 (3) | |
C5 | 0.17115 (7) | 0.38146 (15) | 0.28030 (9) | 0.0250 (3) | |
H5 | 0.1903 | 0.3466 | 0.3456 | 0.03* | |
C6 | 0.22097 (8) | 0.36365 (16) | 0.21806 (9) | 0.0255 (3) | |
H6 | 0.2741 | 0.3171 | 0.2418 | 0.031* | |
C7 | 0.24639 (8) | 0.38725 (16) | 0.05165 (9) | 0.0277 (3) | |
C8 | 0.33683 (8) | 0.37333 (16) | 0.08431 (9) | 0.0280 (3) | |
C9 | 0.37810 (9) | 0.2873 (2) | 0.02651 (11) | 0.0418 (4) | |
H9 | 0.3474 | 0.2209 | −0.0249 | 0.05* | |
C12 | 0.46909 (8) | 0.45890 (18) | 0.18373 (10) | 0.0338 (3) | |
H12 | 0.5002 | 0.5094 | 0.2414 | 0.041* | |
C13 | 0.38483 (8) | 0.45762 (16) | 0.16373 (9) | 0.0280 (3) | |
H13 | 0.3586 | 0.5159 | 0.2053 | 0.034* | |
C14 | −0.03863 (8) | 0.54452 (16) | 0.27895 (11) | 0.0320 (3) | |
H14A | −0.0376 | 0.6301 | 0.2296 | 0.038* | |
H14B | −0.0514 | 0.6008 | 0.3349 | 0.038* | |
C15 | −0.10576 (8) | 0.42046 (18) | 0.23747 (12) | 0.0398 (4) | |
H15A | −0.1086 | 0.3378 | 0.2868 | 0.052* | |
H15B | −0.0937 | 0.3647 | 0.1817 | 0.052* | |
H15C | −0.1584 | 0.4785 | 0.217 | 0.052* | |
C16 | 0.06846 (8) | 0.41796 (18) | 0.41061 (10) | 0.0322 (3) | |
H16A | 0.1012 | 0.3148 | 0.4153 | 0.039* | |
H16B | 0.0194 | 0.3929 | 0.4342 | 0.039* | |
C17 | 0.11913 (10) | 0.5493 (2) | 0.47512 (11) | 0.0480 (4) | |
H17A | 0.0866 | 0.651 | 0.4722 | 0.062* | |
H17B | 0.1684 | 0.5733 | 0.453 | 0.062* | |
H17C | 0.1351 | 0.5086 | 0.5418 | 0.062* | |
N21 | 0.59266 (12) | 0.3978 (3) | 0.13297 (18) | 0.0346 (5) | 0.745 (5) |
C101 | 0.4608 (3) | 0.2954 (4) | 0.0414 (3) | 0.0331 (8) | 0.745 (5) |
H101 | 0.4863 | 0.2388 | −0.0016 | 0.043* | 0.745 (5) |
C111 | 0.5095 (2) | 0.3858 (4) | 0.1191 (3) | 0.0286 (8) | 0.745 (5) |
C181 | 0.63371 (13) | 0.3154 (3) | 0.06763 (16) | 0.0355 (7) | 0.745 (5) |
H18A | 0.6867 | 0.3718 | 0.0716 | 0.046* | 0.745 (5) |
H18B | 0.5996 | 0.3278 | 0.0006 | 0.046* | 0.745 (5) |
C191 | 0.64962 (15) | 0.1329 (3) | 0.0888 (2) | 0.0467 (7) | 0.745 (5) |
H19A | 0.598 | 0.0772 | 0.089 | 0.061* | 0.745 (5) |
H19B | 0.6884 | 0.1198 | 0.1521 | 0.061* | 0.745 (5) |
H19C | 0.6728 | 0.0834 | 0.0389 | 0.061* | 0.745 (5) |
C201 | 0.6426 (3) | 0.5046 (5) | 0.2070 (4) | 0.0395 (11) | 0.745 (5) |
H20A | 0.6101 | 0.604 | 0.2142 | 0.051* | 0.745 (5) |
H20B | 0.6907 | 0.5427 | 0.1848 | 0.051* | 0.745 (5) |
C211 | 0.6729 (7) | 0.4228 (15) | 0.3050 (5) | 0.0508 (14) | 0.745 (5) |
H21A | 0.7075 | 0.3272 | 0.2995 | 0.066* | 0.745 (5) |
H21B | 0.6259 | 0.3853 | 0.3281 | 0.066* | 0.745 (5) |
H21C | 0.705 | 0.503 | 0.3509 | 0.066* | 0.745 (5) |
N22 | 0.5980 (3) | 0.3237 (10) | 0.1681 (5) | 0.0337 (16) | 0.255 (5) |
C102 | 0.4655 (8) | 0.2415 (13) | 0.0661 (8) | 0.036 (2) | 0.255 (5) |
H102 | 0.4883 | 0.15 | 0.04 | 0.047* | 0.255 (5) |
C112 | 0.5143 (6) | 0.3344 (12) | 0.1424 (7) | 0.027 (2) | 0.255 (5) |
C182 | 0.6415 (4) | 0.1982 (8) | 0.1290 (5) | 0.0361 (18) | 0.255 (5) |
H18C | 0.6087 | 0.0947 | 0.1204 | 0.047* | 0.255 (5) |
H18D | 0.6939 | 0.1751 | 0.177 | 0.047* | 0.255 (5) |
C192 | 0.6599 (5) | 0.2417 (10) | 0.0337 (5) | 0.049 (2) | 0.255 (5) |
H19D | 0.6924 | 0.3442 | 0.0411 | 0.064* | 0.255 (5) |
H19E | 0.6084 | 0.2581 | −0.0156 | 0.064* | 0.255 (5) |
H19F | 0.691 | 0.1511 | 0.0139 | 0.064* | 0.255 (5) |
C202 | 0.6463 (9) | 0.4550 (16) | 0.2279 (11) | 0.044 (4) | 0.255 (5) |
H20C | 0.6128 | 0.5573 | 0.222 | 0.057* | 0.255 (5) |
H20D | 0.695 | 0.4801 | 0.2035 | 0.057* | 0.255 (5) |
C212 | 0.674 (2) | 0.407 (5) | 0.3327 (13) | 0.059 (5) | 0.255 (5) |
H21D | 0.7157 | 0.3191 | 0.3406 | 0.076* | 0.255 (5) |
H21E | 0.6271 | 0.3652 | 0.3546 | 0.076* | 0.255 (5) |
H21F | 0.6975 | 0.5036 | 0.3713 | 0.076* | 0.255 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0358 (6) | 0.0525 (6) | 0.0240 (5) | −0.0097 (5) | 0.0058 (4) | −0.0074 (5) |
N1 | 0.0218 (6) | 0.0312 (6) | 0.0303 (6) | 0.0034 (4) | 0.0077 (5) | 0.0001 (5) |
C1 | 0.0237 (7) | 0.0243 (6) | 0.0255 (7) | −0.0039 (5) | 0.0046 (5) | −0.0019 (5) |
C2 | 0.0288 (7) | 0.0282 (7) | 0.0238 (6) | −0.0016 (5) | 0.0014 (5) | 0.0024 (6) |
C3 | 0.0225 (7) | 0.0274 (6) | 0.0320 (7) | 0.0023 (5) | 0.0017 (6) | 0.0008 (6) |
C4 | 0.0221 (7) | 0.0207 (6) | 0.0285 (7) | −0.0024 (5) | 0.0058 (5) | −0.0017 (5) |
C5 | 0.0216 (7) | 0.0283 (6) | 0.0242 (6) | 0.0006 (5) | 0.0044 (5) | 0.0025 (6) |
C6 | 0.0214 (7) | 0.0259 (6) | 0.0280 (7) | 0.0005 (5) | 0.0039 (5) | 0.0004 (6) |
C7 | 0.0303 (7) | 0.0274 (6) | 0.0250 (7) | −0.0075 (5) | 0.0066 (6) | −0.0031 (6) |
C8 | 0.0274 (7) | 0.0315 (7) | 0.0274 (7) | −0.0069 (5) | 0.0109 (6) | −0.0047 (6) |
C9 | 0.0338 (9) | 0.0522 (9) | 0.0421 (8) | −0.0124 (7) | 0.0145 (7) | −0.0230 (8) |
C12 | 0.0291 (8) | 0.0399 (8) | 0.0324 (7) | −0.0070 (6) | 0.0076 (6) | −0.0095 (6) |
C13 | 0.0280 (8) | 0.0305 (7) | 0.0269 (7) | −0.0026 (5) | 0.0093 (6) | −0.0033 (6) |
C14 | 0.0257 (7) | 0.0288 (7) | 0.0430 (8) | 0.0069 (5) | 0.0117 (6) | 0.0025 (6) |
C15 | 0.0245 (8) | 0.0379 (8) | 0.0545 (10) | 0.0048 (6) | 0.0054 (7) | 0.0056 (7) |
C16 | 0.0262 (7) | 0.0411 (8) | 0.0319 (7) | 0.0011 (6) | 0.0121 (6) | 0.0015 (6) |
C17 | 0.0391 (9) | 0.0709 (11) | 0.0366 (8) | −0.0087 (8) | 0.0145 (7) | −0.0130 (8) |
N21 | 0.0243 (10) | 0.0374 (12) | 0.0430 (12) | −0.0042 (8) | 0.0101 (9) | −0.0046 (10) |
C101 | 0.0317 (14) | 0.0358 (19) | 0.0353 (18) | −0.0047 (14) | 0.0149 (13) | −0.0091 (14) |
C111 | 0.0248 (13) | 0.0262 (17) | 0.0357 (19) | −0.0009 (11) | 0.0095 (11) | 0.0028 (12) |
C181 | 0.0272 (11) | 0.0411 (13) | 0.0418 (12) | 0.0015 (9) | 0.0154 (9) | 0.0045 (11) |
C191 | 0.0513 (15) | 0.0457 (15) | 0.0489 (16) | 0.0135 (11) | 0.0233 (12) | 0.0083 (13) |
C201 | 0.0300 (16) | 0.040 (2) | 0.049 (2) | −0.0108 (15) | 0.0091 (15) | −0.0056 (18) |
