# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Mino Caira' _publ_contact_author_email Mino.Caira@uct.ac.za _publ_section_title ; New polymorphs of the cocrystal formers isonicotinamide and nicotinamide ; loop_ _publ_author_name M.Caira J.Li S.Bourne # Attachment 'isonicotinamideFIN.CIF' data_c:\173k\173k _database_code_depnum_ccdc_archive 'CCDC 794755' #TrackingRef 'isonicotinamideFIN.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Isonicotinamide _chemical_melting_point '427 K' _chemical_formula_moiety 'C6 H6 N2 O1' _chemical_formula_sum 'C6 H6 N2 O' _chemical_formula_weight 122.13 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 orthorhombic _symmetry_space_group_name_H-M 'P bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1603(7) _cell_length_b 7.3231(5) _cell_length_c 15.8720(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1180.95(12) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 871 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 26.37 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method 'phi- and omega-scans of 2.00deg.' _diffrn_reflns_number 2126 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1188 _reflns_number_gt 896 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0367P)^2^+0.6598P] 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_number_reflns 1188 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.0960 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 N1 N 0.63287(14) 0.1897(2) 0.72635(9) 0.0290(4) Uani 1 1 d . . . C2 C 0.69796(16) 0.1319(2) 0.86942(11) 0.0273(4) Uani 1 1 d . . . H2 H 0.7604 0.0806 0.9072 0.033 Uiso 1 1 calc R . . O1 O 0.44875(12) 0.2570(2) 1.01940(8) 0.0413(4) Uani 1 1 d . . . C1 C 0.71538(17) 0.1178(2) 0.78307(11) 0.0291(4) Uani 1 1 d . . . H1 H 0.7902 0.0535 0.7630 0.035 Uiso 1 1 calc R . . C4 C 0.49940(17) 0.2933(2) 0.84141(11) 0.0292(4) Uani 1 1 d . . . H3 H 0.4216 0.3534 0.8597 0.035 Uiso 1 1 calc R . . C3 C 0.58778(16) 0.2222(2) 0.89965(11) 0.0257(4) Uani 1 1 d . . . N2 N 0.66788(15) 0.2615(2) 1.04121(9) 0.0349(4) Uani 1 1 d . . . H5 H 0.6587 0.2781 1.0958 0.042 Uiso 1 1 calc R . . H6 H 0.7470 0.2541 1.0190 0.042 Uiso 1 1 calc R . . C5 C 0.52638(17) 0.2751(2) 0.75663(12) 0.0305(4) Uani 1 1 d . . . H4 H 0.4660 0.3262 0.7175 0.037 Uiso 1 1 calc R . . C6 C 0.56228(16) 0.2478(3) 0.99237(11) 0.0288(4) Uani 1 1 d . . . 