Supplementary Material (ESI) for Faraday Discussions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 169 loop_ _publ_author_name 'William Jones' 'Tomislav Friscic' _publ_contact_author_name 'William Jones' _publ_contact_author_address ; Department of Chemistry University of Cambridge Pfizer Institute for Pharmaceutical Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email WJ10@CAM.AC.UK _publ_requested_journal 'Faraday Discussions' _publ_section_title ; Cocrystal architecture and properties: design and building of chiral and racemic structures by solid-solid reactions ; data_wj0638 _database_code_depnum_ccdc_archive 'CCDC 626647' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nicotinamide-D-mandelic acid (1/1) ; _chemical_name_common 1a _chemical_melting_point 362 _chemical_formula_moiety '2(C8 H8 O3) 2(C6 H6 N2 O)' _chemical_formula_sum 'C14 H14 N2 O4' _chemical_formula_weight 274.27 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 32.6557(9) _cell_length_b 5.4751(10) _cell_length_c 14.9264(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.4000(10) _cell_angle_gamma 90.00 _cell_volume 2632.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14638 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.569 _exptl_absorpt_correction_T_max 1.001 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 14285 _diffrn_reflns_av_R_equivalents 0.0759 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 27.43 _reflns_number_total 5773 _reflns_number_gt 4897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogen atoms were included in the refinement following the anisotropic model. Hydrogen atoms bonded to nitrogen and carbon atoms were generated following stereochemical rules applicable to the parent non-hydrogen atom. Coordinates of hydrogen atoms bonded to oxygen were generated so as to establish the best possible hydrogen bond to the neighbouring donor atom. The position of the hydrogen atom H5O was calculated so as to place the aom in the position of maximum electron density in the radius of 0.84 A from the belonging oxygen atom O5. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+2.0274P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.3(11) _refine_ls_number_reflns 5773 _refine_ls_number_parameters 365 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1278 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.29418(6) -0.1324(4) 0.40557(12) 0.0257(4) Uani 1 1 d . . . O2 O 0.23670(6) -0.5853(3) 0.27289(13) 0.0251(4) Uani 1 1 d . . . O3 O 0.15961(6) -1.4919(3) 0.12750(13) 0.0240(4) Uani 1 1 d . . . H3O H 0.1584 -1.3755 0.1636 0.036 Uiso 1 1 calc R . . O4 O 0.21093(6) -1.2694(4) 0.08733(14) 0.0263(4) Uani 1 1 d . . . O5 O 0.21803(6) -1.5760(4) -0.05150(13) 0.0300(5) Uani 1 1 d . . . H5O H 0.2395 -1.6626 -0.0434 0.045 Uiso 1 1 calc R . . O6 O 0.45749(6) 0.2106(4) 0.54623(14) 0.0279(5) Uani 1 1 d . . . H6O H 0.4400 0.2332 0.4991 0.042 Uiso 1 1 calc R . . O7 O 0.44164(7) -0.1839(4) 0.51879(14) 0.0344(5) Uani 1 1 d . . . O8 O 0.50509(7) -0.3359(4) 0.64197(14) 0.0301(5) Uani 1 1 d . . . H8O H 0.4870 -0.4114 0.6059 0.045 Uiso 1 1 calc R . . N1 N 0.40103(7) 0.2790(4) 0.40376(16) 0.0228(5) Uani 1 1 d . . . N2 N 0.28225(7) -0.1388(4) 0.25223(15) 0.0209(5) Uani 1 1 d . . . H2NA H 0.2631 -0.2528 0.2506 0.025 Uiso 1 1 calc R . . H2NB H 0.2885 -0.0797 0.2013 0.025 Uiso 1 1 calc R . . N3 N 0.22950(8) -0.4973(4) 0.41687(16) 0.0268(5) Uani 1 1 d . . . H3NA H 0.2485 -0.3820 0.4211 0.032 Uiso 1 1 calc R . . H3NB H 0.2169 -0.5291 0.4634 0.032 Uiso 1 1 calc R . . N4 N 0.15586(7) -1.1643(4) 0.25247(15) 0.0225(5) Uani 1 1 d . . . C1 C 0.39900(9) 0.4586(5) 0.34164(18) 0.0229(6) Uani 1 1 d . . . H1 H 0.4213 0.5717 0.3455 0.027 Uiso 1 1 calc R . . C2 C 0.36548(9) 0.4840(5) 0.27220(19) 0.0241(6) Uani 1 1 d . . . H2 H 0.3648 0.6128 0.2293 0.029 Uiso 1 1 calc R . . C3 C 0.33286(8) 0.3190(5) 0.26611(18) 0.0208(5) Uani 1 1 d . . . H3C H 0.3096 0.3331 0.2190 0.025 Uiso 1 1 calc R . . C4 C 0.33475(8) 0.1322(5) 0.33008(17) 0.0196(5) Uani 1 1 d . . . C5 C 0.36957(8) 0.1205(5) 0.39719(18) 0.0220(6) Uani 1 1 d . . . H5A H 0.3711 -0.0070 0.4408 0.026 Uiso 1 1 calc R . . C6 C 0.30159(8) -0.0564(5) 0.33117(17) 0.0195(5) Uani 1 1 d . . . C7 C 0.21978(8) -0.6239(5) 0.33983(17) 0.0205(5) Uani 1 1 d . . . C8 C 0.18743(8) -0.8205(5) 0.33598(18) 0.0192(5) Uani 1 1 d . . . C9 C 0.18346(9) -0.9825(5) 0.26314(18) 0.0217(6) Uani 1 1 d . . . H9 H 0.2012 -0.9628 0.2191 0.026 Uiso 1 1 calc R . . C10 C 0.13014(9) -1.1877(5) 0.31338(19) 0.0250(6) Uani 1 1 d . . . H10 H 0.1103 -1.3160 0.3058 0.030 Uiso 1 1 calc R . . C11 C 0.13140(9) -1.0321(6) 0.38701(19) 0.0271(6) Uani 1 1 d . . . H11 H 0.1126 -1.0521 0.4287 0.032 Uiso 1 1 calc R . . C12 C 0.16071(9) -0.8467(5) 0.39871(18) 0.0243(6) Uani 1 1 d . . . H12 H 0.1625 -0.7389 0.4491 0.029 Uiso 1 1 calc R . . C13 C 0.18877(8) -1.4500(5) 0.07957(17) 0.0201(5) Uani 1 1 d . . . C14 C 0.19115(8) -1.6509(5) 0.00928(18) 0.0222(5) Uani 1 1 d . . . H14 H 0.2023 -1.8036 0.0411 0.027 Uiso 1 1 calc R . . C15 C 0.14783(9) -1.6984(5) -0.04132(17) 0.0209(6) Uani 1 1 d . . . C16 C 0.12536(9) -1.9047(5) -0.02401(19) 0.0261(6) Uani 1 1 d . . . H16 H 0.1378 -2.0240 0.0180 0.031 Uiso 1 1 calc R . . C17 C 0.08488(9) -1.9363(5) -0.0679(2) 0.0280(6) Uani 1 1 d . . . H17 H 0.0698 -2.0777 -0.0557 0.034 Uiso 1 1 calc R . . C18 C 0.06615(10) -1.7642(5) -0.1293(2) 0.0283(6) Uani 1 1 d . . . H18 H 0.0383 -1.7864 -0.1586 0.034 Uiso 1 1 calc R . . C19 C 0.08834(9) -1.5588(5) -0.14765(19) 0.0268(6) Uani 1 1 d . . . H19 H 0.0758 -1.4412 -0.1903 0.032 Uiso 1 1 calc R . . C20 C 0.12901(9) -1.5254(5) -0.10339(18) 0.0237(6) Uani 1 1 d . . . H20 H 0.1440 -1.3839 -0.1156 0.028 Uiso 1 1 calc R . . C21 C 0.46152(8) -0.0244(6) 0.56240(18) 0.0239(6) Uani 1 1 d . . . C22 C 0.49367(9) -0.0876(5) 0.64515(18) 0.0248(6) Uani 1 1 d . . . H22 H 0.5189 0.0157 0.6444 0.030 Uiso 1 1 calc