Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620009560/cu3165sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009560/cu3165F1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009560/cu3165S1sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009560/cu3165S2sup4.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620009560/cu3165sup5.pdf |
CCDC references: 1919255; 1919257; 1919259
For all structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015) and WinGX (Farrugia (2012); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2020) and PARST (Nardelli, 1995).
C13H13FN2O3 | F(000) = 1104 |
Mr = 264.25 | Dx = 1.382 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.0881 (15) Å | Cell parameters from 7891 reflections |
b = 7.1958 (8) Å | θ = 2.7–29.9° |
c = 23.177 (3) Å | µ = 0.11 mm−1 |
β = 108.838 (4)° | T = 90 K |
V = 2539.4 (5) Å3 | Plate, colourless |
Z = 8 | 0.40 × 0.25 × 0.09 mm |
Bruker APEXII CCD diffractometer | 2706 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.072 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 30.1°, θmin = 2.7° |
Tmin = 0.647, Tmax = 0.746 | h = −22→22 |
24306 measured reflections | k = −9→10 |
3737 independent reflections | l = −32→32 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0511P)2 + 1.7817P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3737 reflections | Δρmax = 0.39 e Å−3 |
182 parameters | Δρmin = −0.26 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. SCXRD data of all single crystals of (I) were collected on a Bruker AXS SMART APEX CCD diffractometer using Mo Kα radiation (λ = 0.71073 Å) at 100 (2) K. Unit cell measurement, data collection, integration, scaling and absorption correction were performed using Bruker Apex II software and SAINT suite of programs were used for data reduction (Bruker, 2012). Scaling and absorption correction was performed using SADABAS software (Bruker, 2001). Crystal structures were solved using direct methods by SIR 2014 program (Burla et al., 2015) and refined using full matrix least squares method by SHELXL 2014 (Sheldrick, 2015) embedded in the WinGX program suite (Version 2014.1). Geometrical calculations were performed using PLATON (Spek, 2020) and PARST (Nardelli, 1995). Anisotropic refinement was performed for all non-hydrogen atoms. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.02856 (6) | 0.28689 (14) | 0.08155 (5) | 0.0212 (2) | |
O2 | −0.04829 (6) | 0.08374 (13) | 0.11713 (4) | 0.0183 (2) | |
O3 | 0.19561 (6) | −0.43566 (13) | 0.02354 (4) | 0.0159 (2) | |
F1 | 0.42399 (6) | 0.14688 (16) | 0.28731 (4) | 0.0366 (3) | |
N1 | 0.09065 (7) | −0.34590 (17) | 0.06405 (5) | 0.0128 (2) | |
H1A | 0.0744 (10) | −0.464 (3) | 0.0647 (7) | 0.020 (4)* | |
N2 | 0.17380 (7) | −0.12694 (16) | 0.03515 (5) | 0.0126 (2) | |
H2A | 0.2153 (11) | −0.100 (2) | 0.0197 (8) | 0.022 (4)* | |
C1 | 0.27321 (9) | 0.2129 (2) | 0.13482 (6) | 0.0173 (3) | |
H1 | 0.263082 | 0.297493 | 0.101788 | 0.021* | |
C2 | 0.34316 (9) | 0.2433 (2) | 0.18837 (7) | 0.0229 (3) | |
H2 | 0.381219 | 0.346839 | 0.192147 | 0.027* | |
C3 | 0.35521 (9) | 0.1195 (2) | 0.23523 (6) | 0.0233 (3) | |
C4 | 0.30157 (9) | −0.0309 (2) | 0.23263 (6) | 0.0231 (3) | |
H4 | 0.311358 | −0.112770 | 0.266334 | 0.028* | |
C5 | 0.23225 (9) | −0.0593 (2) | 0.17878 (6) | 0.0190 (3) | |
H5 | 0.193881 | −0.161917 | 0.175722 | 0.023* | |
C6 | 0.21849 (8) | 0.06081 (19) | 0.12938 (5) | 0.0129 (3) | |
C7 | 0.14667 (8) | 0.02117 (18) | 0.06901 (5) | 0.0112 (2) | |
H7 | 0.136980 | 0.136887 | 0.043813 | 0.013* | |
C8 | 0.15738 (8) | −0.30750 (19) | 0.04046 (5) | 0.0125 (3) | |
C9 | 0.03494 (8) | −0.21130 (18) | 0.07407 (5) | 0.0117 (3) | |
C10 | −0.04937 (8) | −0.28875 (19) | 0.07810 (6) | 0.0140 (3) | |
H10A | −0.039157 | −0.343228 | 0.118554 | 0.021* | |
H10B | −0.071249 | −0.384804 | 0.046890 | 0.021* | |
H10C | −0.092884 | −0.188923 | 0.071487 | 0.021* | |
C11 | 0.06014 (8) | −0.03197 (19) | 0.07743 (5) | 0.0115 (3) | |
C12 | 0.01232 (8) | 0.12709 (19) | 0.09088 (6) | 0.0131 (3) | |
C13 | −0.09595 (10) | 0.2391 (2) | 0.13041 (7) | 0.0243 (3) | |
H13A | −0.055451 | 0.318714 | 0.161158 | 0.036* | |
H13B | −0.141964 | 0.193158 | 0.145987 | 0.036* | |
H13C | −0.122776 | 0.310988 | 0.093100 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0216 (5) | 0.0117 (5) | 0.0346 (6) | 0.0002 (4) | 0.0152 (4) | 0.0019 (4) |
O2 | 0.0205 (5) | 0.0130 (5) | 0.0274 (5) | 0.0022 (4) | 0.0160 (4) | 0.0009 (4) |
