Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618008719/sk3693sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008719/sk36936csup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008719/sk36936dsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008719/sk36936esup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008719/sk36936csup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008719/sk36936dsup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008719/sk36936esup7.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618008719/sk3693sup8.pdf |
CCDC references: 1849175; 1849174; 1849173
For all structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (6c), (6e); SHELXT (Sheldrick, 2015a) for (6d). For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C19H17IN2O4 | F(000) = 920 |
Mr = 464.24 | Dx = 1.683 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.837 (1) Å | Cell parameters from 9773 reflections |
b = 20.056 (1) Å | θ = 3.2–33.1° |
c = 11.015 (1) Å | µ = 1.77 mm−1 |
β = 110.18 (1)° | T = 100 K |
V = 1832.4 (3) Å3 | Block, colourless |
Z = 4 | 0.42 × 0.20 × 0.16 mm |
Bruker APEXII CCD diffractometer | 4994 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.029 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 30.5°, θmin = 2.8° |
Tmin = 0.627, Tmax = 0.747 | h = −12→12 |
54289 measured reflections | k = −28→28 |
5600 independent reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.022 | H-atom parameters constrained |
wR(F2) = 0.050 | w = 1/[σ2(Fo2) + (0.0212P)2 + 1.2207P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.003 |
5600 reflections | Δρmax = 0.97 e Å−3 |
238 parameters | Δρmin = −0.59 e Å−3 |
0 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. |
x | y | z | Uiso*/Ueq | ||
I1 | 1.02273 (2) | 0.44378 (2) | 0.71043 (2) | 0.02391 (4) | |
O1 | 0.42189 (12) | 0.51004 (5) | 0.22300 (10) | 0.0198 (2) | |
N1 | 0.44105 (14) | 0.63918 (6) | 0.32433 (11) | 0.0172 (2) | |
C1 | 0.81918 (17) | 0.46520 (7) | 0.54844 (14) | 0.0185 (3) | |
O2 | 0.57214 (14) | 0.56173 (6) | 0.12194 (11) | 0.0265 (2) | |
N2 | 0.43632 (14) | 0.70564 (6) | 0.36222 (11) | 0.0170 (2) | |
C2 | 0.75217 (17) | 0.52839 (7) | 0.53642 (13) | 0.0177 (3) | |
H2 | 0.795397 | 0.560319 | 0.603141 | 0.021* | |
O3 | 0.63889 (13) | 0.65492 (5) | 0.51584 (9) | 0.0191 (2) | |
C3 | 0.62097 (16) | 0.54536 (7) | 0.42630 (13) | 0.0162 (2) | |
O4 | 0.31986 (13) | 0.80687 (5) | 0.32597 (11) | 0.0240 (2) | |
C4 | 0.55900 (17) | 0.49706 (7) | 0.33034 (13) | 0.0175 (3) | |
C5 | 0.62622 (19) | 0.43404 (7) | 0.34230 (15) | 0.0221 (3) | |
H5 | 0.582960 | 0.401921 | 0.275960 | 0.027* | |
C6 | 0.75733 (19) | 0.41777 (7) | 0.45167 (15) | 0.0226 (3) | |
H6 | 0.804238 | 0.374628 | 0.460211 | 0.027* | |
C7 | 0.55901 (16) | 0.61343 (7) | 0.41634 (13) | 0.0161 (2) | |
C8 | 0.58015 (17) | 0.72191 (7) | 0.47773 (13) | 0.0165 (2) | |
C9 | 0.70562 (16) | 0.76014 (7) | 0.43953 (13) | 0.0170 (2) | |
C10 | 0.82350 (18) | 0.72550 (8) | 0.40745 (15) | 0.0225 (3) | |
H10 | 0.828901 | 0.678281 | 0.414448 | 0.027* | |
C11 | 0.93294 (19) | 0.75959 (9) | 0.36537 (16) | 0.0289 (3) | |
H11 | 1.012829 | 0.735524 | 0.343917 | 0.035* | |
C12 | 0.92662 (19) | 0.82828 (9) | 0.35443 (16) | 0.0294 (3) | |
H12 | 1.001008 | 0.851359 | 0.324678 | 0.035* | |
C13 | 0.8109 (2) | 0.86321 (9) | 0.38721 (17) | 0.0299 (3) | |
H13 | 0.806516 | 0.910437 | 0.380223 | 0.036* | |
C14 | 0.70118 (18) | 0.82959 (8) | 0.43030 (15) | 0.0235 (3) | |
H14 | 0.623057 | 0.853966 | 0.453485 | 0.028* | |
C15 | 0.44235 (18) | 0.54575 (7) | 0.12345 (14) | 0.0197 (3) | |
C16 | 0.2830 (2) | 0.55892 (8) | 0.02103 (15) | 0.0274 (3) | |
H16A | 0.245772 | 0.518532 | −0.030777 | 0.041* | |
H16B | 0.294126 | 0.595176 | −0.034930 | 0.041* | |
H16C | 0.204476 | 0.571687 | 0.061592 | 0.041* | |
C17 | 0.5379 (2) | 0.75217 (8) | 0.58752 (14) | 0.0236 (3) | |
H17A | 0.456948 | 0.724354 | 0.605601 | 0.035* | |
H17B | 0.494300 | 0.797093 | 0.563247 | 0.035* | |
H17C | 0.634896 | 0.754692 | 0.664922 | 0.035* | |
C18 | 0.31788 (16) | 0.74827 (7) | 0.29343 (13) | 0.0176 (3) | |