C211 | 0.046 (2) | 0.047 (3) | 0.053 (4) | −0.007 (2) | 0.001 (3) | −0.004 (3) |
N22 | 0.021 (3) | 0.040 (4) | 0.042 (4) | 0.000 (2) | 0.012 (2) | −0.006 (3) |
C102 | 0.036 (4) | 0.035 (5) | 0.043 (6) | −0.001 (4) | 0.021 (4) | −0.004 (4) |
C112 | 0.029 (4) | 0.028 (5) | 0.026 (5) | 0.000 (3) | 0.008 (3) | 0.006 (3) |
C182 | 0.039 (4) | 0.035 (4) | 0.036 (4) | 0.003 (3) | 0.013 (3) | 0.004 (3) |
C192 | 0.046 (4) | 0.056 (4) | 0.049 (4) | 0.009 (3) | 0.020 (3) | 0.017 (4) |
C202 | 0.020 (5) | 0.056 (8) | 0.061 (9) | −0.017 (6) | 0.019 (5) | 0.001 (6) |
C212 | 0.061 (7) | 0.048 (8) | 0.057 (10) | −0.003 (5) | −0.003 (9) | −0.002 (9) |
Geometric parameters (Å, º) top
O1—C7 | 1.2350 (15) | C17—H17B | 0.98 |
N1—C4 | 1.3682 (16) | C17—H17C | 0.98 |
N1—C16 | 1.4535 (17) | N21—C111 | 1.368 (4) |
N1—C14 | 1.4596 (16) | N21—C201 | 1.455 (5) |
C1—C6 | 1.3940 (18) | N21—C181 | 1.456 (3) |
C1—C2 | 1.3976 (18) | C101—C111 | 1.407 (4) |
C1—C7 | 1.4742 (17) | C101—H101 | 0.95 |
C2—C3 | 1.3692 (18) | C181—C191 | 1.510 (3) |
C2—H2 | 0.95 | C181—H18A | 0.99 |
C3—C4 | 1.4148 (18) | C181—H18B | 0.99 |
C3—H3 | 0.95 | C191—H19A | 0.98 |
C4—C5 | 1.4066 (17) | C191—H19B | 0.98 |
C5—C6 | 1.3770 (17) | C191—H19C | 0.98 |
C5—H5 | 0.95 | C201—C211 | 1.517 (6) |
C6—H6 | 0.95 | C201—H20A | 0.99 |
C7—C8 | 1.4811 (18) | C201—H20B | 0.99 |
C8—C9 | 1.3919 (19) | C211—H21A | 0.98 |
C8—C13 | 1.3933 (18) | C211—H21B | 0.98 |
C9—C101 | 1.357 (5) | C211—H21C | 0.98 |
C9—C102 | 1.485 (13) | N22—C112 | 1.368 (10) |
C9—H9 | 0.95 | N22—C182 | 1.441 (9) |
C12—C13 | 1.3758 (19) | N22—C202 | 1.470 (12) |
C12—C111 | 1.408 (4) | C102—C112 | 1.405 (12) |
C12—C112 | 1.470 (11) | C102—H102 | 0.95 |
C12—H12 | 0.95 | C182—C192 | 1.515 (9) |
C13—H13 | 0.95 | C182—H18C | 0.99 |
C14—C15 | 1.513 (2) | C182—H18D | 0.99 |
C14—H14A | 0.99 | C192—H19D | 0.98 |
C14—H14B | 0.99 | C192—H19E | 0.98 |
C15—H15A | 0.98 | C192—H19F | 0.98 |
C15—H15B | 0.98 | C202—C212 | 1.505 (14) |
C15—H15C | 0.98 | C202—H20C | 0.99 |
C16—C17 | 1.517 (2) | C202—H20D | 0.99 |
C16—H16A | 0.99 | C212—H21D | 0.98 |
C16—H16B | 0.99 | C212—H21E | 0.98 |
C17—H17A | 0.98 | C212—H21F | 0.98 |
| | | |
C4—N1—C16 | 121.77 (10) | C16—C17—H17B | 109.5 |
C4—N1—C14 | 121.88 (11) | H17A—C17—H17B | 109.5 |
C16—N1—C14 | 116.32 (10) | C16—C17—H17C | 109.5 |
C6—C1—C2 | 116.59 (11) | H17A—C17—H17C | 109.5 |
C6—C1—C7 | 123.79 (12) | H17B—C17—H17C | 109.5 |
C2—C1—C7 | 119.50 (11) | C111—N21—C201 | 122.0 (3) |
C3—C2—C1 | 122.33 (12) | C111—N21—C181 | 120.7 (2) |
C3—C2—H2 | 118.8 | C201—N21—C181 | 117.0 (3) |
C1—C2—H2 | 118.8 | C9—C101—C111 | 121.3 (3) |
C2—C3—C4 | 120.93 (12) | C9—C101—H101 | 119.4 |
C2—C3—H3 | 119.5 | C111—C101—H101 | 119.4 |
C4—C3—H3 | 119.5 | N21—C111—C101 | 121.5 (3) |
N1—C4—C5 | 121.16 (11) | N21—C111—C12 | 121.5 (3) |
N1—C4—C3 | 121.88 (11) | C101—C111—C12 | 116.9 (3) |
C5—C4—C3 | 116.94 (11) | N21—C181—C191 | 113.8 (2) |
C6—C5—C4 | 120.87 (12) | N21—C181—H18A | 108.8 |
C6—C5—H5 | 119.6 | C191—C181—H18A | 108.8 |
C4—C5—H5 | 119.6 | N21—C181—H18B | 108.8 |
C5—C6—C1 | 122.32 (12) | C191—C181—H18B | 108.8 |
C5—C6—H6 | 118.8 | H18A—C181—H18B | 107.7 |
C1—C6—H6 | 118.8 | N21—C201—C211 | 114.5 (5) |
O1—C7—C1 | 119.94 (12) | N21—C201—H20A | 108.6 |
O1—C7—C8 | 118.96 (11) | C211—C201—H20A | 108.6 |
C1—C7—C8 | 121.10 (11) | N21—C201—H20B | 108.6 |
C9—C8—C13 | 116.89 (12) | C211—C201—H20B | 108.6 |
C9—C8—C7 | 118.62 (12) | H20A—C201—H20B | 107.6 |
C13—C8—C7 | 124.02 (11) | C112—N22—C182 | 122.1 (6) |
C101—C9—C8 | 122.1 (2) | C112—N22—C202 | 119.6 (8) |
C8—C9—C102 | 119.6 (5) | C182—N22—C202 | 117.9 (8) |
C101—C9—H9 | 119 | C112—C102—C9 | 119.6 (9) |
C8—C9—H9 | 119 | C112—C102—H102 | 120.2 |
C102—C9—H9 | 116.7 | C9—C102—H102 | 120.2 |
C13—C12—C111 | 120.36 (18) | N22—C112—C102 | 122.5 (10) |
C13—C12—C112 | 121.6 (4) | N22—C112—C12 | 122.6 (7) |
C13—C12—H12 | 119.8 | C102—C112—C12 | 114.5 (8) |
C111—C12—H12 | 119.8 | N22—C182—C192 | 115.3 (7) |
C112—C12—H12 | 114.4 | N22—C182—H18C | 108.5 |
C12—C13—C8 | 121.95 (12) | C192—C182—H18C | 108.5 |
C12—C13—H13 | 119 | N22—C182—H18D | 108.5 |
C8—C13—H13 | 119 | C192—C182—H18D | 108.5 |
N1—C14—C15 | 113.02 (11) | H18C—C182—H18D | 107.5 |
N1—C14—H14A | 109 | C182—C192—H19D | 109.5 |
C15—C14—H14A | 109 | C182—C192—H19E | 109.5 |
N1—C14—H14B | 109 | H19D—C192—H19E | 109.5 |
C15—C14—H14B | 109 | C182—C192—H19F | 109.5 |
H14A—C14—H14B | 107.8 | H19D—C192—H19F | 109.5 |
C14—C15—H15A | 109.5 | H19E—C192—H19F | 109.5 |
C14—C15—H15B | 109.5 | N22—C202—C212 | 112.4 (16) |
H15A—C15—H15B | 109.5 | N22—C202—H20C | 109.1 |
C14—C15—H15C | 109.5 | C212—C202—H20C | 109.1 |
H15A—C15—H15C | 109.5 | N22—C202—H20D | 109.1 |
H15B—C15—H15C | 109.5 | C212—C202—H20D | 109.1 |
N1—C16—C17 | 113.04 (12) | H20C—C202—H20D | 107.9 |
N1—C16—H16A | 109 | C202—C212—H21D | 109.5 |
C17—C16—H16A | 109 | C202—C212—H21E | 109.5 |
N1—C16—H16B | 109 | H21D—C212—H21E | 109.5 |
C17—C16—H16B | 109 | C202—C212—H21F | 109.5 |
H16A—C16—H16B | 107.8 | H21D—C212—H21F | 109.5 |
C16—C17—H17A | 109.5 | H21E—C212—H21F | 109.5 |
| | | |
C6—C1—C2—C3 | 1.28 (19) | C14—N1—C16—C17 | −94.02 (14) |
C7—C1—C2—C3 | 177.60 (12) | C8—C9—C101—C111 | 2.9 (4) |
C1—C2—C3—C4 | −0.3 (2) | C102—C9—C101—C111 | −87.2 (16) |
C16—N1—C4—C5 | 0.45 (18) | C201—N21—C111—C101 | 173.5 (3) |
C14—N1—C4—C5 | 178.07 (11) | C181—N21—C111—C101 | −0.6 (4) |
C16—N1—C4—C3 | 178.87 (12) | C201—N21—C111—C12 | −8.5 (4) |
C14—N1—C4—C3 | −3.51 (19) | C181—N21—C111—C12 | 177.4 (3) |
C2—C3—C4—N1 | −179.50 (12) | C9—C101—C111—N21 | −178.3 (3) |
C2—C3—C4—C5 | −1.01 (18) | C9—C101—C111—C12 | 3.6 (4) |