R . . C23 C 0.47592(8) -0.0309(5) 0.73099(18) 0.0225(6) Uani 1 1 d . . . C24 C 0.44882(9) -0.1987(5) 0.76019(19) 0.0237(6) Uani 1 1 d . . . H24 H 0.4415 -0.3432 0.7261 0.028 Uiso 1 1 calc R . . C25 C 0.43249(9) -0.1557(6) 0.8388(2) 0.0304(7) Uani 1 1 d . . . H25 H 0.4136 -0.2694 0.8577 0.037 Uiso 1 1 calc R . . C26 C 0.44351(11) 0.0521(6) 0.8899(2) 0.0340(7) Uani 1 1 d . . . H26 H 0.4330 0.0786 0.9448 0.041 Uiso 1 1 calc R . . C27 C 0.46991(11) 0.2211(6) 0.8603(2) 0.0331(7) Uani 1 1 d . . . H27 H 0.4770 0.3657 0.8945 0.040 Uiso 1 1 calc R . . C28 C 0.48614(9) 0.1808(5) 0.78076(19) 0.0268(6) Uani 1 1 d . . . H28 H 0.5041 0.2979 0.7607 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0314(11) 0.0282(10) 0.0173(9) 0.0008(8) 0.0032(8) -0.0104(9) O2 0.0306(11) 0.0256(10) 0.0198(9) -0.0008(8) 0.0068(8) -0.0050(8) O3 0.0252(10) 0.0270(11) 0.0210(10) -0.0090(8) 0.0069(8) -0.0058(8) O4 0.0245(10) 0.0283(11) 0.0267(10) -0.0031(8) 0.0064(8) -0.0065(8) O5 0.0263(11) 0.0412(13) 0.0246(10) 0.0049(9) 0.0103(9) 0.0108(9) O6 0.0290(11) 0.0310(11) 0.0210(10) 0.0052(8) -0.0037(8) -0.0018(9) O7 0.0422(13) 0.0302(11) 0.0271(11) -0.0032(9) -0.0051(9) 0.0023(10) O8 0.0271(11) 0.0347(11) 0.0281(11) 0.0000(9) 0.0028(9) 0.0109(9) N1 0.0225(12) 0.0247(12) 0.0205(11) 0.0023(9) 0.0015(9) -0.0035(9) N2 0.0219(11) 0.0223(11) 0.0179(11) -0.0001(9) 0.0017(9) -0.0046(9) N3 0.0333(13) 0.0272(13) 0.0200(12) -0.0036(9) 0.0048(10) -0.0102(10) N4 0.0215(12) 0.0237(11) 0.0217(11) -0.0032(10) 0.0021(9) -0.0017(10) C1 0.0228(14) 0.0213(13) 0.0245(14) 0.0017(11) 0.0043(11) -0.0034(11) C2 0.0288(15) 0.0221(13) 0.0214(13) 0.0038(11) 0.0044(11) -0.0018(11) C3 0.0227(14) 0.0219(13) 0.0176(12) 0.0005(11) 0.0027(10) -0.0008(11) C4 0.0222(13) 0.0208(13) 0.0160(12) -0.0022(10) 0.0038(10) -0.0011(10) C5 0.0241(14) 0.0230(14) 0.0181(13) 0.0018(11) 0.0011(11) -0.0029(11) C6 0.0217(13) 0.0204(13) 0.0164(12) -0.0001(10) 0.0033(10) -0.0009(10) C7 0.0229(14) 0.0189(13) 0.0187(13) -0.0001(10) 0.0005(10) 0.0006(10) C8 0.0198(13) 0.0194(13) 0.0180(12) 0.0008(10) 0.0021(10) -0.0005(10) C9 0.0251(14) 0.0230(14) 0.0171(13) -0.0014(10) 0.0039(10) -0.0010(11) C10 0.0259(14) 0.0244(14) 0.0249(14) -0.0015(12) 0.0045(11) -0.0039(11) C11 0.0296(15) 0.0312(15) 0.0216(14) -0.0011(12) 0.0077(12) -0.0056(12) C12 0.0280(15) 0.0257(14) 0.0195(13) -0.0046(11) 0.0048(11) -0.0023(11) C13 0.0188(13) 0.0250(14) 0.0160(12) 0.0012(10) 0.0007(10) 0.0021(11) C14 0.0239(14) 0.0260(14) 0.0174(12) 0.0006(11) 0.0054(10) 0.0045(11) C15 0.0270(14) 0.0189(13) 0.0168(13) -0.0054(10) 0.0030(10) 0.0049(11) C16 0.0311(16) 0.0227(14) 0.0228(14) -0.0018(11) -0.0004(11) 0.0041(12) C17 0.0326(16) 0.0225(14) 0.0284(15) -0.0005(12) 0.0033(12) -0.0002(12) C18 0.0276(15) 0.0286(15) 0.0266(15) -0.0076(12) -0.0018(12) 0.0021(12) C19 0.0337(16) 0.0247(14) 0.0202(14) -0.0016(11) -0.0011(11) 0.0073(12) C20 0.0311(15) 0.0212(13) 0.0184(13) -0.0023(10) 0.0025(11) 0.0019(11) C21 