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 N1 0.0257(8) 0.0343(8) 0.0269(8) -0.0010(6) 0.0007(6) -0.0048(6) C2 0.0218(8) 0.0314(9) 0.0285(9) -0.0001(7) -0.0033(7) 0.0007(7) O1 0.0219(7) 0.0703(10) 0.0317(7) -0.0021(7) 0.0049(6) 0.0024(7) C1 0.0241(9) 0.0320(9) 0.0312(9) -0.0042(7) 0.0012(7) 0.0015(8) C4 0.0194(8) 0.0379(10) 0.0303(9) 0.0016(8) 0.0010(8) 0.0027(7) C3 0.0187(8) 0.0325(9) 0.0259(9) 0.0007(7) -0.0004(7) -0.0033(7) N2 0.0233(8) 0.0592(11) 0.0222(7) -0.0019(7) 0.0019(6) 0.0017(7) C5 0.0262(9) 0.0373(9) 0.0281(9) 0.0050(8) -0.0029(8) -0.0011(8) C6 0.0221(9) 0.0390(10) 0.0252(9) 0.0022(7) 0.0017(7) 0.0015(8) _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 N1 C1 1.338(2) . ? N1 C5 1.339(2) . ? C2 C1 1.386(2) . ? C2 C3 1.386(2) . ? C2 H2 0.9500 . ? O1 C6 1.2325(19) . ? C1 H1 0.9500 . ? C4 C5 1.380(3) . ? C4 C3 1.390(2) . ? C4 H3 0.9500 . ? C3 C6 1.506(2) . ? N2 C6 1.327(2) . ? N2 H5 0.8800 . ? N2 H6 0.8800 . ? C5 H4 0.9500 . ? 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 N1 C5 116.65(15) . . ? C1 C2 C3 118.75(16) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? N1 C1 C2 123.80(16) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C5 C4 C3 118.96(16) . . ? C5 C4 H3 120.5 . . ? C3 C4 H3 120.5 . . ? C2 C3 C4 118.06(16) . . ? C2 C3 C6 122.46(15) . . ? C4 C3 C6 119.47(15) . . ? C6 N2 H5 120.0 . . ? C6 N2 H6 120.0 . . ? H5 N2 H6 120.0 . . ? N1 C5 C4 123.75(16) . . ? N1 C5 H4 118.1 . . ? C4 C5 H4 118.1 . . ? O1 C6 N2 123.30(16) . . ? O1 C6 C3 120.53(15) . . ? N2 C6 C3 116.17(15) . . ? 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 C5 N1 C1 C2 -1.8(3) . . . . ? C3 C2 C1 N1 1.3(3) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? C1 C2 C3 C6 -178.59(16) . . . . ? C5 C4 C3 C2 -1.6(3) . . . . ? C5 C4 C3 C6 177.51(16) . . . . ? C1 N1 C5 C4 0.6(3) . . . . ? C3 C4 C5 N1 1.1(3) . . . . ? C2 C3 C6 O1 -150.07(18) . . . . ? C4 C3 C6 O1 30.9(3) . . . . ? C2 C3 C6 N2 30.7(3) . . . . ? C4 C3 C6 N2 -148.37(17) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.221 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.045 # Attachment 'nicotinamideFIN.CIF' data_c:\paper\2 _database_code_depnum_ccdc_archive 'CCDC 794756' #TrackingRef 'nicotinamideFIN.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common nicotinamide _chemical_melting_point '379 K' _chemical_formula_moiety 'C6 H6 N2 O1' _chemical_formula_sum 'C6 H6 N2 O' _chemical_formula_weight 122.13 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 P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 15.0634(5) _cell_length_b 10.6976(4) _cell_length_c 