Supplementary Material (ESI) for CrystEngComm This jouranl is (c) The Royal Society of Chemistry 2003 data_global _publ_contact_author_email PARTHOD123@REDIFFMAIL.COM _publ_contact_author_name 'Dr Parthasarathi Dastidar' _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_address ; Department of Analytical Science Central Salt & Marine Chemicals Research Institute G. B. Marg Bhavnagar Gujarat 364 002 INDIA ; _publ_section_title ; Supramolecular Assemblies in Salts and Cocrystals of Imidazoles with Dicarboxylic Acids ; loop_ _publ_author_name 'Parthasarathi Dastidar' 'Amar Ballabh' 'Darshak Trivedi' data_ab0243r _database_code_CSD 213275 _chemical_name_common '2-Phenyl imidazolium hydrogen cyclobutane-1,1-dicarboxylate 1' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 N2 O4' _chemical_formula_weight 288.30 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 Pbca 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 19.763(9) _cell_length_b 13.835(4) _cell_length_c 10.175(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2782.1(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19mm _exptl_crystal_size_mid 0.16mm _exptl_crystal_size_min 0.11mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method 'OMEGA TWO THETA' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1HR _diffrn_standards_decay_% NIL _diffrn_reflns_number 3427 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 22.49 _reflns_number_total 1819 _reflns_number_gt 1200 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4-PC _computing_cell_refinement CAD4-PC _computing_data_reduction NRCVAX _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.1.1' _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 w=1/[\s^2^(Fo^2^)+(0.0655P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1819 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.25756(12) 0.65635(18) -0.0165(2) 0.0299(6) Uani 1 d . . . C2 C 0.30753(12) 0.62816(19) 0.2014(2) 0.0318(6) Uani 1 d . . . C3 C 0.28125(12) 0.57895(17) 0.0766(2) 0.0292(6) Uani 1 d . . . C4 C 0.32956(18) 0.5022(2) 0.0207(3) 0.0474(8) Uani 1 d . . . C5 C 0.2897(2) 0.4242(3) 0.0926(4) 0.0665(11) Uani 1 d . . . C6 C 0.23171(14) 0.4963(2) 0.1104(3) 0.0426(7) Uani 1 d . . . O1 O 0.30599(8) 0.70095(14) -0.07520(19) 0.0442(5) Uani 1 d . . . H1O H 0.2902 0.7388 -0.1291 0.066 Uiso 1 calc R . . O2 O 0.19780(8) 0.67514(14) -0.03425(18) 0.0447(5) Uani 1 d . . . O3 O 0.36338(9) 0.60884(16) 0.2460(2) 0.0595(7) Uani 1 d . . . O4 O 0.26604(9) 0.68701(15) 0.25254(18) 0.0502(6) Uani 1 d . . . H4A H 0.3758(16) 0.512(2) 0.047(3) 0.063(10) Uiso 1 d . . . H4B H 0.3254(13) 0.4965(17) -0.074(3) 0.044(8) Uiso 1 d . . . H5A H 0.3080(17) 0.412(2) 0.180(4) 0.086(12) Uiso 1 d . . . H5B H 0.2775(17) 0.363(3) 0.046(4) 0.092(12) Uiso 1 d . . . H6A H 0.2098(12) 0.5005(17) 0.197(3) 0.038(7) Uiso 1 d . . . H6B H 0.1978(13) 0.4901(19) 0.041(3) 0.049(8) Uiso 1 d . . . N1' N 0.09655(11) 0.65418(16) 0.1439(2) 0.0412(6) Uani 1 d . . . C2' C 0.03180(12) 0.64042(19) 0.1124(3) 0.0369(7) Uani 1 d . . . N3' N -0.00262(12) 0.63867(17) 0.2245(2) 0.0416(6) Uani 1 d . . . C4' C 0.10244(15) 0.6615(2) 0.2775(3) 0.0453(8) Uani 1 d . . . C5' C 0.04071(15) 0.6510(2) 0.3283(3) 0.0457(8) Uani 1 d . . . C6' C 0.00441(12) 0.63127(18) -0.0204(3) 0.0366(7) Uani 1 d . . . C7' C 0.04476(15) 0.6037(2) -0.1246(3) 0.0465(8) Uani 1 d . . . C8' C 0.01858(17) 0.5994(2) -0.2500(3) 0.0541(9) Uani 1 d . . . C9' C -0.04791(17) 0.6231(2) -0.2723(4) 0.0562(9) Uani 1 d . . . C10' C -0.08866(16) 0.6492(2) -0.1687(3) 0.0497(8) Uani 1 d . . . C11' C -0.06338(14) 0.6539(2) -0.0434(3) 0.0454(8) Uani 1 d . . . H1'N H 0.1333(16) 0.661(2) 0.081(3) 0.079(11) Uiso 1 d . . . H3'N H -0.0482(14) 0.629(2) 0.232(3) 0.047(8) Uiso 1 d . . . H4' H 0.1446(14) 0.6715(19) 0.323(3) 0.051(8) Uiso 1 d . . . H5' H 0.0269(12) 0.6528(18) 0.421(3) 0.043(7) Uiso 1 d . . . H7' H 0.0888(16) 0.586(2) -0.112(3) 0.074(11) Uiso 1 d . . . H8' H 0.0444(14) 0.5834(19) -0.325(3) 0.053(9) Uiso 1 d . . . H9' H -0.0675(13) 0.621(2) -0.356(3) 0.049(8) Uiso 1 d . . . H10' H -0.1334(17) 0.665(2) -0.187(3) 0.077(11) Uiso 1 d . . . H11' H -0.0950(13) 0.6713(19) 0.036(3) 0.060(9) Uiso 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 C1 0.0253(15) 0.0403(16) 0.0241(13) -0.0001(12) 0.0003(11) -0.0015(12) C2 0.0242(15) 0.0387(15) 0.0326(15) 0.0051(13) -0.0022(12) -0.0053(13) C3 0.0259(13) 0.0355(15) 0.0262(14) -0.0010(11) 0.0007(11) 0.0010(11) C4 0.056(2) 0.0465(19) 0.0399(19) -0.0017(15) 0.0047(17) 0.0143(16) C5 0.087(3) 0.041(2) 0.072(3) -0.0005(19) 0.004(2) 0.0019(19) C6 0.0458(19) 0.0450(18) 0.0370(17) 0.0014(14) -0.0027(16) -0.0118(15) O1 0.0274(10) 0.0576(13) 0.0474(12) 0.0219(10) 0.0023(9) 0.0022(9) O2 0.0219(11) 0.0663(14) 0.0460(12) 0.0147(10) -0.0022(9) 0.0004(9) O3 0.0312(12) 0.0764(16) 0.0709(16) -0.0139(12) -0.0234(11) 0.0071(10) O4 0.0350(11) 0.0658(13) 0.0498(12) -0.0247(10) -0.0044(9) 0.0084(10) N1' 0.0236(13) 0.0517(15) 0.0482(17) 0.0033(12) 0.0021(11) 0.0017(11) C2' 0.0275(16) 0.0364(16) 0.0467(17) 0.0032(13) 0.0042(14) 0.0031(13) N3' 0.0269(14) 0.0479(15) 0.0499(16) 0.0023(11) 0.0081(13) 0.0030(11) C4' 0.0359(19) 0.0483(19) 0.052(2) 0.0000(14) -0.0053(15) 0.0033(14) C5' 0.044(2) 0.050(2) 0.0430(19) 0.0022(15) 0.0025(16) 0.0057(14) C6' 0.0249(15) 0.0358(16) 0.0492(18) 0.0043(13) 0.0033(13) -0.0028(12) C7' 0.0307(18) 0.0504(19) 0.058(2) -0.0038(16) 0.0007(16) 0.0041(14) C8' 0.051(2) 0.063(2) 0.048(2) -0.0120(17) 0.0010(18) 0.0016(17) C9' 0.055(2) 0.058(2) 0.056(2) -0.0036(17) -0.0153(19) -0.0087(17) C10' 0.0328(18) 0.0517(19) 0.065(2) 0.0090(17) -0.0092(17) -0.0059(15) C11' 0.0298(16) 0.0493(19) 0.057(2) 0.0105(16) 0.0019(15) -0.0004(13) _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 C1 O2 1.223(3) 1 ? C1 O2 1.223(3) . ? C1 O1 1.286(3) . ? C1 C3 1.505(3) . ? C2 O3 1.223(3) . ? C2 O4 1.267(3) . ? C2 C3 1.532(3) . ? C3 C4 1.538(4) . ? C3 C6 1.544(4) . ? C4 C5 1.522(5) . ? C4 H4A 0.96(3) . ? C4 H4B 0.97(3) . ? C4 H5B 2.19(4) . ? C5 C6 1.530(4) . ? C5 H5A 0.97(4) . ? C5 H5B 1.00(4) . ? C6 H5B 2.15(4) . ? C6 H6A 0.99(3) . ? C6 H6B 0.98(3) . ? O1 H1O 0.8200 . ? O2 O2 0.000(6) 1 ? N1' C2' 1.333(3) . ? N1' C4' 1.368(4) . ? N1' H1'N 0.97(3) . ? C2' N3' 1.328(3) . ? C2' C6' 1.461(4) . ? N3' C5' 1.371(4) . ? N3' H3'N 0.91(3) . ? C4' C5' 1.333(4) . ? C4' H4' 0.96(3) . ? C5' H5' 0.98(3) . ? C6' C7' 1.380(4) . ? C6' C11' 1.396(4) . ? C7' C8' 1.378(4) . ? C7' H7' 0.91(3) . ? C8' C9' 1.373(4) . ? C8' H8' 0.94(3) . ? C9' C10' 1.375(5) . ? C9' H9' 0.94(3) . ? C10' C11' 1.371(4) . ? C10' H10' 0.93(3) . ? C11' H11' 1.05(3) . ? 