C19 | 0.18862 (18) | 0.71930 (8) | 0.17778 (15) | 0.0227 (3) | |
H19A | 0.101667 | 0.751907 | 0.143604 | 0.034* | |
H19B | 0.145536 | 0.678758 | 0.203469 | 0.034* | |
H19C | 0.234431 | 0.708341 | 0.110914 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02366 (5) | 0.02116 (5) | 0.02296 (5) | 0.00370 (3) | 0.00299 (4) | 0.00274 (3) |
O1 | 0.0188 (5) | 0.0201 (5) | 0.0183 (5) | −0.0032 (4) | 0.0038 (4) | 0.0003 (4) |
N1 | 0.0175 (5) | 0.0151 (5) | 0.0192 (5) | 0.0000 (4) | 0.0065 (4) | −0.0022 (4) |
C1 | 0.0184 (6) | 0.0178 (6) | 0.0192 (6) | 0.0005 (5) | 0.0064 (5) | 0.0028 (5) |
O2 | 0.0257 (6) | 0.0309 (6) | 0.0238 (5) | −0.0008 (4) | 0.0096 (4) | 0.0042 (4) |
N2 | 0.0163 (5) | 0.0159 (5) | 0.0175 (5) | 0.0010 (4) | 0.0041 (4) | −0.0023 (4) |
C2 | 0.0192 (6) | 0.0171 (6) | 0.0173 (6) | −0.0010 (5) | 0.0070 (5) | 0.0001 (5) |
O3 | 0.0241 (5) | 0.0154 (5) | 0.0148 (4) | 0.0027 (4) | 0.0029 (4) | −0.0007 (4) |
C3 | 0.0167 (6) | 0.0158 (6) | 0.0175 (6) | −0.0008 (5) | 0.0078 (5) | 0.0003 (5) |
O4 | 0.0233 (5) | 0.0190 (5) | 0.0290 (5) | 0.0038 (4) | 0.0083 (4) | 0.0007 (4) |
C4 | 0.0173 (6) | 0.0180 (6) | 0.0172 (6) | −0.0026 (5) | 0.0060 (5) | 0.0009 (5) |
C5 | 0.0257 (7) | 0.0166 (7) | 0.0230 (7) | −0.0025 (5) | 0.0070 (6) | −0.0029 (5) |
C6 | 0.0263 (7) | 0.0145 (6) | 0.0264 (7) | 0.0014 (5) | 0.0082 (6) | 0.0002 (5) |
C7 | 0.0177 (6) | 0.0165 (6) | 0.0151 (6) | −0.0008 (5) | 0.0068 (5) | −0.0013 (5) |
C8 | 0.0182 (6) | 0.0165 (6) | 0.0141 (6) | 0.0028 (5) | 0.0046 (5) | −0.0010 (5) |
C9 | 0.0162 (6) | 0.0197 (6) | 0.0133 (6) | 0.0008 (5) | 0.0028 (5) | −0.0022 (5) |
C10 | 0.0198 (7) | 0.0243 (7) | 0.0235 (7) | 0.0021 (5) | 0.0077 (5) | −0.0033 (6) |
C11 | 0.0195 (7) | 0.0388 (9) | 0.0304 (8) | 0.0001 (6) | 0.0111 (6) | −0.0033 (7) |
C12 | 0.0201 (7) | 0.0400 (9) | 0.0272 (8) | −0.0065 (6) | 0.0071 (6) | 0.0020 (7) |
C13 | 0.0276 (8) | 0.0243 (8) | 0.0361 (9) | −0.0043 (6) | 0.0090 (7) | 0.0014 (7) |
C14 | 0.0214 (7) | 0.0208 (7) | 0.0279 (7) | 0.0015 (5) | 0.0080 (6) | −0.0018 (6) |
C15 | 0.0245 (7) | 0.0168 (6) | 0.0169 (6) | 0.0003 (5) | 0.0058 (5) | −0.0021 (5) |
C16 | 0.0264 (8) | 0.0299 (8) | 0.0206 (7) | 0.0022 (6) | 0.0014 (6) | −0.0003 (6) |
C17 | 0.0307 (8) | 0.0251 (7) | 0.0179 (6) | 0.0042 (6) | 0.0122 (6) | −0.0020 (5) |
C18 | 0.0149 (6) | 0.0204 (6) | 0.0195 (6) | 0.0017 (5) | 0.0085 (5) | 0.0026 (5) |
C19 | 0.0162 (6) | 0.0265 (7) | 0.0231 (7) | 0.0008 (5) | 0.0040 (5) | 0.0013 (6) |
I1—C1 | 2.0951 (14) | C9—C10 | 1.395 (2) |
O1—C4 | 1.3948 (17) | C9—C14 | 1.396 (2) |
O1—C15 | 1.3727 (17) | C10—H10 | 0.9500 |
N1—N2 | 1.4017 (16) | C10—C11 | 1.388 (2) |
N1—C7 | 1.2851 (18) | C11—H11 | 0.9500 |
C1—C2 | 1.386 (2) | C11—C12 | 1.382 (3) |
C1—C6 | 1.392 (2) | C12—H12 | 0.9500 |
O2—C15 | 1.1966 (19) | C12—C13 | 1.386 (2) |
N2—C8 | 1.4917 (18) | C13—H13 | 0.9500 |
N2—C18 | 1.3614 (18) | C13—C14 | 1.392 (2) |
C2—H2 | 0.9500 | C14—H14 | 0.9500 |
C2—C3 | 1.4004 (19) | C15—C16 | 1.493 (2) |
O3—C7 | 1.3631 (16) | C16—H16A | 0.9800 |
O3—C8 | 1.4493 (16) | C16—H16B | 0.9800 |
C3—C4 | 1.3986 (19) | C16—H16C | 0.9800 |
C3—C7 | 1.4610 (19) | C17—H17A | 0.9800 |
O4—C18 | 1.2270 (18) | C17—H17B | 0.9800 |
C4—C5 | 1.383 (2) | C17—H17C | 0.9800 |
C5—H5 | 0.9500 | C18—C19 | 1.504 (2) |
C5—C6 | 1.392 (2) | C19—H19A | 0.9800 |
C6—H6 | 0.9500 | C19—H19B | 0.9800 |
C8—C9 | 1.522 (2) | C19—H19C | 0.9800 |
C8—C17 | 1.5107 (19) | ||
C15—O1—C4 | 117.34 (11) | C11—C10—H10 | 119.8 |
C7—N1—N2 | 104.29 (11) | C10—C11—H11 | 119.7 |
C2—C1—I1 | 118.81 (10) | C12—C11—C10 | 120.55 (15) |
C2—C1—C6 | 120.65 (13) | C12—C11—H11 | 119.7 |
C6—C1—I1 | 120.47 (11) | C11—C12—H12 | 120.3 |
N1—N2—C8 | 110.97 (11) | C11—C12—C13 | 119.49 (15) |
C18—N2—N1 | 121.85 (12) | C13—C12—H12 | 120.3 |
C18—N2—C8 | 127.06 (12) | C12—C13—H13 | 119.8 |
C1—C2—H2 | 119.9 | C12—C13—C14 | 120.47 (16) |
C1—C2—C3 | 120.26 (13) | C14—C13—H13 | 119.8 |
C3—C2—H2 | 119.9 | C9—C14—H14 | 119.9 |
C7—O3—C8 | 107.38 (10) | C13—C14—C9 | 120.17 (15) |
C2—C3—C7 | 117.97 (12) | C13—C14—H14 | 119.9 |
