# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- Lawrence.cif' _audit_creation_method 'APEX2 v2010.1-2' _publ_contact_author_name 'Simon E. Lawrence' _publ_contact_author_address ;Department of Chemistry Analytical and Biological Chemistry Research Facility University College Cork Cork Ireland ; _publ_contact_author_email s.lawrence@ucc.ie _publ_contact_author_fax +353214274097 _publ_contact_author_phone +353214903143 loop_ _publ_author_name _publ_author_address K.S.Eccles ; Department of Chemistry, Analytical and Biological Chemistry Research Facility University College Cork Cork Ireland ; R.E.Deasy ; Department of Chemistry, Analytical and Biological Chemistry Research Facility University College Cork Cork Ireland ; L.Fabian ; School of Pharmacy, University of East Anglia, Earlham, Norwich England ; D.E.Braun ; Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ UK ; A.R.Maguire ; School of Pharmacy and Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork Cork Ireland ; ; S.E.Lawrence ; ; Department of Chemistry, Analytical and Biological Chemistry Research Facility University College Cork Cork Ireland ; _publ_section_title ; Increasing the crystal landscape of isonicotinamide: serendipitous outcome of concomitant co-crystallisation ; #===================================================================== data_Isonicotinamide_Form_IV _database_code_depnum_ccdc_archive 'CCDC 844552' #TrackingRef '- Lawrence.cif' #===================================================================== _chemical_name_systematic ? _chemical_name_common Isonicotinamide _chemical_formula_moiety 'C6 H6 N2 O' _chemical_formula_sum 'C6 H6 N2 O' _chemical_formula_iupac ? _chemical_formula_weight 122.13 _chemical_absolute_configuration syn _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 c 1' _space_group_name_Hall 'P -2yc' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 11.0819(6) _cell_length_b 7.9976(4) _cell_length_c 9.9850(5) _cell_angle_alpha 90 _cell_angle_beta 94.0480(10) _cell_angle_gamma 90 _cell_volume 882.75(8) _cell_formula_units_Z 6 _cell_measurement_reflns_used 4455 _cell_measurement_theta_min 3.1439 _cell_measurement_theta_max 26.4341 _cell_measurement_temperature 100.(2) _exptl_crystal_description Lath _exptl_crystal_colour colorless _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.210 _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.98 _exptl_special_details ; The crystal transforms during the time taken for data collection using CuK\a radiation. The use of MoK\a radiation means that the Flack paramater is not meaningful. ; _diffrn_ambient_temperature 100.