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 O2 C1 O2 0.0(3) 1 . ? O2 C1 O1 123.3(2) 1 . ? O2 C1 O1 123.3(2) . . ? O2 C1 C3 123.0(2) 1 . ? O2 C1 C3 123.0(2) . . ? O1 C1 C3 113.7(2) . . ? O3 C2 O4 124.9(2) . . ? O3 C2 C3 121.1(2) . . ? O4 C2 C3 114.0(2) . . ? C1 C3 C2 108.1(2) . . ? C1 C3 C4 116.9(2) . . ? C2 C3 C4 113.8(2) . . ? C1 C3 C6 118.0(2) . . ? C2 C3 C6 111.0(2) . . ? C4 C3 C6 88.0(2) . . ? C5 C4 C3 89.4(2) . . ? C5 C4 H4A 117.2(18) . . ? C3 C4 H4A 112.9(18) . . ? C5 C4 H4B 112.2(15) . . ? C3 C4 H4B 111.8(15) . . ? H4A C4 H4B 112(2) . . ? C5 C4 H5B 23.3(9) . . ? C3 C4 H5B 105.7(9) . . ? H4A C4 H5B 122(2) . . ? H4B C4 H5B 90.3(18) . . ? C4 C5 C6 89.0(2) . . ? C4 C5 H5A 111(2) . . ? C6 C5 H5A 106(2) . . ? C4 C5 H5B 119(2) . . ? C6 C5 H5B 115(2) . . ? H5A C5 H5B 113(3) . . ? C5 C6 C3 88.9(2) . . ? C5 C6 H5B 24.8(9) . . ? C3 C6 H5B 107.3(9) . . ? C5 C6 H6A 118.3(15) . . ? C3 C6 H6A 115.8(14) . . ? H5B C6 H6A 120.6(17) . . ? C5 C6 H6B 111.8(15) . . ? C3 C6 H6B 109.9(15) . . ? H5B C6 H6B 89.6(18) . . ? H6A C6 H6B 110(2) . . ? C1 O1 H1O 109.5 . . ? O2 O2 C1 0(10) 1 . ? C2' N1' C4' 109.3(2) . . ? C2' N1' H1'N 125(2) . . ? C4' N1' H1'N 126(2) . . ? N3' C2' N1' 106.7(2) . . ? N3' C2' C6' 127.1(2) . . ? N1' C2' C6' 126.2(2) . . ? C2' N3' C5' 109.8(2) . . ? C2' N3' H3'N 125.2(18) . . ? C5' N3' H3'N 124.9(17) . . ? C5' C4' N1' 107.4(3) . . ? C5' C4' H4' 128.5(16) . . ? N1' C4' H4' 124.1(16) . . ? C4' C5' N3' 106.7(3) . . ? C4' C5' H5' 128.5(15) . . ? N3' C5' H5' 124.8(15) . . ? C7' C6' C11' 119.2(3) . . ? C7' C6' C2' 121.4(2) . . ? C11' C6' C2' 119.4(2) . . ? C6' C7' C8' 120.4(3) . . ? C6' C7' H7' 121(2) . . ? C8' C7' H7' 118(2) . . ? C9' C8' C7' 120.1(3) . . ? C9' C8' H8' 116.2(17) . . ? C7' C8' H8' 123.6(17) . . ? C8' C9' C10' 119.8(3) . . ? C8' C9' H9' 122.5(17) . . ? C10' C9' H9' 117.7(17) . . ? C11' C10' C9' 120.8(3) . . ? C11' C10' H10' 121(2) . . ? C9' C10' H10' 118(2) . . ? C10' C11' C6' 119.7(3) . . ? C10' C11' H11' 120.7(15) . . ? C6' C11' H11' 119.6(15) . . ? 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 O1 H1O O4 0.82 1.65 2.469(2) 173.6 8_575 N1' H1'N O2 0.97(3) 1.75(3) 2.716(3) 178(3) 1 N3' H3'N O3 0.91(3) 1.79(3) 2.697(3) 177(3) 6_556 _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.871 _refine_diff_density_max 0.177 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.062 data_dt0526 _database_code_CSD 213276 _chemical_name_common 'imidazolium hydrogen malonate 2' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety ? _chemical_formula_sum 'C6 H7 N2 O5.57' _chemical_formula_weight 196.21 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' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.231(2) _cell_length_b 8.296(4) _cell_length_c 9.235(4) _cell_angle_alpha 115.97(3) _cell_angle_beta 102.84(3) _cell_angle_gamma 91.74(3) _cell_volume 480.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.20mm _exptl_crystal_size_mid 0.17mm _exptl_crystal_size_min 0.13mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 203 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method 'OMEGA TWO THETA' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1HR _diffrn_standards_decay_% NIL _diffrn_reflns_number 1240 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 22.42 _reflns_number_total 1240 _reflns_number_gt 1109 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4-PC _computing_cell_refinement CAD4-PC _computing_data_reduction NRCVAX _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.1.1' _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 w=1/[\s^2^(Fo^2^)+(0.1896P)^2^+1.1921P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1240 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1112 _refine_ls_R_factor_gt 0.1053 _refine_ls_wR_factor_ref 0.2902 _refine_ls_wR_factor_gt 0.2814 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2390(8) 0.8714(6) 0.4858(6) 0.0382(14) Uani 1 d . . . C2 C 