15.2067(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.188(2) _cell_angle_gamma 90.00 _cell_volume 2395.21(14) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 55632 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 26.37 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method 'phi- and omega-scans of 2.00deg.' _diffrn_reflns_number 88974 _diffrn_reflns_av_R_equivalents 0.1173 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 26.38 _reflns_number_total 4881 _reflns_number_gt 3492 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0489P)^2^+0.7737P] 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_number_reflns 4881 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 O1D O 0.61376(9) -0.05481(12) 0.04629(9) 0.0374(4) Uani 1 1 d . . . C1D C 0.75524(12) 0.21563(17) 0.12008(12) 0.0288(4) Uani 1 1 d . . . H1D H 0.7143 0.2793 0.0936 0.035 Uiso 1 1 calc R . . N2D N 0.56885(10) 0.14645(15) 0.04079(11) 0.0343(4) Uani 1 1 d . . . H6D H 0.5135 0.1274 0.0119 0.041 Uiso 1 1 calc R . . H5D H 0.5834 0.2248 0.0545 0.041 Uiso 1 1 calc R . . C2D C 0.72444(12) 0.09300(16) 0.11258(12) 0.0239(4) Uani 1 1 d . . . C4D C 0.87150(13) 0.03359(18) 0.19383(14) 0.0332(5) Uani 1 1 d . . . H3D H 0.9140 -0.0284 0.2203 0.040 Uiso 1 1 calc R . . N1D N 0.83871(10) 0.24996(14) 0.16211(11) 0.0309(4) Uani 1 1 d . . . C5D C 0.89493(13) 0.15781(18) 0.19885(13) 0.0322(5) Uani 1 1 d . . . H4D H 0.9543 0.1798 0.2301 0.039 Uiso 1 1 calc R . . C6D C 0.63076(12) 0.05646(17) 0.06391(12) 0.0270(4) Uani 1 1 d . . . C3D C 0.78489(12) 0.00050(17) 0.14951(13) 0.0298(4) Uani 1 1 d . . . H2D H 0.7672 -0.0849 0.1445 0.036 Uiso 1 1 calc R . . O1C O 0.60622(9) 0.72874(11) 0.32375(9) 0.0338(3) Uani 1 1 d . . . O1B O 0.62027(11) 0.61660(12) 0.54621(9) 0.0430(4) Uani 1 1 d . . . N2B N 0.64114(10) 0.81768(14) 0.51327(10) 0.0311(4) Uani 1 1 d . . . H6B H 0.6415 0.7999 0.4569 0.037 Uiso 1 1 calc R . . H5B H 0.6480 0.8955 0.5322 0.037 Uiso 1 1 calc R . . O1A O 0.38960(10) 0.60142(12) 0.18556(10) 0.0417(4) Uani 1 1 d . . . N2C N 0.61917(11) 0.52608(14) 0.36501(10) 0.0341(4) Uani 1 1 d . . . H6C H 0.6191 0.5444 0.4214 0.041 Uiso 1 1 calc R . . H5C H 0.6236 0.4477 0.3488 0.041 Uiso 1 1 calc R . . N1C N 0.59194(11) 0.42824(15) 0.09082(10) 0.0327(4) Uani 1 1 d . . . N1B N 0.62519(10) 0.91347(14) 0.78063(10) 0.0303(4) Uani 1 1 d . . . N2A N 0.42020(11) 0.80539(14) 0.21442(11) 0.0369(4) Uani 1 1 d . . . H6A H 0.4755 0.7895 0.2449 0.044 Uiso 1 1 calc R . . H5A H 0.4006 0.8830 0.2077 