########################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ########################################################################### # # This CIF contains data generated directly from one or more entries in # the Cambridge Structural Database and will include bibliographic, # chemical, crystal, experimental, refinement, and atomic coordinate data, # as available. # # Copyright 2010 The Cambridge Crystallographic Data Centre # # This CIF is provided on the understanding that it is used for bona fide # research purposes only. It may contain copyright material of the CCDC # or of third parties, and may not be copied or further disseminated in # any form, whether machine-readable or not, except for the purpose of # generating routine backup copies on your local computer system. # # For further information about the CCDC, data deposition and data # retrieval see . Bona fide researchers may freely # download Mercury and enCIFer from this site to visualise CIF-encoded # structures and to carry out CIF format checking respectively. # ########################################################################### data_CSD_CIF_FIFLAI _audit_creation_date 2005-06-02 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD FIFLAI _database_code_depnum_ccdc_archive 'CCDC 263495' _chemical_formula_sum 'C23 H40 N2 O3' _chemical_formula_moiety ; C17 H34 O2,C6 H6 N2 O1 ; _journal_coden_Cambridge 471 _journal_volume 21 _journal_year 2005 _journal_page_first x9 _journal_name_full 'Anal.Sci.:X-Ray Struct.Anal.Online ' loop_ _publ_author_name "M.Amai" "M.Kamijo" "H.Nagase" "T.Endo" "H.Ueda" _chemical_name_systematic ; n-Heptadecanoic acid 3-pyridinecarboxamide ; _chemical_name_common ; Margaric acid nicotinamide ; _cell_volume 1156.128 _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.118 _exptl_special_details ; The cell gamma value =92.357 not 92.0 ; _exptl_crystal_description 'prismatic' _exptl_crystal_preparation 'acetone' _diffrn_ambient_temperature 293.1 #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.058 _refine_ls_wR_factor_gt 0.058 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.37(2) _cell_length_b 5.0229(8) _cell_length_c 61.7(1) _cell_angle_alpha 57.0(2) _cell_angle_beta 63.5(3) _cell_angle_gamma 92.357(1) _cell_formula_units_Z 2 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O -0.0099(7) -0.1370(8) 0.36875(7) O2 O 0.4510(6) 0.1700(7) 0.34742(6) O3 O -0.6561(6) -0.4950(6) 0.47269(6) N1 N 0.2114(7) 0.1636(8) 0.39634(7) N2 N -0.6962(7) -0.1458(7) 0.48485(7) C1 C 0.2470(9) 0.006(1) 0.34824(9) C2 C 0.3870(9) 0.012(1) 0.32065(9) C3 C 0.1749(9) -0.066(1) 0.31357(9) C4 C 0.3394(9) -0.029(1) 0.28410(9) C5 C 0.1465(9) -0.072(1) 0.27385(9) C6 C 0.3176(9) -0.037(1) 0.24454(9) C7 C 0.1322(9) -0.064(1) 0.23302(9) C8 C 0.3047(9) -0.033(1) 0.20391(9) C9 C 0.119(1) -0.060(1) 0.19239(9) C10 C 0.289(1) -0.031(1) 0.16345(9) C11 C 0.103(1) -0.059(1) 0.1520(1) C12 C 0.274(1) -0.029(1) 0.1230(1) C13 C 0.088(1) -0.053(1) 0.1113(1) C14 C 0.261(1) -0.022(1) 0.0823(1) C15 C 0.079(1) -0.040(1) 0.0701(1) C16 C 0.253(1) -0.009(2) 0.0412(1) C17 C 0.074(1) -0.014(2) 0.0284(1) C18 C -0.0759(8) -0.0183(9) 0.41892(8) C19 C -0.2182(8) -0.0210(8) 0.44400(8) C20 C -0.0482(9) 0.1791(9) 0.44507(8) C21 C 0.2478(9) 0.3630(9) 0.42217(9) C22 C 0.3714(9) 0.349(1) 0.39823(9) C23 C -0.5407(8) -0.2393(8) 0.46824(8) H1 H 0.36540 0.18260 0.36270 H2 H -0.90420 -0.27740 0.50070 H3 H -0.59930 0.05280 0.48090 H4 H 0.47870 -0.15170 0.32450 H5 H 0.53630 0.23470 0.30290 H6 H 0.03380 -0.29540 0.33050 H7 H 0.07190 0.08660 0.31100 H8 H 0.42730 -0.19600 0.28760 H9 H 0.49320 0.19390 0.26780 H10 H -0.00890 -0.29390 0.29010 H11 H 0.06040 0.09680 0.27000 H12 H 0.39670 -0.21200 0.24870 H13 H 0.47810 0.18100 0.22860 H14 H -0.02970 -0.28130 0.24910 H15 H 0.05500 0.11230 0.22860 H16 H 0.38130 -0.21020 0.20840 H17 H 0.46690 0.18360 0.18790 H18 H -0.04480 -0.27590 0.20850 H19 H 0.04340 0.11830 0.18780 H20 H 0.36480 -0.20970 0.16810 H21 H 0.45260 0.18440 0.14730 H22 H -0.05990 -0.27510 0.16800 H23 H 0.02670 0.11880 0.14740 H24 H 0.34800 -0.20790 0.12760 H25 H 0.43750 0.18650 0.10700 H26 H -0.07520 -0.26860 0.12730 H27 H 0.01360 0.12570 0.10680 H28 H 0.33320 -0.20300 0.08700 H29 H 0.42670 0.19190 0.06650 H30 H -0.08610 -0.25380 0.08590 H31 H 0.00730 0.14100 0.06540 H32 H 0.31950 -0.19390 0.04600 H33 H 0.42200 0.20180 0.02550 H34 H -0.02360 -0.24420 0.03760 H35 H 0.20280 0.11770 0.00650 H36 H -0.07240 0.07950 0.03320 H37 H -0.19020 -0.15420 0.41780 H38 H -0.13800 0.18790 0.46170 H39 H 0.36820 0.50050 0.42270 H40 H 0.57970 0.47610 0.38230 #END data_CSD_CIF_GOGQID _audit_creation_date 2009-03-31 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD GOGQID _database_code_depnum_ccdc_archive 'CCDC 662940' _chemical_formula_sum 'C15 H16 N2 O4' _chemical_formula_moiety ; C9 H10 O3,C6 H6 N2 O1 ; _journal_coden_Cambridge 83 _journal_volume 97 _journal_year 2008 _journal_page_first 