O3 | 0.0169 (4) | 0.0130 (5) | 0.0209 (5) | 0.0000 (4) | 0.0102 (4) | −0.0027 (4) |
F1 | 0.0219 (4) | 0.0623 (7) | 0.0188 (4) | −0.0054 (5) | −0.0030 (3) | −0.0114 (4) |
N1 | 0.0142 (5) | 0.0089 (6) | 0.0180 (5) | −0.0015 (4) | 0.0089 (4) | −0.0003 (4) |
N2 | 0.0137 (5) | 0.0124 (6) | 0.0144 (5) | −0.0024 (4) | 0.0085 (4) | −0.0021 (4) |
C1 | 0.0168 (6) | 0.0183 (7) | 0.0182 (6) | −0.0034 (5) | 0.0075 (5) | −0.0031 (5) |
C2 | 0.0171 (6) | 0.0280 (8) | 0.0236 (7) | −0.0090 (6) | 0.0066 (5) | −0.0096 (6) |
C3 | 0.0142 (6) | 0.0389 (10) | 0.0151 (6) | −0.0009 (6) | 0.0022 (5) | −0.0107 (6) |
C4 | 0.0223 (7) | 0.0319 (9) | 0.0141 (6) | 0.0031 (6) | 0.0043 (5) | 0.0021 (6) |
C5 | 0.0186 (6) | 0.0212 (8) | 0.0168 (6) | −0.0025 (6) | 0.0054 (5) | 0.0003 (6) |
C6 | 0.0115 (5) | 0.0154 (7) | 0.0128 (5) | 0.0010 (5) | 0.0052 (4) | −0.0023 (5) |
C7 | 0.0119 (5) | 0.0094 (6) | 0.0131 (5) | −0.0002 (5) | 0.0050 (4) | −0.0001 (5) |
C8 | 0.0115 (5) | 0.0146 (7) | 0.0110 (5) | −0.0014 (5) | 0.0033 (4) | −0.0014 (5) |
C9 | 0.0111 (5) | 0.0141 (7) | 0.0103 (5) | 0.0004 (5) | 0.0041 (4) | 0.0012 (5) |
C10 | 0.0125 (6) | 0.0130 (7) | 0.0176 (6) | −0.0016 (5) | 0.0063 (5) | 0.0003 (5) |
C11 | 0.0107 (5) | 0.0133 (7) | 0.0110 (5) | 0.0001 (5) | 0.0043 (4) | 0.0013 (5) |
C12 | 0.0115 (5) | 0.0139 (7) | 0.0139 (5) | −0.0003 (5) | 0.0041 (4) | 0.0005 (5) |
C13 | 0.0252 (7) | 0.0190 (8) | 0.0362 (8) | 0.0047 (6) | 0.0202 (6) | −0.0006 (6) |
O1—C12 | 1.2140 (17) | C4—C5 | 1.3943 (18) |
O2—C12 | 1.3422 (15) | C4—H4 | 0.9500 |
O2—C13 | 1.4441 (17) | C5—C6 | 1.3943 (19) |
O3—C8 | 1.2403 (16) | C5—H5 | 0.9500 |
F1—C3 | 1.3630 (15) | C6—C7 | 1.5265 (16) |
N1—C8 | 1.3809 (16) | C7—C11 | 1.5158 (17) |
N1—C9 | 1.3890 (17) | C7—H7 | 1.0000 |
N1—H1A | 0.891 (18) | C9—C11 | 1.3473 (19) |
N2—C8 | 1.3395 (18) | C9—C10 | 1.4970 (17) |
N2—C7 | 1.4709 (17) | C10—H10A | 0.9800 |
N2—H2A | 0.875 (17) | C10—H10B | 0.9800 |
C1—C6 | 1.3845 (19) | C10—H10C | 0.9800 |
C1—C2 | 1.3975 (19) | C11—C12 | 1.4676 (18) |
C1—H1 | 0.9500 | C13—H13A | 0.9800 |
C2—C3 | 1.370 (2) | C13—H13B | 0.9800 |
C2—H2 | 0.9500 | C13—H13C | 0.9800 |
C3—C4 | 1.373 (2) | ||
C12—O2—C13 | 115.48 (11) | N2—C7—H7 | 108.0 |
C8—N1—C9 | 123.55 (12) | C11—C7—H7 | 108.0 |
C8—N1—H1A | 117.9 (10) | C6—C7—H7 | 108.0 |
C9—N1—H1A | 117.0 (10) | O3—C8—N2 | 124.02 (11) |
C8—N2—C7 | 123.53 (11) | O3—C8—N1 | 120.31 (12) |
C8—N2—H2A | 116.7 (11) | N2—C8—N1 | 115.60 (11) |
C7—N2—H2A | 117.2 (11) | C11—C9—N1 | 118.64 (11) |
C6—C1—C2 | 120.71 (13) | C11—C9—C10 | 127.93 (12) |
C6—C1—H1 | 119.6 | N1—C9—C10 | 113.41 (11) |
C2—C1—H1 | 119.6 | C9—C10—H10A | 109.5 |
C3—C2—C1 | 118.00 (14) | C9—C10—H10B | 109.5 |
C3—C2—H2 | 121.0 | H10A—C10—H10B | 109.5 |
C1—C2—H2 | 121.0 | C9—C10—H10C | 109.5 |
F1—C3—C2 | 118.34 (14) | H10A—C10—H10C | 109.5 |
F1—C3—C4 | 118.16 (14) | H10B—C10—H10C | 109.5 |
C2—C3—C4 | 123.50 (13) | C9—C11—C12 | 126.21 (11) |
C3—C4—C5 | 117.68 (13) | C9—C11—C7 | 120.39 (11) |
C3—C4—H4 | 121.2 | C12—C11—C7 | 113.38 (11) |
C5—C4—H4 | 121.2 | O1—C12—O2 | 122.04 (12) |
C6—C5—C4 | 120.87 (13) | O1—C12—C11 | 122.90 (11) |
C6—C5—H5 | 119.6 | O2—C12—C11 | 114.99 (11) |
C4—C5—H5 | 119.6 | O2—C13—H13A | 109.5 |
C1—C6—C5 | 119.20 (12) | O2—C13—H13B | 109.5 |
C1—C6—C7 | 120.13 (11) | H13A—C13—H13B | 109.5 |
C5—C6—C7 | 120.61 (12) | O2—C13—H13C | 109.5 |
N2—C7—C11 | 109.21 (10) | H13A—C13—H13C | 109.5 |
N2—C7—C6 | 110.93 (10) | H13B—C13—H13C | 109.5 |
C11—C7—C6 | 112.58 (10) | ||
C6—C1—C2—C3 | −0.6 (2) | C9—N1—C8—O3 | −168.46 (11) |
C1—C2—C3—F1 | 179.16 (12) | C9—N1—C8—N2 | 8.77 (17) |
C1—C2—C3—C4 | −1.0 (2) | C8—N1—C9—C11 | −19.04 (18) |
F1—C3—C4—C5 | −179.00 (13) | C8—N1—C9—C10 | 159.33 (11) |
C2—C3—C4—C5 | 1.1 (2) | N1—C9—C11—C12 | −176.58 (11) |
C3—C4—C5—C6 | 0.3 (2) | C10—C9—C11—C12 | 5.3 (2) |
C2—C1—C6—C5 | 2.0 (2) | N1—C9—C11—C7 | 1.35 (17) |
C2—C1—C6—C7 | −175.37 (12) | C10—C9—C11—C7 | −176.76 (11) |
C4—C5—C6—C1 | −1.8 (2) | N2—C7—C11—C9 | 21.92 (15) |
C4—C5—C6—C7 | 175.52 (12) | C6—C7—C11—C9 | −101.77 (13) |
C8—N2—C7—C11 | −33.69 (16) | N2—C7—C11—C12 | −159.91 (10) |
C8—N2—C7—C6 | 90.96 (14) | C6—C7—C11—C12 | 76.41 (13) |
C1—C6—C7—N2 | 100.88 (14) | C13—O2—C12—O1 | 3.22 (18) |
C5—C6—C7—N2 | −76.42 (15) | C13—O2—C12—C11 | −179.83 (11) |
C1—C6—C7—C11 | −136.40 (13) | C9—C11—C12—O1 | −164.90 (13) |
C5—C6—C7—C11 | 46.31 (16) | C7—C11—C12—O1 | 17.05 (17) |
C7—N2—C8—O3 | −163.16 (11) | C9—C11—C12—O2 | 18.17 (18) |