(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II DUO' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 10209 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 26.45 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _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. ; _reflns_number_total 3601 _reflns_number_gt 3375 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_gt 0.0918 _refine_ls_wR_factor_ref 0.0940 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.170 _refine_ls_number_reflns 3601 _refine_ls_number_parameters 268 _refine_ls_number_restraints 3 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.374 _refine_diff_density_min -0.193 _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 -0.3(9) 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2009, 3, 0, 0' _computing_cell_refinement 'SAINT V7.60A (Bruker AXS, 2008)' _computing_data_reduction 'SAINT V7.60A (Bruker AXS, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 2.3 (Macrae et al, 2008)' _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.26667(15) 0.3012(2) 0.64964(17) 0.0143(3) Uani d . 1 . . C C3 0.31997(16) 0.0611(2) 0.78300(17) 0.0178(4) Uani d . 1 . . H H3 0.3595 0.0157 0.8623 0.021 Uiso calc R 1 . . C C2 0.32296(16) 0.2339(2) 0.76556(17) 0.0155(3) Uani d . 1 . . H H2 0.3627 0.3039 0.8317 0.019 Uiso calc R 1 . . N N4 0.26481(14) -0.04455(19) 0.69481(14) 0.0172(3) Uani d . 1 . . C C7 0.26372(16) 0.4867(2) 0.62260(17) 0.0152(3) Uani d . 1 . . C C6 0.21030(16) 0.1927(2) 0.55592(16) 0.0170(4) Uani d . 1 . . H H6 0.172 0.2345 0.4746 0.02 Uiso calc R 1 . . C C5 0.21084(16) 0.0225(2) 0.58305(18) 0.0179(4) Uani d . 1 . . H H5 0.1709 -0.0502 0.5191 0.022 Uiso calc R 1 . . O O8 0.25246(13) 0.53930(16) 0.50535(12) 0.0226(3) Uani d . 1 . . N N9 0.27265(14) 0.58631(19) 0.72931(15) 0.0163(3) Uani d . 1 . . C C10 0.93983(14) 0.2026(2) 0.73283(16) 0.0142(3) Uani d . 1 . . C C11 0.87739(16) 0.2704(2) 0.61929(17) 0.0155(3) Uani d . 1 . . H H11 0.8369 0.2 0.5539 0.019 Uiso calc R 1 . . C C12 0.87588(16) 0.4422(2) 0.60408(19) 0.0180(4) Uani d . 1 . . H H12 0.8334 0.4875 0.5264 0.022 Uiso calc R 1 . . N N13 0.93071(16) 0.5484(2) 0.69223(16) 0.0205(3) Uani d . 1 . . C C14 0.99049(17) 0.4815(2) 0.80088(18) 0.0200(4) Uani d . 1 . . H H14 1.0308 0.5549 0.8641 0.024 Uiso calc R 1 . . C C15 0.99663(15) 0.3117(2) 0.82582(17) 0.0166(4) Uani d . 1 . . H H15 1.0389 0.2702 0.905 0.02 Uiso calc R 1 . . C C16 0.94430(15) 0.0155(2) 0.75956(17) 0.0151(3) Uani d . 1 . . O O17 0.96147(12) -0.03535(16) 0.87606(11) 0.0199(3) Uani d . 1 . . N N18 0.92704(15) -0.08381(18) 0.65359(15) 0.0183(3) Uani d D 1 . . N N22 0.60794(14) 1.04780(18) 0.46116(15) 0.0195(3) Uani d . 1 . . C C23 0.54767(16) 0.9832(2) 0.56132(18) 0.0205(4) Uani d . 1 . . H H23 0.5104 1.0584 0.6194 0.025 Uiso calc R 1 . . C C24 0.53676(16) 0.8131(2) 0.58485(18) 0.0194(4) Uani d . 1 . . H H24 0.4939 0.7737 0.6576 0.023 Uiso calc R 1 . . C C21 0.66017(16) 0.9387(2) 0.38176(18) 0.0194(4) Uani d . 1 . . H H21 0.7049 0.9817 0.3117 0.023 Uiso calc R 1 . . C C20 0.65291(15) 0.7661(2) 0.39566(16) 0.0168(3) Uani d . 