# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Reddy Perumalla' _publ_contact_author_email sperumal@umn.edu loop_ _publ_author_name 'Changquan Sun' S.Perumalla # Attachment '- 2.cif' data_80a _database_code_depnum_ccdc_archive 'CCDC 818654' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Nicotinamide hydrochloride base salt' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 Cl N4 O3' _chemical_formula_weight 298.73 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' Cl Cl 0.1484 0.1585 '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 6.8600(10) _cell_length_b 8.7768(12) _cell_length_c 11.8950(16) _cell_angle_alpha 78.960(2) _cell_angle_beta 82.287(2) _cell_angle_gamma 80.200(2) _cell_volume 688.84(17) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4062 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 26.40 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.291 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9026 _exptl_absorpt_correction_T_max 0.9441 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _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 'Siemens Platform CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7622 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.42 _reflns_number_total 2813 _reflns_number_gt 2352 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0458P)^2^+0.1970P] 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 2813 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _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 O27 O 0.25805(18) 0.63224(13) 0.01498(9) 0.0324(3) Uani 1 1 d . . . O17 O 0.71743(17) 0.80688(13) -0.02775(9) 0.0298(3) Uani 1 1 d . . . N17 N 0.7082(2) 0.66976(16) -0.16896(12) 0.0259(3) Uani 1 1 d . . . N21 N 0.22157(19) 0.92297(15) -0.36406(11) 0.0273(3) Uani 1 1 d . . . N27 N 0.2146(2) 0.50155(16) -0.12385(12) 0.0303(3) Uani 1 1 d . . . N11 N 0.69857(19) 1.09674(15) -0.40426(11) 0.0248(3) Uani 1 1 d . . . C13 C 0.6824(2) 0.95389(17) -0.21438(12) 0.0207(3) Uani 1 1 d . . . C12 C 0.7138(2) 0.95815(17) -0.33210(12) 0.0223(3) Uani 1 1 d . . . C17 C 0.7037(2) 0.80157(17) -0.12943(12) 0.0220(3) Uani 1 1 d . . . C26 C 0.1797(2) 1.05829(18) -0.32290(14) 0.0269(3) Uani 1 1 d . . . C23 C 0.2055(2) 0.78332(17) -0.16930(12) 0.0217(3) Uani 1 1 d . . . C27 C 0.2272(2) 0.63111(17) -0.08480(12) 0.0239(3) Uani 1 1 d . . . C16 C 0.6547(2) 1.23448(18) -0.36644(14) 0.0280(3) Uani 1 1 d . . . C22 C 0.2328(2) 0.78805(18) -0.28771(13) 0.0247(3) Uani 1 1 d . . . C24 C 0.1650(2) 0.92449(18) -0.12874(13) 0.0251(3) Uani 1 1 d . . . C14 C 0.6362(2) 1.09556(18) -0.17369(13) 0.0252(3) Uani 1 1 d . . . C25 C 0.1498(2) 1.06429(18) -0.20655(14) 0.0272(3) Uani 1 1 d . . . C15 C 0.6226(2) 1.23653(18) -0.25016(14) 0.0279(3) Uani 1 1 d . . . O100 O 0.0879(2) 0.46339(17) -0.33795(12) 0.0423(3) Uani 