C7—N2—C8—N1 | 19.72 (17) | C7—C11—C12—O2 | −159.88 (10) |
4C13H13FN2O3·CCl4 | F(000) = 1252 |
Mr = 1210.82 | Dx = 1.508 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
a = 16.2070 (7) Å | Cell parameters from 4823 reflections |
b = 9.1642 (4) Å | θ = 2.5–28.6° |
c = 17.9630 (7) Å | µ = 0.31 mm−1 |
β = 91.607 (2)° | T = 100 K |
V = 2666.89 (19) Å3 | Block, colourless |
Z = 2 | 0.45 × 0.33 × 0.23 mm |
Bruker APEXII CCD diffractometer | 3571 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.051 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.0°, θmin = 1.7° |
Tmin = 0.586, Tmax = 0.746 | h = −16→19 |
20706 measured reflections | k = −10→10 |
4601 independent reflections | l = −19→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.242 | w = 1/[σ2(Fo2) + (0.1858P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4601 reflections | Δρmax = 0.56 e Å−3 |
408 parameters | Δρmin = −0.57 e Å−3 |
22 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. SCXRD data of all single crystals of (I) were collected on a Bruker AXS SMART APEX CCD diffractometer using Mo Kα radiation (λ = 0.71073 Å) at 100 (2) K. Unit cell measurement, data collection, integration, scaling and absorption correction were performed using Bruker Apex II software and SAINT suite of programs were used for data reduction (Bruker, 2012). Scaling and absorption correction was performed using SADABAS software (Bruker, 2001). Crystal structures were solved using direct methods by SIR 2014 program (Burla et al., 2015) and refined using full matrix least squares method by SHELXL 2014 (Sheldrick, 2015) embedded in the WinGX program suite (Version 2014.1). Geometrical calculations were performed using PLATON (Spek, 2020) and PARST (Nardelli, 1995). Anisotropic refinement was performed for all non-hydrogen atoms. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F1 | 0.94589 (12) | 0.7597 (2) | 0.67373 (11) | 0.0330 (5) | |
F2 | 0.39469 (13) | 0.6525 (2) | 0.01540 (11) | 0.0379 (6) | |
C27 | 1.2416 (9) | 0.9780 (7) | 0.2478 (8) | 0.041 (2) | 0.5 |
Cl1 | 1.17515 (17) | 0.9088 (3) | 0.31424 (12) | 0.0496 (6) | 0.5 |
Cl2 | 1.3229 (6) | 1.0678 (8) | 0.2941 (4) | 0.101 (3) | 0.5 |
Cl3 | 1.2793 (2) | 0.8335 (3) | 0.19447 (15) | 0.0682 (8) | 0.5 |
Cl4 | 1.1841 (4) | 1.0981 (5) | 0.1923 (3) | 0.0398 (8) | 0.5 |
O1 | 0.50525 (14) | 0.6145 (2) | 0.65445 (12) | 0.0231 (6) | |
O2 | 0.57460 (14) | 0.4038 (2) | 0.64479 (11) | 0.0192 (5) | |
O3 | 0.67518 (13) | 0.6295 (2) | 0.34185 (11) | 0.0176 (5) | |
O4 | 0.75358 (15) | 1.2304 (2) | 0.09794 (13) | 0.0278 (6) | |
O5 | 0.73355 (13) | 0.9987 (2) | 0.06299 (11) | 0.0186 (5) | |
O6 | 0.56208 (14) | 0.9660 (2) | 0.36331 (11) | 0.0196 (5) | |
N1 | 0.60477 (16) | 0.7117 (3) | 0.44123 (13) | 0.0136 (6) | |
H1A | 0.589 (2) | 0.779 (4) | 0.4184 (19) | 0.017 (9)* | |
N2 | 0.67468 (16) | 0.4950 (3) | 0.44849 (13) | 0.0144 (6) | |
H2A | 0.707 (2) | 0.431 (4) | 0.4249 (17) | 0.012 (8)* | |
N3 | 0.58642 (17) | 1.1304 (3) | 0.27159 (14) | 0.0158 (6) | |
H3A | 0.556 (2) | 1.190 (4) | 0.2983 (18) | 0.024 (9)* | |
N4 | 0.63691 (15) | 0.8970 (2) | 0.26442 (13) | 0.0130 (6) | |
H4A | 0.640 (2) | 0.813 (2) | 0.2853 (16) | 0.016* | |
C1 | 0.7662 (2) | 0.5328 (3) | 0.64108 (17) | 0.0219 (7) | |
H1 | 0.733166 | 0.465609 | 0.667369 | 0.026* | |
C2 | 0.8326 (2) | 0.5994 (4) | 0.67717 (17) | 0.0235 (8) | |
H2 | 0.845317 | 0.579132 | 0.728080 | 0.028* | |
C3 | 0.87968 (19) | 0.6950 (3) | 0.63805 (18) | 0.0218 (8) | |
C4 | 0.8638 (2) | 0.7285 (3) | 0.56485 (17) | 0.0193 (7) | |
H4 | 0.897354 | 0.795600 | 0.539095 | 0.023* | |
C5 | 0.79695 (19) | 0.6610 (3) | 0.52966 (16) | 0.0161 (7) | |
H5 | 0.784825 | 0.682481 | 0.478782 | 0.019* | |
C6 | 0.74721 (18) | 0.5632 (3) | 0.56640 (15) | 0.0139 (7) | |
C7 | 0.67088 (18) | 0.4953 (3) | 0.52939 (16) | 0.0142 (7) | |
H7 | 0.666652 | 0.391916 | 0.546685 | 0.017* | |
C8 | 0.65441 (19) | 0.6121 (3) | 0.40688 (16) | 0.0142 (7) | |
C9 | 0.56612 (18) | 0.6867 (3) | 0.50751 (15) | 0.0134 (7) | |
C10 | 0.4952 (2) | 0.7857 (3) | 0.52126 (17) | 0.0192 (7) | |
H10A | 0.478142 | 0.833938 | 0.474629 | 0.029* | |
H10B | 0.511875 | 0.859532 | 0.558193 | 0.029* | |
H10C | 0.448992 | 0.728843 | 0.540007 | 0.029* | |
C11 | 0.59344 (18) | 0.5765 (3) | 0.55241 (15) | 0.0129 (6) | |
C12 | 0.55275 (19) | 0.5389 (3) | 0.62081 (15) | 0.0150 (7) | |
C13 | 0.5341 (2) | 0.3521 (3) | 0.70969 (17) | 0.0231 (7) | |
H13A | 0.544531 | 0.247353 | 0.715802 | 0.035* | |