4830 _journal_name_full 'J.Pharm.Sci. ' loop_ _publ_author_name "S.Nicoli" "S.Bilzi" "P.Santi" "M.Caira" "J.Li" "R.Bettini" _chemical_name_systematic ; 3-Pyridinecarboxamide 4-hydroxybenzoic acid ethyl ester ; _chemical_name_common ; Nicotinamide ethyl paraben ; _chemical_melting_point 380 _cell_volume 1374.684 _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.393 _exptl_special_details ; ethyl paraben has antimicrobial activity ; _exptl_crystal_description 'prism' _exptl_crystal_preparation 'ethanol' _diffrn_ambient_temperature 113 #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_gt 0.0388 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 -1/2+x,-1/2-y,-1/2+z _cell_length_a 5.1106(2) _cell_length_b 11.5175(5) _cell_length_c 23.3547(9) _cell_angle_alpha 90 _cell_angle_beta 90.148(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z N1 N 0.6535(2) 0.69321(12) 0.63361(6) C1 C 0.8254(3) 0.62797(14) 0.60479(7) H1 H 0.80780 0.54590 0.60650 C2 C 1.0282(3) 0.67415(14) 0.57250(6) C3 C 1.0504(3) 0.79401(14) 0.57012(7) H2 H 1.18560 0.82880 0.54820 C4 C 0.8760(3) 0.86257(15) 0.59967(7) H3 H 0.88910 0.94480 0.59860 C5 C 0.6816(3) 0.80863(15) 0.63086(7) H4 H 0.56170 0.85580 0.65140 C6 C 1.2234(3) 0.60164(15) 0.54056(7) O1 O 1.3584(2) 0.64762(9) 0.50267(5) N2 N 1.2456(2) 0.49038(12) 0.55494(6) H5 H 1.35990 0.44590 0.53730 H6 H 1.14610 0.46130 0.58210 C7 C -0.2073(3) 0.69507(14) 0.80843(7) C8 C -0.2289(3) 0.58028(14) 0.78987(7) H7 H -0.36390 0.53240 0.80480 C9 C -0.0571(3) 0.53517(14) 0.75014(7) H8 H -0.07400 0.45680 0.73800 C10 C 0.1412(3) 0.60483(15) 0.72783(7) C11 C 0.1616(3) 0.72008(14) 0.74536(7) H9 H 0.29500 0.76810 0.72990 C12 C -0.0111(3) 0.76513(15) 0.78510(7) H10 H 0.00370 0.84400 0.79660 O2 O 0.30412(19) 0.55561(10) 0.68935(5) H11 H 0.40810 0.60600 0.67680 C13 C -0.3848(3) 0.74421(15) 0.85191(7) O3 O -0.4022(2) 0.84734(10) 0.86302(5) O4 O -0.52612(19) 0.66283(9) 0.87907(4) C14 C -0.7102(3) 0.70573(14) 0.92147(7) H12 H -0.83700 0.75950 0.90340 H13 H -0.61610 0.74780 0.95220 C15 C -0.8498(3) 0.60204(16) 0.94566(8) H14 H -0.93370 0.55870 0.91450 H15 H -0.98310 0.62800 0.97290 H16 H -0.72360 0.55180 0.96530 #END data_CSD_CIF_IACNCA _audit_creation_date 1979-01-19 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD IACNCA _chemical_formula_sum 'C16 H15 N3 O3' _chemical_formula_moiety ; C10 H9 N1 O2,C6 H6 N2 O1 ; _journal_coden_Cambridge 7 _journal_volume 51 _journal_year 1978 _journal_page_first 1118 _journal_name_full 'Bull.Chem.Soc.Jpn. ' loop_ _publ_author_name "M.Inoue" "T.Sakaki" "T.Fujiwara" "K.Tomita" _chemical_name_systematic ; Indole-3'-acetic acid nicotinamide ; _cell_volume 1455.087 _exptl_crystal_density_diffrn 1.357 _diffrn_ambient_temperature ? _diffrn_special_details ; The study was carried out at room temperature,in the range 283-303K ; #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.069 _refine_ls_wR_factor_gt 0.069 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,-1/2-y,-1/2+z _cell_length_a 11.287(5) _cell_length_b 5.110(3) _cell_length_c 26.391(3) _cell_angle_alpha 90 _cell_angle_beta 107.07(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z N1 N 0.52960 0.41560 0.07210 C2 C 0.40790 0.40360 0.04860 C3 C 0.32490 0.57890 0.05970 C4 C 0.36950 0.77540 0.09660 C5 C 0.49650 0.78660 0.12130 C6 C 0.57110 0.60480 0.10830 C7 C 0.18990 0.54050 0.03380 N8 N 0.11810 0.75080 0.02580 O9 O 0.14780 0.31770 0.02140 N1' N 0.10260 -0.33120 0.23400 C2' C -0.00590 -0.33850 0.19280 C3' C -0.00160 -0.15690 0.15640 C4' C 0.17440 0.18120 0.15680 C5' C 0.29240 0.25410 0.18640 C6' C 0.35240 0.13100 0.23340 C7' C 0.29750 -0.06910 0.25310 C8' C 0.17910 -0.14240 0.22390 C9' C 0.11530 -0.02510 0.17520 C10' C -0.09890 -0.10300 0.10480 C11' C -0.20580 0.06020 0.10820 O12' O -0.28490 0.11090 0.06130 O13' O -0.22390 0.13070 0.14840 H1 H 0.37600 0.25500 0.02000 H2 H 0.30700 0.90900 0.10800 H3 H 0.53200 0.94000 0.15200 H4 H 0.66900 0.60800 0.12600 H5 H 0.02800 0.72900 0.01000 H6 H 0.14600 0.91900 0.02800 H7 H 0.12100 -0.45000 0.26800 H8 H -0.07800 -0.47800 0.19200 H9 H 0.12700 0.28700 0.12100 H10 H 0.33500 0.40800 0.17100 H11 H 0.43900 0.19200 0.25300 H12 H 0.34200 -0.15600 0.28900 H13 H -0.13200 -0.27400 0.08700 H14 H -0.06200 0.00200 0.07800 H15 H -0.35900 0.22300 0.06600 #END data_CSD_CIF_JILZOU _audit_creation_date 2008-02-05 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD JILZOU _database_code_depnum_ccdc_archive 'CCDC 626647' _chemical_formula_sum 'C14 H14 N2 O4' _chemical_formula_moiety ; C6 H6 N2 O1,C8 H8 O3 ; _journal_coden_Cambridge 169 _journal_volume 136 _journal_year 2007 _journal_page_first 167 _journal_name_full 'Faraday Discuss. ' loop_ _publ_author_name "T.Friscic" "W.Jones" _chemical_name_systematic ; Nicotinamide D-mandelic acid ; _chemical_melting_point 362 _cell_volume 2632.904 _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.384 _exptl_crystal_description 'needle' _diffrn_ambient_temperature 