1 1 d . . . Cl1 Cl 0.67390(6) 0.62866(4) -0.43318(3) 0.02983(13) Uani 1 1 d . . . H24 H 0.147(2) 0.9232(19) -0.0478(16) 0.029(4) Uiso 1 1 d . . . H12 H 0.744(2) 0.8671(19) -0.3706(13) 0.021(4) Uiso 1 1 d . . . H14 H 0.615(2) 1.0991(19) -0.0948(15) 0.030(4) Uiso 1 1 d . . . H22 H 0.265(2) 0.696(2) -0.3196(14) 0.026(4) Uiso 1 1 d . . . H25 H 0.121(2) 1.164(2) -0.1827(15) 0.030(4) Uiso 1 1 d . . . H26 H 0.171(3) 1.153(2) -0.3793(16) 0.040(5) Uiso 1 1 d . . . H16 H 0.647(3) 1.326(2) -0.4247(16) 0.040(5) Uiso 1 1 d . . . H102 H 0.160(3) 0.444(3) -0.393(2) 0.051(7) Uiso 1 1 d . . . H15 H 0.592(3) 1.332(2) -0.2245(15) 0.034(5) Uiso 1 1 d . . . H17B H 0.720(3) 0.578(2) -0.1228(17) 0.038(5) Uiso 1 1 d . . . H17A H 0.692(3) 0.665(2) -0.2420(17) 0.035(5) Uiso 1 1 d . . . H27B H 0.223(3) 0.410(2) -0.0776(17) 0.040(5) Uiso 1 1 d . . . H11 H 0.722(3) 1.095(2) -0.482(2) 0.054(6) Uiso 1 1 d . . . H27A H 0.176(3) 0.498(2) -0.1908(19) 0.052(6) Uiso 1 1 d . . . H101 H -0.019(4) 0.508(3) -0.365(2) 0.080(9) Uiso 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 O27 0.0490(7) 0.0280(6) 0.0198(6) 0.0006(4) -0.0080(5) -0.0068(5) O17 0.0441(7) 0.0272(6) 0.0177(5) -0.0006(4) -0.0051(5) -0.0066(5) N17 0.0377(8) 0.0206(7) 0.0183(6) 0.0011(5) -0.0056(6) -0.0044(6) N21 0.0336(7) 0.0256(7) 0.0208(6) 0.0015(5) -0.0029(5) -0.0059(5) N27 0.0478(9) 0.0223(7) 0.0200(7) 0.0034(6) -0.0090(6) -0.0069(6) N11 0.0342(7) 0.0222(6) 0.0185(6) 0.0004(5) -0.0056(5) -0.0078(5) C13 0.0207(7) 0.0218(7) 0.0192(7) -0.0014(6) -0.0031(6) -0.0039(6) C12 0.0289(8) 0.0184(7) 0.0198(7) -0.0012(6) -0.0042(6) -0.0051(6) C17 0.0220(7) 0.0243(8) 0.0186(7) -0.0008(6) -0.0017(6) -0.0038(6) C26 0.0294(8) 0.0220(8) 0.0276(8) 0.0024(6) -0.0045(6) -0.0055(6) C23 0.0207(7) 0.0239(8) 0.0195(7) -0.0006(6) -0.0023(6) -0.0037(6) C27 0.0241(8) 0.0257(8) 0.0201(7) 0.0000(6) -0.0016(6) -0.0034(6) C16 0.0335(9) 0.0205(8) 0.0299(8) 0.0022(6) -0.0097(7) -0.0063(6) C22 0.0302(8) 0.0222(8) 0.0203(7) -0.0018(6) -0.0013(6) -0.0033(6) C24 0.0250(8) 0.0289(8) 0.0217(8) -0.0052(6) -0.0022(6) -0.0043(6) C14 0.0260(8) 0.0284(8) 0.0213(8) -0.0047(6) -0.0034(6) -0.0033(6) C25 0.0279(8) 0.0220(8) 0.0325(8) -0.0056(6) -0.0048(7) -0.0037(6) C15 0.0325(9) 0.0213(8) 0.0312(8) -0.0070(6) -0.0070(7) -0.0013(6) O100 0.0478(8) 0.0506(8) 0.0296(7) -0.0157(6) -0.0089(7) 0.0036(7) Cl1 0.0423(2) 0.0233(2) 0.0248(2) -0.00470(14) -0.00618(16) -0.00465(16) _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 O27 C27 1.2353(18) . ? O17 C17 1.2360(17) . ? N17 C17 1.3238(19) . ? N17 H17B 0.88(2) . ? N17 H17A 0.90(2) . ? N21 C26 1.342(2) . ? N21 C22 1.3449(19) . ? N27 C27 1.328(2) . ? N27 H27B 0.88(2) . ? N27 H27A 0.88(2) . ? N11 C16 1.343(2) . ? N11 C12 1.3447(19) . ? N11 H11 0.92(2) . ? C13 C12 1.382(2) . ? C13 C14 1.391(2) . ? C13 C17 1.5118(19) . ? C12 H12 