H13B | 0.474561 | 0.369020 | 0.703932 | 0.035* | |
H13C | 0.555542 | 0.404460 | 0.753688 | 0.035* | |
C14 | 0.5803 (2) | 0.6954 (3) | 0.12916 (15) | 0.0172 (7) | |
H14 | 0.622852 | 0.637081 | 0.151259 | 0.021* | |
C15 | 0.5164 (2) | 0.6292 (3) | 0.08882 (17) | 0.0255 (8) | |
H15 | 0.514218 | 0.526081 | 0.083460 | 0.031* | |
C16 | 0.4565 (2) | 0.7160 (3) | 0.05699 (17) | 0.0224 (8) | |
C17 | 0.4567 (2) | 0.8652 (4) | 0.06315 (18) | 0.0252 (8) | |
H17 | 0.414351 | 0.922365 | 0.040080 | 0.030* | |
C18 | 0.52112 (19) | 0.9305 (3) | 0.10436 (17) | 0.0188 (7) | |
H18 | 0.522443 | 1.033603 | 0.109570 | 0.023* | |
C19 | 0.58281 (18) | 0.8473 (3) | 0.13762 (15) | 0.0131 (6) | |
C20 | 0.65285 (19) | 0.9133 (3) | 0.18480 (15) | 0.0135 (6) | |
H20 | 0.704406 | 0.858123 | 0.174127 | 0.016* | |
C21 | 0.59323 (19) | 0.9927 (3) | 0.30282 (15) | 0.0140 (7) | |
C22 | 0.63275 (18) | 1.1757 (3) | 0.21263 (15) | 0.0141 (7) | |
C23 | 0.6360 (2) | 1.3381 (3) | 0.20318 (18) | 0.0214 (7) | |
H23A | 0.683940 | 1.377053 | 0.231040 | 0.032* | |
H23B | 0.585455 | 1.381690 | 0.222062 | 0.032* | |
H23C | 0.640621 | 1.361774 | 0.150257 | 0.032* | |
C24 | 0.66910 (18) | 1.0736 (3) | 0.16991 (15) | 0.0132 (6) | |
C25 | 0.72154 (18) | 1.1124 (3) | 0.10920 (16) | 0.0155 (7) | |
C26 | 0.7867 (2) | 1.0271 (4) | 0.00221 (17) | 0.0240 (8) | |
H26A | 0.791001 | 0.939168 | −0.028515 | 0.036* | |
H26B | 0.841668 | 1.054326 | 0.021730 | 0.036* | |
H26C | 0.763902 | 1.107084 | −0.028128 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0209 (11) | 0.0409 (12) | 0.0364 (11) | −0.0103 (9) | −0.0128 (9) | 0.0012 (9) |
F2 | 0.0371 (13) | 0.0349 (12) | 0.0408 (12) | −0.0214 (10) | −0.0149 (10) | −0.0064 (9) |
C27 | 0.050 (6) | 0.040 (3) | 0.033 (3) | 0.002 (7) | 0.004 (4) | −0.002 (8) |
Cl1 | 0.0594 (17) | 0.0571 (16) | 0.0326 (11) | −0.0251 (12) | 0.0036 (11) | 0.0006 (10) |
Cl2 | 0.090 (5) | 0.101 (5) | 0.110 (5) | −0.048 (4) | −0.022 (4) | 0.028 (3) |
Cl3 | 0.098 (3) | 0.0592 (17) | 0.0481 (14) | 0.0329 (17) | 0.0050 (15) | −0.0001 (13) |
Cl4 | 0.0452 (19) | 0.0354 (14) | 0.0382 (13) | 0.0088 (12) | −0.0120 (12) | −0.0167 (12) |
O1 | 0.0282 (14) | 0.0178 (12) | 0.0235 (12) | 0.0040 (10) | 0.0035 (10) | 0.0002 (9) |
O2 | 0.0220 (13) | 0.0145 (11) | 0.0211 (11) | 0.0010 (9) | 0.0012 (9) | 0.0068 (8) |
O3 | 0.0251 (13) | 0.0126 (11) | 0.0152 (11) | 0.0043 (9) | 0.0020 (9) | 0.0002 (8) |
O4 | 0.0321 (14) | 0.0115 (11) | 0.0402 (14) | −0.0077 (10) | 0.0095 (11) | 0.0025 (10) |
O5 | 0.0226 (13) | 0.0140 (11) | 0.0193 (11) | −0.0048 (9) | 0.0024 (9) | 0.0006 (8) |
O6 | 0.0317 (14) | 0.0126 (10) | 0.0146 (10) | 0.0065 (9) | 0.0018 (9) | 0.0018 (8) |
N1 | 0.0201 (15) | 0.0073 (12) | 0.0136 (12) | 0.0047 (10) | 0.0004 (10) | 0.0033 (10) |
N2 | 0.0209 (15) | 0.0075 (12) | 0.0148 (12) | 0.0039 (11) | −0.0011 (11) | −0.0012 (9) |
N3 | 0.0195 (15) | 0.0086 (12) | 0.0190 (13) | 0.0036 (11) | −0.0022 (11) | 0.0001 (10) |
N4 | 0.0165 (14) | 0.0061 (12) | 0.0162 (12) | 0.0007 (10) | −0.0011 (10) | 0.0035 (9) |
C1 | 0.0213 (18) | 0.0234 (17) | 0.0208 (15) | 0.0008 (13) | −0.0012 (13) | 0.0066 (13) |
C2 | 0.0212 (18) | 0.0301 (18) | 0.0190 (15) | −0.0014 (14) | −0.0050 (13) | 0.0055 (13) |
C3 | 0.0144 (17) | 0.0206 (17) | 0.0300 (17) | −0.0003 (13) | −0.0085 (14) | −0.0019 (13) |
C4 | 0.0170 (17) | 0.0139 (15) | 0.0270 (16) | 0.0008 (12) | 0.0039 (13) | 0.0029 (12) |
C5 | 0.0186 (17) | 0.0129 (15) | 0.0168 (15) | 0.0036 (12) | −0.0011 (12) | 0.0033 (11) |
C6 | 0.0140 (16) | 0.0104 (14) | 0.0172 (14) | 0.0075 (12) | −0.0019 (12) | −0.0009 (11) |
C7 | 0.0165 (17) | 0.0084 (14) | 0.0175 (14) | −0.0014 (11) | −0.0015 (12) | 0.0018 (11) |
C8 | 0.0179 (16) | 0.0075 (14) | 0.0167 (15) | −0.0007 (11) | −0.0051 (12) | −0.0018 (11) |
C9 | 0.0153 (16) | 0.0101 (14) | 0.0148 (14) | −0.0038 (12) | −0.0021 (12) | −0.0028 (11) |
C10 | 0.0237 (18) | 0.0148 (15) | 0.0193 (15) | 0.0064 (13) | 0.0007 (13) | 0.0013 (12) |
C11 | 0.0170 (16) | 0.0054 (13) | 0.0161 (14) | −0.0014 (11) | −0.0033 (12) | −0.0003 (11) |
C12 | 0.0160 (16) | 0.0114 (14) | 0.0173 (14) | −0.0020 (12) | −0.0045 (12) | 0.0001 (12) |
C13 | 0.0263 (19) | 0.0213 (17) | 0.0215 (16) | −0.0041 (14) | 0.0004 (14) | 0.0084 (13) |
C14 | 0.0239 (18) | 0.0119 (15) | 0.0159 (14) | −0.0021 (12) | 0.0004 (13) | 0.0016 (11) |
C15 | 0.041 (2) | 0.0121 (16) | 0.0228 (16) | −0.0098 (14) | −0.0019 (15) | −0.0021 (12) |
C16 | 0.0210 (18) | 0.0236 (18) | 0.0222 (16) | −0.0118 (14) | −0.0033 (14) | −0.0047 (13) |