150 #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.055 _refine_ls_wR_factor_gt 0.055 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,-z 3 1/2+x,1/2+y,z 4 1/2-x,1/2+y,-z _cell_length_a 32.6557(9) _cell_length_b 5.4751(10) _cell_length_c 14.9264(5) _cell_angle_alpha 90 _cell_angle_beta 99.400(1) _cell_angle_gamma 90 _cell_formula_units_Z 8 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O 0.29418(6) -0.1324(4) 0.40557(12) O2 O 0.23670(6) -0.5853(3) 0.27289(13) O3 O 0.15961(6) -1.4919(3) 0.12750(13) H1 H 0.15840 -1.37550 0.16360 O4 O 0.21093(6) -1.2694(4) 0.08733(14) O5 O 0.21803(6) -1.5760(4) -0.05150(13) H2 H 0.23950 -1.66260 -0.04340 O6 O 0.45749(6) 0.2106(4) 0.54623(14) H3 H 0.44000 0.23320 0.49910 O7 O 0.44164(7) -0.1839(4) 0.51879(14) O8 O 0.50509(7) -0.3359(4) 0.64197(14) H4 H 0.48700 -0.41140 0.60590 N1 N 0.40103(7) 0.2790(4) 0.40376(16) N2 N 0.28225(7) -0.1388(4) 0.25223(15) H5 H 0.26310 -0.25280 0.25060 H6 H 0.28850 -0.07970 0.20130 N3 N 0.22950(8) -0.4973(4) 0.41687(16) H7 H 0.24850 -0.38200 0.42110 H8 H 0.21690 -0.52910 0.46340 N4 N 0.15586(7) -1.1643(4) 0.25247(15) C1 C 0.39900(9) 0.4586(5) 0.34164(18) H9 H 0.42130 0.57170 0.34550 C2 C 0.36548(9) 0.4840(5) 0.27220(19) H10 H 0.36480 0.61280 0.22930 C3 C 0.33286(8) 0.3190(5) 0.26611(18) H11 H 0.30960 0.33310 0.21900 C4 C 0.33475(8) 0.1322(5) 0.33008(17) C5 C 0.36957(8) 0.1205(5) 0.39719(18) H12 H 0.37110 -0.00700 0.44080 C6 C 0.30159(8) -0.0564(5) 0.33117(17) C7 C 0.21978(8) -0.6239(5) 0.33983(17) C8 C 0.18743(8) -0.8205(5) 0.33598(18) C9 C 0.18346(9) -0.9825(5) 0.26314(18) H13 H 0.20120 -0.96280 0.21910 C10 C 0.13014(9) -1.1877(5) 0.31338(19) H14 H 0.11030 -1.31600 0.30580 C11 C 0.13140(9) -1.0321(6) 0.38701(19) H15 H 0.11260 -1.05210 0.42870 C12 C 0.16071(9) -0.8467(5) 0.39871(18) H16 H 0.16250 -0.73890 0.44910 C13 C 0.18877(8) -1.4500(5) 0.07957(17) C14 C 0.19115(8) -1.6509(5) 0.00928(18) H17 H 0.20230 -1.80360 0.04110 C15 C 0.14783(9) -1.6984(5) -0.04132(17) C16 C 0.12536(9) -1.9047(5) -0.02401(19) H18 H 0.13780 -2.02400 0.01800 C17 C 0.08488(9) -1.9363(5) -0.0679(2) H19 H 0.06980 -2.07770 -0.05570 C18 C 0.06615(10) -1.7642(5) -0.1293(2) H20 H 0.03830 -1.78640 -0.15860 C19 C 0.08834(9) -1.5588(5) -0.14765(19) H21 H 0.07580 -1.44120 -0.19030 C20 C 0.12901(9) -1.5254(5) -0.10339(18) H22 H 0.14400 -1.38390 -0.11560 C21 C 0.46152(8) -0.0244(6) 0.56240(18) C22 C 0.49367(9) -0.0876(5) 0.64515(18) H23 H 0.51890 0.01570 0.64440 C23 C 0.47592(8) -0.0309(5) 0.73099(18) C24 C 0.44882(9) -0.1987(5) 0.76019(19) H24 H 0.44150 -0.34320 0.72610 C25 C 0.43249(9) -0.1557(6) 0.8388(2) H25 H 0.41360 -0.26940 0.85770 C26 C 0.44351(11) 0.0521(6) 0.8899(2) H26 H 0.43300 0.07860 0.94480 C27 C 0.46991(11) 0.2211(6) 0.8603(2) H27 H 0.47700 0.36570 0.89450 C28 C 0.48614(9) 0.1808(5) 0.78076(19) H28 H 0.50410 0.29790 0.76070 #END data_CSD_CIF_PEQBES _audit_creation_date 1998-11-04 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD PEQBES _chemical_formula_sum 'C24 H42 N2 O3' _chemical_formula_moiety ; C18 H36 O2,C6 H6 N2 O1 ; _journal_coeditor_code "IUCr OA1032" _journal_coden_Cambridge 591 _journal_volume 54 _journal_year 1998 _journal_page_first 1367 _journal_name_full 'Acta Crystallogr.,Sect.C:Cryst.Struct.Commun. ' loop_ _publ_author_name "M.Amai" "T.Endo" "H.Nagase" "H.Ueda" "M.Nakagaki" _chemical_name_systematic ; Octadecanoic acid 3-pyridinecarboxamide ; _cell_volume 1232.106 _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.096 _exptl_special_details ; structure has the pharmaceutical advantage of improved hygroscopic activity over nicotinamide ; _exptl_crystal_description 'needle' _exptl_crystal_preparation 'acetone' _diffrn_ambient_temperature ? _diffrn_special_details ; The study was carried out at room temperature,in the range 283-303K ; #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_gt 0.042 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.4313(5) _cell_length_b 45.180(3) _cell_length_c 5.0355(5) _cell_angle_alpha 92.924(6) _cell_angle_beta 92.317(8) _cell_angle_gamma 92.088(6) _cell_formula_units_Z 2 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O -0.1705(2) 0.12529(2) -0.4935(2) O2 O 0.1822(2) 0.14551(2) -0.3260(2) O3 O -0.2936(2) 0.02605(2) -0.1725(2) N1 N 0.1903(2) 0.09880(2) -0.0147(2) N2 N -0.2719(2) 0.01457(2) 0.2565(2) C1 C -0.0164(3) 0.14503(3) -0.4866(3) C2 C -0.0170(3) 0.17111(3) -0.6589(3) C3 C -0.2638(3) 0.17798(3) -0.7844(3) C4 C -0.2483(3) 0.20600(3) -0.9382(3) C5 C -0.4923(3) 0.21596(3) -1.0500(3) C6 C -0.4689(3) 0.24365(3) -1.2060(3) C7 C -0.7113(3) 0.25486(3) -1.3109(3) C8 C -0.6880(3) 0.28244(3) -1.4681(3) C9 C -0.9296(3) 0.29353(3) -1.5726(3) C10 C -0.9062(3) 0.32098(3) -1.7313(3) C11 C -1.1500(3) 0.33207(3) -1.8365(3) C12 C -1.1264(3) 0.35958(4) -1.9940(3) C13 C -1.3698(3) 0.37075(4) -2.0966(4) C14 C -1.3455(3) 0.39829(4) -2.2544(4) C15 C -1.5886(4) 0.40935(4) -2.3579(4) C16 C -1.5680(4) 0.43705(4) -2.5122(4) C17 