0.2351(7) 0.7338(7) 0.6808(6) 0.0329(13) Uani 1 d . . . C3 C 0.1203(8) 0.8099(8) 0.5724(7) 0.0397(14) Uani 1 d . . . O1 O 0.4125(6) 0.9426(7) 0.5712(5) 0.0672(15) Uani 1 d . . . O2 O 0.1705(6) 0.8551(6) 0.3475(5) 0.0611(14) Uani 1 d . . . O3 O 0.2852(6) 0.8286(5) 0.8357(4) 0.0486(12) Uani 1 d . . . O4 O 0.2751(6) 0.5786(5) 0.6104(4) 0.0448(11) Uani 1 d . . . N1' N 0.2052(6) 1.1396(6) 1.0495(5) 0.0390(12) Uani 1 d . . . C2' C 0.2695(8) 1.2108(7) 1.2132(6) 0.0387(14) Uani 1 d . . . N3' N 0.2088(6) 1.3676(6) 1.2816(6) 0.0398(12) Uani 1 d . . . C4' C 0.1016(9) 1.3988(8) 1.1576(7) 0.0457(15) Uani 1 d . . . C5' C 0.0983(8) 1.2573(8) 1.0127(7) 0.0457(15) Uani 1 d . . . O1W O 0.4328(8) 0.5601(9) 0.9206(8) 0.0569(16) Uiso 0.69 d P . . O2W O 0.5275(14) 1.3585(13) 0.9296(13) 0.062(2) Uiso 0.46 d P . . O3W O 0.4631(15) 1.4210(14) 0.8580(13) 0.060(3) Uiso 0.42 d P . . H3A H 0.067(8) 0.913(8) 0.652(7) 0.046(15) Uiso 1 d . . . H3B H 0.011(9) 0.725(8) 0.496(7) 0.043(15) Uiso 1 d . . . H1'N H 0.221(9) 1.036(9) 0.982(8) 0.052(18) Uiso 1 d . . . H2' H 0.339(8) 1.152(7) 1.268(7) 0.040(14) Uiso 1 d . . . H3'N H 0.254(9) 1.439(9) 1.388(9) 0.052(17) Uiso 1 d . . . H4' H 0.033(9) 1.485(9) 1.168(8) 0.059(19) Uiso 1 d . . . H5' H 0.036(11) 1.208(10) 0.884(10) 0.09(2) Uiso 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 C1 0.049(3) 0.032(3) 0.028(3) 0.015(2) -0.001(2) 0.006(2) C2 0.040(3) 0.032(3) 0.025(3) 0.012(2) 0.007(2) 0.006(2) C3 0.042(3) 0.046(3) 0.031(3) 0.022(3) 0.000(3) 0.011(3) O1 0.061(3) 0.096(4) 0.049(3) 0.053(3) -0.015(2) -0.024(2) O2 0.067(3) 0.081(3) 0.031(2) 0.031(2) -0.0058(19) 0.003(2) O3 0.073(3) 0.043(2) 0.025(2) 0.0131(18) 0.0062(18) 0.0195(19) O4 0.068(3) 0.035(2) 0.026(2) 0.0119(17) 0.0058(17) 0.0152(17) N1' 0.048(3) 0.035(3) 0.029(3) 0.011(2) 0.007(2) 0.009(2) C2' 0.044(3) 0.042(3) 0.028(3) 0.016(3) 0.003(2) 0.007(2) N3' 0.047(3) 0.038(3) 0.023(3) 0.007(2) 0.003(2) 0.005(2) C4' 0.056(3) 0.045(3) 0.034(3) 0.018(3) 0.008(3) 0.019(3) C5' 0.054(3) 0.048(3) 0.029(3) 0.017(3) 0.001(2) 0.009(3) _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 C1 O2 1.208(6) . ? C1 O1 1.286(7) . ? C1 C3 1.507(8) . ? C2 O4 1.240(6) . ? C2 O3 1.250(6) 1 ? C2 O3 1.250(6) . ? C2 C3 1.519(7) . ? C3 H3A 1.01(6) . ? C3 H3B 0.95(6) . ? O3 O3 0.000(17) 1 ? N1' C2' 1.319(7) . ? N1' C5' 1.374(7) . ? N1' H1'N 0.84(7) . ? C2' N3' 1.312(7) . ? C2' H2' 0.93(6) . ? N3' C4' 1.362(8) . ? N3' H3'N 0.87(7) . ? C4' C5' 1.334(9) . ? C4' H4' 0.87(7) . ? C5' H5' 1.05(8) . ? O1W O3W 1.096(11) 1_545 ? O1W O2W 1.202(11) 2_677 ? O2W O3W 1.049(13) . ? O2W O1W 1.202(11) 2_677 ? O3W O1W 1.096(11) 1_565 ? 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 O2 C1 O1 124.2(5) . . ? O2 C1 C3 120.8(5) . . ? O1 C1 C3 114.9(4) . . ? O4 C2 O3 122.8(5) . 1 ? O4 C2 O3 122.8(5) . . ? O3 C2 O3 0.0(7) 1 . ? O4 C2 C3 117.9(4) . . ? O3 C2 C3 119.3(5) 1 . ? O3 C2 C3 119.3(5) . . ? C1 C3 C2 113.0(4) . . ? C1 C3 H3A 112(3) . . ? C2 C3 H3A 104(3) . . ? C1 C3 H3B 112(3) . . ? C2 C3 H3B 110(3) . . ? H3A C3 H3B 105(5) . . ? O3 O3 C2 0(10) 1 . ? C2' N1' C5' 108.0(5) . . ? C2' N1' H1'N 125(5) . . ? C5' N1' H1'N 127(5) . . ? N3' C2' N1' 109.1(5) . . ? N3' C2' H2' 127(3) . . ? N1' C2' H2' 124(3) . . ? C2' N3' C4' 108.5(5) . . ? C2' N3' H3'N 120(4) . . ? C4' N3' H3'N 131(4) . . ? C5' C4' N3' 107.5(5) . . ? C5' C4' H4' 125(4) . . ? N3' C4' H4' 127(4) . . ? C4' C5' N1' 106.9(5) . . ? C4' C5' H5' 140(4) . . ? N1' C5' H5' 113(4) . . ? O3W O1W O2W 120.6(9) 1_545 2_677 ? O3W O2W O1W 119.8(11) . 