C17 | 0.0173 (18) | 0.0243 (18) | 0.0334 (18) | −0.0017 (14) | −0.0103 (14) | 0.0002 (14) |
C18 | 0.0170 (17) | 0.0110 (15) | 0.0283 (16) | −0.0006 (12) | −0.0034 (13) | −0.0033 (12) |
C19 | 0.0164 (16) | 0.0094 (14) | 0.0136 (14) | −0.0038 (12) | 0.0030 (11) | 0.0000 (11) |
C20 | 0.0146 (16) | 0.0085 (14) | 0.0171 (14) | 0.0005 (11) | −0.0019 (12) | 0.0017 (11) |
C21 | 0.0181 (16) | 0.0086 (14) | 0.0147 (14) | −0.0001 (12) | −0.0070 (12) | 0.0007 (11) |
C22 | 0.0133 (16) | 0.0094 (14) | 0.0191 (15) | −0.0001 (11) | −0.0070 (12) | 0.0025 (11) |
C23 | 0.0253 (19) | 0.0071 (15) | 0.0315 (17) | 0.0006 (12) | −0.0054 (14) | 0.0021 (12) |
C24 | 0.0129 (15) | 0.0080 (14) | 0.0184 (14) | −0.0030 (11) | −0.0056 (12) | 0.0022 (11) |
C25 | 0.0127 (16) | 0.0103 (15) | 0.0233 (16) | −0.0027 (12) | −0.0040 (12) | 0.0039 (12) |
C26 | 0.0252 (19) | 0.0261 (18) | 0.0210 (16) | −0.0034 (14) | 0.0015 (13) | 0.0033 (13) |
F1—C3 | 1.369 (3) | C5—H5 | 0.9500 |
F2—C16 | 1.364 (3) | C6—C7 | 1.521 (4) |
C27—Cl4 | 1.738 (11) | C7—C11 | 1.526 (4) |
C27—Cl2 | 1.744 (12) | C7—H7 | 1.0000 |
C27—Cl1 | 1.749 (12) | C9—C11 | 1.359 (4) |
C27—Cl3 | 1.754 (10) | C9—C10 | 1.490 (4) |
O1—C12 | 1.209 (4) | C10—H10A | 0.9800 |
O2—C12 | 1.355 (3) | C10—H10B | 0.9800 |
O2—C13 | 1.435 (4) | C10—H10C | 0.9800 |
O3—C8 | 1.235 (4) | C11—C12 | 1.452 (4) |
O4—C25 | 1.219 (4) | C13—H13A | 0.9800 |
O5—C25 | 1.350 (4) | C13—H13B | 0.9800 |
O5—C26 | 1.434 (4) | C13—H13C | 0.9800 |
O6—C21 | 1.235 (4) | C14—C15 | 1.387 (4) |
N1—C8 | 1.374 (4) | C14—C19 | 1.401 (4) |
N1—C9 | 1.380 (4) | C14—H14 | 0.9500 |
N1—H1A | 0.78 (3) | C15—C16 | 1.367 (5) |
N2—C8 | 1.343 (4) | C15—H15 | 0.9500 |
N2—C7 | 1.456 (4) | C16—C17 | 1.372 (5) |
N2—H2A | 0.90 (4) | C17—C18 | 1.397 (4) |
N3—C22 | 1.379 (4) | C17—H17 | 0.9500 |
N3—C21 | 1.385 (4) | C18—C19 | 1.380 (4) |
N3—H3A | 0.88 (4) | C18—H18 | 0.9500 |
N4—C21 | 1.332 (4) | C19—C20 | 1.523 (4) |
N4—C20 | 1.468 (4) | C20—C24 | 1.517 (4) |
N4—H4A | 0.856 (18) | C20—H20 | 1.0000 |
C1—C2 | 1.383 (4) | C22—C24 | 1.355 (4) |
C1—C6 | 1.396 (4) | C22—C23 | 1.499 (4) |
C1—H1 | 0.9500 | C23—H23A | 0.9800 |
C2—C3 | 1.369 (5) | C23—H23B | 0.9800 |
C2—H2 | 0.9500 | C23—H23C | 0.9800 |
C3—C4 | 1.368 (4) | C24—C25 | 1.446 (4) |
C4—C5 | 1.384 (4) | C26—H26A | 0.9800 |
C4—H4 | 0.9500 | C26—H26B | 0.9800 |
C5—C6 | 1.385 (4) | C26—H26C | 0.9800 |
Cl4—C27—Cl2 | 111.1 (4) | C12—C11—C7 | 120.7 (2) |
Cl4—C27—Cl1 | 106.9 (7) | O1—C12—O2 | 121.9 (3) |
Cl2—C27—Cl1 | 108.5 (8) | O1—C12—C11 | 126.7 (3) |
Cl4—C27—Cl3 | 110.7 (8) | O2—C12—C11 | 111.4 (3) |
Cl2—C27—Cl3 | 110.3 (8) | O2—C13—H13A | 109.5 |
Cl1—C27—Cl3 | 109.2 (4) | O2—C13—H13B | 109.5 |
C12—O2—C13 | 116.0 (2) | H13A—C13—H13B | 109.5 |
C25—O5—C26 | 115.4 (2) | O2—C13—H13C | 109.5 |
C8—N1—C9 | 124.3 (3) | H13A—C13—H13C | 109.5 |
C8—N1—H1A | 118 (3) | H13B—C13—H13C | 109.5 |
C9—N1—H1A | 116 (3) | C15—C14—C19 | 120.7 (3) |
C8—N2—C7 | 122.5 (2) | C15—C14—H14 | 119.7 |
C8—N2—H2A | 113.2 (19) | C19—C14—H14 | 119.7 |
C7—N2—H2A | 120.9 (19) | C16—C15—C14 | 118.3 (3) |
C22—N3—C21 | 123.1 (3) | C16—C15—H15 | 120.8 |
C22—N3—H3A | 123 (2) | C14—C15—H15 | 120.8 |
C21—N3—H3A | 113 (2) | F2—C16—C15 | 118.9 (3) |
C21—N4—C20 | 123.2 (2) | F2—C16—C17 | 118.0 (3) |
C21—N4—H4A | 113 (2) | C15—C16—C17 | 123.1 (3) |
C20—N4—H4A | 121 (2) | C16—C17—C18 | 118.0 (3) |
C2—C1—C6 | 120.7 (3) | C16—C17—H17 | 121.0 |
C2—C1—H1 | 119.7 | C18—C17—H17 | 121.0 |
C6—C1—H1 | 119.7 | C19—C18—C17 | 120.9 (3) |
C3—C2—C1 | 118.7 (3) | C19—C18—H18 | 119.5 |
C3—C2—H2 | 120.7 | C17—C18—H18 | 119.5 |
C1—C2—H2 | 120.7 | C18—C19—C14 | 118.9 (3) |
C4—C3—C2 | 123.0 (3) | C18—C19—C20 | 122.8 (2) |
C4—C3—F1 | 118.5 (3) | C14—C19—C20 | 118.3 (3) |
C2—C3—F1 | 118.5 (3) | N4—C20—C24 | 107.9 (2) |
C3—C4—C5 | 117.6 (3) | N4—C20—C19 | 110.7 (2) |
C3—C4—H4 | 121.2 | C24—C20—C19 | 114.6 (2) |
C5—C4—H4 | 121.2 | N4—C20—H20 | 107.8 |
C4—C5—C6 | 122.0 (3) | C24—C20—H20 | 107.8 |
C4—C5—H5 | 119.0 | C19—C20—H20 | 107.8 |
C6—C5—H5 | 119.0 | O6—C21—N4 | 124.2 (3) |
C5—C6—C1 | 118.1 (3) | O6—C21—N3 | 120.4 (3) |
C5—C6—C7 | 122.2 (2) | N4—C21—N3 | 115.3 (3) |
C1—C6—C7 | 119.5 (3) | C24—C22—N3 | 118.8 (3) |
N2—C7—C6 | 112.3 (2) | C24—C22—C23 | 127.2 (3) |
N2—C7—C11 | 109.2 (2) | N3—C22—C23 | 114.0 (3) |
C6—C7—C11 | 110.3 (2) | C22—C23—H23A | 109.5 |
N2—C7—H7 | 108.3 | C22—C23—H23B | 109.5 |
C6—C7—H7 | 108.3 | H23A—C23—H23B | 109.5 |
C11—C7—H7 | 108.3 | C22—C23—H23C | 109.5 |
