Pharmaceutical salt-forming acid 1-hydroxy-2-naphthoic acid (HNA) is widely used in pharmaceutical co-crystal preparation. In this work, we report a new polymorph of HNA obtained during attempted co-crystallization experiments. The reported form and the new form were fully characterized and their thermodynamic relationship was also established to be monotropic with the new form being the more stable form.
Supporting information
CCDC references: 1036605; 1036606
For both compounds, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
Crystal data top
C11H8O3 | F(000) = 392 |
Mr = 188.17 | Dx = 1.436 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9798 (9) Å | Cell parameters from 1909 reflections |
b = 3.8107 (6) Å | θ = 2.5–26.2° |
c = 32.790 (5) Å | µ = 0.11 mm−1 |
β = 93.901 (8)° | T = 296 K |
V = 870.1 (2) Å3 | Columnar, colorless |
Z = 4 | 0.44 × 0.32 × 0.11 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 1020 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
ϕ and ω scans | h = −8→7 |
6187 measured reflections | k = −4→3 |
1491 independent reflections | l = −30→38 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0538P)2] where P = (Fo2 + 2Fc2)/3 |
1491 reflections | (Δ/σ)max = 0.001 |
133 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Crystal data top
C11H8O3 | V = 870.1 (2) Å3 |
Mr = 188.17 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.9798 (9) Å | µ = 0.11 mm−1 |
b = 3.8107 (6) Å | T = 296 K |
c = 32.790 (5) Å | 0.44 × 0.32 × 0.11 mm |
β = 93.901 (8)° | |
Data collection top
Bruker APEX-II CCD diffractometer | 1020 reflections with I > 2σ(I) |
6187 measured reflections | Rint = 0.038 |
1491 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.15 e Å−3 |
1491 reflections | Δρmin = −0.16 e Å−3 |
133 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. |
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.25506 (17) | 0.8378 (3) | 0.99359 (4) | 0.0618 (4) | |
H2 | 0.346 (3) | 0.937 (5) | 1.0124 (7) | 0.093* | |
O2 | 0.48854 (16) | 0.8996 (3) | 0.95134 (3) | 0.0557 (4) | |
O1 | 0.42771 (17) | 0.6877 (3) | 0.87621 (4) | 0.0566 (4) | |
H1 | 0.493 (3) | 0.780 (5) | 0.8993 (7) | 0.085* | |
C11 | 0.3227 (2) | 0.8048 (4) | 0.95749 (5) | 0.0418 (4) | |
C2 | 0.1919 (2) | 0.6527 (3) | 0.92614 (5) | 0.0379 (4) | |
C3 | 0.0036 (2) | 0.5550 (4) | 0.93476 (5) | 0.0441 (4) | |
H3 | −0.0371 | 0.5907 | 0.9609 | 0.053* | |
C4 | −0.1183 (2) | 0.4107 (4) | 0.90569 (5) | 0.0475 (4) | |
H4 | −0.2414 | 0.3479 | 0.9121 | 0.057* | |
C5 | −0.0614 (2) | 0.3540 (3) | 0.86576 (5) | 0.0421 (4) | |
C6 | −0.1863 (3) | 0.2058 (4) | 0.83462 (6) | 0.0541 (5) | |
H5 | −0.3104 | 0.1427 | 0.8403 | 0.065* | |