C4—C3—C2 | 118.53 (13) | O1—C15—C16 | 110.24 (13) |
C4—C3—C7 | 123.48 (13) | O2—C15—O1 | 122.81 (13) |
O1—C4—C3 | 120.69 (12) | O2—C15—C16 | 126.93 (14) |
C5—C4—O1 | 118.05 (12) | C15—C16—H16A | 109.5 |
C5—C4—C3 | 121.16 (13) | C15—C16—H16B | 109.5 |
C4—C5—H5 | 120.0 | C15—C16—H16C | 109.5 |
C4—C5—C6 | 119.91 (14) | H16A—C16—H16B | 109.5 |
C6—C5—H5 | 120.0 | H16A—C16—H16C | 109.5 |
C1—C6—H6 | 120.3 | H16B—C16—H16C | 109.5 |
C5—C6—C1 | 119.49 (14) | C8—C17—H17A | 109.5 |
C5—C6—H6 | 120.3 | C8—C17—H17B | 109.5 |
N1—C7—O3 | 116.29 (12) | C8—C17—H17C | 109.5 |
N1—C7—C3 | 128.01 (13) | H17A—C17—H17B | 109.5 |
O3—C7—C3 | 115.68 (12) | H17A—C17—H17C | 109.5 |
N2—C8—C9 | 111.22 (11) | H17B—C17—H17C | 109.5 |
N2—C8—C17 | 113.42 (12) | N2—C18—C19 | 116.25 (13) |
O3—C8—N2 | 99.15 (10) | O4—C18—N2 | 120.54 (13) |
O3—C8—C9 | 108.96 (11) | O4—C18—C19 | 123.21 (13) |
O3—C8—C17 | 107.66 (11) | C18—C19—H19A | 109.5 |
C17—C8—C9 | 115.08 (12) | C18—C19—H19B | 109.5 |
C10—C9—C8 | 119.86 (13) | C18—C19—H19C | 109.5 |
C10—C9—C14 | 118.89 (14) | H19A—C19—H19B | 109.5 |
C14—C9—C8 | 121.19 (13) | H19A—C19—H19C | 109.5 |
C9—C10—H10 | 119.8 | H19B—C19—H19C | 109.5 |
C11—C10—C9 | 120.41 (15) | ||
I1—C1—C2—C3 | 176.86 (10) | C6—C1—C2—C3 | 0.0 (2) |
I1—C1—C6—C5 | −177.27 (11) | C7—N1—N2—C8 | 9.02 (14) |
O1—C4—C5—C6 | −176.23 (13) | C7—N1—N2—C18 | −174.80 (12) |
N1—N2—C8—O3 | −13.43 (13) | C7—O3—C8—N2 | 12.66 (13) |
N1—N2—C8—C9 | 101.12 (13) | C7—O3—C8—C9 | −103.64 (12) |
N1—N2—C8—C17 | −127.29 (12) | C7—O3—C8—C17 | 130.93 (12) |
N1—N2—C18—O4 | −177.27 (12) | C7—C3—C4—O1 | −6.1 (2) |
N1—N2—C18—C19 | 2.50 (19) | C7—C3—C4—C5 | 177.43 (13) |
C1—C2—C3—C4 | 0.6 (2) | C8—N2—C18—O4 | −1.7 (2) |
C1—C2—C3—C7 | −177.68 (13) | C8—N2—C18—C19 | 178.03 (12) |
N2—N1—C7—O3 | −0.09 (16) | C8—O3—C7—N1 | −8.94 (16) |
N2—N1—C7—C3 | −178.50 (13) | C8—O3—C7—C3 | 169.68 (11) |
N2—C8—C9—C10 | −88.99 (15) | C8—C9—C10—C11 | 176.32 (14) |
N2—C8—C9—C14 | 88.16 (15) | C8—C9—C14—C13 | −175.89 (14) |
C2—C1—C6—C5 | −0.4 (2) | C9—C10—C11—C12 | −0.1 (2) |
C2—C3—C4—O1 | 175.70 (12) | C10—C9—C14—C13 | 1.3 (2) |
C2—C3—C4—C5 | −0.8 (2) | C10—C11—C12—C13 | 0.7 (3) |
C2—C3—C7—N1 | 179.85 (14) | C11—C12—C13—C14 | −0.3 (3) |
C2—C3—C7—O3 | 1.42 (18) | C12—C13—C14—C9 | −0.7 (3) |
O3—C8—C9—C10 | 19.29 (17) | C14—C9—C10—C11 | −0.9 (2) |
O3—C8—C9—C14 | −163.56 (12) | C15—O1—C4—C3 | 81.18 (16) |
C3—C4—C5—C6 | 0.3 (2) | C15—O1—C4—C5 | −102.23 (15) |
C4—O1—C15—O2 | 5.2 (2) | C17—C8—C9—C10 | 140.28 (14) |
C4—O1—C15—C16 | −176.26 (12) | C17—C8—C9—C14 | −42.57 (18) |
C4—C3—C7—N1 | 1.6 (2) | C18—N2—C8—O3 | 170.64 (12) |
C4—C3—C7—O3 | −176.80 (12) | C18—N2—C8—C9 | −74.81 (16) |
C4—C5—C6—C1 | 0.3 (2) | C18—N2—C8—C17 | 56.77 (18) |
Cg3 is the centroid of the C9–C14 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O4i | 0.95 | 2.51 | 3.2828 (19) | 139 |
C16—H16B···O4ii | 0.98 | 2.55 | 3.529 (2) | 177 |
C17—H17C···Cg3iii | 0.98 | 2.70 | 3.5766 (17) | 150 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2. |
C19H16FIN2O4 | F(000) = 952 |
Mr = 482.24 | Dx = 1.732 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1241 (4) Å | Cell parameters from 9994 reflections |
b = 20.0980 (9) Å | θ = 2.9–30.5° |
c = 10.7456 (5) Å | µ = 1.77 mm−1 |
β = 110.224 (2)° | T = 100 K |
V = 1849.00 (15) Å3 | Block, colourless |
Z = 4 | 0.60 × 0.37 × 0.29 mm |
Bruker APEXII CCD diffractometer | 3703 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.048 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 27.0°, θmin = 2.7° |
Tmin = 0.610, Tmax = 0.746 | h = −11→11 |
52242 measured reflections | k = −25→25 |
4033 independent reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H-atom parameters constrained |
wR(F2) = 0.047 | w = 1/[σ2(Fo2) + (0.0179P)2 + 1.3214P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
4033 reflections | Δρmax = 0.56 e Å−3 |
247 parameters | Δρmin = −0.32 e Å−3 |
0 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. |
x | y | z | Uiso*/Ueq | ||
I1 | 1.02927 (2) | 0.43863 (2) | 0.70991 (2) | 0.02562 (5) | |
F1 | 0.99431 (14) | 0.86573 (7) | 0.31186 (15) | 0.0482 (4) | |