0.044 Uiso 1 1 calc R . . C1A C 0.24673(13) 0.86556(17) 0.10002(12) 0.0288(4) Uani 1 1 d . . . H1A H 0.2914 0.9294 0.1128 0.035 Uiso 1 1 calc R . . N1A N 0.16311(11) 0.89754(14) 0.05586(10) 0.0326(4) Uani 1 1 d . . . C2C C 0.61422(12) 0.58079(16) 0.20968(12) 0.0249(4) Uani 1 1 d . . . C6B C 0.63010(12) 0.72664(17) 0.57007(12) 0.0272(4) Uani 1 1 d . . . C2B C 0.62900(11) 0.75995(16) 0.66544(12) 0.0241(4) Uani 1 1 d . . . C2A C 0.27195(13) 0.74523(16) 0.12818(12) 0.0266(4) Uani 1 1 d . . . C6C C 0.61264(12) 0.61661(16) 0.30436(12) 0.0270(4) Uani 1 1 d . . . C1B C 0.62723(12) 0.88211(17) 0.69559(13) 0.0282(4) Uani 1 1 d . . . H1B H 0.6275 0.9476 0.6535 0.034 Uiso 1 1 calc R . . C5B C 0.62586(12) 0.81964(17) 0.83900(13) 0.0285(4) Uani 1 1 d . . . H4B H 0.6260 0.8396 0.8999 0.034 Uiso 1 1 calc R . . C1C C 0.59085(12) 0.46302(17) 0.17507(12) 0.0287(4) Uani 1 1 d . . . H1C H 0.5728 0.4027 0.2137 0.034 Uiso 1 1 calc R . . C3B C 0.62741(12) 0.66477(17) 0.72730(13) 0.0298(4) Uani 1 1 d . . . H2B H 0.6271 0.5797 0.7093 0.036 Uiso 1 1 calc R . . C5A C 0.10165(14) 0.80575(19) 0.03938(14) 0.0372(5) Uani 1 1 d . . . H4A H 0.0416 0.8265 0.0092 0.045 Uiso 1 1 calc R . . C6A C 0.36579(13) 0.71132(17) 0.17821(13) 0.0292(4) Uani 1 1 d . . . C3C C 0.63853(14) 0.66885(18) 0.15265(13) 0.0354(5) Uani 1 1 d . . . H2C H 0.6531 0.7518 0.1729 0.043 Uiso 1 1 calc R . . C4B C 0.62634(13) 0.69537(18) 0.81500(13) 0.0313(5) Uani 1 1 d . . . H3B H 0.6259 0.6317 0.8585 0.038 Uiso 1 1 calc R . . C3A C 0.20670(14) 0.65203(18) 0.10804(14) 0.0354(5) Uani 1 1 d . . . H2A H 0.2215 0.5678 0.1248 0.042 Uiso 1 1 calc R . . C4A C 0.12008(14) 0.6833(2) 0.06345(15) 0.0413(5) Uani 1 1 d . . . H3A H 0.0741 0.6214 0.0497 0.050 Uiso 1 1 calc R . . C5C C 0.61811(14) 0.51473(18) 0.03805(13) 0.0363(5) Uani 1 1 d . . . H4C H 0.6207 0.4920 -0.0217 0.044 Uiso 1 1 calc R . . C4C C 0.64137(16) 0.6346(2) 0.06580(14) 0.0427(5) Uani 1 1 d . . . H3C H 0.6592 0.6931 0.0258 0.051 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 O1D 0.0341(8) 0.0230(8) 0.0514(9) -0.0081(6) 0.0004(7) -0.0046(6) C1D 0.0287(11) 0.0250(10) 0.0314(11) -0.0023(8) 0.0037(9) 0.0026(8) N2D 0.0273(9) 0.0269(9) 0.0445(10) -0.0072(8) -0.0022(7) -0.0022(7) C2D 0.0266(10) 0.0228(10) 0.0232(10) -0.0027(8) 0.0068(8) -0.0014(8) C4D 0.0300(11) 0.0277(11) 0.0400(12) 0.0026(9) 0.0037(9) 0.0059(9) N1D 0.0257(9) 0.0270(9) 0.0385(10) -0.0052(7) 0.0032(7) -0.0028(7) C5D 0.0255(10) 0.0325(11) 0.0372(12) -0.0022(9) 0.0036(9) 0.0000(9) C6D 