0.974(16) . ? C26 C25 1.381(2) . ? C26 H26 0.960(19) . ? C23 C24 1.386(2) . ? C23 C22 1.389(2) . ? C23 C27 1.508(2) . ? C16 C15 1.374(2) . ? C16 H16 0.953(19) . ? C22 H22 0.941(17) . ? C24 C25 1.386(2) . ? C24 H24 0.953(18) . ? C14 C15 1.385(2) . ? C14 H14 0.936(17) . ? C25 H25 0.950(17) . ? C15 H15 0.929(18) . ? O100 H102 0.79(2) . ? O100 H101 0.84(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 C17 N17 H17B 121.2(12) . . ? C17 N17 H17A 124.3(12) . . ? H17B N17 H17A 114.4(17) . . ? C26 N21 C22 117.91(13) . . ? C27 N27 H27B 120.7(12) . . ? C27 N27 H27A 125.4(13) . . ? H27B N27 H27A 112.8(18) . . ? C16 N11 C12 122.36(14) . . ? C16 N11 H11 119.9(13) . . ? C12 N11 H11 117.7(13) . . ? C12 C13 C14 118.32(13) . . ? C12 C13 C17 122.22(13) . . ? C14 C13 C17 119.42(13) . . ? N11 C12 C13 120.07(14) . . ? N11 C12 H12 114.2(9) . . ? C13 C12 H12 125.8(9) . . ? O17 C17 N17 123.84(14) . . ? O17 C17 C13 118.42(13) . . ? N17 C17 C13 117.74(13) . . ? N21 C26 C25 122.92(14) . . ? N21 C26 H26 116.1(11) . . ? C25 C26 H26 120.9(11) . . ? C24 C23 C22 118.15(13) . . ? C24 C23 C27 119.51(13) . . ? C22 C23 C27 122.29(13) . . ? O27 C27 N27 123.62(14) . . ? O27 C27 C23 119.38(13) . . ? N27 C27 C23 117.00(13) . . ? N11 C16 C15 119.80(14) . . ? N11 C16 H16 115.6(11) . . ? C15 C16 H16 124.6(11) . . ? N21 C22 C23 122.95(14) . . ? N21 C22 H22 115.6(10) . . ? C23 C22 H22 121.4(10) . . ? C25 C24 C23 119.44(14) . . ? C25 C24 H24 121.4(10) . . ? C23 C24 H24 119.2(10) . . ? C15 C14 C13 120.28(14) . . ? C15 C14 H14 118.0(10) . . ? C13 C14 H14 121.7(10) . . ? C26 C25 C24 118.62(15) . . ? C26 C25 H25 119.0(10) . . ? C24 C25 H25 122.4(10) . . ? C16 C15 C14 119.16(15) . . ? C16 C15 H15 119.4(11) . . ? C14 C15 H15 121.4(11) . . ? H102 O100 H101 104(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.210 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.047 data_77a _database_code_depnum_ccdc_archive 'CCDC 818655' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Sodium hydrogen bis(naproxate) methanol solvate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H35 Na O8' _chemical_formula_weight 546.57 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 '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(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.8921(12) _cell_length_b 5.7750(8) _cell_length_c 26.920(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.899(3) _cell_angle_gamma 90.00 _cell_volume 1375.