N1—C4—C5—C6 | 179.85 (12) | C13—C12—C111—N21 | 174.3 (2) |
C3—C4—C5—C6 | 1.36 (18) | C112—C12—C111—N21 | −86.1 (13) |
C4—C5—C6—C1 | −0.39 (19) | C13—C12—C111—C101 | −7.7 (3) |
C2—C1—C6—C5 | −0.93 (18) | C112—C12—C111—C101 | 91.9 (13) |
C7—C1—C6—C5 | −177.08 (12) | C111—N21—C181—C191 | −81.1 (3) |
C6—C1—C7—O1 | 155.74 (13) | C201—N21—C181—C191 | 104.5 (3) |
C2—C1—C7—O1 | −20.30 (18) | C111—N21—C201—C211 | 88.3 (7) |
C6—C1—C7—C8 | −24.64 (18) | C181—N21—C201—C211 | −97.4 (7) |
C2—C1—C7—C8 | 159.32 (12) | C101—C9—C102—C112 | 78.4 (15) |
O1—C7—C8—C9 | −25.90 (19) | C8—C9—C102—C112 | −24.6 (10) |
C1—C7—C8—C9 | 154.48 (13) | C182—N22—C112—C102 | −10.0 (12) |
O1—C7—C8—C13 | 146.07 (13) | C202—N22—C112—C102 | 162.5 (9) |
C1—C7—C8—C13 | −33.55 (19) | C182—N22—C112—C12 | 178.3 (7) |
C13—C8—C9—C101 | −5.3 (3) | C202—N22—C112—C12 | −9.3 (12) |
C7—C8—C9—C101 | 167.2 (2) | C9—C102—C112—N22 | −165.2 (7) |
C13—C8—C9—C102 | 20.0 (5) | C9—C102—C112—C12 | 7.2 (11) |
C7—C8—C9—C102 | −167.4 (5) | C13—C12—C112—N22 | −173.9 (6) |
C111—C12—C13—C8 | 5.4 (2) | C111—C12—C112—N22 | 93.1 (15) |
C112—C12—C13—C8 | −18.9 (5) | C13—C12—C112—C102 | 13.8 (8) |
C9—C8—C13—C12 | 1.1 (2) | C111—C12—C112—C102 | −79.3 (14) |
C7—C8—C13—C12 | −170.99 (13) | C112—N22—C182—C192 | 86.2 (9) |
C4—N1—C14—C15 | 89.47 (15) | C202—N22—C182—C192 | −86.3 (10) |
C16—N1—C14—C15 | −92.79 (15) | C112—N22—C202—C212 | 100 (2) |
C4—N1—C16—C17 | 83.72 (15) | C182—N22—C202—C212 | −88 (2) |
Crystal data top
C13H10O3 | F(000) = 896 |
Mr = 214.21 | Dx = 1.404 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 24.4619 (9) Å | Cell parameters from 11394 reflections |
b = 7.3737 (2) Å | θ = 2.9–27.5° |
c = 12.3961 (4) Å | µ = 0.1 mm−1 |
β = 115.019 (2)° | T = 120 K |
V = 2026.14 (11) Å3 | Plate, colourless |
Z = 8 | 0.24 × 0.14 × 0.03 mm |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 1733 reflections with I > 2σ(I) |
ϕ and ω scans to fill Ewald sphere | Rint = 0.074 |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | θmax = 27.5°, θmin = 2.9° |
Tmin = 0.913, Tmax = 0.997 | h = −31→31 |
16476 measured reflections | k = −9→9 |
2319 independent reflections | l = −15→16 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0555P)2 + 1.1706P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.19 e Å−3 |
2319 reflections | Δρmin = −0.29 e Å−3 |
152 parameters | |
Crystal data top
C13H10O3 | V = 2026.14 (11) Å3 |
Mr = 214.21 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 24.4619 (9) Å | µ = 0.1 mm−1 |
b = 7.3737 (2) Å | T = 120 K |
c = 12.3961 (4) Å | 0.24 × 0.14 × 0.03 mm |
β = 115.019 (2)° | |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 2319 independent reflections |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | 1733 reflections with I > 2σ(I) |
Tmin = 0.913, Tmax = 0.997 | Rint = 0.074 |
16476 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.19 e Å−3 |
2319 reflections | Δρmin = −0.29 e Å−3 |
152 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 | |
O1 | 0.66586 (5) | 0.08148 (16) | 0.40009 (9) | 0.0243 (3) | |
O2 | 0.56113 (5) | 0.05271 (16) | 0.75039 (10) | 0.0242 (3) | |
H2 | 0.5968 (9) | −0.006 (3) | 0.8012 (16) | 0.029* | |
O3 | 0.46801 (5) | 0.24018 (16) | 0.58310 (10) | 0.0270 (3) | |
H3 | 0.4682 (8) | 0.172 (3) | 0.6473 (17) | 0.032* | |
C1 | 0.62252 (7) | 0.1488 (2) | 0.53207 (13) | 0.0185 (3) | |
C2 | 0.61879 (7) | 0.0841 (2) | 0.63465 (13) | 0.0185 (3) | |
H2A | 0.6517 | 0.0193 | 0.6925 | 0.022* | |
C3 | 0.56755 (7) | 0.1140 (2) | 0.65227 (13) | 0.0188 (3) | |
C4 | 0.51906 (7) | 0.2092 (2) | 0.56816 (14) | 0.0204 (3) | |
C5 | 0.52305 (7) | 0.2761 (2) | 0.46731 (14) | 0.0220 (3) | |
H5 | 0.4905 | 0.3437 | 0.4106 | 0.026* | |
C6 | 0.57402 (7) | 0.2450 (2) | 0.44867 (13) | 0.0217 (4) | |
H6A | 0.5761 | 0.2895 | 0.3785 | 0.026* | |
C7 | 0.67428 (7) | 0.1048 (2) | 0.50480 (13) | 0.0193 (3) | |
C8 | 0.73631 (7) | 0.0819 (2) | 0.60007 (13) | 0.0194 (3) | |
C9 | 0.77717 (7) | −0.0204 (2) | 0.57393 (14) | 0.0232 (4) | |
H9 | 0.7649 | −0.072 | 0.497 | 0.028* | |
C10 | 0.83534 (7) | −0.0471 (2) | 0.65921 (15) | 0.0268 (4) | |
H10 | 0.8629 | −0.118 | 0.6413 | 0.032* | |
C11 | 0.85344 (7) | 0.0300 (2) | 0.77117 (15) | 0.0273 (4) | |
H11 | 0.8932 | 0.0102 | 0.8302 | 0.033* | |
C12 | 0.81387 (7) | 0.1355 (2) | 0.79721 (14) | 0.0248 (4) | |
H12 | 0.8268 | 0.1901 | 0.8735 | 0.03* | |
C13 | 0.75534 (7) | 0.1618 (2) | 0.71223 (13) | 0.0210 (3) | |
H13 | 0.7282 | 0.2342 | 0.7303 | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0232 (6) | 0.0325 (6) | 0.0190 (6) | −0.0024 (5) | 0.0106 (5) | −0.0016 (5) |
O2 | 0.0197 (6) | 0.0345 (7) | 0.0208 (6) | 0.0036 (5) | 0.0109 (5) | 0.0058 (5) |
O3 | 0.0187 (6) | 0.0359 (7) | 0.0290 (6) | 0.0052 (5) | 0.0126 (5) | 0.0051 (5) |
C1 | 0.0173 (7) | 0.0202 (8) | 0.0177 (7) | −0.0019 (6) | 0.0071 (6) | −0.0013 (6) |
C2 | 0.0163 (7) | 0.0203 (8) | 0.0172 (7) | 0.0004 (6) | 0.0056 (6) | −0.0009 (6) |
C3 | 0.0191 (7) | 0.0208 (8) | 0.0167 (7) | −0.0023 (6) | 0.0080 (6) | −0.0010 (6) |
C4 | 0.0166 (8) | 0.0211 (8) | 0.0239 (8) | −0.0010 (6) | 0.0089 (7) | −0.0023 (6) |
C5 | 0.0184 (8) | 0.0236 (8) | 0.0202 (8) | 0.0032 (6) | 0.0046 (6) | 0.0018 (6) |
C6 | 0.0242 (8) | 0.0236 (8) | 0.0172 (7) | −0.0007 (6) | 0.0086 (7) | 0.0011 (6) |
C7 | 0.0216 (8) | 0.0181 (8) | 0.0192 (8) | −0.0028 (6) | 0.0096 (6) | −0.0004 (6) |
C8 | 0.0189 (8) | 0.0195 (8) | 0.0214 (8) | −0.0018 (6) | 0.0099 (6) | 0.0020 (6) |
C9 | 0.0230 (8) | 0.0227 (9) | 0.0266 (8) | −0.0005 (6) | 0.0133 (7) | 0.0017 (6) |
C10 | 0.0219 (8) | 0.0240 (9) | 0.0373 (9) | 0.0035 (7) | 0.0152 (7) | 0.0059 (7) |
C11 | 0.0170 (8) | 0.0262 (9) | 0.0340 (9) | −0.0022 (7) | 0.0063 (7) | 0.0091 (7) |