0.0296(10) 0.0241(11) 0.0276(10) -0.0035(8) 0.0065(8) -0.0032(8) C3D 0.0338(11) 0.0221(10) 0.0345(11) -0.0010(8) 0.0092(9) -0.0021(8) O1C 0.0490(9) 0.0200(7) 0.0298(7) -0.0028(6) 0.0028(6) 0.0019(6) O1B 0.0759(11) 0.0236(8) 0.0303(8) -0.0018(6) 0.0128(7) 0.0036(7) N2B 0.0414(10) 0.0279(9) 0.0249(9) -0.0010(7) 0.0089(7) -0.0022(7) O1A 0.0467(9) 0.0204(8) 0.0546(10) 0.0006(6) 0.0031(7) 0.0048(6) N2C 0.0522(10) 0.0223(9) 0.0272(9) -0.0001(7) 0.0073(8) 0.0050(7) N1C 0.0392(10) 0.0264(9) 0.0287(9) -0.0020(7) -0.0013(7) 0.0053(7) N1B 0.0345(9) 0.0254(9) 0.0306(9) -0.0041(7) 0.0059(7) -0.0048(7) N2A 0.0363(10) 0.0235(9) 0.0451(11) -0.0015(8) -0.0047(8) 0.0027(7) C1A 0.0323(11) 0.0241(10) 0.0291(10) -0.0036(8) 0.0043(9) -0.0009(8) N1A 0.0355(9) 0.0286(9) 0.0321(9) -0.0052(7) 0.0032(7) 0.0045(8) C2C 0.0255(9) 0.0211(9) 0.0258(10) 0.0010(8) 0.0003(8) 0.0019(8) C6B 0.0297(10) 0.0232(11) 0.0281(10) 0.0013(8) 0.0045(8) 0.0027(8) C2B 0.0225(9) 0.0230(10) 0.0262(10) 0.0005(8) 0.0035(8) 0.0002(8) C2A 0.0338(10) 0.0214(10) 0.0254(10) -0.0029(8) 0.0079(8) 0.0001(8) C6C 0.0294(10) 0.0210(10) 0.0283(10) 0.0003(8) 0.0011(8) 0.0006(8) C1B 0.0332(11) 0.0230(10) 0.0290(11) 0.0016(8) 0.0079(8) -0.0035(8) C5B 0.0304(10) 0.0299(11) 0.0245(10) -0.0014(8) 0.0047(8) -0.0016(8) C1C 0.0331(11) 0.0231(10) 0.0282(11) 0.0015(8) 0.0023(8) 0.0006(8) C3B 0.0347(11) 0.0220(10) 0.0315(11) 0.0004(8) 0.0046(9) 0.0031(8) C5A 0.0305(11) 0.0381(12) 0.0412(12) -0.0108(10) 0.0033(9) 0.0014(9) C6A 0.0376(11) 0.0216(10) 0.0295(11) -0.0005(8) 0.0093(9) -0.0001(9) C3C 0.0489(13) 0.0237(10) 0.0326(12) -0.0005(9) 0.0062(10) -0.0032(9) C4B 0.0408(12) 0.0269(10) 0.0256(11) 0.0044(8) 0.0060(9) 0.0021(9) C3A 0.0422(12) 0.0239(10) 0.0409(12) -0.0017(9) 0.0108(10) -0.0027(9) C4A 0.0365(12) 0.0332(12) 0.0539(14) -0.0081(10) 0.0090(10) -0.0076(9) C5C 0.0500(13) 0.0331(12) 0.0246(11) 0.0014(9) 0.0052(9) 0.0071(10) C4C 0.0658(15) 0.0336(12) 0.0307(12) 0.0042(9) 0.0143(11) -0.0044(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 O1D C6D 1.235(2) . ? C1D N1D 1.336(2) . ? C1D C2D 1.388(2) . ? C1D H1D 0.9500 . ? N2D C6D 1.335(2) . ? N2D H6D 0.8800 . ? N2D H5D 0.8800 . ? C2D C3D 1.381(3) . ? C2D C6D 1.500(3) . ? C4D C5D 1.373(3) . ? C4D C3D 1.382(3) . ? C4D H3D 0.9500 . ? N1D C5D 1.342(2) . ? C5D H4D 0.9500 . ? C3D H2D 0.9500 . ? O1C C6C 1.244(2) . ? O1B C6B 1.232(2) . ? N2B C6B 1.335(2) . ? N2B H6B 0.8800 . ? N2B H5B 0.8800 . ? O1A C6A 1.227(2) . ? N2C C6C 1.327(2) . ? N2C H6C 0.8800 . ? N2C