O3—C8—N2 | 124.1 (3) | H23A—C23—H23C | 109.5 |
O3—C8—N1 | 121.2 (3) | H23B—C23—H23C | 109.5 |
N2—C8—N1 | 114.7 (3) | C22—C24—C25 | 122.1 (3) |
C11—C9—N1 | 119.1 (3) | C22—C24—C20 | 119.2 (3) |
C11—C9—C10 | 126.5 (3) | C25—C24—C20 | 118.7 (3) |
N1—C9—C10 | 114.4 (2) | O4—C25—O5 | 120.9 (3) |
C9—C10—H10A | 109.5 | O4—C25—C24 | 127.3 (3) |
C9—C10—H10B | 109.5 | O5—C25—C24 | 111.8 (2) |
H10A—C10—H10B | 109.5 | O5—C26—H26A | 109.5 |
C9—C10—H10C | 109.5 | O5—C26—H26B | 109.5 |
H10A—C10—H10C | 109.5 | H26A—C26—H26B | 109.5 |
H10B—C10—H10C | 109.5 | O5—C26—H26C | 109.5 |
C9—C11—C12 | 122.0 (3) | H26A—C26—H26C | 109.5 |
C9—C11—C7 | 117.3 (3) | H26B—C26—H26C | 109.5 |
C6—C1—C2—C3 | −0.4 (5) | C19—C14—C15—C16 | 0.7 (5) |
C1—C2—C3—C4 | 0.4 (5) | C14—C15—C16—F2 | 178.1 (3) |
C1—C2—C3—F1 | −179.3 (3) | C14—C15—C16—C17 | −0.1 (5) |
C2—C3—C4—C5 | −0.2 (5) | F2—C16—C17—C18 | −178.6 (3) |
F1—C3—C4—C5 | 179.5 (3) | C15—C16—C17—C18 | −0.4 (5) |
C3—C4—C5—C6 | 0.1 (4) | C16—C17—C18—C19 | 0.2 (5) |
C4—C5—C6—C1 | −0.2 (4) | C17—C18—C19—C14 | 0.3 (5) |
C4—C5—C6—C7 | 176.4 (3) | C17—C18—C19—C20 | −178.3 (3) |
C2—C1—C6—C5 | 0.3 (5) | C15—C14—C19—C18 | −0.8 (5) |
C2—C1—C6—C7 | −176.4 (3) | C15—C14—C19—C20 | 177.8 (3) |
C8—N2—C7—C6 | −82.3 (3) | C21—N4—C20—C24 | 39.2 (4) |
C8—N2—C7—C11 | 40.4 (4) | C21—N4—C20—C19 | −86.9 (3) |
C5—C6—C7—N2 | 23.3 (4) | C18—C19—C20—N4 | 100.4 (3) |
C1—C6—C7—N2 | −160.1 (3) | C14—C19—C20—N4 | −78.2 (3) |
C5—C6—C7—C11 | −98.9 (3) | C18—C19—C20—C24 | −21.8 (4) |
C1—C6—C7—C11 | 77.7 (3) | C14—C19—C20—C24 | 159.5 (3) |
C7—N2—C8—O3 | 161.6 (3) | C20—N4—C21—O6 | 161.6 (3) |
C7—N2—C8—N1 | −21.0 (4) | C20—N4—C21—N3 | −20.5 (4) |
C9—N1—C8—O3 | 166.8 (3) | C22—N3—C21—O6 | 166.7 (3) |
C9—N1—C8—N2 | −10.7 (4) | C22—N3—C21—N4 | −11.2 (4) |
C8—N1—C9—C11 | 18.0 (4) | C21—N3—C22—C24 | 18.9 (4) |
C8—N1—C9—C10 | −160.6 (3) | C21—N3—C22—C23 | −161.6 (3) |
N1—C9—C11—C12 | −176.5 (2) | N3—C22—C24—C25 | −177.2 (2) |
C10—C9—C11—C12 | 2.0 (4) | C23—C22—C24—C25 | 3.4 (4) |
N1—C9—C11—C7 | 5.3 (4) | N3—C22—C24—C20 | 4.3 (4) |
C10—C9—C11—C7 | −176.2 (3) | C23—C22—C24—C20 | −175.1 (3) |
N2—C7—C11—C9 | −30.9 (3) | N4—C20—C24—C22 | −29.6 (3) |
C6—C7—C11—C9 | 93.0 (3) | C19—C20—C24—C22 | 94.1 (3) |
N2—C7—C11—C12 | 150.8 (2) | N4—C20—C24—C25 | 151.8 (2) |
C6—C7—C11—C12 | −85.2 (3) | C19—C20—C24—C25 | −84.4 (3) |
C13—O2—C12—O1 | 3.8 (4) | C26—O5—C25—O4 | 1.0 (4) |
C13—O2—C12—C11 | −176.4 (2) | C26—O5—C25—C24 | −178.4 (2) |
C9—C11—C12—O1 | −17.8 (4) | C22—C24—C25—O4 | 16.5 (5) |
C7—C11—C12—O1 | 160.3 (3) | C20—C24—C25—O4 | −165.0 (3) |
C9—C11—C12—O2 | 162.4 (2) | C22—C24—C25—O5 | −164.0 (2) |
C7—C11—C12—O2 | −19.4 (3) | C20—C24—C25—O5 | 14.5 (3) |
C13H13FN2O3·0.5C4H8O2 | Z = 2 |
Mr = 308.30 | F(000) = 324 |
Triclinic, P1 | Dx = 1.400 Mg m−3 |
a = 7.3353 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9091 (2) Å | Cell parameters from 3724 reflections |
c = 12.5006 (4) Å | θ = 2.5–28.7° |
α = 82.389 (2)° | µ = 0.11 mm−1 |
β = 79.380 (2)° | T = 100 K |
γ = 65.898 (2)° | Rod, colourless |
V = 731.44 (4) Å3 | 0.43 × 0.36 × 0.27 mm |
Bruker APEXII CCD diffractometer | 2647 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.034 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 27.9°, θmin = 1.7° |
Tmin = 0.706, Tmax = 0.746 | h = −9→9 |
14325 measured reflections | k = −11→11 |
3475 independent reflections | l = −16→16 |
Refinement on F2 | 118 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.061P)2 + 0.449P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3475 reflections | Δρmax = 0.65 e Å−3 |
238 parameters | Δρmin = −0.34 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. SCXRD data of all single crystals of (I) were collected on a Bruker AXS SMART APEX CCD diffractometer using Mo Kα radiation (λ = 0.71073 Å) at 100 (2) K. Unit cell measurement, data collection, integration, scaling and absorption correction were performed using Bruker Apex II software and SAINT suite of programs were used for data reduction (Bruker, 2012). Scaling and absorption correction was performed using SADABAS software (Bruker, 2001). Crystal structures were solved using direct methods by SIR 2014 program (Burla et al., 2015) and refined using full matrix least squares method by SHELXL 2014 (Sheldrick, 2015) embedded in the WinGX program suite (Version 2014.1). Geometrical calculations were performed using PLATON (Spek, 2020) and PARST (Nardelli, 1995). Anisotropic refinement was performed for all non-hydrogen atoms. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F1 | 0.71212 (18) | −0.00939 (16) | −0.00525 (9) | 0.0395 (3) | |