C12 | 0.0238 (8) | 0.0251 (8) | 0.0223 (8) | −0.0045 (7) | 0.0067 (7) | 0.0028 (6) |
C13 | 0.0202 (8) | 0.0201 (8) | 0.0232 (8) | −0.0019 (6) | 0.0098 (6) | 0.0007 (6) |
Geometric parameters (Å, º) top
O1—C7 | 1.2373 (18) | C6—H6A | 0.95 |
O2—C3 | 1.3675 (18) | C7—C8 | 1.487 (2) |
O2—H2 | 0.94 (2) | C8—C9 | 1.395 (2) |
O3—C4 | 1.3571 (18) | C8—C13 | 1.396 (2) |
O3—H3 | 0.94 (2) | C9—C10 | 1.382 (2) |
C1—C6 | 1.394 (2) | C9—H9 | 0.95 |
C1—C2 | 1.397 (2) | C10—C11 | 1.388 (2) |
C1—C7 | 1.478 (2) | C10—H10 | 0.95 |
C2—C3 | 1.378 (2) | C11—C12 | 1.382 (2) |
C2—H2A | 0.95 | C11—H11 | 0.95 |
C3—C4 | 1.393 (2) | C12—C13 | 1.386 (2) |
C4—C5 | 1.385 (2) | C12—H12 | 0.95 |
C5—C6 | 1.380 (2) | C13—H13 | 0.95 |
C5—H5 | 0.95 | | |
| | | |
C3—O2—H2 | 108.9 (11) | O1—C7—C8 | 118.60 (13) |
C4—O3—H3 | 110.4 (11) | C1—C7—C8 | 121.91 (12) |
C6—C1—C2 | 119.11 (14) | C9—C8—C13 | 119.30 (14) |
C6—C1—C7 | 118.99 (13) | C9—C8—C7 | 117.89 (13) |
C2—C1—C7 | 121.70 (13) | C13—C8—C7 | 122.79 (14) |
C3—C2—C1 | 120.25 (14) | C10—C9—C8 | 120.44 (15) |
C3—C2—H2A | 119.9 | C10—C9—H9 | 119.8 |
C1—C2—H2A | 119.9 | C8—C9—H9 | 119.8 |
O2—C3—C2 | 122.86 (14) | C9—C10—C11 | 119.76 (15) |
O2—C3—C4 | 116.77 (13) | C9—C10—H10 | 120.1 |
C2—C3—C4 | 120.37 (14) | C11—C10—H10 | 120.1 |
O3—C4—C5 | 118.92 (14) | C12—C11—C10 | 120.36 (15) |
O3—C4—C3 | 121.60 (14) | C12—C11—H11 | 119.8 |
C5—C4—C3 | 119.47 (14) | C10—C11—H11 | 119.8 |
C6—C5—C4 | 120.38 (14) | C11—C12—C13 | 120.10 (15) |
C6—C5—H5 | 119.8 | C11—C12—H12 | 119.9 |
C4—C5—H5 | 119.8 | C13—C12—H12 | 119.9 |
C5—C6—C1 | 120.41 (14) | C12—C13—C8 | 119.99 (15) |
C5—C6—H6A | 119.8 | C12—C13—H13 | 120 |
C1—C6—H6A | 119.8 | C8—C13—H13 | 120 |
O1—C7—C1 | 119.47 (13) | | |
| | | |
C6—C1—C2—C3 | 0.6 (2) | C6—C1—C7—C8 | 151.66 (14) |
C7—C1—C2—C3 | −174.22 (14) | C2—C1—C7—C8 | −33.5 (2) |
C1—C2—C3—O2 | 179.45 (14) | O1—C7—C8—C9 | −20.9 (2) |
C1—C2—C3—C4 | −0.1 (2) | C1—C7—C8—C9 | 157.17 (14) |
O2—C3—C4—O3 | 0.2 (2) | O1—C7—C8—C13 | 157.44 (15) |
C2—C3—C4—O3 | 179.83 (14) | C1—C7—C8—C13 | −24.5 (2) |
O2—C3—C4—C5 | 179.46 (14) | C13—C8—C9—C10 | 2.0 (2) |
C2—C3—C4—C5 | −0.9 (2) | C7—C8—C9—C10 | −179.63 (14) |
O3—C4—C5—C6 | −179.18 (14) | C8—C9—C10—C11 | −0.7 (2) |
C3—C4—C5—C6 | 1.6 (2) | C9—C10—C11—C12 | −0.9 (2) |
C4—C5—C6—C1 | −1.1 (2) | C10—C11—C12—C13 | 1.4 (2) |
C2—C1—C6—C5 | 0.1 (2) | C11—C12—C13—C8 | −0.1 (2) |
C7—C1—C6—C5 | 174.99 (14) | C9—C8—C13—C12 | −1.5 (2) |
C6—C1—C7—O1 | −30.3 (2) | C7—C8—C13—C12 | −179.88 (14) |
C2—C1—C7—O1 | 144.53 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.94 (2) | 1.71 (2) | 2.6391 (16) | 171.7 (18) |
O3—H3···O2ii | 0.94 (2) | 1.91 (2) | 2.8149 (16) | 159.6 (16) |
C2—H2A···O1i | 0.95 | 2.56 | 3.2309 (18) | 128 |
Symmetry codes: (i) x, −y, z+1/2; (ii) −x+1, y, −z+3/2. |
Crystal data top
C13H10O2 | F(000) = 416 |
Mr = 198.21 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.0462 (1) Å | Cell parameters from 2247 reflections |
b = 20.2165 (6) Å | θ = 2.9–27.5° |
c = 11.8058 (3) Å | µ = 0.09 mm−1 |
β = 90.929 (2)° | T = 120 K |
V = 965.59 (4) Å3 | Lath, colourless |
Z = 4 | 0.16 × 0.1 × 0.04 mm |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 1795 reflections with I > 2σ(I) |
ϕ and ω scans to fill Ewald sphere | Rint = 0.049 |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | θmax = 27.5°, θmin = 3.5° |
Tmin = 0.729, Tmax = 0.996 | h = −5→5 |
13634 measured reflections | k = −24→26 |
2197 independent reflections | l = −15→15 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.074 | w = 1/[σ2(Fo2) + (0.0718P)2 + 2.095P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.216 | (Δ/σ)max = 0.001 |
S = 1.17 | Δρmax = 0.42 e Å−3 |
2197 reflections | Δρmin = −0.30 e Å−3 |
140 parameters | |
Crystal data top
C13H10O2 | V = 965.59 (4) Å3 |
Mr = 198.21 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.0462 (1) Å | µ = 0.09 mm−1 |
b = 20.2165 (6) Å | T = 120 K |
c = 11.8058 (3) Å | 0.16 × 0.1 × 0.04 mm |
β = 90.929 (2)° | |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 2197 independent reflections |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | 1795 reflections with I > 2σ(I) |
Tmin = 0.729, Tmax = 0.996 | Rint = 0.049 |
13634 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.074 | 0 restraints |
wR(F2) = 0.216 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 0.42 e Å−3 |
2197 reflections | Δρmin = −0.30 e Å−3 |
140 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 | |
O1 | 0.9906 (7) | 0.21701 (11) | 0.39677 (18) | 0.0345 (6) | |
O2 | 0.7594 (6) | 0.39136 (11) | 0.79324 (19) | 0.0328 (6) | |
H2 | 0.663 (13) | 0.347 (3) | 0.832 (5) | 0.076 (16)* | |
C1 | 1.0098 (7) | 0.29194 (14) | 0.5484 (2) | 0.0229 (6) | |
C2 | 0.8767 (7) | 0.30776 (15) | 0.6536 (2) | 0.0234 (6) | |
H21 | 0.7778 | 0.2743 | 0.6983 | 0.028* | |
C3 | 0.8897 (8) | 0.37273 (15) | 0.6925 (2) | 0.0240 (6) | |
C4 | 1.0392 (8) | 0.42159 (15) | 0.6276 (3) | 0.0271 (7) | |
H4 | 1.0482 | 0.4659 | 0.6543 | 0.032* | |
C5 | 1.1750 (8) | 0.40546 (15) | 0.5239 (3) | 0.0290 (7) | |
H5 | 1.2795 | 0.4388 | 0.4804 | 0.035* | |
C6 | 1.1593 (8) | 0.34118 (15) | 0.4831 (2) | 0.0260 (7) | |
H6 | 1.2492 | 0.3306 | 0.4115 | 0.031* | |
C7 | 0.9927 (8) | 0.22421 (15) | 0.5002 (2) | 0.0254 (6) | |
C8 | 0.9787 (7) | 0.16500 (14) | 0.5754 (2) | 0.0222 (6) | |
C9 | 0.8240 (8) | 0.10799 (15) | 0.5333 (3) | 0.0262 (6) | |
H9 | 0.7225 | 0.1082 | 0.4602 | 0.031* | |
C10 | 0.8197 (8) | 0.05098 (15) | 0.5991 (3) | 0.0278 (7) | |
H10 | 0.7105 | 0.0125 | 0.5716 | 0.033* | |
C11 | 0.9747 (8) | 0.05024 (15) | 0.7047 (3) | 0.0280 (7) | |