H5C 0.8800 . ? N1C C1C 1.338(2) . ? N1C C5C 1.337(3) . ? N1B C5B 1.339(2) . ? N1B C1B 1.343(2) . ? N2A C6A 1.341(2) . ? N2A H6A 0.8800 . ? N2A H5A 0.8800 . ? C1A N1A 1.341(2) . ? C1A C2A 1.384(3) . ? C1A H1A 0.9500 . ? N1A C5A 1.336(2) . ? C2C C3C 1.381(3) . ? C2C C1C 1.382(2) . ? C2C C6C 1.495(3) . ? C6B C2B 1.497(3) . ? C2B C1B 1.387(2) . ? C2B C3B 1.390(3) . ? C2A C3A 1.388(3) . ? C2A C6A 1.502(3) . ? C1B H1B 0.9500 . ? C5B C4B 1.379(3) . ? C5B H4B 0.9500 . ? C1C H1C 0.9500 . ? C3B C4B 1.377(3) . ? C3B H2B 0.9500 . ? C5A C4A 1.372(3) . ? C5A H4A 0.9500 . ? C3C C4C 1.380(3) . ? C3C H2C 0.9500 . ? C4B H3B 0.9500 . ? C3A C4A 1.379(3) . ? C3A H2A 0.9500 . ? C4A H3A 0.9500 . ? C5C C4C 1.372(3) . ? C5C H4C 0.9500 . ? C4C H3C 0.9500 . ? 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 N1D C1D C2D 124.30(17) . . ? N1D C1D H1D 117.8 . . ? C2D C1D H1D 117.8 . . ? C6D N2D H6D 120.0 . . ? C6D N2D H5D 120.0 . . ? H6D N2D H5D 120.0 . . ? C3D C2D C1D 117.61(16) . . ? C3D C2D C6D 118.99(16) . . ? C1D C2D C6D 123.36(16) . . ? C5D C4D C3D 118.70(18) . . ? C5D C4D H3D 120.7 . . ? C3D C4D H3D 120.7 . . ? C1D N1D C5D 116.40(16) . . ? N1D C5D C4D 123.75(18) . . ? N1D C5D H4D 118.1 . . ? C4D C5D H4D 118.1 . . ? O1D C6D N2D 122.45(17) . . ? O1D C6D C2D 119.24(16) . . ? N2D C6D C2D 118.30(16) . . ? C2D C3D C4D 119.22(17) . . ? C2D C3D H2D 120.4 . . ? C4D C3D H2D 120.4 . . ? C6B N2B H6B 120.0 . . ? C6B N2B H5B 120.0 . . ? H6B N2B H5B 120.0 . . ? C6C N2C H6C 120.0 . . ? C6C N2C H5C 120.0 . . ? H6C N2C H5C 120.0 . . ? C1C N1C C5C 116.56(16) . . ? C5B N1B C1B 116.93(16) . . ? C6A N2A H6A 120.0 . . ? C6A N2A H5A 120.0 . . ? H6A N2A H5A 120.0 . . ? N1A C1A C2A 124.03(17) . . ? N1A C1A H1A 118.0 . . ? C2A C1A H1A 118.0 . . ? C5A N1A C1A 116.54(17) . . ? C3C C2C C1C 117.55(17) . . ? C3C C2C C6C 119.35(16) . . ? C1C C2C C6C 123.09(16) . . ? O1B C6B N2B 122.02(17) . . ? O1B C6B C2B 119.20(16) . . ? N2B C6B C2B 118.78(16) . . ? C1B C2B C3B 117.53(17) . . ? C1B C2B C6B 123.33(16) . . ? C3B C2B C6B 119.12(16) . . ? C1A C2A C3A 117.68(18) . . ? C1A C2A C6A 123.29(17) . . ? C3A C2A C6A 119.03(16) . . ? O1C C6C N2C 122.50(17) . . ? O1C C6C C2C 119.56(16) . . ? N2C C6C C2C 117.93(16) . . ? N1B C1B C2B 124.04(17) . . ? N1B C1B H1B 118.0 . . ? C2B C1B H1B 118.0 . . ? N1B C5B C4B 123.17(17) . . ? N1B C5B H4B 118.4 . . ? C4B C5B H4B 118.4 . . ? N1C C1C C2C 124.38(17) . . ? N1C C1C H1C 117.8 . . ? C2C C1C H1C 117.8 . . ? C4B C3B C2B 119.14(17) . . ? C4B C3B H2B 120.4 . . ? C2B