2_677 ? O2W O3W O1W 119.7(12) . 1_565 ? 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 N1' H1'N O3 0.84(7) 1.81(7) 2.651(6) 172(6) 1 N3' H3'N O4 0.87(7) 1.83(7) 2.676(6) 163(6) 1_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 22.42 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.083 _refine_diff_density_min -0.856 _refine_diff_density_rms 0.166 data_dt0529r _database_code_CSD 213277 _chemical_name_common 'Benzimidazole / succinic acid (1:1) cocrystal 3' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9.50 N2 O4' _chemical_formula_weight 233.71 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' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21/C 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 9.639(2) _cell_length_b 5.083(3) _cell_length_c 23.066(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.817(19) _cell_angle_gamma 90.00 _cell_volume 1081.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.25mm _exptl_crystal_size_mid 0.18mm _exptl_crystal_size_min 0.12mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 486 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method 'OMEGA TWO THETA' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1HR _diffrn_standards_decay_% NIL _diffrn_reflns_number 1415 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 22.42 _reflns_number_total 1415 _reflns_number_gt 933 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4-PC _computing_cell_refinement CAD4-PC _computing_data_reduction NRCVAX _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.1.1' _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 w=1/[\s^2^(Fo^2^)+(0.0920P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1415 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1454 _refine_ls_wR_factor_gt 0.1344 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0813(4) 0.8114(7) 0.05937(16) 0.0397(9) Uani 1 d . . . C2 C 0.4250(4) 0.8663(7) 0.07407(16) 0.0394(9) Uani 1 d . . . C3 C 0.3071(4) 1.0656(8) 0.05534(19) 0.0411(9) Uani 1 d . . . C4 C 0.1870(4) 1.0288(8) 0.08481(17) 0.0427(9) Uani 1 d . . . O1 O -0.0247(3) 0.7829(5) 0.07899(13) 0.0603(8) Uani 1 d . . . O2 O 0.1024(2) 0.6654(5) 0.01806(11) 0.0495(7) Uani 1 d . . . O3 O 0.4388(3) 0.7277(5) 0.11875(11) 0.0520(8) Uani 1 d . . . O4 O 0.5150(3) 0.8456(5) 0.04212(11) 0.0540(7) Uani 1 d . . . N1' N 0.6615(3) 0.4035(6) 0.13474(14) 0.0495(8) Uani 1 d . . . C2' C 0.7392(5) 0.3375(9) 0.09817(19) 0.0566(11) Uani 1 d . . . N3' N 0.8276(3) 0.1370(6) 0.11857(13) 0.0471(8) Uani 1 d . . . C4' C 0.8071(3) 0.0670(7) 0.17349(15) 0.0389(9) Uani 1 d . . . C5' C 0.7030(3) 0.2348(6) 0.18402(16) 0.0401(9) Uani 1 d . . . C6' C 0.6620(4) 0.2117(9) 0.2371(2) 0.0539(11) Uani 1 d . . . C7' C 0.7260(4) 0.0209(9) 0.2769(2) 0.0578(11) Uani 1 d . . . C8' C 0.8288(4) -0.1458(8) 0.26575(18) 0.0540(10) Uani 1 d . . . C9' C 0.8699(4) -0.1285(8) 0.21457(17) 0.0471(10) Uani 1 d . . . H3A H 0.347(4) 1.206(7) 0.0692(16) 0.041(11) Uiso 1 d . . . H3B H 0.266(4) 1.074(7) 0.0093(17) 0.046(10) Uiso 1 d . . . H4A H 0.129(4) 1.181(8) 0.0822(17) 0.060(11) Uiso 1 d . . . H4B H 0.230(4) 0.985(7) 0.1322(17) 0.059(10) Uiso 1 d . . . H2' H 0.725(4) 0.427(7) 0.0648(15) 0.039(10) Uiso 1 d . . . H6' H 0.601(4) 0.323(7) 0.2428(17) 0.052(11) Uiso 1 d . . . H7' H 0.714(4) 0.005(7) 0.3166(18) 0.057(11) Uiso 1 d . . . H8' H 0.871(4) -0.302(8) 0.2965(18) 0.068(12) Uiso 1 d . . . H9' H 0.931(4) -0.235(8) 0.2057(16) 0.054(12) Uiso 1 d . . . H4O H 0.5000 1.0000 0.0000 0.079(17) Uiso 1 d S . . 