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4027 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.51 _chemical_absolute_configuration rm _exptl_crystal_description Rods _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9530 _exptl_absorpt_correction_T_max 0.9652 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _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 'Siemens Platform CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16083 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 0.76 _diffrn_reflns_theta_max 27.52 _reflns_number_total 6255 _reflns_number_gt 5232 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0501P)^2^+0.1700P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(4) _refine_ls_number_reflns 6255 _refine_ls_number_parameters 468 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0957 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _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 Na1 Na 0.74622(10) 0.80134(16) 0.24858(3) 0.03737(17) Uani 1 1 d . . . C210 C 0.76794(19) 0.5387(3) 0.47887(6) 0.0236(4) Uani 1 1 d . . . O261 O 0.94108(14) 0.5004(2) 0.60998(4) 0.0311(3) Uani 1 1 d . . . O4 O 0.67303(16) 0.3938(2) 0.27712(5) 0.0363(3) Uani 1 1 d . . . C29 C 0.67982(19) 0.3328(3) 0.47657(6) 0.0234(4) Uani 1 1 d . . . C23 C 0.6766(2) 0.6178(3) 0.39264(7) 0.0291(4) Uani 1 1 d . . . C21 C 0.59278(19) 0.2725(3) 0.43124(6) 0.0236(3) Uani 1 1 d . . . C28 C 0.6821(2) 0.1962(3) 0.52026(7) 0.0284(4) Uani 1 1 d . . . C22 C 0.59110(18) 0.4104(3) 0.38957(6) 0.0239(4) Uani 1 1 d . . . C24 C 0.7623(2) 0.6792(3) 0.43554(7) 0.0301(4) Uani 1 1 d . . . C26 C 0.85814(18) 0.4600(3) 0.56490(6) 0.0259(4) Uani 1 1 d . . . C25 C 0.85838(19) 0.5989(3) 0.52370(7) 0.0266(4) Uani 1 1 d . . . O3 O 0.63735(16) 0.0381(2) 0.30426(5) 0.0353(3) Uani 1 1 d . . . C223 C 0.61173(19) 0.2469(3) 0.30475(6) 0.0253(4) Uani 1 1 d . . . C27 C 0.7683(2) 0.2573(3) 0.56313(7) 0.0296(4) Uani 1 1 d . . . C222 C 0.5025(2) 0.3488(3) 0.33996(6) 0.0259(4) Uani 1 1 d . . . C261 C 1.0269(2) 0.7110(4) 0.61481(8) 0.0352(4) Uani 1 1 d . . . C221 C 0.3719(2) 0.1837(4) 0.34440(7) 0.0358(4) Uani 1 1 d . . . O2 O 0.83393(16) 0.2056(2) 0.21895(5) 0.0366(3) Uani 1 1 d . . . C19 C 0.8275(2) 0.2238(3) 0.01917(6) 0.0256(4) Uani 1 1 d . . . C12 C 0.9141(2) 0.1884(3) 0.10754(6) 0.0276(4) Uani 1 1 d . . . C14 C 0.7536(2) -0.1086(3) 0.06632(7) 0.0329(4) Uani 1 1 d . . . C11 C 0.9104(2) 0.3069(3) 0.06324(6) 0.0268(4) Uani 1 1 d . . . C15 C 0.6572(2) -0.0661(3) -0.02336(7) 0.0313(4) Uani 1 1 d . . . O161 O 0.57566(16) -0.0039(3) -0.11137(5) 0.0437(4) Uani 1 1 d . . . C13 C 0.8356(2) -0.0246(3) 0.10807(6) 0.0326(4) Uani 1 1 d . . . C17 C 0.7420(2) 0.2608(4) -0.06876(7) 0.0356(5) Uani 1 1 d . . . O1 O 0.84738(18) 0.5658(2) 0.19225(5) 0.0417(4) Uani 1 1 d . . . C16 C 0.6564(2) 0.0566(4) -0.06666(7) 0.0331(4) Uani 1 1 d . . . C123 C 0.8844(2) 0.3626(3) 0.19092(6) 0.0273(4) Uani 1 1 d . . . C122 C 0.9975(2) 0.2866(4) 0.15500(7) 0.0309(4) Uani 1 1 d . . . C18 C 0.8241(2) 0.3437(3) -0.02732(7) 0.0317(4) Uani 1 1 d . . . C110 C 0.7450(2) 0.0148(3) 0.02043(7) 0.0280(4) Uani 1 1 d . . . C121 C 1.1154(2) 0.1210(5) 0.18041(8) 0.0445(5) Uani 1 1 d . . . C161 C 