#------------------------------------------------------------------------------ #$Date: 2012-02-26 23:34:47 +0200 (Sun, 26 Feb 2012) $ #$Revision: 35909 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/66/7206693.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7206693 loop_ _publ_author_name 'Majumder, Mridul' 'Buckton, Graham' 'Rawlinson-Malone, Clare' 'Williams, Adrian C.' 'Spillman, Mark J.' 'Shankland, Norman' 'Shankland, Kenneth' _publ_section_title ; A carbamazepine-indomethacin (1 : 1) cocrystal produced by milling ; _journal_issue 21 _journal_name_full CrystEngComm _journal_page_first 6327 _journal_volume 13 _journal_year 2011 _chemical_formula_moiety 'C15 H12 N2 O1, C19 H16 Cl1 N1 O4' _chemical_formula_sum 'C34 H28 Cl N3 O5' _chemical_formula_weight 594.055 _chemical_melting_point 417 _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) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 106.636(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.2447(3) _cell_length_b 29.148(1) _cell_length_c 10.2114(3) _cell_measurement_temperature 293 _cell_volume 2921.62(16) _diffrn_ambient_temperature 293 _diffrn_measurement_device_type ; Bruker AXS D8 Advance X-ray powder diffractometer ; _diffrn_radiation_type 'Cu K\a~1~' _diffrn_radiation_wavelength 1.54056 _exptl_crystal_colour off-white _exptl_crystal_density_diffrn 1.3505 _exptl_crystal_description powder _pd_proc_ls_prof_wR_factor 3.99 _[local]_cod_data_source_file c1ce05650f.txt _[local]_cod_data_source_block CBZ-INDO _[local]_cod_cif_authors_sg_H-M P21/c _[local]_cod_chemical_formula_sum_orig 'C34 H28 Cl1 N3 O5' _cod_original_cell_volume 2921.6(2) _cod_database_code 7206693 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' 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 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _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_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _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_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_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