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 C1 0.0354(19) 0.037(2) 0.049(2) 0.0070(17) 0.0163(17) 0.0061(16) C2 0.0347(19) 0.040(2) 0.043(2) 0.0020(18) 0.0097(17) -0.0039(17) C3 0.037(2) 0.035(2) 0.048(2) -0.0008(19) 0.0069(18) -0.0023(19) C4 0.040(2) 0.042(2) 0.047(2) -0.0056(18) 0.0138(19) 0.0060(19) O1 0.0517(16) 0.0572(17) 0.0850(19) -0.0053(14) 0.0404(16) -0.0045(14) O2 0.0464(15) 0.0476(15) 0.0600(16) -0.0143(14) 0.0239(13) -0.0038(12) O3 0.0480(16) 0.0611(17) 0.0496(15) 0.0209(14) 0.0186(13) 0.0143(13) O4 0.0481(15) 0.0617(17) 0.0610(16) 0.0158(14) 0.0295(14) 0.0102(13) N1' 0.0500(19) 0.0508(19) 0.0454(18) 0.0034(16) 0.0101(16) -0.0008(15) C2' 0.054(3) 0.066(3) 0.041(2) 0.014(2) -0.001(2) -0.016(2) N3' 0.0383(17) 0.062(2) 0.0383(17) 0.0000(16) 0.0069(14) -0.0091(16) C4' 0.0316(19) 0.045(2) 0.042(2) -0.0087(18) 0.0126(16) -0.0068(17) C5' 0.0319(19) 0.037(2) 0.050(2) -0.0063(17) 0.0097(17) -0.0042(16) C6' 0.042(2) 0.056(3) 0.070(3) -0.017(2) 0.025(2) 0.000(2) C7' 0.060(3) 0.064(3) 0.052(3) 0.002(2) 0.021(2) -0.008(3) C8' 0.055(2) 0.052(3) 0.053(2) 0.004(2) 0.014(2) -0.004(2) C9' 0.038(2) 0.046(2) 0.056(3) -0.005(2) 0.0101(19) 0.0031(19) _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 C1 O1 1.240(4) . ? C1 O2 1.270(4) . ? C1 C4 1.503(5) . ? C2 O3 1.223(4) 1 ? C2 O3 1.223(4) . ? C2 O4 1.295(4) . ? C2 C3 1.490(5) . ? C3 C4 1.514(5) . ? C3 H3A 0.83(4) . ? C3 H3B 1.02(3) . ? C4 H4A 0.95(4) . ? C4 H4B 1.07(4) . ? O3 O3 0.000(10) 1 ? O4 H4O 1.224(2) . ? N1' C2' 1.323(5) . ? N1' C5' 1.387(4) . ? C2' N3' 1.324(5) . ? C2' H2' 0.87(3) . ? N3' C4' 1.384(4) . ? C4' C9' 1.386(5) . ? C4' C5' 1.391(5) . ? C5' C6' 1.396(5) . ? C6' C7' 1.355(6) . ? C6' H6' 0.85(4) . ? C7' C8' 1.383(6) . ? C7' H7' 0.96(4) . ? C8' C9' 1.352(5) . ? C8' H8' 1.06(4) . ? C9' H9' 0.87(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 O1 C1 O2 122.3(3) . . ? O1 C1 C4 118.7(3) . . ? O2 C1 C4 119.0(3) . . ? O3 C2 O3 0.0(4) 1 . ? O3 C2 O4 120.3(3) 1 . ? O3 C2 O4 120.3(3) . . ? O3 C2 C3 121.6(3) 1 . ? O3 C2 C3 121.6(3) . . ? O4 C2 C3 118.1(3) . . ? C2 C3 C4 113.8(3) . . ? C2 C3 H3A 104(2) . . ? C4 C3 H3A 105(2) . . ? C2 C3 H3B 111.5(19) . . ? C4 C3 H3B 110.6(19) . . ? H3A C3 H3B 111(3) . . ? C1 C4 C3 115.9(3) . . ? C1 C4 H4A 105(2) . . ? C3 C4 H4A 113(2) . . ? C1 C4 H4B 105(2) . . ? C3 C4 H4B 111.5(18) . . ? H4A C4 H4B 106(3) . . ? O3 O3 C2 0(10) 1 . ? C2 O4 H4O 117.1(2) . . ? C2' N1' C5' 106.5(3) . . ? N1' C2' N3' 113.1(4) . . ? N1' C2' H2' 117(2) . . ? N3' C2' H2' 129(2) . . ? C2' N3' C4' 106.0(3) . . ? N3' C4' C9' 131.4(3) . . ? N3' C4' C5' 107.7(3) . . ? C9' C4' C5' 121.0(3) . . ? N1' C5' C4' 106.7(3) . . ? N1' C5' C6' 133.1(3) . . ? C4' C5' C6' 120.2(4) . . ? C7' C6' C5' 117.7(4) . . ? C7' C6' H6' 125(3) . . ? C5' C6' H6' 117(3) . . ? C6' C7' C8' 121.5(4) . . ? C6' C7' H7' 123(2) . . ? C8' C7' H7' 115(2) . . ? C9' C8' C7' 121.9(4) . . ? C9' C8' H8' 119(2) . . ? C7' C8' H8' 119(2) . . ? C8' C9' C4' 117.6(4) . . ? C8' C9' H9' 124(3) . . ? C4' C9' H9' 119(3) . . ? 