C3B H2B 120.4 . . ? N1A C5A C4A 123.92(19) . . ? N1A C5A H4A 118.0 . . ? C4A C5A H4A 118.0 . . ? O1A C6A N2A 122.69(18) . . ? O1A C6A C2A 120.21(17) . . ? N2A C6A C2A 117.09(16) . . ? C4C C3C C2C 119.06(18) . . ? C4C C3C H2C 120.5 . . ? C2C C3C H2C 120.5 . . ? C3B C4B C5B 119.17(18) . . ? C3B C4B H3B 120.4 . . ? C5B C4B H3B 120.4 . . ? C4A C3A C2A 119.12(18) . . ? C4A C3A H2A 120.4 . . ? C2A C3A H2A 120.4 . . ? C5A C4A C3A 118.69(19) . . ? C5A C4A H3A 120.7 . . ? C3A C4A H3A 120.7 . . ? N1C C5C C4C 123.40(19) . . ? N1C C5C H4C 118.3 . . ? C4C C5C H4C 118.3 . . ? C5C C4C C3C 119.01(19) . . ? C5C C4C H3C 120.5 . . ? C3C C4C H3C 120.5 . . ? 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 N1D C1D C2D C3D -1.4(3) . . . . ? N1D C1D C2D C6D -179.11(16) . . . . ? C2D C1D N1D C5D 0.0(3) . . . . ? C1D N1D C5D C4D 1.2(3) . . . . ? C3D C4D C5D N1D -0.8(3) . . . . ? C3D C2D C6D O1D -10.6(3) . . . . ? C1D C2D C6D O1D 167.12(18) . . . . ? C3D C2D C6D N2D 169.81(17) . . . . ? C1D C2D C6D N2D -12.5(3) . . . . ? C1D C2D C3D C4D 1.7(3) . . . . ? C6D C2D C3D C4D 179.52(16) . . . . ? C5D C4D C3D C2D -0.7(3) . . . . ? C2A C1A N1A C5A 0.4(3) . . . . ? O1B C6B C2B C1B -171.03(18) . . . . ? N2B C6B C2B C1B 8.5(3) . . . . ? O1B C6B C2B C3B 7.3(3) . . . . ? N2B C6B C2B C3B -173.12(17) . . . . ? N1A C1A C2A C3A 1.0(3) . . . . ? N1A C1A C2A C6A -179.52(17) . . . . ? C3C C2C C6C O1C 21.3(3) . . . . ? C1C C2C C6C O1C -157.59(18) . . . . ? C3C C2C C6C N2C -158.05(18) . . . . ? C1C C2C C6C N2C 23.1(3) . . . . ? C5B N1B C1B C2B 0.7(3) . . . . ? C3B C2B C1B N1B 0.8(3) . . . . ? C6B C2B C1B N1B 179.22(16) . . . . ? C1B N1B C5B C4B -1.6(3) . . . . ? C5C N1C C1C C2C 0.4(3) . . . . ? C3C C2C C1C N1C 1.4(3) . . . . ? C6C C2C C1C N1C -179.75(17) . . . . ? C1B C2B C3B C4B -1.5(3) . . . . ? C6B C2B C3B C4B -179.96(17) . . . . ? C1A N1A C5A C4A -1.2(3) . . . . ? C1A C2A C6A O1A -165.27(18) . . . . ? C3A C2A C6A O1A 14.2(3) . . . . ? C1A C2A C6A N2A 15.6(3) . . . . ? C3A C2A C6A N2A -164.99(17) . . . . ? C1C C2C C3C C4C -2.2(3) . . . . ? C6C C2C C3C C4C 178.89(18) . . . . ? C2B C3B C4B C5B 0.7(3) . . . . ? N1B C5B C4B C3B 0.9(3) . . . . ? C1A C2A C3A C4A -1.6(3) . . . . ? C6A C2A C3A C4A 178.90(18) . . . . ? N1A C5A C4A C3A 0.6(3) . . . . ? C2A C3A C4A C5A 0.9(3) . . . . ? C1C N1C C5C C4C -1.3(3) . . . . ? N1C C5C C4C C3C 0.4(3) . . . . ? C2C C3C C4C C5C 1.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.188 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.049