C -1.8128(5) 0.44807(5) -2.6106(5) C18 C -1.7939(7) 0.47540(6) -2.7647(7) C19 C 0.0152(2) 0.07732(3) -0.0479(2) C20 C -0.0006(2) 0.05348(2) 0.1133(2) C21 C 0.1746(3) 0.05217(3) 0.3202(2) C22 C 0.3564(3) 0.07424(3) 0.3551(3) C23 C 0.3592(3) 0.09697(3) 0.1836(3) C24 C -0.2003(2) 0.03032(3) 0.0551(2) H1 H 0.177(3) 0.1273(4) -0.214(4) H2 H 0.048(3) 0.1877(4) -0.542(4) H3 H 0.104(4) 0.1669(5) -0.808(4) H4 H -0.383(3) 0.1803(4) -0.638(3) H5 H -0.331(3) 0.1606(4) -0.905(4) H6 H -0.164(3) 0.2227(4) -0.824(3) H7 H -0.129(3) 0.2035(4) -1.089(4) H8 H -0.609(3) 0.2198(4) -0.902(3) H9 H -0.573(3) 0.1993(4) -1.152(4) H10 H -0.377(3) 0.2599(4) -1.090(3) H11 H -0.367(3) 0.2397(4) -1.371(4) H12 H -0.819(3) 0.2583(4) -1.146(4) H13 H -0.794(3) 0.2391(4) -1.433(4) H14 H -0.591(3) 0.2989(4) -1.361(3) H15 H -0.586(3) 0.2779(4) -1.612(4) H16 H -1.034(3) 0.2975(4) -1.427(3) H17 H -1.012(3) 0.2772(4) -1.694(4) H18 H -0.818(3) 0.3365(4) -1.606(4) H19 H -0.809(3) 0.3162(4) -1.886(4) H20 H -1.252(4) 0.3363(4) -1.681(4) H21 H -1.234(3) 0.3151(4) -1.952(4) H22 H -1.041(3) 0.3761(4) -1.879(4) H23 H -1.015(4) 0.3558(4) -2.137(4) H24 H -1.481(4) 0.3758(4) -1.939(4) H25 H -1.460(4) 0.3542(5) -2.205(4) H26 H -1.255(4) 0.4150(4) -2.132(4) H27 H -1.231(3) 0.3952(4) -2.419(4) H28 H -1.702(4) 0.4129(4) -2.186(4) H29 H -1.679(4) 0.3925(4) -2.477(4) H30 H -1.472(4) 0.4544(5) -2.410(4) H31 H -1.456(4) 0.4333(5) -2.667(4) H32 H -1.914(5) 0.4539(6) -2.445(5) H33 H -1.880(6) 0.4315(7) -2.751(6) H34 H -1.709(6) 0.4936(8) -2.630(7) H35 H -1.666(6) 0.4745(6) -2.897(6) H36 H -1.947(5) 0.4831(5) -2.850(5) H37 H -0.113(3) 0.0791(3) -0.195(3) H38 H 0.174(3) 0.0356(3) 0.439(3) H39 H 0.479(3) 0.0729(4) 0.506(3) H40 H 0.496(3) 0.1140(3) 0.191(3) H41 H -0.404(3) 0.0002(4) 0.224(3) H42 H -0.228(3) 0.0207(3) 0.433(3) #END data_CSD_CIF_SODDIZ _audit_creation_date 2008-10-28 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD SODDIZ _database_code_depnum_ccdc_archive 'CCDC 678915' _chemical_formula_sum 'C19 H24 N2 O3' _chemical_formula_moiety ; C6 H6 N2 O1,C13 H18 O2 ; _journal_coden_Cambridge 1147 _journal_volume 8 _journal_year 2008 _journal_page_first 1697 _journal_name_full 'Cryst.Growth Des. ' loop_ _publ_author_name "D.J.Berry" "C.C.Seaton" "W.Clegg" "R.W.Harrington" "S.J.Coles" "P.N.Horton" "M.B.Hursthouse" "R.Storey" "W.Jones" "T.Friscic" "N.Blagden" _chemical_name_systematic ; Nicotinamide rac-ibuprofen ; _cell_volume 3592.956 _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.214 _exptl_special_details ; ibuprofen is an anti-inflammatory drug almost isostructural with the (S)-ibuprofen analogue powder data at room temperature a=11.830, b=5.554 and c=56.455 ; _exptl_crystal_description 'Slab' _diffrn_ambient_temperature 120 #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_gt 0.0582 loop_ _citation_database_id_CSD _citation_special_details SOGLAC "is a stereoisomer of this entry" _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2+x,-y,z 4 1/2-x,y,1/2+z _cell_length_a 11.652(2) _cell_length_b 5.4473(11) _cell_length_c 56.607(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1 C -0.0058(6) 0.2123(12) 0.51678(10) C2 C -0.0950(6) 0.1858(13) 0.53667(10) H1 H -0.13600 0.34600 0.53840 C3 C -0.1795(11) -0.0022(12) 0.5309(2) H2 H -0.14060 -0.15970 0.52850 H3 H -0.22030 0.04400 0.51650 H4 H -0.23450 -0.01720 0.54400 C4 C -0.0329(7) 0.1315(14) 0.55995(10) C5 C -0.0445(6) 0.2884(13) 0.5792(1) H5 H -0.08900 0.43360 0.57760 C6 C 0.0074(6) 0.2367(12) 0.60046(11) H6 H -0.00190 0.34830 0.61320 C7 C 0.0731(10) 0.0260(13) 0.60391(16) C8 C 0.0857(6) -0.1304(12) 0.58452(11) H7 H 0.13150 -0.27390 0.58590 C9 C 0.0306(7) -0.077(2) 0.56263(11) H8 H 0.03820 -0.18740 0.54980 C10 C 0.1298(11) -0.0251(14) 0.62796(15) H9 H 0.09540 0.08420 0.64000 H10 H 0.11370 -0.19670 0.63270 C11 C 0.2592(13) 0.0148(13) 0.6275(2) H11 H 0.29480 -0.09770 0.61560 C12 C 0.2891(7) 0.2757(15) 0.62161(17) H12 H 0.25530 0.31940 0.60630 H13 H 0.37270 0.29310 0.62080 H14 H 0.25880 0.38480 0.63390 C13 C 0.3064(12) -0.047(2) 0.6526(2) H15 H 0.26700 0.05380 0.66440 H16 H 0.38900 -0.01380 0.65320 H17 H 0.29280 -0.22130 0.65610 O1 O 0.0686(4) 0.3893(11) 0.52130(7) H18 H 0.11820 0.39410 0.51050 O2 O -0.0053(4) 0.0877(11) 0.49882(8) C14 C 0.2581(6) 0.2888(12) 0.31753(10) C15 C 0.3451(6) 0.3153(13) 0.2975(1) H19 H 0.38300 0.15170 0.29570 C16 C 0.4418(10) 0.5029(14) 0.3026(2) H20 H 0.49940 0.49460 0.29000 H21 H 0.47790 0.46400 0.31780 H22 H 0.40930 0.66870 0.30320 C17 C 0.2846(6) 0.3690(13) 0.2741(1) C18 C 0.2938(6) 0.2121(13) 0.25515(11) H23 H 0.33800 0.06660 0.25680 C19 C 0.2401(6) 0.2602(13) 0.23360(11) H24 H 0.24830 0.14660 0.22100 C20 C 0.1755(11) 0.4698(15) 0.2303(2) C21 C 0.1651(6) 0.6283(13) 0.24963(12) H25 H 0.12030 0.77320 0.24810 C22 C 0.2186(7) 0.579(2) 0.27093(13) H26 H 0.21010 0.69090 0.28370 C23 C 0.1195(11) 0.5241(15) 0.2074(2) H27 H 0.15790 0.42450 0.19510 H28 H 0.13400 0.69870 0.20360 C24 C -0.0073(12) 0.4795(14) 0.2056(2) H29 H -0.04430 0.59270 0.21720 C25 C -0.0399(8) 0.2197(16) 0.21313(17) H30 H -0.12320 0.19900 0.21190 H31 H -0.01590 0.19260 0.22950 H32 H -0.00140 0.10080 0.20280 C26 C -0.0569(12) 0.5401(19) 0.1823(2) H33 H -0.02070 0.43870 0.17010 H34 H -0.04340 0.71390 0.17880 H35 H -0.13970 0.50810 0.18260 O3 O 0.1839(4) 0.1126(10) 0.31303(7) H36 H 0.13950 0.09570 0.32460 O4 O 0.2563(4) 0.4109(11) 0.33543(8) C27 C 0.1738(8) -0.0420(14) 0.43848(15) C28 C 0.2202(5) -0.2486(10) 0.45253(10) C29 C 0.1751(5) -0.3262(12) 0.47407(10) H37 H 0.11080 -0.23970 0.48020 C30 C 0.3084(5) -0.6313(12) 0.47781(10) H38 H 0.33930 -0.76560 0.48640 C31 C 0.3594(6) -0.5644(17) 0.45668(11) H39 H 0.42550 -0.64920 0.45120 C32 C 0.3144(5) -0.3762(12) 0.44381(11) H40 H 0.34710 -0.33260 0.42900 N1 N 0.0902(5) 0.0971(12) 0.44741(9) H41 H 0.06100 0.21750 0.43900 H42 H 0.06430 0.06860 0.46180 N2 N 0.2156(9) -0.5118(9) 0.48668(16) O5 O 0.2127(8) -0.0067(7) 0.41818(11) C33 C 0.0795(8) 0.5441(14) 0.39637(14) C34 C 0.0313(5) 0.7489(10) 0.38160(9) C35 C 0.0770(5) 0.8249(12) 0.36007(10) H43 H 0.14190 0.73970 0.35410 C36 C -0.0563(6) 1.1303(12) 0.35612(10) H44 H -0.08830 1.26090 0.34720 C37 C -0.1065(7) 1.0735(17) 0.37758(13) H45 H -0.16930 1.16660 0.38340 C38 C -0.0630(5) 0.8782(12) 0.39031(11) H46 H -0.09710 0.83220 0.40490 N3 N 0.1618(4) 0.4042(12) 0.38686(8) H47 H 0.19020 0.27990 0.39490 H48 H 0.18750 0.43640 0.37260 N4 N 0.0343(8) 1.0122(10) 0.34729(15) O6 O 0.0401(7) 0.5073(7) 0.41640(12) #END data_CSD_CIF_SODDOF _audit_creation_date 2008-10-28 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD SODDOF _database_code_depnum_ccdc_archive 'CCDC 678917' _chemical_formula_sum 'C13 H12 N2 O4' _chemical_formula_moiety ; C6 H6 N2 O1,C7 H6 O3 ; _journal_coden_Cambridge 1147 _journal_volume 8 _journal_year 2008 _journal_page_first 1697 _journal_name_full 'Cryst.Growth Des. ' loop_ _publ_author_name "D.J.Berry" "C.C.Seaton" "W.Clegg" "R.W.Harrington" "S.J.Coles" "P.N.Horton" "M.B.Hursthouse" "R.Storey" "W.Jones" "T.Friscic" "N.Blagden" _chemical_name_systematic ; Nicotinamide salicylic acid ; _cell_volume 1240.157 _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.394 _exptl_special_details ; salicylic acid is an anti-inflammatory drug ; _exptl_crystal_description 'blade' _diffrn_ambient_temperature 120 #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_gt 0.0461 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 -1/2+x,-1/2-y,-1/2+z _cell_length_a 11.0751(2) _cell_length_b 4.9441(1) _cell_length_c 22.8470(5) _cell_angle_alpha 90 _cell_angle_beta 97.556(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1 C 1.00826(13) 1.0462(3) 0.28292(6) C2 C 0.97753(13) 1.2578(3) 0.32436(6) C3 C 1.06209(14) 1.3245(3) 0.37376(7) C4 C 1.03362(16) 1.5208(4) 0.41354(7) H1 H 1.09030 1.56440 0.44710 C5 C 0.92264(16) 1.6515(4) 0.40391(8) H2 H 0.90360 1.78570 0.43100 C6 C 0.83812(16) 1.5891(4) 0.35495(8) H3 H 0.76210 1.68080 0.34860 C7 C 0.86587(14) 1.3929(3) 0.31573(7) H4 H 0.80830 1.34940 0.28250 O1 O 0.92465(9) 0.9936(2) 0.23870(5) H5 H 0.94960 0.87190 0.21760 O2 O 1.10869(10) 0.9304(2) 0.28991(5) O3 O 1.17286(10) 1.2023(3) 0.38394(5) H6 H 1.17880 1.08690 0.35750 H7 H 0.7566(17) 0.397(4) -0.0351(9) H8 H 0.8177(17) 0.623(4) 0.0093(8) C8 C 0.86250(14) 0.2510(3) 0.03241(7) C9 C 0.94553(14) 0.3305(3) 0.08699(6) C10 C 0.91886(14) 0.5446(3) 0.12247(6) H9 H 0.84720 0.64760 0.11100 C11 C 1.09316(14) 0.4703(3) 0.18771(7) H10 H 1.14520 0.52050 0.22240 C12 C 1.12631(14) 0.2530(3) 0.15477(7) H11 H 1.19930 0.15580 0.16680 C13 C 1.05055(14) 0.1810(3) 0.10393(7) H12 H 1.07020 0.03110 0.08100 N1 N 0.99087(12) 0.6117(3) 0.17251(6) N2 N 0.80259(13) 0.4487(3) 0.00129(6) O4 O 0.85171(11) 0.0098(2) 0.01844(5) #END data_CSD_CIF_SOGLAC _audit_creation_date 2008-10-28 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD SOGLAC _database_code_depnum_ccdc_archive 'CCDC 678916' _chemical_formula_sum 'C19 H24 N2 O3' _chemical_formula_moiety ; C6 H6 N2 O1,C13 H18 O2 ; _journal_coden_Cambridge 1147 _journal_volume 8 _journal_year 2008 _journal_page_first 1697 _journal_name_full 'Cryst.Growth Des. ' loop_ _publ_author_name "D.J.Berry" "C.C.Seaton" "W.Clegg" "R.W.Harrington" "S.J.Coles" "P.N.Horton" "M.B.Hursthouse" "R.Storey" "W.Jones" "T.Friscic" "N.Blagden" _chemical_name_systematic ; Nicotinamide (S)-ibuprofen ; _cell_volume 3598.538 _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.212 _exptl_special_details ; ibuprofen is an anti-inflammatory drug almost isostructural with the rac-ibuprofen analogue powder data at room temperature a=5.525, b=56.088, c=11.804 and beta=91.12 ; _exptl_crystal_description 'rod' _diffrn_ambient_temperature 120 _diffrn_radiation_probe x-ray _diffrn_source synchrotron #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_gt 0.0507 loop_ _citation_database_id_CSD _citation_special_details SODDIZ "is a racemate of this entry" _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 