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 O4 H4O O4 1.224(2) 1.224(2) 2.449(5) 180.0 3_675 _diffrn_measured_fraction_theta_max 0.877 _diffrn_reflns_theta_full 22.42 _diffrn_measured_fraction_theta_full 0.877 _refine_diff_density_max 0.359 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.055 data_dt0563r _database_code_CSD 213278 _chemical_name_common 'Benzimidazole / isophthalic acid (1:1) cocrystal 4' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 N2 O4' _chemical_formula_weight 282.25 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 10.157(4) _cell_length_b 5.130(7) _cell_length_c 26.067(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.98(4) _cell_angle_gamma 90.00 _cell_volume 1358(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17mm _exptl_crystal_size_mid 0.14mm _exptl_crystal_size_min 0.11mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method 'omega two theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1hr _diffrn_standards_decay_% nil _diffrn_reflns_number 1773 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 22.42 _reflns_number_total 1773 _reflns_number_gt 1320 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4-PC _computing_cell_refinement CAD4-PC _computing_data_reduction NRCVAX _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.1.1' _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 w=1/[\s^2^(Fo^2^)+(0.1602P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1773 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.2045 _refine_ls_wR_factor_gt 0.1925 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0126(3) 0.2211(7) 0.55966(14) 0.0517(9) Uani 1 d . . . C2 C -0.3725(3) -0.4432(7) 0.56233(14) 0.0542(10) Uani 1 d . . . C3 C -0.2631(3) -0.2992(7) 0.58812(11) 0.0448(9) Uani 1 d . . . C4 C -0.2352(4) -0.3478(8) 0.63932(14) 0.0629(11) Uani 1 d . . . C5 C -0.1338(4) -0.2168(9) 0.66423(14) 0.0696(12) Uani 1 d . . . C6 C -0.0623(4) -0.0322(8) 0.63823(13) 0.0604(10) Uani 1 d . . . C7 C -0.0901(3) 0.0208(6) 0.58707(12) 0.0439(8) Uani 1 d . . . C8 C -0.1897(3) -0.1158(7) 0.56240(13) 0.0451(9) Uani 1 d . . . O1 O 0.0939(2) 0.2944(6) 0.57905(11) 0.0784(10) Uani 1 d . . . O2 O -0.0609(2) 0.3113(5) 0.51809(9) 0.0572(8) Uani 1 d . . . O3 O -0.4300(3) -0.6136(7) 0.58579(13) 0.0929(11) Uani 1 d . . . O4 O -0.4030(2) -0.3764(6) 0.51638(9) 0.0655(9) Uani 1 d . . . H4 H -0.291(4) -0.463(8) 0.6562(14) 0.062(10) Uiso 1 d . . . H5 H -0.109(4) -0.278(8) 0.7007(17) 0.079(12) Uiso 1 d . . . H6 H 0.001(3) 0.087(7) 0.6553(14) 0.062(10) Uiso 1 d . . . H8 H -0.206(3) -0.081(7) 0.5243(15) 0.067(11) Uiso 1 d . . . N1' N 0.2513(3) 0.6915(6) 0.58933(12) 0.0588(9) Uani 1 d . . . C2' C 0.3213(3) 0.8471(7) 0.56010(14) 0.0578(10) Uani 1 d . . . H2' H 0.3204 0.8410 0.5244 0.069 Uiso 1 calc R . . N3' N 0.3924(3) 1.0116(6) 0.58750(11) 0.0545(8) Uani 1 d . . . C4' C 0.3670(3) 0.9609(7) 0.63887(12) 0.0489(9) Uani 1 d . . . C5' C 0.2791(3) 0.7591(7) 0.63964(13) 0.0526(9) Uani 1 d . . . C6' C 0.2332(4) 0.6645(9) 0.68621(18) 0.0735(13) Uani 1 d . . . C7' C 0.2814(5) 0.7832(10) 0.72933(16) 0.0806(13) Uani 1 d . . . H7' H 0.2524 0.7261 0.7611 0.097 Uiso 1 calc R . . C8' C 0.3703(5) 0.9818(11) 0.72804(17) 0.0849(14) Uani 1 d . . . C9' C 0.4159(4) 1.0803(9) 0.68284(15) 0.0675(11) Uani 1 d . . . H6' H 0.176(4) 0.520(8) 0.6839(13) 0.062(10) Uiso 1 d . . . H9' H 0.463(4) 1.267(9) 0.6789(15) 0.082(12) Uiso 1 d . . . H8' H 0.401(4) 1.044(10) 0.763(2) 0.104(15) Uiso 1 d . . . H2O H 0.0000 0.5000 0.5000 0.092(19) Uiso 1 d S . . H4O H -0.5000 -0.5000 0.5000 0.096(19) Uiso 1 d S . . 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 C1 0.0409(19) 0.057(2) 0.057(2) 0.0015(18) -0.0036(16) -0.0201(17) C2 0.0400(18) 0.059(2) 0.063(2) 0.0009(19) 0.0055(16) -0.0230(17) C3 0.0359(17) 0.058(2) 0.0404(18) -0.0017(16) 0.0004(13) -0.0143(16) C4 0.060(2) 0.077(3) 0.052(2) 0.013(2) 0.0043(17) -0.030(2) C5 0.070(3) 0.093(3) 0.046(2) 0.009(2) -0.0073(18) -0.025(2) C6 0.053(2) 0.078(3) 0.049(2) -0.002(2) -0.0111(16) -0.020(2) C7 0.0351(16) 0.0518(19) 0.0448(19) -0.0040(16) -0.0019(13) -0.0139(15) C8 0.0364(17) 0.059(2) 0.040(2) -0.0002(16) -0.0011(13) -0.0112(16) O1 0.0569(17) 0.088(2) 0.090(2) 0.0193(16) -0.0238(14) -0.0409(16) O2 0.0496(14) 0.0684(16) 0.0534(15) 0.0107(12) -0.0053(11) -0.0251(12) O3 0.0757(19) 0.106(2) 0.096(2) 0.0300(19) -0.0234(15) -0.0591(19) O4 0.0528(14) 0.093(2) 0.0500(16) -0.0045(13) -0.0059(11) -0.0376(14) N1' 0.0447(16) 0.069(2) 0.063(2) -0.0018(16) -0.0075(14) -0.0201(16) C2' 0.049(2) 0.070(2) 0.054(2) -0.0033(19) -0.0073(16) -0.0117(19) N3' 0.0459(16) 0.0639(18) 0.0536(18) -0.0019(15) -0.0025(13) -0.0175(15) C4' 0.0384(17) 0.061(2) 0.0471(19) 0.0019(17) -0.0047(13) -0.0085(17) C5' 0.0381(18) 0.062(2) 0.058(2) 0.0044(18) -0.0049(15) -0.0073(17) C6' 0.058(2) 0.079(3) 0.084(3) 0.022(3) 0.014(2) -0.015(2) C7' 0.091(3) 0.101(3) 0.050(3) 0.011(2) 0.008(2) -0.002(3) C8' 0.101(3) 0.096(4) 0.057(3) -0.007(3) -0.011(2) 0.000(3) C9' 0.069(2) 0.074(3) 0.060(3) -0.006(2) -0.0120(19) -0.015(2) _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 C1 O1 1.244(4) 1 ? C1 O1 1.244(4) . ? C1 O2 1.269(4) . ? C1 C7 1.485(5) . ? C2 O3 1.221(4) . ? C2 O4 1.279(4) . ? C2 C3 1.486(5) . ? C3 C8 1.381(5) . ? C3 C4 1.382(5) . ? C4 C5 1.382(5) . ? C4 H4 0.93(4) . ? C5 C6 1.379(6) . ? C5 H5 1.03(4) . ? C6 C7 1.385(5) . ? C6 H6 0.99(4) . ? C7 C8 1.380(4) . ? C8 H8 1.02(4) . ? O1 O1 0.000(9) 1 ? O2 H2O 1.246(2) . ? O4 H4O 1.241(2) . ? N1' C2' 1.320(5) . ? N1' C5' 1.381(4) . ? C2' N3' 1.314(5) . ? C2' H2' 0.9300 . ? N3' C4' 1.392(4) . ? C4' C5' 1.367(5) . ? C4' C9' 1.384(5) . ? C5' C6' 1.395(5) . ? C6' C7' 1.362(6) . ? C6' H6' 0.95(4) . ? C7' C8' 1.361(7) . ? C7' H7' 0.9300 . ? C8' C9' 1.370(6) . ? C8' H8' 1.01(5) . ? C9' H9' 1.08(5) . ? 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 O1 C1 O1 0.0(4) 1 . ? O1 C1 O2 123.9(3) 1 . ? O1 C1 O2 123.9(3) . . ? O1 C1 C7 118.5(3) 1 . ? O1 C1 C7 118.5(3) . . ? O2 C1 C7 117.6(3) . . ? O3 C2 O4 123.4(3) . . ? O3 C2 C3 119.3(4) . . ? O4 C2 C3 117.2(3) . . ? C8 C3 C4 119.2(3) . . ? C8 C3 C2 121.7(3) . . ? C4 C3 C2 119.1(3) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 123(2) . . ? C3 C4 H4 117(2) . . ? C6 C5 C4 119.8(4) . . ? C6 C5 H5 123(2) . . ? C4 C5 H5 117(2) . . ? C5 C6 C7 120.5(3) . . ? C5 C6 H6 123(2) . . ? C7 C6 H6 116(2) . . ? C8 C7 C6 119.0(3) . . ? C8 C7 C1 121.2(3) . . ? C6 C7 C1 119.9(3) . . ? C3 C8 C7 121.1(3) . . ? C3 C8 H8 121(2) . . ? C7 C8 H8 118(2) . . ? O1 O1 C1 0(10) 1 . ? C1 O2 H2O 114.8(2) . . ? C2 O4 H4O 111.3(2) . . ? C2' N1' C5' 107.0(3) . . ? N3' C2' N1' 111.8(3) . . ? N3' C2' H2' 124.1 . . ? N1' C2' H2' 124.1 . . ? C2' N3' C4' 107.1(3) . . ? C5' C4' C9' 123.2(3) . . ? C5' C4' N3' 106.7(3) . . ? C9' C4' N3' 130.1(3) . . ? C4' C5' N1' 107.4(3) . . ? C4' C5' C6' 120.3(4) . . ? N1' C5' C6' 132.3(4) . . ? C7' C6' C5' 116.2(4) . . ? C7' C6' H6' 128(2) . . ? C5' C6' H6' 116(2) . . ? C8' C7' C6' 122.9(4) . . ? C8' C7' H7' 118.6 . . ? C6' C7' H7' 118.6 . . ? C7' C8' C9' 122.1(4) . . ? C7' C8' H8' 114(3) . . ? C9' C8' H8' 124(3) . . ? C8' C9' C4' 115.3(4) . . ? C8' C9' H9' 125(2) . . ? C4' C9' H9' 118(2) . . ? 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 O2 H2O O2 1.246(2) 1.246(2) 2.492(5) 180.0 3_566 O4 H4O O4 1.241(2) 1.241(2) 2.482(4) 180.0 3_446 _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 22.42 _diffrn_measured_fraction_theta_full 0.880 _refine_diff_density_max 0.631 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.087