# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- CBZ-INDO CCDC Deposition version.cif' _publ_contact_author 'Kenneth Shankland' _publ_contact_author_email k.shankland@reading.ac.uk loop_ _publ_author_name 'Mridul Majumder' 'Graham Buckton' 'Clare Rawlinson-Malone' 'Adrian C. Williams' ; M.J.Spillman ; 'Kenneth Shankland' _publ_contact_author_name 'Kenneth Shankland' data_CBZ-INDO _database_code_depnum_ccdc_archive 'CCDC 827277' _chemical_name_common ; 5H-dibenz(b,f)azepine-5-carboxamide 2-(1-((4- chlorophenyl)carbonyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (1/1) ; _chemical_name_systematic ; 5H-dibenz[b,f]azepine-5-carboxamide 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid (1/1) ; _chemical_formula_moiety 'C15 H12 N2 O1, C19 H16 Cl1 N1 O4' _chemical_formula_sum 'C34 H28 Cl1 N3 O5' _chemical_formula_weight 594.055 _exptl_crystal_colour off-white _chemical_melting_point 417 _exptl_crystal_description powder _exptl_special_details ; laboratory-based powder diffraction data ; _refine_special_details ; Pawley refinement Rwp = 1.58 Rietveld refinement Rwp = 3.99 Errors on unit cell parameter from Pawley refinement Errors on atomic coordinate via 'bootstrap method' of TOPAS ; _cell_length_a 10.2447(3) _cell_length_b 29.148(1) _cell_length_c 10.2114(3) _cell_angle_alpha 90 _cell_angle_beta 106.636(2) _cell_angle_gamma 90 _cell_volume 2921.6(2) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y+1/2, z+1/2' _cell_formula_units_Z 4 _cell_measurement_temperature 293 _exptl_crystal_density_diffrn 1.3505 _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Cu K\a~1~' _diffrn_radiation_wavelength 1.54056 _diffrn_measurement_device_type ; Bruker AXS D8 Advance X-ray powder diffractometer ; _pd_proc_ls_prof_wR_factor 3.99 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv N2 N Uiso 0.68413(46) 0.071467(80) 0.26161(23) 1 0.0514 C33 C Uiso 0.55557(42) 0.055179(88) 0.17657(26) 1 0.0514 C20 C Uiso 0.79826(43) 0.040902(94) 0.28227(24) 1 0.0514 C34 C Uiso 0.69567(53) 0.112311(70) 0.33236(28) 1 0.0514 C32 C Uiso 0.49611(40) 0.07659(11) 0.05189(28) 1 0.0514 C28 C Uiso 0.48936(44) 0.019493(87) 0.22222(30) 1 0.0514 C21 C Uiso 0.90690(40) 0.05205(13) 0.23326(28) 1 0.0514 C25 C Uiso 0.79654(47) -0.000378(80) 0.35142(28) 1 0.0514 N3 N Uiso 0.58020(58) 0.13631(13) 0.31433(78) 1 0.0514 O5 O Uiso 0.80572(58) 0.12544(11) 0.40762(36) 1 0.0514 C31 C Uiso 0.36789(38) 0.06366(13) -0.02641(33) 1 0.0514 H26 H Uiso 0.54632(43) 0.10237(12) 0.03190(28) 1 0.0621 C27 C Uiso 0.55127(51) -0.005978(81) 0.34792(31) 1 0.0514 C29 C Uiso 0.35920(42) 0.00716(11) 0.14071(36) 1 0.0514 C22 C Uiso 1.01633(39) 0.02271(16) 0.25322(36) 1 0.0514 H17 H Uiso 0.90432(41) 0.07990(15) 0.18237(28) 1 0.0621 C24 C Uiso 0.90997(47) -0.02946(10) 0.37043(37) 1 0.0514 C26 C Uiso 0.68319(53) -0.014748(69) 0.40175(29) 1 0.0514 H27 H Uiso 0.58625(63) 0.16186(14) 0.34949(82) 1 0.0621 H28 H Uiso 0.50516(58) 0.12600(18) 0.2575(11) 1 0.0621 C30 C Uiso 0.29938(38) 0.02902(13) 0.01854(37) 1 0.0514 H25 H Uiso 0.32774(39) 0.08055(15) -0.11445(35) 1 0.0621 H22 H Uiso 0.48814(55) -0.022525(99) 0.37997(36) 1 0.0621 H23 H Uiso 0.30673(45) -0.01817(12) 0.17291(42) 1 0.0621 C23 C Uiso 1.01784(42) -0.01817(14) 0.32201(41) 1 0.0514 H18 H Uiso 1.09479(37) 0.02999(19) 0.21859(41) 1 0.0621 H20 H Uiso 0.90820(52) -0.056369(93) 0.41972(41) 1 0.0621 H21 H Uiso 0.71167(58) -0.036986(75) 0.48245(33) 1 0.0621 H24 H Uiso 0.20535(36) 0.01966(15) -0.04590(42) 1 0.0621 H19 H Uiso 1.09527(43) -0.03870(16) 0.33887(49) 1 0.0621 N1 N Uiso 1.09562(15) 0.319057(99) 0.73980(18) 1 0.0514 C1 C Uiso 1.00318(28) 0.28746(12) 0.77036(23) 1 0.0514 C8 C Uiso 1.02574(13) 0.343046(75) 0.61944(15) 1 0.0514 C9 C Uiso 1.22729(13) 0.32823(15) 0.82619(23) 1 0.0514 C2 C Uiso 0.88258(26) 0.29008(14) 0.67058(21) 1 0.0514 C16 C Uiso 1.04416(45) 0.25556(16) 0.88899(35) 1 0.0514 C3 C Uiso 0.89361(14) 0.32522(12) 0.57555(13) 1 0.0514 C7 C Uiso 1.06493(27) 0.379060(70) 0.55035(24) 1 0.0514 O1 O Uiso 1.31696(12) 0.34253(22) 0.78057(28) 1 0.0514 C10 C Uiso 1.24848(23) 0.32210(12) 0.97572(22) 1 0.0514 C17 C Uiso 0.75645(39) 0.26278(20) 0.65770(30) 1 0.0514 H9 H Uiso 0.97572(57) 0.23126(17) 0.87820(43) 1 0.0621 H10 H Uiso 1.05118(40) 0.27253(20) 0.97353(29) 1 0.0621 H11 H Uiso 1.13265(51) 0.24184(16) 0.89336(44) 1 0.0621 C4 C Uiso 0.79770(17) 0.34241(17) 0.45813(14) 1 0.0514 C6 C Uiso 0.97043(37) 0.39558(11) 0.43418(29) 1 0.0514 H4 H Uiso 1.15359(33) 0.391982(84) 0.58157(29) 1 0.0621 C11 C Uiso 1.15766(37) 0.34053(28) 1.04032(25) 1 0.0514 C15 C Uiso 1.36712(52) 0.30091(21) 1.05317(25) 1 0.0514 H12 H Uiso 0.67681(30) 0.28369(23) 0.63523(38) 1 0.0621 H13 H Uiso 0.76207(52) 0.24814(27) 0.74657(35) 1 0.0621 C18 C Uiso 0.73506(49) 0.22632(16) 0.54932(47) 1 0.0514 H2 H Uiso 0.70799(17) 0.33027(22) 0.42839(16) 1 0.0621 C5 C Uiso 0.83815(31) 0.37737(16) 0.38777(23) 1 0.0514 H3 H Uiso 0.99571(50) 0.41990(12) 0.38443(37) 1 0.0621 H5 H Uiso 1.07621(56) 0.35474(43) 0.98732(31) 1 0.0621 C12 C Uiso 1.18509(45) 0.33834(28) 1.18123(25) 1 0.0514 C14 C Uiso 1.39377(57) 0.29750(20) 1.19309(24) 1 0.0514 H8 H Uiso 1.43000(73) 0.28872(35) 1.00952(31) 1 0.0621 O3 O Uiso 0.82337(60) 0.19258(19) 0.58216(69) 1 0.0514 O4 O Uiso 0.64306(64) 0.22778(20) 0.44291(54) 1 0.0514 O2 O Uiso 0.75640(43) 0.39783(22) 0.27207(32) 1 0.0514 H6 H Uiso 1.12430(67) 0.35144(42) 1.22571(31) 1 0.0621 C13 C Uiso 1.30343(40) 0.31653(10) 1.25587(21) 1 0.0514 H7 H Uiso 1.47338(81) 0.28226(34) 1.24580(30) 1 0.0621 H1 H Uiso 0.80307(67) 0.17188(17) 0.51277(84) 1 0.0621 C19 C Uiso 0.62823(75) 0.37664(37) 0.20696(76) 1 0.0514 Cl1 Cl Uiso 1.34178(52) 0.31450(11) 1.43316(20) 1 0.0514 H14 H Uiso 0.57700(45) 0.37246(64) 0.2738(12) 1 0.0621 H15 H Uiso 0.6439(16) 0.34671(30) 0.17034(99) 1 0.0621 H16 H Uiso 0.57612(69) 0.39621(40) 0.13224(70) 1 0.0621 _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C13 1.740(3) . . yes O1 C9 1.216(3) . . yes O2 C5 1.373(5) . . yes O2 C19 1.431(10) . . yes O3 C18 1.313(8) . . yes O4 C18 1.218(7) . . yes O3 H1 0.908(9) . . no O5 C34 1.229(7) . . yes N1 C8 1.417(3) . . yes N1 C9 1.410(3) . . yes N1 C1 1.418(4) . . yes N2 C33 1.434(5) . . yes N2 C34 1.380(3) . . yes N2 C20 1.437(6) . . yes N3 C34 1.341(7) . . yes N3 H27 0.822(7) . . no N3 H28 0.873(11) . . no C1 C2 1.360(4) . . no C1 C16 1.489(5) . . no C2 C3 1.438(4) . . no C2 C17 1.490(6) . . no C3 C4 1.407(3) . . no C3 C8 1.399(2) . . no C4 C5 1.377(5) . . no C5 C6 1.405(5) . . no C6 C7 1.385(4) . . no C7 C8 1.386(3) . . no C9 C10 1.490(3) . . no C10 C15 1.391(5) . . no C10 C11 1.393(5) . . no C11 C12 1.386(4) . . no C12 C13 1.387(6) . . no C13 C14 1.384(7) . . no C14 C15 1.379(4) . . no C17 C18 1.505(7) . . no C4 H2 0.950(4) . . no C6 H3 0.951(5) . . no C7 H4 0.950(4) . . no C11 H5 0.950(9) . . no C12 H6 0.950(9) . . no C14 H7 0.949(9) . . no C15 H8 0.952(8) . . no C16 H9 0.981(7) . . no C16 H10 0.979(5) . . no C16 H11 0.980(7) . . no C17 H12 0.992(7) . . no C17 H13 0.991(6) . . no C19 H14 0.980(12) . . no C19 H15 0.980(15) . . no C19 H16 0.980(13) . . no C20 C25 1.398(4) . . no C20 C21 1.383(6) . . no C21 C22 1.378(6) . . no C22 C23 1.381(6) . . no C23 C24 1.373(7) . . no C24 C25 1.407(6) . . no C25 C26 1.459(7) . . no C26 C27 1.330(7) . . no C27 C28 1.461(4) . . no C28 C33 1.393(5) . . no C28 C29 1.402(6) . . no C29 C30 1.379(5) . . no C30 C31 1.381(6) . . no C31 C32 1.380(5) . . no C32 C33 1.392(4) . . no C21 H17 0.960(5) . . no C22 H18 0.990(6) . . no C23 H19 0.969(6) . . no C24 H20 0.935(5) . . no C26 H21 1.023(4) . . no C27 H22 0.939(6) . . no C29 H23 1.022(5) . . no C30 H24 1.035(6) . . no C31 H25 1.005(5) . . no C32 H26 0.965(5) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O2 C19 117.7(6) . . . yes C18 O3 H1 108.1(8) . . . no C1 N1 C9 124.4(2) . . . yes C8 N1 C9 127.2(2) . . . yes C1 N1 C8 107.95(16) . . . yes C33 N2 C34 121.9(4) . . . yes C20 N2 C34 120.9(4) . . . yes C20 N2 C33 116.8(2) . . . yes H27 N3 H28 123.0(9) . . . no C34 N3 H28 119.1(6) . . . no C34 N3 H27 117.3(8) . . . no N1 C1 C2 108.6(2) . . . yes C2 C1 C16 129.0(3) . . . no N1 C1 C16 122.3(3) . . . yes C1 C2 C3 108.4(3) . . . no C1 C2 C17 127.9(3) . . . no C3 C2 C17 123.7(2) . . . no C2 C3 C4 131.2(2) . . . no C4 C3 C8 121.1(3) . . . no C2 C3 C8 107.71(17) . . . no C3 C4 C5 117.8(2) . . . no O2 C5 C4 124.7(3) . . . yes O2 C5 C6 114.7(4) . . . yes C4 C5 C6 120.6(2) . . . no C5 C6 C7 121.8(3) . . . no C6 C7 C8 117.8(3) . . . no N1 C8 C3 107.27(18) . . . yes N1 C8 C7 131.82(18) . . . yes C3 C8 C7 120.86(19) . . . no O1 C9 C10 121.9(2) . . . yes O1 C9 N1 121.2(2) . . . yes N1 C9 C10 116.82(17) . . . yes C11 C10 C15 119.7(3) . . . no C9 C10 C11 121.2(3) . . . no C9 C10 C15 118.9(2) . . . no C10 C11 C12 120.6(4) . . . no C11 C12 C13 118.5(4) . . . no Cl1 C13 C12 119.3(3) . . . yes Cl1 C13 C14 119.1(3) . . . yes C12 C13 C14 121.6(2) . . . no C13 C14 C15 119.4(4) . . . no C10 C15 C14 120.2(4) . . . no C2 C17 C18 112.5(3) . . . no O3 C18 O4 123.7(6) . . . yes O3 C18 C17 113.4(5) . . . yes O4 C18 C17 122.9(5) . . . yes C5 C4 H2 121.1(3) . . . no C3 C4 H2 121.1(4) . . . no C5 C6 H3 119.1(4) . . . no C7 C6 H3 119.1(5) . . . no C8 C7 H4 121.2(3) . . . no C6 C7 H4 121.1(3) . . . no C10 C11 H5 119.7(4) . . . no C12 C11 H5 119.7(6) . . . no C11 C12 H6 120.8(6) . . . no C13 C12 H6 120.7(4) . . . no C15 C14 H7 120.3(6) . . . no C13 C14 H7 120.3(4) . . . no C10 C15 H8 119.9(4) . . . no C14 C15 H8 119.9(5) . . . no H10 C16 H11 109.4(5) . . . no C1 C16 H10 109.5(5) . . . no C1 C16 H9 109.5(4) . . . no H9 C16 H11 109.5(6) . . . no C1 C16 H11 109.5(4) . . . no H9 C16 H10 109.5(5) . . . no C2 C17 H12 109.2(6) . . . no C18 C17 H13 109.1(7) . . . no C2 C17 H13 109.2(4) . . . no C18 C17 H12 109.1(4) . . . no H12 C17 H13 107.8(6) . . . no O2 C19 H16 109.4(11) . . . no O2 C19 H14 109.4(10) . . . no O2 C19 H15 109.4(12) . . . no H14 C19 H15 109.7(17) . . . no H14 C19 H16 109.5(12) . . . no H15 C19 H16 109.4(11) . . . no N2 C20 C21 120.4(3) . . . yes N2 C20 C25 118.7(4) . . . yes C21 C20 C25 120.9(4) . . . no C20 C21 C22 120.4(3) . . . no C21 C22 C23 120.0(4) . . . no C22 C23 C24 119.8(4) . . . no C23 C24 C25 121.6(3) . . . no C20 C25 C24 117.3(4) . . . no C20 C25 C26 123.5(4) . . . no C24 C25 C26 119.2(3) . . . no C25 C26 C27 128.0(3) . . . no C26 C27 C28 126.5(4) . . . no C29 C28 C33 117.7(3) . . . no C27 C28 C33 122.9(3) . . . no C27 C28 C29 119.4(3) . . . no C28 C29 C30 121.3(3) . . . no C29 C30 C31 120.1(4) . . . no C30 C31 C32 119.8(3) . . . no C31 C32 C33 120.2(3) . . . no C28 C33 C32 120.9(3) . . . no N2 C33 C28 119.7(3) . . . yes N2 C33 C32 119.4(3) . . . yes O5 C34 N2 121.5(4) . . . yes O5 C34 N3 122.6(4) . . . yes N2 C34 N3 115.9(4) . . . yes C20 C21 H17 119.6(5) . . . no C22 C21 H17 120.0(5) . . . no C21 C22 H18 121.6(5) . . . no C23 C22 H18 118.4(5) . . . no C22 C23 H19 120.8(5) . . . no C24 C23 H19 119.4(5) . . . no C23 C24 H20 122.5(6) . . . no C25 C24 H20 115.9(6) . . . no C25 C26 H21 113.2(5) . . . no C27 C26 H21 118.5(5) . . . no C26 C27 H22 118.5(4) . . . no C28 C27 H22 113.5(5) . . . no C28 C29 H23 119.6(4) . . . no C30 C29 H23 119.1(4) . . . no C29 C30 H24 123.0(4) . . . no C31 C30 H24 116.8(4) . . . no C30 C31 H25 122.6(4) . . . no C32 C31 H25 117.6(4) . . . no C31 C32 H26 124.5(4) . . . no C33 C32 H26 115.0(4) . . . no 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 C19 O2 C5 C6 170.5(5) . . . . no C19 O2 C5 C4 -10.9(7) . . . . no C9 N1 C1 C2 175.0(3) . . . . no C9 N1 C1 C16 -9.2(5) . . . . no C1 N1 C8 C3 -1.7(3) . . . . no C1 N1 C8 C7 175.6(2) . . . . no C9 N1 C8 C3 -173.8(2) . . . . no C9 N1 C8 C7 3.4(4) . . . . no C8 N1 C1 C16 178.3(3) . . . . no C1 N1 C9 C10 -28.5(5) . . . . no C8 N1 C9 O1 -34.1(6) . . . . no C8 N1 C9 C10 142.6(3) . . . . no C1 N1 C9 O1 154.9(4) . . . . no C8 N1 C1 C2 2.5(3) . . . . no C34 N2 C33 C32 72.9(5) . . . . no C20 N2 C33 C32 -114.0(3) . . . . no C34 N2 C33 C28 -104.5(4) . . . . no C33 N2 C34 O5 178.2(4) . . . . no C33 N2 C34 N3 -1.5(5) . . . . no C20 N2 C33 C28 68.7(4) . . . . no C33 N2 C20 C25 -64.4(3) . . . . no C34 N2 C20 C21 -71.8(4) . . . . no C33 N2 C20 C21 114.9(3) . . . . no C20 N2 C34 N3 -174.4(4) . . . . no C34 N2 C20 C25 108.9(4) . . . . no C20 N2 C34 O5 5.3(5) . . . . no N1 C1 C2 C17 178.7(3) . . . . no N1 C1 C2 C3 -2.3(4) . . . . no C16 C1 C2 C17 3.2(6) . . . . no C16 C1 C2 C3 -177.8(3) . . . . no C1 C2 C17 C18 -104.8(4) . . . . no C3 C2 C17 C18 76.3(5) . . . . no C17 C2 C3 C8 -179.7(3) . . . . no C17 C2 C3 C4 1.4(6) . . . . no C1 C2 C3 C8 1.3(3) . . . . no C1 C2 C3 C4 -177.7(3) . . . . no C4 C3 C8 N1 179.3(3) . . . . no C2 C3 C8 C7 -177.4(2) . . . . no C2 C3 C4 C5 178.9(3) . . . . no C4 C3 C8 C7 1.7(4) . . . . no C8 C3 C4 C5 0.0(5) . . . . no C2 C3 C8 N1 0.3(3) . . . . no C3 C4 C5 C6 -1.2(5) . . . . no C3 C4 C5 O2 -179.7(4) . . . . no C4 C5 C6 C7 0.7(5) . . . . no O2 C5 C6 C7 179.3(3) . . . . no C5 C6 C7 C8 1.1(4) . . . . no C6 C7 C8 C3 -2.2(3) . . . . no C6 C7 C8 N1 -179.2(3) . . . . no O1 C9 C10 C11 128.9(6) . . . . no O1 C9 C10 C15 -45.7(6) . . . . no N1 C9 C10 C11 -47.7(6) . . . . no N1 C9 C10 C15 137.6(4) . . . . no C15 C10 C11 C12 0.7(9) . . . . no C9 C10 C15 C14 175.7(5) . . . . no C11 C10 C15 C14 1.0(8) . . . . no C9 C10 C11 C12 -173.9(6) . . . . no C10 C11 C12 C13 -1.4(11) . . . . no C11 C12 C13 Cl1 178.6(6) . . . . no C11 C12 C13 C14 0.5(9) . . . . no C12 C13 C14 C15 1.1(8) . . . . no Cl1 C13 C14 C15 -177.0(4) . . . . no C13 C14 C15 C10 -1.8(8) . . . . no C2 C17 C18 O4 -111.3(6) . . . . no C2 C17 C18 O3 70.0(6) . . . . no N2 C20 C21 C22 -180.0(3) . . . . no C25 C20 C21 C22 -0.7(5) . . . . no N2 C20 C25 C24 -179.8(3) . . . . no N2 C20 C25 C26 1.3(4) . . . . no C21 C20 C25 C24 0.9(4) . . . . no C21 C20 C25 C26 -178.1(3) . . . . no C20 C21 C22 C23 0.2(5) . . . . no C21 C22 C23 C24 0.0(6) . . . . no C22 C23 C24 C25 0.2(6) . . . . no C23 C24 C25 C20 -0.7(5) . . . . no C23 C24 C25 C26 178.3(3) . . . . no C20 C25 C26 C27 32.3(4) . . . . no C24 C25 C26 C27 -146.6(3) . . . . no C25 C26 C27 C28 1.7(4) . . . . no C26 C27 C28 C29 146.8(3) . . . . no C26 C27 C28 C33 -31.5(5) . . . . no C27 C28 C29 C30 -177.3(3) . . . . no C33 C28 C29 C30 1.1(5) . . . . no C27 C28 C33 N2 -6.7(5) . . . . no C27 C28 C33 C32 176.0(3) . . . . no C29 C28 C33 N2 175.0(3) . . . . no C29 C28 C33 C32 -2.3(5) . . . . no C28 C29 C30 C31 0.3(6) . . . . no C29 C30 C31 C32 -0.5(6) . . . . no C30 C31 C32 C33 -0.8(5) . . . . no C31 C32 C33 N2 -175.1(3) . . . . no C31 C32 C33 C28 2.2(5) . . . . no