O2 | 0.37279 (18) | 0.71184 (14) | 0.29141 (11) | 0.0255 (3) | |
O1 | 0.25071 (18) | 0.52266 (15) | 0.36519 (11) | 0.0257 (3) | |
O3 | 1.12712 (17) | 0.13882 (14) | 0.46283 (10) | 0.0221 (3) | |
N1 | 0.9368 (2) | 0.38577 (17) | 0.38433 (12) | 0.0200 (3) | |
H1A | 1.033 (4) | 0.413 (3) | 0.3854 (18) | 0.033 (6)* | |
N2 | 0.8049 (2) | 0.18943 (17) | 0.44248 (12) | 0.0199 (3) | |
H2A | 0.828 (3) | 0.088 (3) | 0.4704 (17) | 0.029 (5)* | |
C1 | 0.7875 (3) | 0.2155 (2) | 0.18991 (15) | 0.0253 (4) | |
H1 | 0.865664 | 0.276590 | 0.194367 | 0.030* | |
C2 | 0.8095 (3) | 0.1448 (2) | 0.09401 (16) | 0.0283 (4) | |
H2 | 0.901582 | 0.156310 | 0.032471 | 0.034* | |
C3 | 0.6944 (3) | 0.0573 (2) | 0.09024 (15) | 0.0272 (4) | |
C4 | 0.5615 (3) | 0.0362 (2) | 0.17711 (16) | 0.0299 (4) | |
H4 | 0.485602 | −0.026428 | 0.171991 | 0.036* | |
C5 | 0.5402 (3) | 0.1084 (2) | 0.27287 (15) | 0.0245 (4) | |
H5 | 0.447920 | 0.095876 | 0.333925 | 0.029* | |
C6 | 0.6525 (2) | 0.19882 (19) | 0.28032 (14) | 0.0192 (3) | |
C7 | 0.6294 (2) | 0.27781 (19) | 0.38548 (14) | 0.0177 (3) | |
H7 | 0.507910 | 0.271437 | 0.434183 | 0.021* | |
C8 | 0.9645 (2) | 0.2302 (2) | 0.43101 (13) | 0.0187 (3) | |
C9 | 0.7506 (2) | 0.5048 (2) | 0.36381 (14) | 0.0196 (4) | |
C10 | 0.7483 (3) | 0.6749 (2) | 0.34535 (16) | 0.0258 (4) | |
H10A | 0.804397 | 0.692116 | 0.269541 | 0.039* | |
H10B | 0.829798 | 0.688143 | 0.394445 | 0.039* | |
H10C | 0.609107 | 0.755813 | 0.359969 | 0.039* | |
C11 | 0.5968 (2) | 0.45782 (19) | 0.36440 (13) | 0.0178 (3) | |
C12 | 0.3918 (2) | 0.5651 (2) | 0.34235 (14) | 0.0197 (3) | |
C13 | 0.1708 (3) | 0.8203 (2) | 0.27048 (18) | 0.0324 (5) | |
H13A | 0.126618 | 0.769881 | 0.220773 | 0.049* | |
H13B | 0.171257 | 0.926174 | 0.237192 | 0.049* | |
H13C | 0.078133 | 0.838225 | 0.339317 | 0.049* | |
O4 | 1.0043 (7) | 0.3710 (6) | −0.0909 (4) | 0.0739 (11) | 0.5 |
O5 | 1.0156 (9) | 0.5286 (9) | 0.0250 (7) | 0.0752 (13) | 0.5 |
C14 | 0.7037 (14) | 0.6047 (12) | −0.0313 (11) | 0.101 (2) | 0.5 |
H14A | 0.672799 | 0.670807 | −0.099785 | 0.152* | 0.5 |
H14B | 0.677212 | 0.677588 | 0.026965 | 0.152* | 0.5 |
H14C | 0.618647 | 0.541383 | −0.012401 | 0.152* | 0.5 |
C15 | 0.9215 (17) | 0.4887 (15) | −0.0446 (11) | 0.0760 (15) | 0.5 |
C16 | 1.2183 (13) | 0.4257 (11) | 0.0214 (9) | 0.0803 (15) | 0.5 |
H16A | 1.290889 | 0.431253 | −0.053141 | 0.096* | 0.5 |
H16B | 1.233320 | 0.310345 | 0.041144 | 0.096* | 0.5 |
C17 | 1.3007 (11) | 0.4794 (8) | 0.0976 (7) | 0.0792 (17) | 0.5 |
H17A | 1.272184 | 0.596988 | 0.082200 | 0.119* | 0.5 |
H17B | 1.447050 | 0.416554 | 0.090528 | 0.119* | 0.5 |
H17C | 1.239131 | 0.461259 | 0.172016 | 0.119* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0383 (7) | 0.0549 (8) | 0.0311 (6) | −0.0213 (6) | −0.0024 (5) | −0.0157 (6) |
O2 | 0.0149 (6) | 0.0179 (6) | 0.0404 (7) | −0.0053 (5) | −0.0059 (5) | 0.0081 (5) |
O1 | 0.0163 (6) | 0.0201 (6) | 0.0419 (8) | −0.0090 (5) | −0.0070 (5) | 0.0032 (5) |
O3 | 0.0171 (6) | 0.0187 (6) | 0.0301 (7) | −0.0061 (5) | −0.0079 (5) | 0.0033 (5) |
N1 | 0.0145 (7) | 0.0171 (7) | 0.0302 (8) | −0.0081 (6) | −0.0061 (6) | 0.0026 (6) |
N2 | 0.0180 (7) | 0.0149 (7) | 0.0282 (8) | −0.0076 (5) | −0.0085 (6) | 0.0041 (6) |
C1 | 0.0214 (9) | 0.0241 (9) | 0.0320 (10) | −0.0112 (7) | −0.0004 (7) | −0.0044 (7) |
C2 | 0.0231 (9) | 0.0304 (9) | 0.0292 (10) | −0.0104 (8) | 0.0019 (7) | −0.0031 (8) |
C3 | 0.0258 (9) | 0.0294 (9) | 0.0260 (9) | −0.0084 (8) | −0.0047 (7) | −0.0072 (7) |
C4 | 0.0308 (10) | 0.0355 (10) | 0.0314 (10) | −0.0206 (8) | −0.0052 (8) | −0.0036 (8) |
C5 | 0.0253 (9) | 0.0276 (9) | 0.0248 (9) | −0.0155 (7) | −0.0043 (7) | 0.0020 (7) |
C6 | 0.0162 (8) | 0.0149 (7) | 0.0253 (8) | −0.0046 (6) | −0.0058 (6) | 0.0014 (6) |
C7 | 0.0133 (7) | 0.0155 (7) | 0.0243 (8) | −0.0057 (6) | −0.0042 (6) | 0.0007 (6) |
C8 | 0.0170 (8) | 0.0171 (7) | 0.0216 (8) | −0.0064 (6) | −0.0027 (6) | −0.0015 (6) |
C9 | 0.0165 (8) | 0.0155 (7) | 0.0257 (9) | −0.0053 (6) | −0.0037 (7) | 0.0010 (6) |
C10 | 0.0203 (9) | 0.0167 (8) | 0.0416 (11) | −0.0081 (7) | −0.0081 (8) | 0.0021 (7) |
C11 | 0.0150 (8) | 0.0145 (7) | 0.0228 (8) | −0.0051 (6) | −0.0027 (6) | 0.0003 (6) |
C12 | 0.0164 (8) | 0.0164 (8) | 0.0256 (8) | −0.0061 (6) | −0.0029 (7) | −0.0005 (6) |