1 . . H H20 0.6902 0.6939 0.3353 0.02 Uiso calc R 1 . . C C19 0.59001(15) 0.7012(2) 0.49954(16) 0.0154(3) Uani d . 1 . . N N27 0.58490(15) 0.41738(19) 0.41757(17) 0.0202(3) Uani d . 1 . . C C25 0.57946(16) 0.5155(2) 0.52439(17) 0.0167(3) Uani d . 1 . . O O26 0.56909(12) 0.46280(15) 0.63886(12) 0.0217(3) Uani d . 1 . . H H18A 0.918(2) -0.048(3) 0.569(2) 0.022(6) Uiso d . 1 . . H H18B 0.924(2) -0.196(2) 0.665(2) 0.024(5) Uiso d D 1 . . H H9B 0.263(2) 0.688(3) 0.719(2) 0.030(6) Uiso d . 1 . . H H9A 0.267(3) 0.544(3) 0.815(3) 0.034(7) Uiso d . 1 . . H H27A 0.581(2) 0.462(3) 0.336(2) 0.020(5) Uiso d . 1 . . H H27B 0.579(2) 0.305(3) 0.439(3) 0.044(7) Uiso d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0169(8) 0.0134(8) 0.0134(8) 0.0008(7) 0.0056(6) 0.0002(7) C3 0.0225(9) 0.0174(8) 0.0137(9) 0.0043(7) 0.0028(7) 0.0023(7) C2 0.0188(8) 0.0151(8) 0.0127(8) 0.0006(7) 0.0026(6) -0.0024(7) N4 0.0211(7) 0.0120(7) 0.0192(8) 0.0006(6) 0.0062(6) -0.0002(6) C7 0.0178(8) 0.0128(9) 0.0152(9) -0.0003(7) 0.0033(7) 0.0024(7) C6 0.0203(8) 0.0177(9) 0.0130(8) 0.0005(7) 0.0018(6) 0.0003(7) C5 0.0205(9) 0.0167(9) 0.0167(8) -0.0031(7) 0.0030(7) -0.0035(7) O8 0.0405(8) 0.0152(7) 0.0122(6) -0.0007(5) 0.0016(6) 0.0028(5) N9 0.0264(8) 0.0091(7) 0.0136(8) -0.0002(6) 0.0022(6) 0.0013(6) C10 0.0134(8) 0.0143(8) 0.0152(8) 0.0001(6) 0.0032(7) 0.0015(7) C11 0.0181(8) 0.0151(8) 0.0132(8) 0.0005(6) 0.0001(7) -0.0011(7) C12 0.0198(9) 0.0175(9) 0.0169(9) 0.0027(7) 0.0029(7) 0.0018(7) N13 0.0257(8) 0.0146(7) 0.0218(8) -0.0008(6) 0.0055(6) -0.0005(6) C14 0.0242(9) 0.0160(9) 0.0201(9) -0.0052(7) 0.0033(8) -0.0041(7) C15 0.0185(8) 0.0180(9) 0.0134(8) -0.0011(7) 0.0007(6) -0.0013(7) C16 0.0159(8) 0.0162(9) 0.0131(8) 0.0003(7) 0.0010(7) -0.0005(7) O17 0.0299(7) 0.0174(6) 0.0123(6) 0.0025(5) 0.0017(5) 0.0027(5) N18 0.0309(9) 0.0104(7) 0.0135(8) -0.0006(7) 0.0014(6) 0.0008(6) N22 0.0258(8) 0.0131(7) 0.0190(7) -0.0001(6) -0.0020(6) -0.0002(6) C23 0.0245(9) 0.0199(8) 0.0170(9) 0.0041(7) 0.0013(7) -0.0016(7) C24 0.0230(8) 0.0196(8) 0.0156(8) 0.0030(7) 0.0023(7) 0.0001(6) C21 0.0198(8) 0.0215(9) 0.0171(9) -0.0036(7) 0.0026(7) -0.0004(7) C20 0.0199(8) 0.0171(8) 0.0135(8) 0.0010(6) 0.0015(7) -0.0006(7) C19 0.0172(8) 0.0160(8) 0.0126(8) 0.0010(6) -0.0016(6) 0.0001(6) N27 0.0331(9) 0.0132(7) 0.0143(7) -0.0001(6) 0.0023(6) 0.0022(6) C25 0.0168(8) 0.0190(9) 0.0143(8) 0.0022(7) 0.0001(6) 0.0030(7) O26 0.0319(7) 0.0183(6) 0.0153(6) 0.0012(5) 0.0030(5) 0.0021(5) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.384(2) ? C1 C6 . 1.392(2) ? C1 C7 . 1.508(2) ? C3 N4 . 1.337(2) ? C3 C2 . 1.393(2) ? C3 H3 . 0.95 ? C2 H2 . 0.95 ? N4 C5 . 1.340(2) ? C7 O8 . 1.242(2) ? C7 N9 . 1.328(2) ? C6 C5 . 1.387(2) ? C6 H6 . 0.95 ? C5 H5 . 0.95 ? N9 H9B . 0.83(2) ? N9 H9A . 0.92(3) ? C10 C15 . 1.392(2) ? C10 C11 . 1.395(2) ? C10 C16 . 1.520(2) ? C11 C12 . 