C7 | −0.1271 (3) | 0.1547 (4) | 0.79662 (6) | 0.0632 (6) | |
H6 | −0.2113 | 0.0571 | 0.7765 | 0.076* | |
C10 | 0.1249 (2) | 0.4484 (3) | 0.85586 (5) | 0.0397 (4) | |
C9 | 0.1826 (3) | 0.3905 (4) | 0.81634 (5) | 0.0545 (5) | |
H8 | 0.3062 | 0.4504 | 0.8099 | 0.065* | |
C8 | 0.0574 (3) | 0.2457 (5) | 0.78713 (5) | 0.0632 (5) | |
H7 | 0.0958 | 0.2083 | 0.7609 | 0.076* | |
C1 | 0.2516 (2) | 0.6003 (3) | 0.88710 (5) | 0.0392 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0531 (8) | 0.0938 (9) | 0.0384 (8) | −0.0212 (6) | 0.0023 (6) | −0.0106 (6) |
O2 | 0.0422 (7) | 0.0784 (8) | 0.0462 (8) | −0.0145 (6) | 0.0010 (5) | −0.0081 (5) |
O1 | 0.0428 (7) | 0.0800 (8) | 0.0474 (8) | −0.0089 (6) | 0.0068 (6) | −0.0060 (6) |
C11 | 0.0442 (10) | 0.0446 (8) | 0.0362 (10) | −0.0011 (7) | 0.0004 (7) | 0.0003 (7) |
C2 | 0.0394 (9) | 0.0374 (8) | 0.0364 (9) | −0.0012 (6) | −0.0018 (7) | 0.0024 (6) |
C3 | 0.0438 (10) | 0.0489 (9) | 0.0397 (10) | −0.0026 (7) | 0.0033 (7) | 0.0039 (7) |
C4 | 0.0392 (9) | 0.0502 (9) | 0.0524 (12) | −0.0051 (7) | −0.0006 (8) | 0.0043 (8) |
C5 | 0.0465 (10) | 0.0330 (7) | 0.0454 (11) | 0.0009 (7) | −0.0082 (8) | 0.0047 (6) |
C6 | 0.0600 (12) | 0.0445 (9) | 0.0550 (13) | −0.0038 (8) | −0.0153 (9) | 0.0021 (8) |
C7 | 0.0859 (16) | 0.0434 (9) | 0.0564 (13) | −0.0023 (9) | −0.0246 (11) | −0.0041 (8) |
C10 | 0.0479 (10) | 0.0336 (7) | 0.0367 (9) | 0.0043 (6) | −0.0028 (7) | 0.0023 (6) |
C9 | 0.0642 (12) | 0.0532 (10) | 0.0457 (11) | 0.0047 (8) | 0.0006 (9) | −0.0018 (8) |
C8 | 0.0905 (16) | 0.0577 (10) | 0.0400 (12) | 0.0082 (10) | −0.0066 (10) | −0.0068 (8) |
C1 | 0.0366 (9) | 0.0384 (8) | 0.0422 (10) | 0.0009 (7) | 0.0000 (7) | 0.0031 (7) |
Geometric parameters (Å, º) top
O3—C11 | 1.3102 (19) | C5—C10 | 1.408 (2) |
O3—H2 | 0.93 (2) | C5—C6 | 1.414 (2) |
O2—C11 | 1.2417 (17) | C6—C7 | 1.353 (3) |
O1—C1 | 1.3447 (18) | C6—H5 | 0.9300 |
O1—H1 | 0.92 (2) | C7—C8 | 1.389 (3) |
C11—C2 | 1.449 (2) | C7—H6 | 0.9300 |
C2—C1 | 1.388 (2) | C10—C9 | 1.400 (2) |
C2—C3 | 1.413 (2) | C10—C1 | 1.430 (2) |
C3—C4 | 1.351 (2) | C9—C8 | 1.368 (3) |
C3—H3 | 0.9300 | C9—H8 | 0.9300 |
C4—C5 | 1.410 (2) | C8—H7 | 0.9300 |
C4—H4 | 0.9300 | | |
| | | |
C11—O3—H2 | 111.4 (13) | C7—C6—H5 | 119.7 |
C1—O1—H1 | 106.4 (13) | C5—C6—H5 | 119.7 |
O2—C11—O3 | 121.08 (15) | C6—C7—C8 | 121.08 (17) |
O2—C11—C2 | 123.41 (14) | C6—C7—H6 | 119.5 |
O3—C11—C2 | 115.51 (14) | C8—C7—H6 | 119.5 |
C1—C2—C3 | 119.26 (14) | C9—C10—C5 | 120.07 (15) |
C1—C2—C11 | 119.84 (14) | C9—C10—C1 | 121.61 (15) |
C3—C2—C11 | 120.90 (14) | C5—C10—C1 | 118.32 (14) |
C4—C3—C2 | 121.05 (15) | C8—C9—C10 | 120.07 (18) |
C4—C3—H3 | 119.5 | C8—C9—H8 | 120.0 |
C2—C3—H3 | 119.5 | C10—C9—H8 | 120.0 |
C3—C4—C5 | 120.94 (15) | C9—C8—C7 | 120.11 (18) |
C3—C4—H4 | 119.5 | C9—C8—H7 | 119.9 |
C5—C4—H4 | 119.5 | C7—C8—H7 | 119.9 |
C10—C5—C4 | 119.83 (14) | O1—C1—C2 | 123.15 (14) |
C10—C5—C6 | 117.98 (15) | O1—C1—C10 | 116.24 (14) |
C4—C5—C6 | 122.19 (16) | C2—C1—C10 | 120.61 (14) |
C7—C6—C5 | 120.68 (18) | | |
| | | |
O2—C11—C2—C1 | 1.3 (2) | C4—C5—C10—C1 | 0.1 (2) |
O3—C11—C2—C1 | −178.66 (13) | C6—C5—C10—C1 | 179.64 (12) |
O2—C11—C2—C3 | −178.95 (14) | C5—C10—C9—C8 | 0.8 (2) |
O3—C11—C2—C3 | 1.1 (2) | C1—C10—C9—C8 | −179.76 (14) |
C1—C2—C3—C4 | 0.2 (2) | C10—C9—C8—C7 | −0.2 (2) |
C11—C2—C3—C4 | −179.49 (13) | C6—C7—C8—C9 | −0.2 (3) |
C2—C3—C4—C5 | −0.2 (2) | C3—C2—C1—O1 | 179.56 (12) |
C3—C4—C5—C10 | 0.0 (2) | C11—C2—C1—O1 | −0.7 (2) |
C3—C4—C5—C6 | −179.54 (13) | C3—C2—C1—C10 | −0.2 (2) |
C10—C5—C6—C7 | 0.5 (2) | C11—C2—C1—C10 | 179.58 (12) |
C4—C5—C6—C7 | −179.97 (14) | C9—C10—C1—O1 | 0.8 (2) |
C5—C6—C7—C8 | 0.1 (2) | C5—C10—C1—O1 | −179.73 (11) |
C4—C5—C10—C9 | 179.55 (13) | C9—C10—C1—C2 | −179.47 (13) |
C6—C5—C10—C9 | −0.9 (2) | C5—C10—C1—C2 | 0.0 (2) |
Crystal data top
C11H8O3 | F(000) = 784 |
Mr = 188.17 | Dx = 1.426 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.920 (5) Å | Cell parameters from 2087 reflections |
b = 6.9926 (14) Å | θ = 2.4–27.4° |
c = 14.688 (3) Å | µ = 0.11 mm−1 |
β = 125.339 (10)° | T = 296 K |
V = 1752.7 (6) Å3 | Columnar, colorless |
Z = 8 | 0.42 × 0.34 × 0.11 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 1239 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 27.5°, θmin = 2.4° |
ϕ and ω scans | h = −22→27 |
7678 measured reflections | k = −9→8 |
2015 independent reflections | l = −19→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.226 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1338P)2 + 0.4921P] where P = (Fo2 + 2Fc2)/3 |
2015 reflections | (Δ/σ)max < 0.001 |
133 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C11H8O3 | V = 1752.7 (6) Å3 |
Mr = 188.17 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 20.920 (5) Å | µ = 0.11 mm−1 |
b = 6.9926 (14) Å | T = 296 K |
c = 14.688 (3) Å | 0.42 × 0.34 × 0.11 mm |
β = 125.339 (10)° | |
Data collection top
Bruker APEX-II CCD diffractometer | 1239 reflections with I > 2σ(I) |
7678 measured reflections | Rint = 0.034 |
2015 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.226 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.49 e Å−3 |
2015 reflections | Δρmin = −0.27 e Å−3 |
133 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. |
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.51230 (9) | 0.1297 (2) | 0.13772 (13) | 0.0546 (5) | |
H2 | 0.474 (2) | 0.137 (3) | 0.152 (2) | 0.082* | |
O2 | 0.59661 (9) | 0.1364 (2) | 0.32339 (13) | 0.0473 (5) | |