H11 | 0.9739 | 0.011 | 0.749 | 0.034* | |
C12 | 1.1300 (8) | 0.10633 (15) | 0.7457 (3) | 0.0257 (6) | |
H12 | 1.2371 | 0.1054 | 0.8178 | 0.031* | |
C13 | 1.1310 (7) | 0.16412 (14) | 0.6823 (2) | 0.0233 (6) | |
H13 | 1.2347 | 0.2028 | 0.7114 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0619 (16) | 0.0256 (12) | 0.0163 (11) | 0.0033 (10) | 0.0036 (10) | 0.0004 (8) |
O2 | 0.0522 (15) | 0.0232 (12) | 0.0233 (11) | −0.0008 (10) | 0.0054 (10) | −0.0032 (9) |
C1 | 0.0289 (15) | 0.0208 (14) | 0.0189 (13) | 0.0022 (11) | −0.0005 (11) | 0.0010 (11) |
C2 | 0.0297 (15) | 0.0215 (14) | 0.0192 (13) | −0.0001 (11) | 0.0011 (11) | 0.0022 (11) |
C3 | 0.0310 (15) | 0.0222 (14) | 0.0189 (13) | 0.0020 (11) | −0.0004 (11) | −0.0005 (11) |
C4 | 0.0349 (16) | 0.0199 (14) | 0.0263 (15) | −0.0020 (12) | −0.0037 (12) | 0.0011 (11) |
C5 | 0.0339 (16) | 0.0247 (15) | 0.0284 (16) | −0.0045 (12) | 0.0010 (12) | 0.0075 (12) |
C6 | 0.0325 (16) | 0.0255 (15) | 0.0201 (14) | 0.0007 (12) | 0.0026 (12) | 0.0038 (11) |
C7 | 0.0316 (15) | 0.0239 (15) | 0.0208 (14) | 0.0033 (12) | 0.0047 (11) | 0.0004 (11) |
C8 | 0.0284 (15) | 0.0204 (14) | 0.0180 (13) | 0.0038 (11) | 0.0045 (11) | 0.0004 (10) |
C9 | 0.0305 (15) | 0.0268 (15) | 0.0213 (14) | 0.0006 (12) | 0.0021 (11) | −0.0036 (11) |
C10 | 0.0316 (15) | 0.0216 (15) | 0.0304 (16) | −0.0005 (12) | 0.0060 (12) | −0.0047 (12) |
C11 | 0.0330 (16) | 0.0214 (15) | 0.0298 (16) | 0.0050 (12) | 0.0058 (12) | 0.0022 (12) |
C12 | 0.0300 (15) | 0.0270 (15) | 0.0200 (14) | 0.0062 (12) | 0.0032 (11) | 0.0017 (11) |
C13 | 0.0276 (14) | 0.0215 (14) | 0.0209 (14) | 0.0018 (11) | 0.0037 (11) | −0.0030 (11) |
Geometric parameters (Å, º) top
O1—C7 | 1.230 (4) | C6—H6 | 0.95 |
O2—C3 | 1.362 (4) | C7—C8 | 1.491 (4) |
O2—H2 | 1.09 (6) | C8—C13 | 1.395 (4) |
C1—C2 | 1.399 (4) | C8—C9 | 1.399 (4) |
C1—C6 | 1.402 (4) | C9—C10 | 1.390 (4) |
C1—C7 | 1.484 (4) | C9—H9 | 0.95 |
C2—C3 | 1.392 (4) | C10—C11 | 1.387 (5) |
C2—H21 | 0.95 | C10—H10 | 0.95 |
C3—C4 | 1.394 (4) | C11—C12 | 1.380 (4) |
C4—C5 | 1.390 (4) | C11—H11 | 0.95 |
C4—H4 | 0.95 | C12—C13 | 1.388 (4) |
C5—C6 | 1.387 (4) | C12—H12 | 0.95 |
C5—H5 | 0.95 | C13—H13 | 0.95 |
| | | |
C3—O2—H2 | 107 (3) | O1—C7—C8 | 119.7 (3) |
C2—C1—C6 | 120.1 (3) | C1—C7—C8 | 121.0 (3) |
C2—C1—C7 | 122.3 (3) | C13—C8—C9 | 119.9 (3) |
C6—C1—C7 | 117.6 (3) | C13—C8—C7 | 121.8 (3) |
C3—C2—C1 | 119.7 (3) | C9—C8—C7 | 118.1 (3) |
C3—C2—H21 | 120.1 | C10—C9—C8 | 119.7 (3) |
C1—C2—H21 | 120.1 | C10—C9—H9 | 120.2 |
O2—C3—C2 | 122.4 (3) | C8—C9—H9 | 120.2 |
O2—C3—C4 | 117.5 (3) | C11—C10—C9 | 120.1 (3) |
C2—C3—C4 | 120.1 (3) | C11—C10—H10 | 119.9 |
C5—C4—C3 | 120.0 (3) | C9—C10—H10 | 119.9 |
C5—C4—H4 | 120 | C12—C11—C10 | 120.2 (3) |
C3—C4—H4 | 120 | C12—C11—H11 | 119.9 |
C6—C5—C4 | 120.6 (3) | C10—C11—H11 | 119.9 |
C6—C5—H5 | 119.7 | C11—C12—C13 | 120.6 (3) |
C4—C5—H5 | 119.7 | C11—C12—H12 | 119.7 |
C5—C6—C1 | 119.5 (3) | C13—C12—H12 | 119.7 |
C5—C6—H6 | 120.2 | C12—C13—C8 | 119.6 (3) |
C1—C6—H6 | 120.2 | C12—C13—H13 | 120.2 |
O1—C7—C1 | 119.3 (3) | C8—C13—H13 | 120.2 |
| | | |
C6—C1—C2—C3 | 0.8 (4) | C6—C1—C7—C8 | 153.4 (3) |
C7—C1—C2—C3 | −177.7 (3) | O1—C7—C8—C13 | 148.7 (3) |
C1—C2—C3—O2 | 178.8 (3) | C1—C7—C8—C13 | −31.1 (4) |
C1—C2—C3—C4 | −0.9 (4) | O1—C7—C8—C9 | −27.5 (4) |
O2—C3—C4—C5 | −179.7 (3) | C1—C7—C8—C9 | 152.7 (3) |
C2—C3—C4—C5 | 0.1 (5) | C13—C8—C9—C10 | 0.8 (4) |
C3—C4—C5—C6 | 0.9 (5) | C7—C8—C9—C10 | 177.1 (3) |
C4—C5—C6—C1 | −1.1 (5) | C8—C9—C10—C11 | −1.5 (4) |
C2—C1—C6—C5 | 0.2 (4) | C9—C10—C11—C12 | 0.9 (5) |
C7—C1—C6—C5 | 178.8 (3) | C10—C11—C12—C13 | 0.5 (5) |
C2—C1—C7—O1 | 152.0 (3) | C11—C12—C13—C8 | −1.2 (4) |
C6—C1—C7—O1 | −26.5 (4) | C9—C8—C13—C12 | 0.5 (4) |
C2—C1—C7—C8 | −28.1 (4) | C7—C8—C13—C12 | −175.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 1.09 (6) | 1.66 (6) | 2.742 (3) | 175 (5) |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
Crystal data top
C13H9ClO2 | Dx = 1.435 Mg m−3 |
Mr = 232.65 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 17704 reflections |
a = 23.3058 (11) Å | θ = 2.9–27.5° |
b = 5.5770 (2) Å | µ = 0.33 mm−1 |
c = 8.2847 (4) Å | T = 120 K |
V = 1076.82 (8) Å3 | Prism, colourless |
Z = 4 | 0.2 × 0.15 × 0.1 mm |
F(000) = 480 | |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 1681 reflections with I > 2σ(I) |
ϕ and ω scans to fill Ewald sphere | Rint = 0.064 |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | θmax = 27.5°, θmin = 3.0° |
Tmin = 0.881, Tmax = 0.967 | h = −30→29 |
9569 measured reflections | k = −6→7 |
2143 independent reflections | l = −10→8 |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.043P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.038 | (Δ/σ)max < 0.001 |
wR(F2) = 0.085 | Δρmax = 0.20 e Å−3 |
S = 1.04 | Δρmin = −0.26 e Å−3 |
2143 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
149 parameters | Absolute structure parameter: −0.13 (7) |
1 restraint | |
Crystal data top
C13H9ClO2 | V = 1076.82 (8) Å3 |
Mr = 232.65 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 23.3058 (11) Å | µ = 0.33 mm−1 |
b = 5.5770 (2) Å | T = 120 K |
c = 8.2847 (4) Å | 0.2 × 0.15 × 0.1 mm |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 2143 independent reflections |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | 1681 reflections with I > 2σ(I) |
Tmin = 0.881, Tmax = 0.967 | Rint = 0.064 |
9569 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.085 | Δρmax = 0.20 e Å−3 |
S = 1.04 | Δρmin = −0.26 e Å−3 |
2143 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
149 parameters | Absolute structure parameter: −0.13 (7) |
1 restraint | |