1.383(2) ? C11 H11 . 0.95 ? C12 N13 . 1.338(2) ? C12 H12 . 0.95 ? N13 C14 . 1.342(2) ? C14 C15 . 1.381(3) ? C14 H14 . 0.95 ? C15 H15 . 0.95 ? C16 O17 . 1.234(2) ? C16 N18 . 1.326(2) ? N18 H18A . 0.89(2) ? N18 H18B . 0.907(16) ? N22 C21 . 1.338(2) ? N22 C23 . 1.344(2) ? C23 C24 . 1.387(2) ? C23 H23 . 0.95 ? C24 C19 . 1.395(2) ? C24 H24 . 0.95 ? C21 C20 . 1.389(2) ? C21 H21 . 0.95 ? C20 C19 . 1.391(2) ? C20 H20 . 0.95 ? C19 C25 . 1.511(2) ? N27 C25 . 1.329(2) ? N27 H27A . 0.88(2) ? N27 H27B . 0.93(3) ? C25 O26 . 1.231(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 C6 . . 118.30(15) ? C2 C1 C7 . . 122.34(15) ? C6 C1 C7 . . 119.35(15) ? N4 C3 C2 . . 123.94(16) ? N4 C3 H3 . . 118.0 ? C2 C3 H3 . . 118.0 ? C1 C2 C3 . . 118.47(16) ? C1 C2 H2 . . 120.8 ? C3 C2 H2 . . 120.8 ? C3 N4 C5 . . 116.86(15) ? O8 C7 N9 . . 123.38(16) ? O8 C7 C1 . . 120.08(15) ? N9 C7 C1 . . 116.54(15) ? C5 C6 C1 . . 119.00(16) ? C5 C6 H6 . . 120.5 ? C1 C6 H6 . . 120.5 ? N4 C5 C6 . . 123.41(16) ? N4 C5 H5 . . 118.3 ? C6 C5 H5 . . 118.3 ? C7 N9 H9B . . 119.3(17) ? C7 N9 H9A . . 121.0(15) ? H9B N9 H9A . . 117.(2) ? C15 C10 C11 . . 118.26(16) ? C15 C10 C16 . . 119.50(15) ? C11 C10 C16 . . 122.21(15) ? C12 C11 C10 . . 118.48(16) ? C12 C11 H11 . . 120.8 ? C10 C11 H11 . . 120.8 ? N13 C12 C11 . . 123.88(17) ? N13 C12 H12 . . 118.1 ? C11 C12 H12 . . 118.1 ? C12 N13 C14 . . 116.99(16) ? N13 C14 C15 . . 123.58(16) ? N13 C14 H14 . . 118.2 ? C15 C14 H14 . . 118.2 ? C14 C15 C10 . . 118.80(16) ? C14 C15 H15 . . 120.6 ? C10 C15 H15 . . 120.6 ? O17 C16 N18 . . 123.95(16) ? O17 C16 C10 . . 119.39(15) ? N18 C16 C10 . . 116.65(15) ? C16 N18 H18A . . 124.4(14) ? C16 N18 H18B . . 120.1(14) ? H18A N18 H18B . . 115.(2) ? C21 N22 C23 . . 116.65(15) ? N22 C23 C24 . . 123.82(16) ? N22 C23 H23 . . 118.1 ? C24 C23 H23 . . 118.1 ? C23 C24 C19 . . 118.71(16) ? C23 C24 H24 . . 120.6 ? C19 C24 H24 . . 120.6 ? N22 C21 C20 . . 123.92(16) ? N22 C21 H21 . . 118.0 ? C20 C21 H21 . . 118.0 ? C21 C20 C19 . . 118.77(16) ? C21 C20 H20 . . 120.6 ? C19 C20 H20 . . 120.6 ? C20 C19 C24 . . 118.12(15) ? C20 C19 C25 . . 122.57(15) ? C24 C19 C25 . . 119.30(15) ? C25 N27 H27A . . 119.5(13) ? C25 N27 H27B . . 112.1(16) ? H27A N27 H27B . . 127.(2) ? O26 C25 N27 . . 123.76(16) ? O26 C25 C19 . . 120.13(15) ? N27 C25 C19 . . 116.10(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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . . . . -0.3(3) ? C7 C1 C2 C3 . . . . 179.21(16) ? N4 C3 C2 C1 . . . . -0.6(3) ? C2 C3 N4 C5 . . . . 0.7(3) ? C2 C1 C7 O8 . . . . 154.70(17) ? C6 C1 C7 O8 . . . . -25.8(3) ? C2 C1 C7 N9 . . . . -25.8(3) ? C6 C1 C7 N9 . . . . 153.65(16) ? C2 C1 C6 C5 . . . . 1.1(2) ? C7 C1 C6 C5 . . . . -178.43(16) ? C3 N4 C5 C6 . . . . 0.2(2) ? C1 C6 C5 N4 . . . . -1.1(3) ? C15 C10 C11 C12 . . . . 0.6(2) ? C16 C10 C11 C12 . . . . 178.70(16) ? C10 C11 C12 N13 . . . . -0.2(3) ? C11 C12 N13 C14 . . . . 0.2(3) ? C12 N13 C14 C15 . . . . -0.7(3) ? N13 C14 C15 C10 . . . . 1.1(3) ? C11 C10 C15 C14 . . . . -1.0(2) ? C16 C10 C15 C14 . . . . -179.21(16) ? C15 C10 C16 O17 . . . . 23.4(2) ? C11 C10 C16 O17 . . . . -154.74(17) ? C15 C10 C16 N18 . . . . -157.74(16) ? C11 C10 C16 N18 . . . . 24.2(2) ? C21 N22 C23 C24 . . . . -0.5(3) ? N22 C23 C24 C19 . . . . -0.7(3) ? C23 N22 C21 C20 . . . . 1.5(3) ? N22 C21 C20 C19 . . . . -1.4(3) ? C21 C20 C19 C24 . . . . 0.2(2) ? C21 C20 C19 C25 . . . . -178.69(15) ? C23 C24 C19 C20 . . . . 0.8(2) ? C23 C24 C19 C25 . . . . 179.67(16) ? C20 C19 C25 O26 . . . . 150.55(17) ? C24 C19 C25 O26 . . . . -28.3(2) ? C20 C19 C25 N27 . . . . -28.0(2) ? C24 C19 C25 N27 . . . . 153.16(17) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N18 H18A O17 2_554 0.89(2) 2.13(2) 2.980(2) 160.(2) ? N18 H18B N13 1_545 0.907(16) 2.061(16) 2.966(2) 176.(2) ? N9 H9B N4 1_565 0.83(2) 2.15(2) 2.973(2) 172.(2) ? N9 H9A O8 2_565 0.92(3) 2.04(3) 2.957(2) 178.(2) ? N27 H27A O26 2_564 0.88(2) 2.06(2) 2.937(2) 172.9(19) ? N27 H27B N22 1_545 0.93(3) 2.09(3) 2.996(2) 164.(2) ? #===END #===================================================================== data_Isonicotinamide_Form_V _database_code_depnum_ccdc_archive 'CCDC 844553' #TrackingRef '- Lawrence.cif' #===================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O1' _chemical_formula_sum 'C6 H6 N2 O1' _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' _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.1923(11) _cell_length_b 9.466(3) _cell_length_c 12.259(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.217(7) _cell_angle_gamma 90.00 _cell_volume 602.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 916 _cell_measurement_theta_min 2.7189 _cell_measurement_theta_max 24.3271 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.6479 _exptl_absorpt_correction_T_max 0.7452 _diffrn_ambient_temperature 300(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 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 3129 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1048 _reflns_number_gt 762 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 2.3 (Macrae et al, 2008)' _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^)+(0.0396P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.030(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1048 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.353 _refine_ls_restrained_S_all 1.353 _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 O8 O 0.9228(2) 0.07420(12) 0.81663(8) 0.0615(4) Uani 1 1 d . . . N9 N 1.0246(3) 0.30274(13) 0.79749(10) 0.0569(4) Uani 1 1 d . . . H9A H 1.1314 0.3002 0.8521 0.068 Uiso 1 1 calc R . . H9B H 1.0013 0.3801 0.7619 0.068 Uiso 1 1 calc R . . N4 N 0.3496(3) 0.20356(15) 0.50146(11) 0.0572(4) Uani 1 