O1 | 0.74661 (9) | 0.1404 (2) | 0.41035 (12) | 0.0465 (5) | |
H1 | 0.704 (2) | 0.140 (3) | 0.408 (2) | 0.070* | |
C11 | 0.58435 (12) | 0.1317 (3) | 0.22991 (17) | 0.0373 (5) | |
C2 | 0.64602 (12) | 0.1281 (2) | 0.21269 (17) | 0.0349 (5) | |
C1 | 0.72398 (12) | 0.1329 (2) | 0.30434 (17) | 0.0343 (5) | |
C10 | 0.78555 (12) | 0.1295 (2) | 0.28829 (17) | 0.0359 (5) | |
C9 | 0.86499 (13) | 0.1328 (3) | 0.3797 (2) | 0.0464 (6) | |
H8 | 0.8787 | 0.1364 | 0.4522 | 0.056* | |
C8 | 0.92190 (15) | 0.1306 (3) | 0.3609 (3) | 0.0589 (7) | |
H7 | 0.9744 | 0.1346 | 0.4211 | 0.071* | |
C7 | 0.90208 (15) | 0.1224 (3) | 0.2531 (3) | 0.0609 (8) | |
H6 | 0.9416 | 0.1193 | 0.2422 | 0.073* | |
C6 | 0.82553 (15) | 0.1186 (3) | 0.1625 (2) | 0.0532 (6) | |
H5 | 0.8134 | 0.1141 | 0.0908 | 0.064* | |
C5 | 0.76483 (13) | 0.1216 (2) | 0.17838 (18) | 0.0397 (5) | |
C4 | 0.68447 (14) | 0.1170 (3) | 0.08643 (18) | 0.0455 (6) | |
H4 | 0.6711 | 0.1125 | 0.0141 | 0.055* | |
C3 | 0.62756 (12) | 0.1190 (3) | 0.10299 (17) | 0.0406 (5) | |
H3 | 0.5754 | 0.1143 | 0.0419 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0321 (9) | 0.0918 (13) | 0.0424 (9) | 0.0012 (7) | 0.0231 (8) | −0.0018 (7) |
O2 | 0.0349 (8) | 0.0739 (11) | 0.0394 (8) | −0.0016 (6) | 0.0250 (7) | −0.0003 (6) |
O1 | 0.0360 (8) | 0.0718 (11) | 0.0332 (8) | −0.0019 (7) | 0.0209 (7) | −0.0014 (6) |
C11 | 0.0310 (10) | 0.0445 (11) | 0.0392 (11) | −0.0011 (8) | 0.0219 (9) | −0.0012 (8) |
C2 | 0.0322 (11) | 0.0381 (10) | 0.0365 (11) | −0.0003 (7) | 0.0211 (9) | 0.0001 (7) |
C1 | 0.0357 (11) | 0.0367 (10) | 0.0343 (10) | −0.0009 (8) | 0.0224 (9) | −0.0015 (7) |
C10 | 0.0367 (11) | 0.0305 (10) | 0.0467 (12) | −0.0004 (7) | 0.0277 (10) | −0.0001 (7) |
C9 | 0.0367 (12) | 0.0473 (12) | 0.0543 (13) | −0.0038 (9) | 0.0257 (11) | −0.0040 (9) |
C8 | 0.0351 (13) | 0.0576 (14) | 0.0808 (19) | −0.0066 (10) | 0.0317 (13) | −0.0055 (12) |
C7 | 0.0507 (16) | 0.0627 (15) | 0.094 (2) | −0.0070 (11) | 0.0560 (16) | −0.0072 (13) |
C6 | 0.0624 (16) | 0.0528 (13) | 0.0700 (15) | −0.0018 (10) | 0.0531 (14) | −0.0017 (10) |
C5 | 0.0449 (12) | 0.0354 (10) | 0.0509 (13) | −0.0033 (8) | 0.0348 (11) | −0.0024 (8) |
C4 | 0.0519 (13) | 0.0546 (13) | 0.0393 (11) | 0.0017 (9) | 0.0317 (11) | −0.0003 (9) |
C3 | 0.0352 (11) | 0.0513 (12) | 0.0331 (10) | −0.0001 (8) | 0.0185 (9) | −0.0010 (8) |
Geometric parameters (Å, º) top
O3—C11 | 1.321 (3) | C9—H8 | 0.9300 |
O3—H2 | 0.93 (4) | C8—C7 | 1.387 (4) |
O2—C11 | 1.243 (2) | C8—H7 | 0.9300 |
O1—C1 | 1.341 (2) | C7—C6 | 1.368 (4) |
O1—H1 | 0.86 (3) | C7—H6 | 0.9300 |
C11—C2 | 1.451 (3) | C6—C5 | 1.418 (3) |
C2—C1 | 1.391 (3) | C6—H5 | 0.9300 |
C2—C3 | 1.425 (3) | C5—C4 | 1.423 (3) |