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 | |
Cl1 | 0.20287 (3) | −0.16954 (11) | 0.42794 (10) | 0.0447 (2) | |
O1 | 0.43169 (7) | 0.5397 (3) | 0.4458 (2) | 0.0374 (4) | |
O2 | 0.46228 (8) | 0.7846 (3) | 1.1812 (2) | 0.0362 (5) | |
H2 | 0.4502 (13) | 0.694 (5) | 1.257 (3) | 0.043* | |
C1 | 0.35389 (10) | 0.3051 (4) | 0.5321 (3) | 0.0281 (5) | |
C2 | 0.36014 (10) | 0.1095 (4) | 0.4304 (3) | 0.0316 (5) | |
H2A | 0.3962 | 0.0782 | 0.3812 | 0.038* | |
C3 | 0.31403 (11) | −0.0407 (4) | 0.4000 (3) | 0.0348 (6) | |
H3 | 0.3186 | −0.1787 | 0.3341 | 0.042* | |
C4 | 0.26151 (10) | 0.0130 (4) | 0.4667 (3) | 0.0321 (6) | |
C5 | 0.25378 (11) | 0.2102 (4) | 0.5654 (3) | 0.0312 (6) | |
H5 | 0.217 | 0.2469 | 0.6081 | 0.037* | |
C6 | 0.30041 (10) | 0.3528 (5) | 0.6007 (3) | 0.0299 (6) | |
H6 | 0.2961 | 0.4846 | 0.6723 | 0.036* | |
C7 | 0.40295 (10) | 0.4708 (4) | 0.5614 (3) | 0.0273 (5) | |
C8 | 0.41568 (9) | 0.5508 (4) | 0.7258 (3) | 0.0262 (5) | |
C9 | 0.44722 (11) | 0.7632 (5) | 0.7488 (3) | 0.0288 (6) | |
H9 | 0.4589 | 0.855 | 0.658 | 0.035* | |
C10 | 0.46132 (9) | 0.8388 (4) | 0.9013 (3) | 0.0282 (6) | |
H10 | 0.4814 | 0.9854 | 0.9156 | 0.034* | |
C11 | 0.44630 (10) | 0.7019 (4) | 1.0350 (3) | 0.0276 (5) | |
C12 | 0.41600 (10) | 0.4884 (4) | 1.0139 (3) | 0.0284 (6) | |
H12 | 0.4061 | 0.3929 | 1.1047 | 0.034* | |
C13 | 0.40060 (10) | 0.4171 (4) | 0.8607 (3) | 0.0274 (5) | |
H13 | 0.3792 | 0.2735 | 0.8471 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0423 (4) | 0.0388 (4) | 0.0530 (4) | −0.0074 (3) | −0.0099 (3) | −0.0088 (3) |
O1 | 0.0379 (9) | 0.0445 (10) | 0.0297 (9) | −0.0006 (7) | 0.0069 (9) | 0.0014 (9) |
O2 | 0.0442 (11) | 0.0350 (11) | 0.0294 (11) | −0.0105 (8) | −0.0017 (8) | −0.0013 (8) |
C1 | 0.0311 (13) | 0.0276 (12) | 0.0255 (12) | 0.0024 (10) | −0.0034 (11) | 0.0010 (11) |
C2 | 0.0340 (12) | 0.0360 (13) | 0.0247 (12) | 0.0075 (10) | 0.0018 (13) | −0.0032 (12) |
C3 | 0.0452 (15) | 0.0286 (13) | 0.0307 (16) | 0.0046 (11) | −0.0054 (12) | −0.0064 (11) |
C4 | 0.0364 (14) | 0.0287 (13) | 0.0313 (14) | −0.0039 (10) | −0.0086 (12) | −0.0004 (11) |
C5 | 0.0319 (14) | 0.0292 (13) | 0.0326 (15) | −0.0003 (11) | 0.0002 (10) | −0.0021 (11) |
C6 | 0.0313 (14) | 0.0322 (14) | 0.0263 (13) | 0.0005 (11) | −0.0004 (10) | −0.0036 (10) |
C7 | 0.0270 (13) | 0.0298 (12) | 0.0249 (13) | 0.0050 (10) | 0.0017 (10) | 0.0024 (11) |
C8 | 0.0251 (12) | 0.0256 (13) | 0.0280 (13) | 0.0022 (10) | 0.0009 (10) | −0.0019 (11) |
C9 | 0.0282 (13) | 0.0301 (13) | 0.0280 (14) | 0.0015 (10) | −0.0012 (10) | 0.0033 (12) |
C10 | 0.0272 (11) | 0.0238 (11) | 0.0337 (16) | −0.0042 (9) | −0.0006 (11) | 0.0029 (11) |
C11 | 0.0248 (12) | 0.0315 (13) | 0.0265 (13) | 0.0015 (10) | −0.0025 (11) | −0.0019 (11) |
C12 | 0.0294 (13) | 0.0267 (13) | 0.0290 (14) | −0.0014 (10) | 0.0052 (10) | 0.0038 (11) |
C13 | 0.0267 (12) | 0.0243 (12) | 0.0312 (13) | −0.0003 (10) | 0.0005 (10) | 0.0006 (11) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.734 (2) | C5—H5 | 0.95 |
O1—C7 | 1.230 (3) | C6—H6 | 0.95 |
O2—C11 | 1.349 (3) | C7—C8 | 1.463 (3) |
O2—H2 | 0.86 (3) | C8—C13 | 1.389 (3) |
C1—C2 | 1.386 (3) | C8—C9 | 1.407 (4) |
C1—C6 | 1.396 (3) | C9—C10 | 1.372 (3) |
C1—C7 | 1.490 (3) | C9—H9 | 0.95 |
C2—C3 | 1.385 (3) | C10—C11 | 1.390 (3) |
C2—H2A | 0.95 | C10—H10 | 0.95 |
C3—C4 | 1.376 (3) | C11—C12 | 1.395 (3) |
C3—H3 | 0.95 | C12—C13 | 1.378 (3) |
C4—C5 | 1.382 (3) | C12—H12 | 0.95 |
C5—C6 | 1.378 (3) | C13—H13 | 0.95 |
| | | |
C11—O2—H2 | 112 (2) | O1—C7—C1 | 119.0 (2) |
C2—C1—C6 | 119.4 (2) | C8—C7—C1 | 119.7 (2) |
C2—C1—C7 | 120.4 (2) | C13—C8—C9 | 118.3 (2) |
C6—C1—C7 | 120.0 (2) | C13—C8—C7 | 122.3 (2) |
C3—C2—C1 | 120.3 (2) | C9—C8—C7 | 119.3 (2) |
C3—C2—H2A | 119.9 | C10—C9—C8 | 120.6 (2) |
C1—C2—H2A | 119.9 | C10—C9—H9 | 119.7 |
C4—C3—C2 | 119.1 (2) | C8—C9—H9 | 119.7 |
C4—C3—H3 | 120.5 | C9—C10—C11 | 120.3 (2) |
C2—C3—H3 | 120.5 | C9—C10—H10 | 119.9 |
C3—C4—C5 | 121.8 (2) | C11—C10—H10 | 119.9 |
C3—C4—Cl1 | 119.94 (19) | O2—C11—C10 | 117.2 (2) |
C5—C4—Cl1 | 118.30 (19) | O2—C11—C12 | 122.9 (2) |
C6—C5—C4 | 118.8 (2) | C10—C11—C12 | 119.8 (2) |
C6—C5—H5 | 120.6 | C13—C12—C11 | 119.6 (2) |
C4—C5—H5 | 120.6 | C13—C12—H12 | 120.2 |
C5—C6—C1 | 120.5 (2) | C11—C12—H12 | 120.2 |
C5—C6—H6 | 119.7 | C12—C13—C8 | 121.4 (2) |
C1—C6—H6 | 119.7 | C12—C13—H13 | 119.3 |
O1—C7—C8 | 121.3 (2) | C8—C13—H13 | 119.3 |
| | | |
C6—C1—C2—C3 | −1.5 (4) | O1—C7—C8—C13 | −155.0 (2) |
C7—C1—C2—C3 | −178.3 (2) | C1—C7—C8—C13 | 25.8 (3) |
C1—C2—C3—C4 | 2.7 (3) | O1—C7—C8—C9 | 21.2 (3) |
C2—C3—C4—C5 | −1.1 (3) | C1—C7—C8—C9 | −158.1 (2) |
C2—C3—C4—Cl1 | 178.97 (19) | C13—C8—C9—C10 | −1.7 (3) |
C3—C4—C5—C6 | −1.7 (4) | C7—C8—C9—C10 | −178.0 (2) |
Cl1—C4—C5—C6 | 178.2 (2) | C8—C9—C10—C11 | 2.2 (3) |
C4—C5—C6—C1 | 2.9 (4) | C9—C10—C11—O2 | 178.9 (2) |
C2—C1—C6—C5 | −1.4 (4) | C9—C10—C11—C12 | −1.0 (3) |
C7—C1—C6—C5 | 175.5 (2) | O2—C11—C12—C13 | 179.2 (2) |
C2—C1—C7—O1 | 45.3 (3) | C10—C11—C12—C13 | −0.9 (3) |
C6—C1—C7—O1 | −131.4 (3) | C11—C12—C13—C8 | 1.4 (4) |
C2—C1—C7—C8 | −135.4 (2) | C9—C8—C13—C12 | −0.2 (3) |
C6—C1—C7—C8 | 47.8 (3) | C7—C8—C13—C12 | 176.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.86 (3) | 1.83 (3) | 2.679 (3) | 169 (3) |
Symmetry code: (i) x, y, z+1. |
Crystal data top
C13H9Cl2NO | F(000) = 544 |
Mr = 266.11 | Dx = 1.464 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8897 (3) Å | Cell parameters from 8581 reflections |
b = 9.5581 (4) Å | θ = 2.9–27.5° |
c = 16.1101 (5) Å | µ = 0.52 mm−1 |
β = 96.416 (2)° | T = 120 K |
V = 1207.26 (8) Å3 | Shard, yellow |
Z = 4 | 0.24 × 0.16 × 0.06 mm |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 2133 reflections with I > 2σ(I) |