0.0217(14) 0.0315(15) 0.0192(13) -0.0002(11) 0.0057(11) 0.0032(12) C22 0.0226(14) 0.0315(16) 0.0206(14) 0.0036(11) 0.0044(11) 0.0006(11) C23 0.0212(13) 0.0274(14) 0.0174(12) 0.0032(11) -0.0008(10) 0.0033(11) C24 0.0227(14) 0.0228(14) 0.0255(14) 0.0031(11) 0.0036(11) 0.0018(11) C25 0.0319(17) 0.0317(15) 0.0293(16) 0.0075(13) 0.0099(13) 0.0052(13) C26 0.0450(19) 0.0375(17) 0.0206(14) 0.0046(13) 0.0092(13) 0.0109(14) C27 0.0439(19) 0.0265(16) 0.0267(15) -0.0039(12) -0.0007(14) 0.0053(13) C28 0.0286(15) 0.0243(14) 0.0261(15) 0.0042(12) 0.0003(12) 0.0037(11) _geom_special_details ; 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. ; 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 C6 1.246(3) . ? O2 C7 1.236(3) . ? O3 C13 1.301(3) . ? O4 C13 1.219(3) . ? O5 C14 1.422(3) . ? O6 C21 1.312(4) . ? O7 C21 1.213(4) . ? O8 C22 1.413(4) . ? N1 C5 1.336(3) . ? N1 C1 1.346(3) . ? N2 C6 1.322(3) . ? N3 C7 1.336(3) . ? N4 C9 1.335(4) . ? N4 C10 1.341(4) . ? C1 C2 1.386(4) . ? C2 C3 1.389(4) . ? C3 C4 1.393(4) . ? C4 C5 1.389(4) . ? C4 C6 1.498(4) . ? C7 C8 1.503(4) . ? C8 C12 1.388(4) . ? C8 C9 1.393(4) . ? C10 C11 1.386(4) . ? C11 C12 1.387(4) . ? C13 C14 1.531(4) . ? C14 C15 1.513(4) . ? C15 C16 1.394(4) . ? C15 C20 1.395(4) . ? C16 C17 1.387(4) . ? C17 C18 1.385(4) . ? C18 C19 1.389(4) . ? C19 C20 1.395(4) . ? C21 C22 1.524(4) . ? C22 C23 1.522(4) . ? C23 C28 1.388(4) . ? C23 C24 1.394(4) . ? C24 C25 1.386(4) . ? C25 C26 1.384(5) . ? C26 C27 1.385(5) . ? C27 C28 1.395(4) . ? 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 C5 N1 C1 118.3(2) . . ? C9 N4 C10 118.4(2) . . ? N1 C1 C2 122.2(3) . . ? C1 C2 C3 119.2(3) . . ? C2 C3 C4 119.0(2) . . ? C5 C4 C3 117.9(2) . . ? C5 C4 C6 117.9(2) . . ? C3 C4 C6 124.2(2) . . ? N1 C5 C4 123.5(2) . . ? O1 C6 N2 123.1(2) . . ? O1 C6 C4 119.1(2) . . ? N2 C6 C4 117.8(2) . . ? O2 C7 N3 122.2(3) . . ? O2 C7 C8 119.7(2) . . ? N3 C7 C8 118.1(2) . . ? C12 C8 C9 118.2(2) . . ? C12 C8 C7 124.3(2) . . ? C9 C8 C7 117.5(2) . . ? N4 C9 C8 122.9(2) . . ? N4 C10 C11 122.6(3) . . ? C10 C11 C12 118.7(3) . . ? C11 C12 C8 119.2(2) . . ? O4 C13 O3 124.5(2) . . ? O4 C13 C14 123.5(2) . . ? O3 C13 C14 111.9(2) . . ? O5 C14 C15 110.8(2) . . ? O5 C14 C13 109.6(2) . . ? C15 C14 C13 108.5(2) . . ? C16 C15 C20 119.0(3) . . ? C16 C15 C14 121.6(2) . . ? C20 C15 C14 119.3(3) . . ? C17 C16 C15 120.2(3) . . ? C18 C17 C16 120.7(3) . . ? C17 C18 C19 119.6(3) . . ? C18 C19 C20 119.9(3) . . ? C15 C20 C19 120.5(3) . . ? O7 C21 O6 125.4(3) . . ? O7 C21 C22 120.6(3) . . ? O6 C21 C22 114.0(2) . . ? O8 C22 C23 111.3(2) . . ? O8 C22 C21 110.0(2) . . ? C23 C22 C21 109.2(2) . . ? C28 C23 C24 119.5(3) . . ? C28 C23 C22 122.0(3) . . ? C24 C23 C22 118.5(3) . . ? C25 C24 C23 120.3(3) . . ? C26 C25 C24 120.3(3) . . ? C25 C26 C27 119.6(3) . . ? C26 C27 C28 120.5(3) . . ? C23 C28 C27 119.8(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.291 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.093