C13 | 0.0167 (9) | 0.0235 (9) | 0.0502 (12) | −0.0042 (7) | −0.0078 (8) | 0.0128 (8) |
O4 | 0.072 (3) | 0.063 (2) | 0.095 (3) | −0.038 (2) | −0.005 (2) | −0.005 (2) |
O5 | 0.068 (3) | 0.042 (2) | 0.126 (3) | −0.025 (3) | −0.036 (3) | −0.002 (2) |
C14 | 0.086 (4) | 0.059 (4) | 0.155 (5) | −0.002 (3) | −0.067 (4) | −0.009 (4) |
C15 | 0.070 (4) | 0.044 (2) | 0.124 (3) | −0.027 (3) | −0.032 (3) | 0.000 (2) |
C16 | 0.071 (3) | 0.047 (3) | 0.128 (4) | −0.019 (3) | −0.038 (3) | −0.002 (3) |
C17 | 0.074 (4) | 0.053 (3) | 0.109 (4) | −0.014 (3) | −0.044 (3) | 0.008 (3) |
F1—C3 | 1.365 (2) | C7—H7 | 1.0000 |
O2—C12 | 1.340 (2) | C9—C11 | 1.352 (2) |
O2—C13 | 1.451 (2) | C9—C10 | 1.496 (2) |
O1—C12 | 1.216 (2) | C10—H10A | 0.9800 |
O3—C8 | 1.2410 (19) | C10—H10B | 0.9800 |
N1—C8 | 1.379 (2) | C10—H10C | 0.9800 |
N1—C9 | 1.389 (2) | C11—C12 | 1.470 (2) |
N1—H1A | 0.84 (2) | C13—H13A | 0.9800 |
N2—C8 | 1.340 (2) | C13—H13B | 0.9800 |
N2—C7 | 1.465 (2) | C13—H13C | 0.9800 |
N2—H2A | 0.88 (2) | O4—C15 | 1.147 (14) |
C1—C2 | 1.380 (3) | O5—C15 | 1.364 (9) |
C1—C6 | 1.394 (2) | O5—C16 | 1.388 (10) |
C1—H1 | 0.9500 | C14—C15 | 1.499 (12) |
C2—C3 | 1.373 (3) | C14—H14A | 0.9800 |
C2—H2 | 0.9500 | C14—H14B | 0.9800 |
C3—C4 | 1.367 (3) | C14—H14C | 0.9800 |
C4—C5 | 1.387 (3) | C16—C17 | 1.439 (12) |
C4—H4 | 0.9500 | C16—H16A | 0.9900 |
C5—C6 | 1.387 (2) | C16—H16B | 0.9900 |
C5—H5 | 0.9500 | C17—H17A | 0.9800 |
C6—C7 | 1.522 (2) | C17—H17B | 0.9800 |
C7—C11 | 1.516 (2) | C17—H17C | 0.9800 |
C12—O2—C13 | 115.75 (13) | H10A—C10—H10B | 109.5 |
C8—N1—C9 | 123.70 (14) | C9—C10—H10C | 109.5 |
C8—N1—H1A | 114.2 (15) | H10A—C10—H10C | 109.5 |
C9—N1—H1A | 119.9 (15) | H10B—C10—H10C | 109.5 |
C8—N2—C7 | 124.17 (14) | C9—C11—C12 | 126.50 (15) |
C8—N2—H2A | 114.0 (14) | C9—C11—C7 | 120.20 (14) |
C7—N2—H2A | 119.3 (14) | C12—C11—C7 | 113.27 (14) |
C2—C1—C6 | 121.10 (17) | O1—C12—O2 | 122.16 (15) |
C2—C1—H1 | 119.4 | O1—C12—C11 | 122.79 (15) |
C6—C1—H1 | 119.4 | O2—C12—C11 | 115.01 (14) |
C3—C2—C1 | 118.00 (17) | O2—C13—H13A | 109.5 |
C3—C2—H2 | 121.0 | O2—C13—H13B | 109.5 |
C1—C2—H2 | 121.0 | H13A—C13—H13B | 109.5 |
F1—C3—C4 | 118.82 (17) | O2—C13—H13C | 109.5 |
F1—C3—C2 | 118.19 (17) | H13A—C13—H13C | 109.5 |
C4—C3—C2 | 122.99 (17) | H13B—C13—H13C | 109.5 |
C3—C4—C5 | 118.44 (17) | C15—O5—C16 | 113.2 (6) |
C3—C4—H4 | 120.8 | C15—C14—H14A | 109.5 |
C5—C4—H4 | 120.8 | C15—C14—H14B | 109.5 |
C6—C5—C4 | 120.63 (17) | H14A—C14—H14B | 109.5 |
C6—C5—H5 | 119.7 | C15—C14—H14C | 109.5 |
C4—C5—H5 | 119.7 | H14A—C14—H14C | 109.5 |
C5—C6—C1 | 118.83 (16) | H14B—C14—H14C | 109.5 |
C5—C6—C7 | 120.63 (15) | O4—C15—O5 | 120.3 (8) |
C1—C6—C7 | 120.54 (15) | O4—C15—C14 | 130.7 (8) |
N2—C7—C11 | 109.82 (13) | O5—C15—C14 | 108.3 (8) |
N2—C7—C6 | 111.24 (13) | O5—C16—C17 | 108.1 (7) |
C11—C7—C6 | 111.57 (13) | O5—C16—H16A | 110.1 |
N2—C7—H7 | 108.0 | C17—C16—H16A | 110.1 |
C11—C7—H7 | 108.0 | O5—C16—H16B | 110.1 |
C6—C7—H7 | 108.0 | C17—C16—H16B | 110.1 |
O3—C8—N2 | 123.59 (15) | H16A—C16—H16B | 108.4 |
O3—C8—N1 | 120.46 (15) | C16—C17—H17A | 109.5 |
N2—C8—N1 | 115.90 (14) | C16—C17—H17B | 109.5 |
C11—C9—N1 | 118.86 (14) | H17A—C17—H17B | 109.5 |
C11—C9—C10 | 128.14 (15) | C16—C17—H17C | 109.5 |
N1—C9—C10 | 112.99 (14) | H17A—C17—H17C | 109.5 |
C9—C10—H10A | 109.5 | H17B—C17—H17C | 109.5 |
C9—C10—H10B | 109.5 | ||
C6—C1—C2—C3 | 0.0 (3) | C8—N1—C9—C11 | −16.4 (3) |
C1—C2—C3—F1 | 178.43 (16) | C8—N1—C9—C10 | 162.49 (16) |
C1—C2—C3—C4 | −0.7 (3) | N1—C9—C11—C12 | −178.65 (16) |
F1—C3—C4—C5 | −178.17 (16) | C10—C9—C11—C12 | 2.6 (3) |
C2—C3—C4—C5 | 0.9 (3) | N1—C9—C11—C7 | −0.9 (2) |
C3—C4—C5—C6 | −0.5 (3) | C10—C9—C11—C7 | −179.65 (17) |
C4—C5—C6—C1 | −0.1 (3) | N2—C7—C11—C9 | 21.5 (2) |
C4—C5—C6—C7 | −179.88 (16) | C6—C7—C11—C9 | −102.35 (18) |
C2—C1—C6—C5 | 0.4 (3) | N2—C7—C11—C12 | −160.51 (14) |
C2—C1—C6—C7 | −179.86 (16) | C6—C7—C11—C12 | 75.67 (18) |
C8—N2—C7—C11 | −30.2 (2) | C13—O2—C12—O1 | 3.2 (3) |
C8—N2—C7—C6 | 93.77 (18) | C13—O2—C12—C11 | −179.11 (16) |
C5—C6—C7—N2 | 106.84 (17) | C9—C11—C12—O1 | −164.82 (18) |
C1—C6—C7—N2 | −72.89 (19) | C7—C11—C12—O1 | 17.3 (2) |
C5—C6—C7—C11 | −130.15 (16) | C9—C11—C12—O2 | 17.5 (3) |
C1—C6—C7—C11 | 50.1 (2) | C7—C11—C12—O2 | −160.38 (14) |
C7—N2—C8—O3 | −166.08 (16) | C16—O5—C15—O4 | 7.2 (12) |
C7—N2—C8—N1 | 16.3 (2) | C16—O5—C15—C14 | 178.5 (10) |
C9—N1—C8—O3 | −168.65 (16) | C15—O5—C16—C17 | −180.0 (6) |
C9—N1—C8—N2 | 9.1 (2) |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register