1 d . . . C5 C 0.3444(3) 0.10508(19) 0.57799(14) 0.0569(5) Uani 1 1 d . . . H5 H 0.2160 0.0367 0.5731 0.068 Uiso 1 1 calc R . . C6 C 0.5175(3) 0.09768(17) 0.66447(12) 0.0503(5) Uani 1 1 d . . . H6 H 0.5058 0.0258 0.7158 0.060 Uiso 1 1 calc R . . C1 C 0.7084(3) 0.19854(15) 0.67375(12) 0.0424(4) Uani 1 1 d . . . C7 C 0.8966(3) 0.18790(16) 0.76840(12) 0.0454(4) Uani 1 1 d . . . C3 C 0.5346(4) 0.30024(18) 0.51114(14) 0.0577(5) Uani 1 1 d . . . H3 H 0.5414 0.3707 0.4584 0.069 Uiso 1 1 calc R . . C2 C 0.7170(3) 0.30254(16) 0.59458(13) 0.0517(5) Uani 1 1 d . . . H2 H 0.8429 0.3724 0.5976 0.062 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 O8 0.0835(9) 0.0420(7) 0.0580(7) 0.0031(5) -0.0236(6) 0.0062(6) N9 0.0696(10) 0.0424(8) 0.0574(9) -0.0021(6) -0.0290(7) 0.0026(7) N4 0.0593(10) 0.0569(9) 0.0545(9) -0.0049(7) -0.0188(7) 0.0075(8) C5 0.0487(10) 0.0595(11) 0.0619(11) -0.0041(9) -0.0108(9) -0.0036(8) C6 0.0519(10) 0.0494(10) 0.0493(10) 0.0014(7) -0.0049(8) -0.0004(8) C1 0.0451(10) 0.0385(9) 0.0434(9) -0.0057(6) -0.0059(7) 0.0069(7) C7 0.0515(10) 0.0408(9) 0.0436(9) -0.0041(7) -0.0080(8) 0.0081(7) C3 0.0734(12) 0.0505(10) 0.0486(10) 0.0050(8) -0.0142(9) 0.0045(9) C2 0.0591(11) 0.0444(10) 0.0512(10) 0.0008(7) -0.0121(8) -0.0031(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 O8 C7 1.2341(17) . ? N9 C7 1.3194(19) . ? N9 H9A 0.8600 . ? N9 H9B 0.8600 . ? N4 C5 1.323(2) . ? N4 C3 1.330(2) . ? C5 C6 1.377(2) . ? C5 H5 0.9300 . ? C6 C1 1.379(2) . ? C6 H6 0.9300 . ? C1 C2 1.384(2) . ? C1 C7 1.504(2) . ? C3 C2 1.379(2) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? 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 C7 N9 H9A 120.0 . . ? C7 N9 H9B 120.0 . . ? H9A N9 H9B 120.0 . . ? C5 N4 C3 116.55(14) . . ? N4 C5 C6 123.98(16) . . ? N4 C5 H5 118.0 . . ? C6 C5 H5 118.0 . . ? C5 C6 C1 118.98(15) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C6 C1 C2 117.93(14) . . ? C6 C1 C7 118.11(14) . . ? C2 C1 C7 123.96(14) . . ? O8 C7 N9 122.64(14) . . ? O8 C7 C1 119.41(14) . . ? N9 C7 C1 117.94(13) . . ? N4 C3 C2 124.07(15) . . ? N4 C3 H3 118.0 . . ? C2 C3 H3 118.0 . . ? C3 C2 C1 118.49(15) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? 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 C3 N4 C5 C6 -0.4(3) . . . . ? N4 C5 C6 C1 0.4(3) . . . . ? C5 C6 C1 C2 -0.3(2) . . . . ? C5 C6 C1 C7 -179.58(14) . . . . ? C6 C1 C7 O8 19.6(2) . . . . ? C2 C1 C7 O8 -159.61(15) . . . . ? C6 C1 C7 N9 -159.31(15) . . . . ? C2 C1 C7 N9 21.5(2) . . . . ? C5 N4 C3 C2 0.2(3) . . . . ? N4 C3 C2 C1 -0.2(3) . . . . ? C6 C1 C2 C3 0.2(2) . . . . ? C7 C1 C2 C3 179.44(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H9A N4 0.86 2.13 2.9872(19) 171.9 4_666 N9 H9B O8 0.86 2.11 2.9412(19) 161.0 2_756 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.137 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.031 #===END