5.4110(6) _cell_length_b 55.883(6) _cell_length_c 11.9006(13) _cell_angle_alpha 90 _cell_angle_beta 90.004(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O -0.3869(7) 0.56487(6) 0.2522(3) O2 O -0.1281(7) 0.53880(6) 0.3305(3) H1 H -0.07520 0.55100 0.36380 O3 O 0.5255(6) 0.64382(6) 0.4606(3) N1 N 0.0169(7) 0.57449(9) 0.4617(4) N2 N 0.6283(7) 0.61457(7) 0.3407(3) H2 H 0.74700 0.62310 0.31000 H3 H 0.59890 0.60000 0.31640 C1 C -0.3032(9) 0.54498(8) 0.2599(4) C2 C -0.3931(12) 0.52513(9) 0.1846(4) H4 H -0.56120 0.52980 0.15740 C3 C -0.221(2) 0.52441(11) 0.0800(5) H5 H -0.05190 0.52080 0.10390 H6 H -0.22430 0.54000 0.04230 H7 H -0.27870 0.51200 0.02800 C4 C -0.4198(10) 0.50104(9) 0.2426(4) C5 C -0.2442(10) 0.48277(9) 0.2316(4) H8 H -0.10010 0.48540 0.18760 C6 C -0.2789(9) 0.46113(9) 0.2839(4) H9 H -0.15920 0.44890 0.27460 C7 C -0.4868(10) 0.4568(1) 0.3505(4) C8 C -0.6561(10) 0.47511(9) 0.3629(4) H10 H -0.79760 0.47280 0.40890 C9 C -0.6222(11) 0.49691(9) 0.3092(5) H11 H -0.74160 0.50920 0.31870 C10 C -0.5247(11) 0.43292(11) 0.4073(5) H12 H -0.41160 0.42110 0.37250 H13 H -0.69590 0.42750 0.39260 C11 C -0.4815(11) 0.43284(12) 0.5342(5) H14 H -0.59770 0.44460 0.56900 C12 C -0.2163(13) 0.44066(14) 0.5623(5) H15 H -0.18590 0.45660 0.53110 H16 H -0.09900 0.42920 0.52960 H17 H -0.19480 0.44110 0.64400 C13 C -0.5350(13) 0.40851(12) 0.5837(6) H18 H -0.41500 0.39690 0.55490 H19 H -0.70230 0.40350 0.56250 H20 H -0.52250 0.40930 0.66580 C14 C 0.2029(8) 0.58744(8) 0.4216(4) H21 H 0.28830 0.58170 0.35740 C15 C 0.2789(8) 0.60888(8) 0.4684(3) C16 C 0.1584(8) 0.61711(8) 0.5632(4) H22 H 0.20740 0.63170 0.59760 C17 C -0.0354(9) 0.6038(1) 0.6075(4) H23 H -0.12000 0.60910 0.67300 C18 C -0.1033(9) 0.58256(8) 0.5541(4) H24 H -0.23730 0.57350 0.58330 C19 C 0.4934(8) 0.62369(9) 0.4235(4) O4 O 1.4556(7) 0.56164(7) 0.7430(3) O5 O 1.1532(7) 0.53960(6) 0.8185(3) H25 H 1.11760 0.55240 0.85140 O6 O 0.5445(6) 0.64311(6) 0.9610(3) N3 N 1.0640(8) 0.57478(8) 0.9589(4) N4 N 0.4472(8) 0.61383(7) 0.8396(3) H26 H 0.32570 0.62210 0.80960 H27 H 0.48020 0.59940 0.81460 C20 C 1.3336(9) 0.54360(8) 0.7442(4) C21 C 1.3550(9) 0.52290(8) 0.6625(4) H28 H 1.19340 0.52140 0.62240 C22 C 1.5543(11) 0.52733(9) 0.5744(4) H29 H 1.56450 0.51350 0.52390 H30 H 1.71390 0.52970 0.61170 H31 H 1.51250 0.54170 0.53090 C23 C 1.3981(8) 0.49973(8) 0.7276(4) C24 C 1.6063(9) 0.49661(8) 0.7933(4) H32 H 1.72450 0.50910 0.79920 C25 C 1.6432(9) 0.47528(8) 0.8507(4) H33 H 1.78580 0.47360 0.89660 C26 C 1.4776(10) 0.45634(10) 0.8428(5) C27 C 1.2659(9) 0.45990(8) 0.7774(4) H34 H 1.14590 0.44750 0.77260 C28 C 1.2277(9) 0.48106(8) 0.7195(4) H35 H 1.08470 0.48290 0.67400 C29 C 1.5171(11) 0.43326(11) 0.9044(5) H36 H 1.68750 0.42770 0.88960 H37 H 1.40230 0.42110 0.87350 C30 C 1.4787(10) 0.43473(12) 1.0313(5) H38 H 1.59900 0.44670 1.06180 C31 C 1.2198(12) 0.44318(15) 1.0617(5) H39 H 1.20400 0.44420 1.14360 H40 H 1.09800 0.43180 1.03220 H41 H 1.19060 0.45900 1.02880 C32 C 1.5343(14) 0.41076(12) 1.0853(5) H42 H 1.70450 0.40610 1.06800 H43 H 1.42010 0.39870 1.05600 H44 H 1.51400 0.41200 1.16690 C33 C 0.8736(9) 0.58731(8) 0.9195(4) H45 H 0.78890 0.58150 0.85510 C34 C 0.7933(8) 0.60850(8) 0.9684(3) C35 C 0.9136(9) 0.61668(8) 1.0630(4) H46 H 0.86090 0.63100 1.09890 C36 C 1.1139(9) 0.60375(9) 1.1056(4) H47 H 1.20010 0.60910 1.17040 C37 C 1.1841(9) 0.58283(8) 1.0509(4) H48 H 1.32040 0.57400 1.07900 C38 C 0.5817(8) 0.62321(8) 0.9231(3) O7 O 0.1160(8) 0.72299(6) 0.9958(3) O8 O 0.3739(7) 0.74921(6) 0.9176(3) H49 H 0.41310 0.73730 0.87830 O9 O 1.0233(6) 0.64415(6) 0.7851(3) N5 N 0.5158(8) 0.71366(8) 0.7847(4) N6 N 1.1296(7) 0.67337(7) 0.9072(3) H50 H 1.25180 0.66480 0.93510 H51 H 1.09990 0.68780 0.93340 C39 C 0.1975(9) 0.74309(8) 0.9883(4) C40 C 0.1090(13) 0.76303(9) 1.0651(4) H52 H -0.05980 0.75840 1.09150 C41 C 0.274(2) 0.76329(12) 1.1681(5) H53 H 0.22590 0.77650 1.21740 H54 H 0.44670 0.76540 1.14480 H55 H 0.25720 0.74810 1.20860 C42 C 0.0828(10) 0.78679(8) 1.0069(4) C43 C -0.1221(11) 0.79122(9) 0.9396(4) H56 H -0.24220 0.77900 0.92990 C44 C -0.1557(9) 0.81294(9) 0.8863(4) H57 H -0.29700 0.81540 0.84040 C45 C 0.0191(9) 0.83140(11) 0.9001(4) C46 C 0.2239(10) 0.82691(9) 0.9652(4) H58 H 0.34480 0.83910 0.97400 C47 C 0.2588(10) 0.80517(8) 1.0182(4) H59 H 0.40230 0.80260 1.06260 C48 C -0.0200(12) 0.85536(11) 0.8448(5) H60 H 0.09480 0.86710 0.87890 H61 H -0.19060 0.86080 0.86070 C49 C 0.0193(10) 0.85530(12) 0.7182(5) H62 H -0.09860 0.84350 0.68480 C50 C 0.2762(12) 0.84772(13) 0.6868(5) H63 H 0.30780 0.83160 0.71580 H64 H 0.39580 0.85890 0.71920 H65 H 0.29270 0.84770 0.60480 C51 C -0.0410(15) 0.88001(13) 0.6689(6) H66 H -0.02750 0.87940 0.58680 H67 H 0.07570 0.89190 0.69840 H68 H -0.20970 0.88460 0.68990 C52 C 0.7037(8) 0.70053(8) 0.8271(4) H69 H 0.78530 0.70620 0.89260 C53 C 0.7837(8) 0.67916(7) 0.7799(3) C54 C 0.6568(9) 0.67075(8) 0.6857(4) H70 H 0.70160 0.65600 0.65190 C55 C 0.4657(10) 0.6842(1) 