O1 | 0.43234 (14) | 0.50760 (6) | 0.22482 (12) | 0.0221 (3) | |
N1 | 0.45186 (17) | 0.63451 (7) | 0.33434 (14) | 0.0196 (3) | |
C1 | 0.8281 (2) | 0.46130 (9) | 0.54780 (17) | 0.0208 (3) | |
O2 | 0.56974 (16) | 0.56291 (6) | 0.11907 (14) | 0.0287 (3) | |
N2 | 0.44708 (17) | 0.70043 (7) | 0.37438 (14) | 0.0193 (3) | |
C2 | 0.7610 (2) | 0.52365 (8) | 0.54173 (17) | 0.0193 (3) | |
H2 | 0.803774 | 0.554529 | 0.611907 | 0.023* | |
O3 | 0.64636 (15) | 0.64956 (6) | 0.52903 (12) | 0.0221 (3) | |
C3 | 0.6303 (2) | 0.54116 (8) | 0.43227 (17) | 0.0185 (3) | |
O4 | 0.33470 (15) | 0.80138 (6) | 0.34228 (13) | 0.0275 (3) | |
C4 | 0.5691 (2) | 0.49418 (8) | 0.33133 (17) | 0.0197 (3) | |
C5 | 0.6368 (2) | 0.43237 (8) | 0.33789 (19) | 0.0244 (4) | |
H5 | 0.594019 | 0.401213 | 0.268247 | 0.029* | |
C6 | 0.7674 (2) | 0.41554 (9) | 0.44590 (19) | 0.0247 (4) | |
H6 | 0.814835 | 0.373124 | 0.450193 | 0.030* | |
C7 | 0.5681 (2) | 0.60868 (8) | 0.42603 (16) | 0.0185 (3) | |
C8 | 0.5860 (2) | 0.71636 (8) | 0.49331 (17) | 0.0197 (3) | |
C9 | 0.7052 (2) | 0.75722 (8) | 0.45591 (16) | 0.0190 (3) | |
C10 | 0.8228 (2) | 0.72585 (9) | 0.42326 (19) | 0.0254 (4) | |
H10 | 0.835259 | 0.678999 | 0.433228 | 0.030* | |
C11 | 0.9221 (2) | 0.76212 (10) | 0.3763 (2) | 0.0327 (4) | |
H11 | 1.002324 | 0.740675 | 0.353709 | 0.039* | |
C12 | 0.9018 (2) | 0.82967 (10) | 0.3632 (2) | 0.0301 (4) | |
C13 | 0.7907 (2) | 0.86302 (9) | 0.3985 (2) | 0.0293 (4) | |
H13 | 0.781470 | 0.910050 | 0.390699 | 0.035* | |
C14 | 0.6923 (2) | 0.82630 (9) | 0.44565 (18) | 0.0242 (4) | |
H14 | 0.615284 | 0.848465 | 0.471304 | 0.029* | |
C15 | 0.4463 (2) | 0.54563 (9) | 0.12336 (18) | 0.0221 (4) | |
C16 | 0.2891 (2) | 0.55914 (10) | 0.02252 (19) | 0.0298 (4) | |
H16A | 0.294383 | 0.599001 | −0.028300 | 0.045* | |
H16B | 0.213370 | 0.566258 | 0.067348 | 0.045* | |
H16C | 0.256482 | 0.521035 | −0.037665 | 0.045* | |
C17 | 0.5423 (2) | 0.74413 (10) | 0.60655 (18) | 0.0274 (4) | |
H17A | 0.463240 | 0.715531 | 0.621914 | 0.041* | |
H17B | 0.500112 | 0.789140 | 0.584128 | 0.041* | |
H17C | 0.635236 | 0.745718 | 0.686984 | 0.041* | |
C18 | 0.3312 (2) | 0.74345 (9) | 0.30679 (17) | 0.0207 (3) | |
C19 | 0.2035 (2) | 0.71544 (10) | 0.1893 (2) | 0.0281 (4) | |
H19A | 0.119864 | 0.748393 | 0.156118 | 0.042* | |
H19B | 0.161775 | 0.675041 | 0.215776 | 0.042* | |
H19C | 0.245578 | 0.704600 | 0.119275 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02788 (7) | 0.02021 (7) | 0.02625 (7) | 0.00422 (5) | 0.00614 (5) | 0.00214 (5) |
F1 | 0.0294 (6) | 0.0459 (8) | 0.0738 (10) | −0.0073 (6) | 0.0236 (7) | 0.0089 (7) |
O1 | 0.0241 (6) | 0.0200 (6) | 0.0208 (6) | −0.0051 (5) | 0.0061 (5) | 0.0002 (5) |
N1 | 0.0225 (7) | 0.0160 (7) | 0.0217 (7) | 0.0003 (5) | 0.0094 (6) | −0.0008 (6) |
C1 | 0.0221 (8) | 0.0187 (8) | 0.0227 (9) | 0.0002 (7) | 0.0091 (7) | 0.0035 (7) |
O2 | 0.0305 (7) | 0.0300 (7) | 0.0275 (7) | −0.0029 (6) | 0.0125 (6) | 0.0043 (6) |
N2 | 0.0216 (7) | 0.0172 (7) | 0.0184 (7) | 0.0024 (5) | 0.0062 (6) | −0.0010 (6) |
C2 | 0.0240 (9) | 0.0172 (8) | 0.0194 (8) | −0.0015 (6) | 0.0109 (7) | −0.0002 (6) |
O3 | 0.0313 (7) | 0.0163 (6) | 0.0156 (6) | 0.0061 (5) | 0.0043 (5) | −0.0008 (5) |
C3 | 0.0224 (8) | 0.0170 (8) | 0.0197 (8) | −0.0004 (6) | 0.0118 (7) | 0.0020 (6) |
O4 | 0.0282 (7) | 0.0218 (7) | 0.0317 (7) | 0.0070 (5) | 0.0092 (6) | 0.0012 (5) |
C4 | 0.0215 (8) | 0.0190 (8) | 0.0199 (8) | −0.0036 (6) | 0.0087 (7) | 0.0016 (7) |
C5 | 0.0319 (10) | 0.0163 (8) | 0.0257 (9) | −0.0052 (7) | 0.0106 (8) | −0.0036 (7) |
C6 | 0.0313 (10) | 0.0138 (8) | 0.0308 (10) | 0.0010 (7) | 0.0131 (8) | 0.0006 (7) |
C7 | 0.0226 (8) | 0.0180 (8) | 0.0172 (8) | −0.0013 (6) | 0.0098 (7) | −0.0008 (6) |
C8 | 0.0248 (9) | 0.0175 (8) | 0.0152 (8) | 0.0065 (7) | 0.0050 (7) | 0.0004 (6) |
C9 | 0.0197 (8) | 0.0201 (8) | 0.0135 (8) | 0.0027 (6) | 0.0009 (6) | −0.0036 (6) |
C10 | 0.0225 (9) | 0.0230 (9) | 0.0281 (10) | 0.0061 (7) | 0.0056 (7) | −0.0018 (7) |
C11 | 0.0209 (9) | 0.0361 (11) | 0.0420 (12) | 0.0058 (8) | 0.0118 (9) | −0.0014 (9) |