C1—C10 | 1.437 (3) | C4—C3 | 1.346 (3) |
C10—C9 | 1.408 (3) | C4—H4 | 0.9300 |
C10—C5 | 1.410 (3) | C3—H3 | 0.9300 |
C9—C8 | 1.368 (3) | | |
| | | |
C11—O3—H2 | 112.9 (19) | C9—C8—H7 | 119.7 |
C1—O1—H1 | 107 (2) | C7—C8—H7 | 119.7 |
O2—C11—O3 | 121.11 (18) | C6—C7—C8 | 121.4 (2) |
O2—C11—C2 | 123.83 (18) | C6—C7—H6 | 119.3 |
O3—C11—C2 | 115.06 (18) | C8—C7—H6 | 119.3 |
C1—C2—C3 | 119.65 (18) | C7—C6—C5 | 119.7 (2) |
C1—C2—C11 | 119.61 (18) | C7—C6—H5 | 120.1 |
C3—C2—C11 | 120.73 (18) | C5—C6—H5 | 120.1 |
O1—C1—C2 | 123.61 (19) | C10—C5—C6 | 118.5 (2) |
O1—C1—C10 | 116.29 (18) | C10—C5—C4 | 119.98 (18) |
C2—C1—C10 | 120.10 (19) | C6—C5—C4 | 121.5 (2) |
C9—C10—C5 | 120.23 (19) | C3—C4—C5 | 120.7 (2) |
C9—C10—C1 | 121.3 (2) | C3—C4—H4 | 119.6 |
C5—C10—C1 | 118.50 (19) | C5—C4—H4 | 119.6 |
C8—C9—C10 | 119.5 (2) | C4—C3—C2 | 121.0 (2) |
C8—C9—H8 | 120.2 | C4—C3—H3 | 119.5 |
C10—C9—H8 | 120.2 | C2—C3—H3 | 119.5 |
C9—C8—C7 | 120.6 (2) | | |
| | | |
O2—C11—C2—C1 | −1.0 (3) | C10—C9—C8—C7 | −1.0 (3) |
O3—C11—C2—C1 | 179.00 (15) | C9—C8—C7—C6 | 0.8 (3) |
O2—C11—C2—C3 | 178.75 (16) | C8—C7—C6—C5 | −0.5 (3) |
O3—C11—C2—C3 | −1.3 (2) | C9—C10—C5—C6 | −0.5 (2) |
C3—C2—C1—O1 | −179.61 (15) | C1—C10—C5—C6 | 179.90 (16) |
C11—C2—C1—O1 | 0.1 (3) | C9—C10—C5—C4 | 179.56 (16) |
C3—C2—C1—C10 | 0.3 (2) | C1—C10—C5—C4 | 0.0 (2) |
C11—C2—C1—C10 | −179.97 (15) | C7—C6—C5—C10 | 0.4 (3) |
O1—C1—C10—C9 | 0.4 (2) | C7—C6—C5—C4 | −179.72 (18) |
C2—C1—C10—C9 | −179.53 (15) | C10—C5—C4—C3 | −0.4 (3) |
O1—C1—C10—C5 | 179.99 (14) | C6—C5—C4—C3 | 179.68 (18) |
C2—C1—C10—C5 | 0.1 (2) | C5—C4—C3—C2 | 0.8 (3) |
C5—C10—C9—C8 | 0.8 (3) | C1—C2—C3—C4 | −0.7 (3) |
C1—C10—C9—C8 | −179.61 (16) | C11—C2—C3—C4 | 179.53 (17) |
Experimental details
| (mo_I) | (mo_II) |
Crystal data |
Chemical formula | C11H8O3 | C11H8O3 |
Mr | 188.17 | 188.17 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, C2/c |
Temperature (K) | 296 | 296 |
a, b, c (Å) | 6.9798 (9), 3.8107 (6), 32.790 (5) | 20.920 (5), 6.9926 (14), 14.688 (3) |
β (°) | 93.901 (8) | 125.339 (10) |
V (Å3) | 870.1 (2) | 1752.7 (6) |
Z | 4 | 8 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.11 |
Crystal size (mm) | 0.44 × 0.32 × 0.11 | 0.42 × 0.34 × 0.11 |
|
Data collection |
Diffractometer | Bruker APEX-II CCD diffractometer | Bruker APEX-II CCD diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6187, 1491, 1020 | 7678, 2015, 1239 |
Rint | 0.038 | 0.034 |
(sin θ/λ)max (Å−1) | 0.594 | 0.651 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.097, 0.96 | 0.068, 0.226, 1.04 |
No. of reflections | 1491 | 2015 |
No. of parameters | 133 | 133 |
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) | 0.15, −0.16 | 0.49, −0.27 |