ϕ and ω scans to fill Ewald sphere | Rint = 0.075 |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | θmax = 27.5°, θmin = 3.3° |
Tmin = 0.849, Tmax = 0.970 | h = −10→10 |
16326 measured reflections | k = −12→12 |
2765 independent reflections | l = −20→20 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0547P)2 + 0.2206P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.103 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.38 e Å−3 |
2765 reflections | Δρmin = −0.46 e Å−3 |
161 parameters | |
Crystal data top
C13H9Cl2NO | V = 1207.26 (8) Å3 |
Mr = 266.11 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.8897 (3) Å | µ = 0.52 mm−1 |
b = 9.5581 (4) Å | T = 120 K |
c = 16.1101 (5) Å | 0.24 × 0.16 × 0.06 mm |
β = 96.416 (2)° | |
Data collection top
Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | 2765 independent reflections |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | 2133 reflections with I > 2σ(I) |
Tmin = 0.849, Tmax = 0.970 | Rint = 0.075 |
16326 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.38 e Å−3 |
2765 reflections | Δρmin = −0.46 e Å−3 |
161 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 | |
Cl1 | 0.10399 (6) | 0.05770 (5) | −0.13621 (3) | 0.02752 (15) | |
Cl2 | 0.39712 (7) | 0.46355 (5) | 0.08406 (3) | 0.03637 (16) | |
O1 | 0.35091 (17) | 0.19480 (14) | 0.24038 (8) | 0.0284 (3) | |
N1 | 0.4739 (2) | −0.05029 (19) | 0.19551 (11) | 0.0295 (4) | |
H1A | 0.534 (3) | −0.125 (3) | 0.2006 (14) | 0.035* | |
H1B | 0.475 (3) | 0.013 (3) | 0.2325 (15) | 0.035* | |
C1 | 0.2857 (2) | 0.09936 (18) | 0.10484 (11) | 0.0203 (4) | |
C2 | 0.3840 (2) | −0.02415 (19) | 0.12098 (11) | 0.0224 (4) | |
C3 | 0.3836 (2) | −0.12392 (19) | 0.05608 (12) | 0.0258 (4) | |
H3 | 0.4436 | −0.2094 | 0.0664 | 0.031* | |
C4 | 0.2983 (2) | −0.09969 (19) | −0.02131 (12) | 0.0253 (4) | |
H4 | 0.3015 | −0.1672 | −0.0644 | 0.03* | |
C5 | 0.2066 (2) | 0.02441 (19) | −0.03684 (11) | 0.0234 (4) | |
C6 | 0.1991 (2) | 0.12077 (18) | 0.02498 (11) | 0.0207 (4) | |
H6 | 0.1341 | 0.2037 | 0.0138 | 0.025* | |
C7 | 0.2727 (2) | 0.20316 (18) | 0.16985 (11) | 0.0214 (4) | |
C8 | 0.1505 (2) | 0.32416 (18) | 0.15294 (10) | 0.0226 (4) | |
C9 | 0.1950 (3) | 0.44843 (19) | 0.11733 (12) | 0.0265 (4) | |
C10 | 0.0842 (3) | 0.5611 (2) | 0.10734 (13) | 0.0326 (5) | |
H10 | 0.1178 | 0.6457 | 0.0828 | 0.039* | |
C11 | −0.0755 (3) | 0.5486 (2) | 0.13359 (12) | 0.0312 (5) | |
H11 | −0.1524 | 0.6253 | 0.1275 | 0.037* | |
C12 | −0.1244 (3) | 0.4251 (2) | 0.16884 (13) | 0.0302 (4) | |
H12 | −0.2354 | 0.4171 | 0.1859 | 0.036* | |
C13 | −0.0136 (3) | 0.3135 (2) | 0.17935 (12) | 0.0272 (4) | |
H13 | −0.0476 | 0.2295 | 0.2043 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0319 (3) | 0.0278 (3) | 0.0222 (2) | −0.00214 (18) | 0.00011 (19) | −0.00133 (17) |
Cl2 | 0.0316 (3) | 0.0343 (3) | 0.0449 (3) | −0.0007 (2) | 0.0120 (2) | 0.0089 (2) |
O1 | 0.0329 (8) | 0.0260 (7) | 0.0247 (7) | 0.0007 (6) | −0.0034 (6) | −0.0010 (5) |
N1 | 0.0311 (10) | 0.0287 (9) | 0.0276 (9) | 0.0097 (7) | −0.0006 (8) | 0.0018 (7) |
C1 | 0.0179 (9) | 0.0193 (9) | 0.0239 (8) | −0.0004 (7) | 0.0027 (7) | 0.0010 (7) |
C2 | 0.0191 (9) | 0.0232 (9) | 0.0258 (9) | 0.0005 (7) | 0.0067 (7) | 0.0032 (7) |
C3 | 0.0264 (10) | 0.0182 (9) | 0.0335 (10) | 0.0023 (7) | 0.0071 (8) | 0.0004 (7) |
C4 | 0.0280 (10) | 0.0203 (9) | 0.0285 (9) | −0.0013 (8) | 0.0070 (8) | −0.0041 (7) |
C5 | 0.0225 (9) | 0.0256 (9) | 0.0222 (9) | −0.0030 (7) | 0.0026 (7) | 0.0005 (7) |
C6 | 0.0181 (9) | 0.0186 (8) | 0.0258 (9) | 0.0002 (7) | 0.0046 (7) | 0.0007 (7) |
C7 | 0.0194 (9) | 0.0206 (9) | 0.0245 (9) | −0.0021 (7) | 0.0031 (7) | 0.0007 (7) |
C8 | 0.0253 (10) | 0.0218 (9) | 0.0199 (8) | 0.0009 (7) | −0.0004 (8) | −0.0031 (7) |
C9 | 0.0254 (10) | 0.0276 (10) | 0.0270 (9) | −0.0009 (8) | 0.0046 (8) | −0.0011 (7) |
C10 | 0.0386 (12) | 0.0248 (10) | 0.0335 (10) | 0.0048 (9) | 0.0010 (9) | 0.0030 (8) |
C11 | 0.0335 (11) | 0.0257 (10) | 0.0335 (11) | 0.0078 (8) | −0.0006 (9) | −0.0050 (8) |
C12 | 0.0256 (10) | 0.0328 (11) | 0.0326 (10) | 0.0021 (8) | 0.0052 (9) | −0.0079 (8) |
C13 | 0.0307 (11) | 0.0229 (9) | 0.0269 (9) | −0.0009 (8) | −0.0016 (8) | −0.0032 (7) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.7407 (18) | C5—C6 | 1.363 (3) |
Cl2—C9 | 1.744 (2) | C6—H6 | 0.95 |
O1—C7 | 1.233 (2) | C7—C8 | 1.511 (3) |
N1—C2 | 1.348 (2) | C8—C9 | 1.381 (3) |
N1—H1A | 0.86 (3) | C8—C13 | 1.411 (3) |
N1—H1B | 0.85 (3) | C9—C10 | 1.385 (3) |
C1—C6 | 1.403 (2) | C10—C11 | 1.378 (3) |
C1—C2 | 1.420 (3) | C10—H10 | 0.95 |
C1—C7 | 1.455 (2) | C11—C12 | 1.384 (3) |
C2—C3 | 1.415 (3) | C11—H11 | 0.95 |
C3—C4 | 1.369 (3) | C12—C13 | 1.377 (3) |
C3—H3 | 0.95 | C12—H12 | 0.95 |
C4—C5 | 1.397 (3) | C13—H13 | 0.95 |
C4—H4 | 0.95 | | |
| | | |
C2—N1—H1A | 118.1 (16) | O1—C7—C1 | 123.42 (16) |
C2—N1—H1B | 117.3 (16) | O1—C7—C8 | 117.33 (16) |
H1A—N1—H1B | 124 (2) | C1—C7—C8 | 119.16 (15) |
C6—C1—C2 | 119.29 (16) | C9—C8—C13 | 118.13 (17) |
C6—C1—C7 | 119.64 (15) | C9—C8—C7 | 123.14 (17) |
C2—C1—C7 | 121.07 (16) | C13—C8—C7 | 118.62 (16) |
N1—C2—C3 | 119.41 (17) | C8—C9—C10 | 122.04 (19) |
N1—C2—C1 | 122.63 (17) | C8—C9—Cl2 | 118.84 (15) |
C3—C2—C1 | 117.95 (16) | C10—C9—Cl2 | 119.12 (15) |
C4—C3—C2 | 121.30 (17) | C11—C10—C9 | 118.91 (18) |
C4—C3—H3 | 119.3 | C11—C10—H10 | 120.5 |
C2—C3—H3 | 119.3 | C9—C10—H10 | 120.5 |
C3—C4—C5 | 119.91 (17) | C10—C11—C12 | 120.43 (18) |
C3—C4—H4 | 120 | C10—C11—H11 | 119.8 |
C5—C4—H4 | 120 | C12—C11—H11 | 119.8 |
C6—C5—C4 | 120.46 (17) | C13—C12—C11 | 120.59 (19) |
C6—C5—Cl1 | 119.66 (14) | C13—C12—H12 | 119.7 |