0.6426(4) H71 H 0.37800 0.67880 0.57830 C56 C 0.4033(9) 0.70525(8) 0.6928(4) H72 H 0.27330 0.71440 0.66080 C57 C 0.9894(8) 0.66440(9) 0.8251(4) O10 O 0.9576(6) 0.72640(7) 0.5073(3) O11 O 0.6593(8) 0.74832(6) 0.4297(3) H73 H 0.65660 0.73710 0.38300 O12 O 0.0450(6) 0.64489(6) 0.2849(3) N7 N 0.5675(8) 0.71317(8) 0.2886(3) N8 N -0.0539(8) 0.67395(7) 0.4090(3) H74 H -0.17770 0.66560 0.43640 H75 H -0.02110 0.68820 0.43630 C58 C 0.8336(9) 0.74437(8) 0.5043(4) C59 C 0.8581(9) 0.76510(8) 0.5859(4) H76 H 0.69630 0.76670 0.62590 C60 C 1.0537(11) 0.76046(9) 0.6744(4) H77 H 1.05790 0.77390 0.72750 H78 H 1.21540 0.75890 0.63810 H79 H 1.01430 0.74570 0.71480 C61 C 0.9017(9) 0.78826(8) 0.5216(4) C62 C 1.1100(9) 0.79112(9) 0.4549(4) H80 H 1.22480 0.77830 0.44770 C63 C 1.1516(9) 0.81242(8) 0.3986(4) H81 H 1.29570 0.81410 0.35370 C64 C 0.9883(10) 0.83136(11) 0.4064(4) C65 C 0.7775(9) 0.82820(9) 0.4718(4) H82 H 0.66000 0.84080 0.47670 C66 C 0.7351(10) 0.80703(8) 0.5299(4) H83 H 0.59180 0.80540 0.57540 C67 C 1.0335(11) 0.85466(11) 0.3451(4) H84 H 1.20510 0.85990 0.36010 H85 H 0.92130 0.86700 0.37620 C68 C 0.9953(11) 0.85337(12) 0.2176(5) H86 H 1.11370 0.84140 0.18630 C69 C 0.7336(13) 0.84528(15) 0.1891(5) H87 H 0.61440 0.85660 0.22090 H88 H 0.70440 0.82930 0.22090 H89 H 0.71360 0.84470 0.10730 C70 C 1.0524(14) 0.87761(12) 0.1651(5) H90 H 0.94680 0.88990 0.19920 H91 H 1.02080 0.87690 0.08410 H92 H 1.22630 0.88160 0.17820 C71 C 0.3752(8) 0.70055(8) 0.3300(4) H93 H 0.29330 0.70620 0.39540 C72 C 0.2933(8) 0.67958(8) 0.2804(3) C73 C 0.4200(9) 0.67127(8) 0.1857(4) H94 H 0.37220 0.65670 0.15080 C74 C 0.6134(10) 0.68426(9) 0.1437(4) H95 H 0.69860 0.67900 0.07840 C75 C 0.6827(9) 0.70502(8) 0.1973(4) H96 H 0.81800 0.71390 0.16810 C76 C 0.0849(8) 0.66495(8) 0.3257(4) #END data_CSD_CIF_UCOTUC _audit_creation_date 2006-06-27 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD UCOTUC _database_code_depnum_ccdc_archive 'CCDC 290748' _chemical_formula_sum 'C18 H30 N2 O3' _chemical_formula_moiety ; C12 H24 O2,C6 H6 N2 O1 ; _journal_coden_Cambridge 471 _journal_volume 22 _journal_year 2006 _journal_page_first x27 _journal_name_full 'Anal.Sci.:X-Ray Struct.Anal.Online ' loop_ _publ_author_name "D.Chakrabarty" "H.Nagase" "M.Kamijo" "T.Endo" "H.Ueda" _chemical_name_systematic ; Nicotinamide lauric acid ; _chemical_name_common ; 3-pyridinecarboxamide n-dodecanoic acid ; _cell_volume 954.425 _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.122 _exptl_crystal_description 'plate' _diffrn_ambient_temperature 298.1 #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.055 _refine_ls_wR_factor_gt 0.055 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.4694(7) _cell_length_b 34.636(7) _cell_length_c 5.045(1) _cell_angle_alpha 91.94(2) _cell_angle_beta 92.19(2) _cell_angle_gamma 90.48(1) _cell_formula_units_Z 2 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O 0.7759(7) 0.3373(1) 0.9073(7) O2 O 1.1184(6) 0.3108(1) 1.0563(7) O3 O 0.6960(5) 0.46653(9) 1.3051(5) N1 N 1.1471(8) 0.3715(1) 1.4047(7) N2 N 0.7211(6) 0.4810(1) 1.7433(6) C1 C 0.920(1) 0.3117(2) 0.896(1) C2 C 0.9089(9) 0.2778(1) 0.7065(9) C3 C 0.6634(9) 0.2690(1) 0.571(1) C4 C 0.6642(9) 0.2323(1) 0.402(1) C5 C 0.4203(9) 0.2197(1) 0.276(1) C6 C 0.4288(9) 0.1834(1) 0.107(1) C7 C 0.1878(9) 0.1689(2) -0.015(1) C8 C 0.1972(9) 0.1324(2) -0.180(1) C9 C -0.045(1) 0.1182(2) -0.301(1) C10 C -0.038(1) 0.0814(2) -0.466(1) C11 C -0.283(1) 0.0676(2) -0.581(1) C12 C -0.279(1) 0.0315(2) -0.745(2) C13 C 1.3167(8) 0.3739(1) 1.6071(9) C14 C 1.3233(9) 0.4035(2) 1.7895(9) C15 C 1.1536(9) 0.4320(1) 1.7767(8) C16 C 0.9753(8) 0.4306(1) 1.5673(7) C17 C 0.9852(9) 0.3995(1) 1.3928(8) C18 C 0.7878(8) 0.4605(1) 1.5305(9) H1 H 1.13(1) 0.338(2) 1.17(1) H2 H 0.79400 0.47610 1.91270 H3 H 0.60070 0.50040 1.72580 H4 H -0.25160 0.03750 -0.92440 H5 H -0.42540 0.01680 -0.73770 H6 H -0.14510 0.01700 -0.67760 H7 H 0.95670 0.25570 0.80180 H8 H 1.02260 0.28220 0.57280 H9 H 0.54500 0.26640 0.70200 H10 H 0.62040 0.28980 0.46060 H11 H 0.72150 0.21210 0.51070 H12 H 0.77440 0.23590 0.26370 H13 H 0.31000 0.21560 0.41320 H14 H 0.36140 0.23980 0.16780 H15 H 0.49430 0.16360 0.21400 H16 H 0.53520 0.18790 -0.03350 H17 H 0.08060 0.16470 0.12520 H18 H 0.12340 0.18850 -0.12420 H19 H 0.26120 0.11280 -0.07120 H20 H 0.30450 0.13660 -0.32050 H21 H -0.15230 0.11440 -0.16100 H22 H -0.10780 0.13780 -0.41170 H23 H 0.02700 0.06190 -0.35670 H24 H 0.06700 0.08530 -0.60820 H25 H -0.38940 0.06310 -0.43990 H26 H -0.35060 0.08690 -0.69000 H27 H 1.43530 0.35420 1.62180 H28 H 1.44710 0.40440 1.92700 H29 H 1.15540 0.45240 1.90700 H30 H 0.86520 0.39780 1.25150 #END data_CSD_CIF_UNEZES _audit_creation_date 2004-04-19 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD UNEZES _database_code_depnum_ccdc_archive 'CCDC 212375' _chemical_formula_sum 'C21 H18 N4 O2' _chemical_formula_moiety ; C15 H12 N2 O1,C6 H6 N2 O1 ; _journal_coden_Cambridge 1147 _journal_volume 3 _journal_year 2003 _journal_page_first 909 _journal_name_full 'Cryst.Growth Des. ' loop_ _publ_author_name "S.G.Fleischman" "S.S.Kuduva" "J.A.McMahon" "B.Moulton" "R.D.B.Walsh" "N.Rodriguez-Hornedo" "M.J.Zaworotko" _chemical_name_systematic ; Carbamazepine nicotinamide solvate ; _chemical_name_common ; 5H-dibenz(b,f)azepine-5-carboxamide nicotinamide solvate ; _chemical_melting_point 424.15 _cell_volume 1761.440 _exptl_crystal_density_diffrn 1.351 _exptl_special_details ; Melting point range 424.15-434.15K boat conformer treatment for epilepsy and trigeminal neuralgia. ; _exptl_crystal_preparation 'dimethylsulfoxide/methanol' _diffrn_ambient_temperature 200 #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_gt 0.0522 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2+x,1/2-y,1/2+z 3 -x,-y,-z 4 -1/2-x,-1/2+y,-1/2-z _cell_length_a 5.0961(8) _cell_length_b 17.595(3) _cell_length_c 19.647(3) _cell_angle_alpha 90 _cell_angle_beta 90.917(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O 0.3136(3) 0.07814(8) 1.03533(7) O2 O -0.1762(3) 0.05924(11) 0.20151(8) N1 N 0.2731(4) 0.02654(10) 0.93082(9) H1 H 0.37060 -0.01280 0.94230 H2 H 0.20720 0.03010 0.88930 N2 N 0.0747(3) 0.14132(10) 0.95543(8) N3 N 0.2486(4) 0.08373(11) 0.18011(9) H3 H 0.21660 0.09060 0.13640 H4 H 0.40970 0.08830 0.19640 N4 N 0.0028(4) -0.00171(12) 0.40079(10) C1 C 0.2251(4) 0.08083(12) 0.97642(10) C2 C 0.0134(4) 0.15562(12) 0.88509(10) C3 C -0.1869(4) 0.11550(13) 0.85346(11) H5 H -0.28740 0.08020 0.87880 C4 C -0.2411(5) 0.12656(14) 0.78529(12) H6 H -0.37930 0.09910 0.76350 C5 C -0.0940(5) 0.17759(14) 0.74882(12) H7 H -0.13050 0.18520 0.70170 C6 C 0.1053(5) 0.21760(14) 0.78028(11) H8 H 0.20650 0.25200 0.75430 C7 C 0.1625(4) 0.20880(12) 0.84952(11) C8 C 0.3709(5) 0.25377(13) 0.88151(12) H9 H 0.51400 0.26710 0.85350 C9 C 0.3823(5) 0.27825(12) 0.94593(12) H10 H 0.53460 0.30630 0.95870 C10 C 0.1890(5) 0.26707(12) 0.99886(11) C11 C 0.1491(6) 0.32397(14) 1.04713(12) H11 H 0.25700 0.36800 1.04710 C12 C -0.0446(6) 0.31714(17) 1.09472(13) H12 H -0.07230 0.35690 1.12660 C13 C -0.1991(5) 0.25258(17) 1.09629(12) H13 H -0.33270 0.24790 1.12920 C14 C -0.1592(5) 0.19551(15) 1.05048(11) H14 H -0.26370 0.15080 1.05190 C15 C 0.0327(4) 0.20272(12) 1.00213(10) C16 C 0.0541(5) 0.06642(13) 0.22144(11) C17 C 0.1241(4) 0.05604(12) 0.29465(11) C18 C 0.3382(5) 0.08967(13) 0.32651(11) H15 H 0.45490 0.12070 0.30150 C19 C 0.3800(5) 0.07760(14) 0.39514(11) H16 H 0.52540 0.10030 0.41810 C20 C 0.2096(5) 0.03258(14) 0.42962(12) H17 H 0.24020 0.02520 0.47700 C21 C -0.0348(5) 0.01077(13) 0.33446(11) H18 H -0.18110 -0.01310 0.31290 #END data_CSD_CIF_XAQQIQ _audit_creation_date 2005-11-15 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD XAQQIQ _database_code_depnum_ccdc_archive 'CCDC 240489' _chemical_formula_sum 'C13 H12 N2 O4' _chemical_formula_moiety ; C6 H6 N2 O1,C7 H6 O3 ; _journal_coden_Cambridge 643 _journal_volume 220 _journal_year 2005 _journal_page_first 340 _journal_name_full 'Z.Kristallogr. ' loop_ _publ_author_name "J.A.McMahon" "J.A.Bis" "P.Vishweshwar" "T.R.Shattock" "O.L.McLaughlin" "M.J.Zaworotko" _chemical_name_systematic ; Nicotinamide 3-hydroxybenzoic acid ; _chemical_melting_point 395 _cell_volume 1202.915 _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.437 _exptl_special_details ; Melting point range 395-398K ; _exptl_crystal_description 'plate' _exptl_crystal_preparation 'acetonitrile' _diffrn_ambient_temperature 100 #These two values have been output from a single CSD field. _refine_ls_R_factor_gt 0.048 _refine_ls_wR_factor_gt 0.048 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,-1/2-y,-1/2+z _cell_length_a 7.3699(13) _cell_length_b 7.1977(13) _cell_length_c 22.688(4) _cell_angle_alpha 90 _cell_angle_beta 91.809(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 N 0.68 O 0.68 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O 0.87275(18) 1.05743(17) 0.10353(5) N1 N 0.9092(2) 1.06248(19) 0.20231(6) H1 H 0.95880 1.17230 0.19760 H2 H 0.90410 1.00880 0.23550 N2 N 0.6500(2) 0.53831(19) 0.20951(6) C1 C 0.8544(2) 0.9814(2) 0.15225(7) C2 C 0.7702(2) 0.7927(2) 0.15428(7) C3 C 0.7224(2) 0.7087(2) 0.20652(8) H3 H 0.74210 0.77580 0.24220 C4 C 0.6209(2) 0.4471(2) 0.15888(8) H4 H 0.57040 0.32580 0.16020 C5 C 0.6611(2) 0.5210(2) 0.10435(8) H5 H 0.63710 0.45220 0.06920 C6 C 0.7365(2) 0.6966(2) 0.10194(7) H6 H 0.76480 0.75060 0.06520 O2 O 0.41484(18) 1.04372(16) 0.17435(5) H7 H 0.39900 1.00110 0.21290 O3 O 0.08812(17) 0.41606(16) 0.17653(5) O4 O 0.06856(17) 0.34622(16) 0.08047(5) H8 H 0.00840 0.25450 0.09080 C7 C 0.3414(2) 0.9223(2) 0.13432(8) C8 C 0.2653(2) 0.7541(2) 0.15042(7) H9 H 0.26040 0.72050 0.19080 C9 C 0.1960(2) 0.6350(2) 0.10688(7) C10 C 0.2018(2) 0.6840(3) 0.04769(8) H10 H 0.15430 0.60250 0.01810 C11 C 0.2775(3) 0.8527(3) 0.03217(8) H11 H 0.28140 0.88730 -0.00820 C12 C 0.3472(3) 0.9705(2) 0.07518(8) H12 H 0.39950 1.08550 0.06420 C13 C 0.1136(2) 0.4562(2) 0.12489(7) #END