C12 | 0.0173 (9) | 0.0344 (10) | 0.0357 (11) | −0.0063 (8) | 0.0056 (8) | 0.0015 (9) |
C13 | 0.0273 (10) | 0.0207 (9) | 0.0348 (11) | −0.0020 (7) | 0.0044 (8) | −0.0012 (8) |
C14 | 0.0233 (9) | 0.0223 (9) | 0.0243 (9) | 0.0030 (7) | 0.0048 (7) | −0.0044 (7) |
C15 | 0.0305 (10) | 0.0163 (8) | 0.0203 (8) | −0.0011 (7) | 0.0098 (7) | −0.0024 (7) |
C16 | 0.0310 (10) | 0.0299 (10) | 0.0239 (9) | −0.0013 (8) | 0.0037 (8) | 0.0001 (8) |
C17 | 0.0402 (11) | 0.0280 (10) | 0.0172 (9) | 0.0084 (8) | 0.0139 (8) | −0.0006 (7) |
C18 | 0.0190 (8) | 0.0228 (9) | 0.0229 (9) | 0.0032 (7) | 0.0107 (7) | 0.0045 (7) |
C19 | 0.0189 (9) | 0.0312 (10) | 0.0318 (10) | 0.0006 (7) | 0.0055 (8) | 0.0035 (8) |
I1—C1 | 2.0979 (18) | C8—C17 | 1.512 (2) |
F1—C12 | 1.365 (2) | C9—C10 | 1.390 (2) |
O1—C4 | 1.397 (2) | C9—C14 | 1.395 (2) |
O1—C15 | 1.373 (2) | C10—H10 | 0.9500 |
N1—N2 | 1.3983 (19) | C10—C11 | 1.387 (3) |
N1—C7 | 1.281 (2) | C11—H11 | 0.9500 |
C1—C2 | 1.386 (2) | C11—C12 | 1.371 (3) |
C1—C6 | 1.390 (3) | C12—C13 | 1.373 (3) |
O2—C15 | 1.195 (2) | C13—H13 | 0.9500 |
N2—C8 | 1.491 (2) | C13—C14 | 1.386 (3) |
N2—C18 | 1.364 (2) | C14—H14 | 0.9500 |
C2—H2 | 0.9500 | C15—C16 | 1.493 (3) |
C2—C3 | 1.400 (2) | C16—H16A | 0.9800 |
O3—C7 | 1.365 (2) | C16—H16B | 0.9800 |
O3—C8 | 1.4515 (19) | C16—H16C | 0.9800 |
C3—C4 | 1.400 (2) | C17—H17A | 0.9800 |
C3—C7 | 1.464 (2) | C17—H17B | 0.9800 |
O4—C18 | 1.222 (2) | C17—H17C | 0.9800 |
C4—C5 | 1.379 (2) | C18—C19 | 1.500 (3) |
C5—H5 | 0.9500 | C19—H19A | 0.9800 |
C5—C6 | 1.387 (3) | C19—H19B | 0.9800 |
C6—H6 | 0.9500 | C19—H19C | 0.9800 |
C8—C9 | 1.523 (2) | ||
C15—O1—C4 | 117.16 (13) | C11—C10—H10 | 119.6 |
C7—N1—N2 | 104.65 (14) | C10—C11—H11 | 120.8 |
C2—C1—I1 | 118.74 (13) | C12—C11—C10 | 118.38 (18) |
C2—C1—C6 | 120.79 (17) | C12—C11—H11 | 120.8 |
C6—C1—I1 | 120.42 (13) | F1—C12—C11 | 119.10 (18) |
N1—N2—C8 | 111.07 (13) | F1—C12—C13 | 118.09 (18) |
C18—N2—N1 | 122.51 (14) | C11—C12—C13 | 122.81 (19) |
C18—N2—C8 | 126.37 (14) | C12—C13—H13 | 120.9 |
C1—C2—H2 | 120.0 | C12—C13—C14 | 118.30 (18) |
C1—C2—C3 | 120.05 (16) | C14—C13—H13 | 120.9 |
C3—C2—H2 | 120.0 | C9—C14—H14 | 119.6 |
C7—O3—C8 | 107.33 (12) | C13—C14—C9 | 120.78 (17) |
C2—C3—C4 | 118.51 (16) | C13—C14—H14 | 119.6 |
C2—C3—C7 | 118.41 (15) | O1—C15—C16 | 110.38 (15) |
C4—C3—C7 | 123.02 (16) | O2—C15—O1 | 122.66 (17) |
O1—C4—C3 | 120.58 (15) | O2—C15—C16 | 126.93 (17) |
C5—C4—O1 | 118.26 (15) | C15—C16—H16A | 109.5 |
C5—C4—C3 | 121.07 (16) | C15—C16—H16B | 109.5 |
C4—C5—H5 | 119.9 | C15—C16—H16C | 109.5 |
C4—C5—C6 | 120.18 (17) | H16A—C16—H16B | 109.5 |
C6—C5—H5 | 119.9 | H16A—C16—H16C | 109.5 |
C1—C6—H6 | 120.3 | H16B—C16—H16C | 109.5 |
C5—C6—C1 | 119.39 (16) | C8—C17—H17A | 109.5 |
C5—C6—H6 | 120.3 | C8—C17—H17B | 109.5 |
N1—C7—O3 | 116.20 (15) | C8—C17—H17C | 109.5 |
N1—C7—C3 | 128.00 (16) | H17A—C17—H17B | 109.5 |
O3—C7—C3 | 115.78 (15) | H17A—C17—H17C | 109.5 |
N2—C8—C9 | 111.26 (13) | H17B—C17—H17C | 109.5 |
N2—C8—C17 | 112.74 (15) | N2—C18—C19 | 116.33 (16) |
O3—C8—N2 | 99.24 (12) | O4—C18—N2 | 120.39 (17) |
O3—C8—C9 | 109.17 (13) | O4—C18—C19 | 123.28 (16) |
O3—C8—C17 | 108.06 (14) | C18—C19—H19A | 109.5 |
C17—C8—C9 | 115.09 (15) | C18—C19—H19B | 109.5 |
C10—C9—C8 | 120.38 (15) | C18—C19—H19C | 109.5 |
C10—C9—C14 | 118.86 (17) | H19A—C19—H19B | 109.5 |
C14—C9—C8 | 120.64 (15) | H19A—C19—H19C | 109.5 |
C9—C10—H10 | 119.6 | H19B—C19—H19C | 109.5 |
C11—C10—C9 | 120.80 (17) | ||
I1—C1—C2—C3 | 177.52 (12) | C6—C1—C2—C3 | 0.2 (3) |
I1—C1—C6—C5 | −178.17 (13) | C7—N1—N2—C8 | 7.40 (18) |
F1—C12—C13—C14 | 177.44 (17) | C7—N1—N2—C18 | −175.13 (15) |
O1—C4—C5—C6 | −176.19 (16) | C7—O3—C8—N2 | 11.41 (16) |
N1—N2—C8—O3 | −11.66 (16) | C7—O3—C8—C9 | −105.04 (15) |
N1—N2—C8—C9 | 103.18 (15) | C7—O3—C8—C17 | 129.12 (15) |
N1—N2—C8—C17 | −125.79 (15) | C7—C3—C4—O1 | −7.2 (2) |
N1—N2—C18—O4 | −177.18 (15) | C7—C3—C4—C5 | 176.30 (16) |
N1—N2—C18—C19 | 2.7 (2) | C8—N2—C18—O4 | −0.1 (3) |
C1—C2—C3—C4 | 0.8 (2) | C8—N2—C18—C19 | 179.75 (15) |
C1—C2—C3—C7 | −176.69 (15) | C8—O3—C7—N1 | −8.6 (2) |
N2—N1—C7—O3 | 0.70 (19) | C8—O3—C7—C3 | 169.74 (14) |
N2—N1—C7—C3 | −177.36 (16) | C8—C9—C10—C11 | 173.47 (17) |
N2—C8—C9—C10 | −90.33 (18) | C8—C9—C14—C13 | −173.28 (16) |
N2—C8—C9—C14 | 85.57 (19) | C9—C10—C11—C12 | 0.2 (3) |
C2—C1—C6—C5 | −0.9 (3) | C10—C9—C14—C13 | 2.7 (3) |
C2—C3—C4—O1 | 175.43 (14) | C10—C11—C12—F1 | −177.25 (18) |
C2—C3—C4—C5 | −1.0 (2) | C10—C11—C12—C13 | 2.1 (3) |
C2—C3—C7—N1 | 178.95 (17) | C11—C12—C13—C14 | −1.9 (3) |
C2—C3—C7—O3 | 0.9 (2) | C12—C13—C14—C9 | −0.6 (3) |
O3—C8—C9—C10 | 18.2 (2) | C14—C9—C10—C11 | −2.5 (3) |
O3—C8—C9—C14 | −165.92 (15) | C15—O1—C4—C3 | 81.4 (2) |
C3—C4—C5—C6 | 0.3 (3) | C15—O1—C4—C5 | −102.02 (18) |
C4—O1—C15—O2 | 5.6 (2) | C17—C8—C9—C10 | 139.87 (17) |
C4—O1—C15—C16 | −176.14 (14) | C17—C8—C9—C14 | −44.2 (2) |
C4—C3—C7—N1 | 1.6 (3) | C18—N2—C8—O3 | 170.99 (15) |
C4—C3—C7—O3 | −176.45 (15) | C18—N2—C8—C9 | −74.2 (2) |
C4—C5—C6—C1 | 0.6 (3) | C18—N2—C8—C17 | 56.9 (2) |
Cg3 is the centroid of the C9–C14 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O4i | 0.95 | 2.53 | 3.331 (2) | 142 |
C14—H14···O2ii | 0.95 | 2.51 | 3.335 (2) | 145 |
C16—H16A···O4iii | 0.98 | 2.54 | 3.513 (2) | 174 |
C17—H17C···Cg3ii | 0.98 | 2.50 | 3.407 (2) | 154 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2. |
C19H16ClIN2O4 | F(000) = 984 |
Mr = 498.69 | Dx = 1.736 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.703 (2) Å | Cell parameters from 9499 reflections |
b = 22.037 (4) Å | θ = 2.9–31.1° |
c = 7.4073 (12) Å | µ = 1.85 mm−1 |
β = 92.888 (8)° | T = 100 K |
V = 1907.9 (5) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.12 × 0.12 mm |
Bruker APEXII CCD diffractometer | 3863 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.042 |
Absorption correction: multi-scan SADABS2014/2 (Bruker, 2014) | θmax = 27.5°, θmin = 2.9° |
Tmin = 0.640, Tmax = 0.746 | h = −15→15 |
62840 measured reflections | k = −28→28 |
4387 independent reflections | l = −9→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.021 | H-atom parameters constrained |
wR(F2) = 0.051 | w = 1/[σ2(Fo2) + (0.0233P)2 + 1.3951P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
4387 reflections | Δρmax = 0.40 e Å−3 |
247 parameters | Δρmin = −0.66 e Å−3 |
0 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. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.89006 (2) | 0.30547 (2) | 0.88485 (2) | 0.03207 (5) | |
Cl1 | 0.06374 (4) | 0.34278 (2) | 0.41999 (8) | 0.03241 (12) | |
O1 | 0.77394 (10) | 0.50823 (5) | 0.31612 (16) | 0.0169 (2) | |
N1 | 0.64395 (12) | 0.42152 (6) | 0.12176 (18) | 0.0155 (3) | |
C1 | 0.84397 (15) | 0.37358 (8) | 0.6975 (2) | 0.0175 (3) | |
O2 | 0.91227 (11) | 0.47025 (6) | 0.14881 (17) | 0.0219 (3) | |
N2 | 0.56147 (13) | 0.38760 (6) | 0.02279 (19) | 0.0165 (3) | |
C2 | 0.77370 (14) | 0.35965 (7) | 0.5465 (2) | 0.0156 (3) | |
H2 | 0.742501 | 0.320035 | 0.532421 | 0.019* | |
O3 | 0.61627 (10) | 0.33434 (5) | 0.27089 (16) | 0.0156 (2) | |
C3 | 0.74881 (14) | 0.40416 (7) | 0.4147 (2) | 0.0135 (3) | |
O4 | 0.44240 (12) | 0.37370 (6) | −0.22008 (18) | 0.0279 (3) | |
C4 | 0.79720 (14) | 0.46180 (7) | 0.4405 (2) | 0.0147 (3) | |
C5 | 0.86500 (15) | 0.47563 (8) | 0.5935 (2) | 0.0176 (3) | |
H5 | 0.895568 | 0.515324 | 0.609208 | 0.021* | |
C6 | 0.88836 (15) | 0.43149 (8) | 0.7241 (2) | 0.0183 (3) | |
H6 | 0.934058 | 0.440805 | 0.830114 | 0.022* | |
C7 | 0.67047 (14) | 0.38903 (7) | 0.2610 (2) | 0.0137 (3) | |
C8 | 0.53275 (14) | 0.33051 (7) | 0.1187 (2) | 0.0145 (3) | |
C9 | 0.41367 (14) | 0.33227 (7) | 0.1917 (2) | 0.0142 (3) | |
C10 | 0.39456 (15) | 0.36749 (8) | 0.3436 (2) | 0.0193 (4) | |
H10 | 0.456042 | 0.389965 | 0.399203 | 0.023* | |
C11 | 0.28763 (16) | 0.37029 (8) | 0.4149 (2) | 0.0209 (4) | |
H11 | 0.275442 | 0.394248 | 0.518796 | 0.025* | |
C12 | 0.19911 (15) | 0.33766 (8) | 0.3323 (2) | 0.0191 (4) | |
C13 | 0.21483 (16) | 0.30168 (8) | 0.1829 (3) | 0.0226 (4) | |
H13 | 0.152988 | 0.279055 | 0.129009 | 0.027* | |
C14 | 0.32285 (16) | 0.29914 (8) | 0.1126 (2) | 0.0198 (4) | |
H14 | 0.334764 | 0.274592 | 0.009782 | 0.024* | |