C4—C5—Cl1 | 119.88 (14) | C11—C12—H12 | 119.7 |
C5—C6—C1 | 121.00 (16) | C12—C13—C8 | 119.88 (18) |
C5—C6—H6 | 119.5 | C12—C13—H13 | 120.1 |
C1—C6—H6 | 119.5 | C8—C13—H13 | 120.1 |
| | | |
C6—C1—C2—N1 | 178.38 (17) | C2—C1—C7—C8 | −172.82 (16) |
C7—C1—C2—N1 | −2.0 (3) | O1—C7—C8—C9 | 94.9 (2) |
C6—C1—C2—C3 | −2.9 (3) | C1—C7—C8—C9 | −88.4 (2) |
C7—C1—C2—C3 | 176.71 (16) | O1—C7—C8—C13 | −81.1 (2) |
N1—C2—C3—C4 | −177.97 (18) | C1—C7—C8—C13 | 95.7 (2) |
C1—C2—C3—C4 | 3.2 (3) | C13—C8—C9—C10 | 0.2 (3) |
C2—C3—C4—C5 | −1.3 (3) | C7—C8—C9—C10 | −175.78 (18) |
C3—C4—C5—C6 | −1.1 (3) | C13—C8—C9—Cl2 | −179.84 (14) |
C3—C4—C5—Cl1 | 177.91 (14) | C7—C8—C9—Cl2 | 4.2 (2) |
C4—C5—C6—C1 | 1.4 (3) | C8—C9—C10—C11 | −0.2 (3) |
Cl1—C5—C6—C1 | −177.58 (13) | Cl2—C9—C10—C11 | 179.88 (15) |
C2—C1—C6—C5 | 0.6 (3) | C9—C10—C11—C12 | −0.4 (3) |
C7—C1—C6—C5 | −178.96 (17) | C10—C11—C12—C13 | 0.9 (3) |
C6—C1—C7—O1 | −176.73 (17) | C11—C12—C13—C8 | −0.9 (3) |
C2—C1—C7—O1 | 3.7 (3) | C9—C8—C13—C12 | 0.3 (3) |
C6—C1—C7—C8 | 6.7 (2) | C7—C8—C13—C12 | 176.49 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.86 (3) | 2.12 (3) | 2.932 (2) | 158 (2) |
N1—H1B···O1 | 0.85 (3) | 2.01 (3) | 2.666 (2) | 134 (2) |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Experimental details
| (2d4d) | (orla1) | (orla2) | (3hbz2) |
Crystal data |
Chemical formula | C15H14O5 | C21H28N2O | C13H10O3 | C13H10O2 |
Mr | 274.26 | 324.45 | 214.21 | 198.21 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/c | Monoclinic, C2/c | Monoclinic, P21/n |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 3.8466 (1), 25.1521 (12), 12.9802 (6) | 16.8519 (6), 8.0488 (3), 14.3060 (5) | 24.4619 (9), 7.3737 (2), 12.3961 (4) | 4.0462 (1), 20.2165 (6), 11.8058 (3) |
α, β, γ (°) | 90, 92.545 (3), 90 | 90, 104.6390 (18), 90 | 90, 115.019 (2), 90 | 90, 90.929 (2), 90 |
V (Å3) | 1254.60 (9) | 1877.44 (12) | 2026.14 (11) | 965.59 (4) |
Z | 4 | 4 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.07 | 0.1 | 0.09 |
Crystal size (mm) | 0.52 × 0.08 × 0.06 | 0.4 × 0.35 × 0.3 | 0.24 × 0.14 × 0.03 | 0.16 × 0.1 × 0.04 |
|
Data collection |
Diffractometer | Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer |
Absorption correction | Multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | Multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | Multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | Multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) |
Tmin, Tmax | 0.727, 0.994 | 0.948, 0.979 | 0.913, 0.997 | 0.729, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13532, 2798, 1759 | 18012, 4315, 2862 | 16476, 2319, 1733 | 13634, 2197, 1795 |
Rint | 0.083 | 0.077 | 0.074 | 0.049 |
(sin θ/λ)max (Å−1) | 0.649 | 0.652 | 0.649 | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.119, 0.99 | 0.047, 0.122, 1.01 | 0.048, 0.114, 1.03 | 0.074, 0.216, 1.17 |
No. of reflections | 2798 | 4315 | 2319 | 2197 |
No. of parameters | 189 | 288 | 152 | 140 |
No. of restraints | 0 | 12 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.30 | 0.21, −0.22 | 0.19, −0.29 | 0.42, −0.30 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
| (dimit1) | (dimit2) |
Crystal data |
Chemical formula | C13H9ClO2 | C13H9Cl2NO |
Mr | 232.65 | 266.11 |
Crystal system, space group | Orthorhombic, Pca21 | Monoclinic, P21/c |
Temperature (K) | 120 | 120 |
a, b, c (Å) | 23.3058 (11), 5.5770 (2), 8.2847 (4) | 7.8897 (3), 9.5581 (4), 16.1101 (5) |
α, β, γ (°) | 90, 90, 90 | 90, 96.416 (2), 90 |
V (Å3) | 1076.82 (8) | 1207.26 (8) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.33 | 0.52 |
Crystal size (mm) | 0.2 × 0.15 × 0.1 | 0.24 × 0.16 × 0.06 |
|
Data collection |
Diffractometer | Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer | Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer |
Absorption correction | Multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) | Multi-scan using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997) |
Tmin, Tmax | 0.881, 0.967 | 0.849, 0.970 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9569, 2143, 1681 | 16326, 2765, 2133 |
Rint | 0.064 | 0.075 |
(sin θ/λ)max (Å−1) | 0.649 | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.085, 1.04 | 0.040, 0.103, 1.03 |
No. of reflections | 2143 | 2765 |
No. of parameters | 149 | 161 |
No. of restraints | 1 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.26 | 0.38, −0.46 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? |
Absolute structure parameter | −0.13 (7) | ? |
Hydrogen-bond geometry (Å, º) for (2d4d) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.92 (2) | 1.68 (2) | 2.5278 (18) | 150.4 (19) |
O3—H3···O1 | 0.92 (2) | 1.75 (2) | 2.5733 (18) | 147 (2) |
Hydrogen-bond geometry (Å, º) for (orla2) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.94 (2) | 1.71 (2) | 2.6391 (16) | 171.7 (18) |
O3—H3···O2ii | 0.94 (2) | 1.91 (2) | 2.8149 (16) | 159.6 (16) |
C2—H2A···O1i | 0.95 | 2.56 | 3.2309 (18) | 128.1 |
Symmetry codes: (i) x, −y, z+1/2; (ii) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) for (3hbz2) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 1.09 (6) | 1.66 (6) | 2.742 (3) | 175 (5) |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) for (dimit1) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.86 (3) | 1.83 (3) | 2.679 (3) | 169 (3) |
Symmetry code: (i) x, y, z+1. |
Hydrogen-bond geometry (Å, º) for (dimit2) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.86 (3) | 2.12 (3) | 2.932 (2) | 158 (2) |
N1—H1B···O1 | 0.85 (3) | 2.01 (3) | 2.666 (2) | 134 (2) |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |