Crystal Structures of Intermediates in a New Synthesis of Antitumor Drug Cabozantinib (2016)

All s.u.'s (except the s.u. in the dihedral angle between two l.s.planes) are estimated using the full covariance matrix.The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry.An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s.planes.; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.309(6) .?O1 C11 1.430(5) .?O2 C9 1.315(5) .?O2 C10 1.431(5) .?O3 C4 1.273(5) .?N1 C6 1.331(6) .?N1 C7 1.366(5) .?N1 H1 0.85(2) .?C10 H10A 0.98 .?C10 H10B 0.98 .?C10 H10C 0.98 .?C9 C8 1.370(7) .?C9 C1 1.431(6) .?C7 C3 1.392(5) .?C7 C8 1.418(6) .?C6 C5 1.371(6) .?C6 H6 0.95 .?C5 C4 1.430(6) .?C5 H5 0.95 .?C3 C2 1.421(6) .?C3 C4 1.451(6) .?C1 C2 1.378(6) .?C2 H2 0.95 .?C11 H11A 0.98 .?C11 H11B 0.98 .?C11 H11C 0.98 .?C8 H8 0.95 .?O4 H41 0.8588 .?O4 H42 0.8538 .? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C11 116.5(3) . .?C9 O2 C10 117.6(4) . .?C6 N1 C7 121.7(3) . .?C6 N1 H1 120(4) . .?C7 N1 H1 117(4) . .?O2 C10 H10A 109.5 . .?O2 C10 H10B 109.5 . .?H10A C10 H10B 109.5 . .?O2 C10 H10C 109.5 . .?H10A C10 H10C 109.5 . .?H10B C10 H10C 109.5 . .?O2 C9 C8 123.8(4) . .?O2 C9 C1 115.9(4) . .?C8 C9 C1 120.2(4) . .?N1 C7 C3 119.9(4) . .?N1 C7 C8 118.3(4) . .?C3 C7 C8 121.8(4) . .?N1 C6 C5 122.0(4) . .?N1 C6 H6 119 . .?C5 C6 H6 119 . .?C6 C5 C4 120.3(4) . .?C6 C5 H5 119.9 . .?C4 C5 H5 119.9 . .?C7 C3 C2 117.1(4) . .?C7 C3 C4 120.0(4) . .?C2 C3 C4 122.9(3) . .?O1 C1 C2 126.3(4) . .?O1 C1 C9 114.9(3) . .?C2 C1 C9 118.9(4) . .?O3 C4 C5 122.7(4) . .?O3 C4 C3 121.3(4) . .?C5 C4 C3 116.1(3) . .?C1 C2 C3 122.4(3) . .?C1 C2 H2 118.8 . .?C3 C2 H2 118.8 . .?O1 C11 H11A 109.5 . .?O1 C11 H11B 109.5 . .?H11A C11 H11B 109.5 . .?O1 C11 H11C 109.5 . .?H11A C11 H11C 109.5 . .?H11B C11 H11C 109.5 . .?C9 C8 C7 119.7(4) . .?C9 C8 H8 120.1 . .?C7 C8 H8 120.1 . .?H41 O4 H42 109.3 . .?C14 C15 C10 120.97(17) . .?C14 C15 H15 119.5 . .?C10 C15 H15 119.5 . .?C2 C2 C1 61.28(6) 8_565 .?C2 C2 H2A 117.6 8_565 .?C1 C2 H2A 117.6 . .?C2 C2 H2B 117.6 8_565 .?C1 C2 H2B 117.6 . .?H2A C2 H2B 114.7 . .?C13 C12 C11 118.97(18) . .?C13 C12 H12 120.5 . .?C11 C12 H12 120.5 . .?C3 C1 C6 121.53(15) . .?C3 C1 C2 116.75(13) .8_565 ?C6 C1 C2 113.96(13) .8_565 ?C3 C1 C2 116.75(13) . .?C6 C1 C2 113.96(13) . .?C2 C1 C2 57.44(13) 8_565 .?C15 C10 C11 119.49(16) . .?C15 C10 N1 116.74(16) . .?C11 C10 N1 123.77(16) . .?C13 C14 C15 118.13(18) . .?C13 C14 H14 120.9 . .?C15 C14 H14 120.9 . .?O2 C3 O1 122.68(16) . .?O2 C3 C1 125.37(16) . .?O1 C3 C1 111.96(15) . .?F1 C13 C12 118.34(17) . .?F1 C13 C14 118.95(17) . .?C12 C13 C14 122.70(18) . .?O3 C6 N1 124.07(17) . .?O3 C6 C1 119.68(16) . .?N1 C6 C1 116.25(16) . .?O1 C5 H5B 109.8(10) . .?O1 C5 H5A 105.5(13) . .?H5B C5 H5A 109.47(16) . .? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C11 C12 C13 0 . . . .?C2 C2 C1 C3 -106.03(10)8_565 . . .?C2 C2 C1 C6