C15 | 0.84064 (15) | 0.50789 (8) | 0.1683 (2) | 0.0172 (3) | |
C16 | 0.81145 (19) | 0.56051 (9) | 0.0475 (3) | 0.0292 (4) | |
H16A | 0.801965 | 0.596984 | 0.120947 | 0.044* | |
H16B | 0.740015 | 0.552037 | −0.022698 | 0.044* | |
H16C | 0.873208 | 0.567020 | −0.034917 | 0.044* | |
C17 | 0.55813 (15) | 0.27428 (8) | 0.0106 (2) | 0.0197 (4) | |
H17A | 0.548298 | 0.238187 | 0.085534 | 0.029* | |
H17B | 0.637073 | 0.276005 | −0.027385 | 0.029* | |
H17C | 0.505453 | 0.272232 | −0.096334 | 0.029* | |
C18 | 0.51525 (15) | 0.40515 (8) | −0.1420 (2) | 0.0190 (4) | |
C19 | 0.55873 (17) | 0.46367 (9) | −0.2175 (2) | 0.0239 (4) | |
H19A | 0.516126 | 0.473014 | −0.331441 | 0.036* | |
H19B | 0.640246 | 0.459579 | −0.239569 | 0.036* | |
H19C | 0.548147 | 0.496532 | −0.130830 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02554 (8) | 0.03502 (8) | 0.03427 (8) | −0.00758 (5) | −0.01207 (5) | 0.02000 (6) |
Cl1 | 0.0206 (2) | 0.0319 (3) | 0.0460 (3) | 0.00113 (19) | 0.0134 (2) | −0.0002 (2) |
O1 | 0.0224 (6) | 0.0132 (5) | 0.0153 (6) | 0.0002 (5) | 0.0019 (5) | 0.0013 (4) |
N1 | 0.0162 (7) | 0.0158 (7) | 0.0143 (7) | −0.0012 (5) | −0.0003 (5) | −0.0009 (5) |
C1 | 0.0145 (8) | 0.0224 (9) | 0.0156 (8) | −0.0002 (7) | 0.0005 (6) | 0.0049 (7) |
O2 | 0.0227 (7) | 0.0242 (7) | 0.0192 (6) | −0.0005 (5) | 0.0047 (5) | 0.0013 (5) |
N2 | 0.0183 (7) | 0.0169 (7) | 0.0140 (7) | −0.0030 (6) | −0.0019 (6) | 0.0012 (5) |
C2 | 0.0144 (8) | 0.0151 (8) | 0.0174 (8) | −0.0022 (6) | 0.0011 (6) | 0.0005 (6) |
O3 | 0.0157 (6) | 0.0147 (6) | 0.0158 (6) | −0.0030 (5) | −0.0048 (5) | 0.0014 (4) |
C3 | 0.0114 (8) | 0.0156 (8) | 0.0135 (7) | −0.0004 (6) | 0.0018 (6) | −0.0005 (6) |
O4 | 0.0291 (8) | 0.0343 (8) | 0.0191 (7) | −0.0041 (6) | −0.0088 (6) | 0.0005 (6) |
C4 | 0.0152 (8) | 0.0155 (8) | 0.0137 (8) | 0.0010 (6) | 0.0034 (6) | 0.0007 (6) |
C5 | 0.0190 (9) | 0.0168 (8) | 0.0173 (8) | −0.0037 (7) | 0.0030 (7) | −0.0032 (6) |
C6 | 0.0149 (8) | 0.0259 (9) | 0.0141 (8) | −0.0037 (7) | 0.0001 (6) | −0.0018 (7) |
C7 | 0.0130 (8) | 0.0131 (7) | 0.0152 (8) | −0.0004 (6) | 0.0026 (6) | −0.0010 (6) |
C8 | 0.0150 (8) | 0.0156 (8) | 0.0125 (8) | −0.0013 (6) | −0.0023 (6) | −0.0004 (6) |
C9 | 0.0165 (8) | 0.0127 (7) | 0.0131 (8) | 0.0012 (6) | −0.0018 (6) | 0.0009 (6) |
C10 | 0.0196 (9) | 0.0206 (8) | 0.0174 (8) | −0.0013 (7) | −0.0018 (7) | −0.0049 (7) |
C11 | 0.0243 (9) | 0.0205 (9) | 0.0179 (9) | 0.0040 (7) | 0.0023 (7) | −0.0044 (7) |
C12 | 0.0158 (8) | 0.0188 (8) | 0.0231 (9) | 0.0027 (7) | 0.0047 (7) | 0.0055 (7) |
C13 | 0.0176 (9) | 0.0226 (9) | 0.0273 (10) | −0.0036 (7) | −0.0012 (7) | −0.0031 (7) |
C14 | 0.0197 (9) | 0.0207 (9) | 0.0189 (8) | −0.0012 (7) | −0.0008 (7) | −0.0062 (7) |
C15 | 0.0180 (8) | 0.0179 (8) | 0.0155 (8) | −0.0062 (7) | −0.0002 (7) | 0.0010 (6) |
C16 | 0.0346 (11) | 0.0273 (10) | 0.0258 (10) | −0.0006 (8) | 0.0021 (8) | 0.0121 (8) |
C17 | 0.0191 (9) | 0.0193 (8) | 0.0208 (9) | 0.0004 (7) | 0.0023 (7) | −0.0054 (7) |
C18 | 0.0196 (9) | 0.0228 (9) | 0.0146 (8) | 0.0048 (7) | 0.0011 (7) | −0.0002 (7) |
C19 | 0.0308 (10) | 0.0254 (9) | 0.0156 (9) | 0.0029 (8) | 0.0022 (7) | 0.0053 (7) |
I1—C1 | 2.0963 (17) | C8—C17 | 1.513 (2) |
Cl1—C12 | 1.7459 (18) | C9—C10 | 1.395 (2) |
O1—C4 | 1.395 (2) | C9—C14 | 1.394 (2) |
O1—C15 | 1.377 (2) | C10—H10 | 0.9500 |
N1—N2 | 1.399 (2) | C10—C11 | 1.384 (3) |
N1—C7 | 1.281 (2) | C11—H11 | 0.9500 |
C1—C2 | 1.389 (2) | C11—C12 | 1.379 (3) |
C1—C6 | 1.388 (2) | C12—C13 | 1.381 (3) |
O2—C15 | 1.193 (2) | C13—H13 | 0.9500 |
N2—C8 | 1.491 (2) | C13—C14 | 1.392 (3) |
N2—C18 | 1.366 (2) | C14—H14 | 0.9500 |
C2—H2 | 0.9500 | C15—C16 | 1.493 (2) |
C2—C3 | 1.404 (2) | C16—H16A | 0.9800 |
O3—C7 | 1.366 (2) | C16—H16B | 0.9800 |
O3—C8 | 1.4568 (19) | C16—H16C | 0.9800 |
C3—C4 | 1.400 (2) | C17—H17A | 0.9800 |
C3—C7 | 1.464 (2) | C17—H17B | 0.9800 |
O4—C18 | 1.221 (2) | C17—H17C | 0.9800 |
C4—C5 | 1.384 (2) | C18—C19 | 1.505 (3) |
C5—H5 | 0.9500 | C19—H19A | 0.9800 |
C5—C6 | 1.389 (2) | C19—H19B | 0.9800 |
C6—H6 | 0.9500 | C19—H19C | 0.9800 |
C8—C9 | 1.520 (2) | ||
C15—O1—C4 | 114.96 (13) | C11—C10—H10 | 119.4 |
C7—N1—N2 | 104.84 (14) | C10—C11—H11 | 120.6 |
C2—C1—I1 | 119.80 (13) | C12—C11—C10 | 118.76 (16) |
C6—C1—I1 | 118.83 (13) | C12—C11—H11 | 120.6 |
C6—C1—C2 | 121.32 (16) | C11—C12—Cl1 | 118.47 (14) |
N1—N2—C8 | 111.55 (13) | C11—C12—C13 | 121.84 (16) |
C18—N2—N1 | 123.28 (14) | C13—C12—Cl1 | 119.69 (14) |
C18—N2—C8 | 125.17 (14) | C12—C13—H13 | 120.6 |
C1—C2—H2 | 120.0 | C12—C13—C14 | 118.87 (17) |
C1—C2—C3 | 119.95 (15) | C14—C13—H13 | 120.6 |
C3—C2—H2 | 120.0 | C9—C14—H14 | 119.7 |
C7—O3—C8 | 107.76 (12) | C13—C14—C9 | 120.60 (16) |
C2—C3—C7 | 118.79 (15) | C13—C14—H14 | 119.7 |
C4—C3—C2 | 118.07 (15) | O1—C15—C16 | 110.52 (15) |
C4—C3—C7 | 123.10 (15) | O2—C15—O1 | 122.00 (15) |
O1—C4—C3 | 120.76 (15) | O2—C15—C16 | 127.46 (17) |
C5—C4—O1 | 117.65 (15) | C15—C16—H16A | 109.5 |
C5—C4—C3 | 121.53 (15) | C15—C16—H16B | 109.5 |
C4—C5—H5 | 120.0 | C15—C16—H16C | 109.5 |
C4—C5—C6 | 120.03 (16) | H16A—C16—H16B | 109.5 |
C6—C5—H5 | 120.0 | H16A—C16—H16C | 109.5 |
C1—C6—C5 | 119.06 (16) | H16B—C16—H16C | 109.5 |
C1—C6—H6 | 120.5 | C8—C17—H17A | 109.5 |
C5—C6—H6 | 120.5 | C8—C17—H17B | 109.5 |
N1—C7—O3 | 116.24 (15) | C8—C17—H17C | 109.5 |
N1—C7—C3 | 128.02 (15) | H17A—C17—H17B | 109.5 |
O3—C7—C3 | 115.71 (14) | H17A—C17—H17C | 109.5 |
N2—C8—C9 | 112.35 (14) | H17B—C17—H17C | 109.5 |
N2—C8—C17 | 112.57 (14) | N2—C18—C19 | 116.68 (16) |
O3—C8—N2 | 99.28 (12) | O4—C18—N2 | 119.87 (16) |
O3—C8—C9 | 108.34 (13) | O4—C18—C19 | 123.46 (16) |
O3—C8—C17 | 108.37 (13) | C18—C19—H19A | 109.5 |
C17—C8—C9 | 114.64 (14) | C18—C19—H19B | 109.5 |
C10—C9—C8 | 119.22 (15) | C18—C19—H19C | 109.5 |
C14—C9—C8 | 122.03 (15) | H19A—C19—H19B | 109.5 |
C14—C9—C10 | 118.74 (16) | H19A—C19—H19C | 109.5 |
C9—C10—H10 | 119.4 | H19B—C19—H19C | 109.5 |
C11—C10—C9 | 121.16 (16) | ||
I1—C1—C2—C3 | −175.79 (12) | C6—C1—C2—C3 | 1.7 (3) |
I1—C1—C6—C5 | 175.24 (13) | C7—N1—N2—C8 | 2.98 (18) |
Cl1—C12—C13—C14 | 178.69 (14) | C7—N1—N2—C18 | −176.27 (16) |
O1—C4—C5—C6 | 178.30 (15) | C7—O3—C8—N2 | 5.51 (15) |
N1—N2—C8—O3 | −5.26 (16) | C7—O3—C8—C9 | −111.89 (14) |
N1—N2—C8—C9 | 109.07 (15) | C7—O3—C8—C17 | 123.16 (14) |
N1—N2—C8—C17 | −119.69 (15) | C7—C3—C4—O1 | −1.2 (2) |
N1—N2—C18—O4 | −179.05 (16) | C7—C3—C4—C5 | 175.70 (15) |
N1—N2—C18—C19 | 0.9 (2) | C8—N2—C18—O4 | 1.8 (3) |
C1—C2—C3—C4 | 0.4 (2) | C8—N2—C18—C19 | −178.20 (15) |
C1—C2—C3—C7 | −177.32 (15) | C8—O3—C7—N1 | −4.56 (19) |
N2—N1—C7—O3 | 0.98 (19) | C8—O3—C7—C3 | 173.32 (13) |
N2—N1—C7—C3 | −176.59 (16) | C8—C9—C10—C11 | −179.82 (16) |
N2—C8—C9—C10 | −74.07 (19) | C8—C9—C14—C13 | 179.91 (16) |
N2—C8—C9—C14 | 106.70 (18) | C9—C10—C11—C12 | −0.3 (3) |
C2—C1—C6—C5 | −2.3 (3) | C10—C9—C14—C13 | 0.7 (3) |
C2—C3—C4—O1 | −178.77 (14) | C10—C11—C12—Cl1 | −178.58 (14) |
C2—C3—C4—C5 | −1.9 (2) | C10—C11—C12—C13 | 1.1 (3) |
C2—C3—C7—N1 | −174.43 (16) | C11—C12—C13—C14 | −1.0 (3) |
C2—C3—C7—O3 | 8.0 (2) | C12—C13—C14—C9 | 0.1 (3) |
O3—C8—C9—C10 | 34.6 (2) | C14—C9—C10—C11 | −0.6 (3) |
O3—C8—C9—C14 | −144.63 (15) | C15—O1—C4—C3 | −83.54 (19) |
C3—C4—C5—C6 | 1.3 (3) | C15—O1—C4—C5 | 99.47 (17) |
C4—O1—C15—O2 | 0.4 (2) | C17—C8—C9—C10 | 155.75 (16) |
C4—O1—C15—C16 | −178.08 (15) | C17—C8—C9—C14 | −23.5 (2) |
C4—C3—C7—N1 | 8.0 (3) | C18—N2—C8—O3 | 173.97 (15) |
C4—C3—C7—O3 | −169.58 (15) | C18—N2—C8—C9 | −71.7 (2) |
C4—C5—C6—C1 | 0.8 (3) | C18—N2—C8—C17 | 59.5 (2) |
Cg2 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.95 | 2.47 | 3.258 (2) | 140 |
C11—H11···O1ii | 0.95 | 2.55 | 3.435 (2) | 155 |
C19—H19B···Cg2iii | 0.98 | 2.75 | 3.649 (2) | 153 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y, z−1. |
Compound | KB | Hep-G2 |
6a | 3.733±0.472 | 12.574±0.766 |
6b | 9.214±0.884 | 14.735±0.727 |
6c | 5.280±0.819 | 12.284±0.625 |
6d | 1.867±0.568 | 4.564±0.539 |
6e | 4.012±0.622 | 3.811±0.822 |
6f | 0.921±0.360 | 3.315±0.552 |
6g | 6.262±0.645 | 13.260±0.866 |
6h | 3.166±0.398 | 3.983±0.482 |
6i | 12.476±0.979 | 11.900±1.036 |
Elipcitine | 1.260±0,528 | 2.358±0.407 |
Note: (a) IC50 is the concentration of the compound required to inhibit cell growth by 50%. |