0.4837(3) -0.2062(4) -0.11199(9) 0.0436(5) Uani 1 1 d . . . O6 O 0.51701(18) 0.7996(3) 0.19391(6) 0.0510(4) Uani 1 1 d . . . O5 O 0.96468(18) 0.7349(4) 0.30430(6) 0.0609(5) Uani 1 1 d . . . C100 C 1.0999(3) 0.6523(6) 0.29100(9) 0.0598(7) Uani 1 1 d . . . H10A H 1.1725 0.6393 0.3208 0.090 Uiso 1 1 calc R . . H10B H 1.1394 0.7592 0.2672 0.090 Uiso 1 1 calc R . . H10C H 1.0842 0.4996 0.2755 0.090 Uiso 1 1 calc R . . C200 C 0.3967(3) 0.7123(5) 0.21805(8) 0.0592(7) Uani 1 1 d . . . H20A H 0.3042 0.7134 0.1949 0.089 Uiso 1 1 calc R . . H20B H 0.3822 0.8092 0.2471 0.089 Uiso 1 1 calc R . . H20C H 0.4195 0.5533 0.2291 0.089 Uiso 1 1 calc R . . H15 H 0.598(2) -0.202(4) -0.0210(7) 0.035(5) Uiso 1 1 d . . . H21 H 0.5381(19) 0.124(4) 0.4297(6) 0.022(4) Uiso 1 1 d . . . H18 H 0.883(2) 0.479(4) -0.0268(7) 0.031(5) Uiso 1 1 d . . . H25 H 0.9196(19) 0.734(4) 0.5243(6) 0.021(4) Uiso 1 1 d . . . H27 H 0.7662(19) 0.167(3) 0.5921(7) 0.025(5) Uiso 1 1 d . . . H11 H 0.964(2) 0.451(4) 0.0604(7) 0.029(5) Uiso 1 1 d . . . H23 H 0.673(2) 0.721(4) 0.3639(7) 0.041(6) Uiso 1 1 d . . . H14 H 0.698(2) -0.257(4) 0.0675(6) 0.024(5) Uiso 1 1 d . . . H28 H 0.626(2) 0.064(4) 0.5212(7) 0.038(6) Uiso 1 1 d . . . H17 H 0.745(2) 0.344(4) -0.1016(8) 0.040(6) Uiso 1 1 d . . . H13 H 0.837(2) -0.115(4) 0.1393(7) 0.036(5) Uiso 1 1 d . . . H24 H 0.823(2) 0.819(4) 0.4372(7) 0.040(6) Uiso 1 1 d . . . H26C H 1.071(2) 0.713(4) 0.6482(8) 0.034(5) Uiso 1 1 d . . . H26B H 1.106(2) 0.702(4) 0.5909(8) 0.047(6) Uiso 1 1 d . . . H16C H 0.409(3) -0.187(5) -0.0884(9) 0.054(7) Uiso 1 1 d . . . H16B H 0.550(3) -0.336(5) -0.1017(9) 0.055(7) Uiso 1 1 d . . . H16A H 0.439(2) -0.219(4) -0.1465(9) 0.046(6) Uiso 1 1 d . . . H22C H 0.311(2) 0.160(4) 0.3115(7) 0.032(5) Uiso 1 1 d . . . H22D H 0.467(2) 0.488(4) 0.3230(7) 0.034(5) Uiso 1 1 d . . . H12D H 1.053(2) 0.436(4) 0.1469(7) 0.035(5) Uiso 1 1 d . . . H22B H 0.408(3) 0.043(5) 0.3531(8) 0.047(6) Uiso 1 1 d . . . H22A H 0.304(2) 0.252(4) 0.3681(8) 0.044(6) Uiso 1 1 d . . . H12C H 1.065(2) -0.046(5) 0.1843(8) 0.051(6) Uiso 1 1 d . . . H26A H 0.958(3) 0.845(5) 0.6094(8) 0.049(7) Uiso 1 1 d . . . H12B H 1.160(2) 0.183(4) 0.2149(8) 0.049(6) Uiso 1 1 d . . . H6 H 0.507(3) 0.732(6) 0.1647(10) 0.064(8) Uiso 1 1 d . . . H12A H 1.191(3) 0.101(5) 0.1580(8) 0.050(6) Uiso 1 1 d . . . H5A H 0.987(4) 0.823(8) 0.3359(13) 0.128(14) Uiso 1 1 d . . . H2 H 0.755(3) 0.296(7) 0.2457(11) 0.084(9) Uiso 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 Na1 0.0399(4) 0.0356(4) 0.0363(3) -0.0099(3) 0.0025(3) 0.0113(3) C210 0.0265(8) 0.0207(8) 0.0247(8) -0.0001(6) 0.0081(7) 0.0023(7) O261 0.0289(6) 0.0363(7) 0.0274(6) -0.0007(5) 0.0000(5) -0.0030(5) O4 0.0511(8) 0.0256(7) 0.0361(7) 0.0036(5) 0.0232(6) 0.0058(6) C29 0.0245(8) 0.0211(8) 0.0253(8) 0.0011(7) 0.0067(6) 0.0028(7) C23 0.0361(10) 0.0240(9) 0.0286(9) 0.0047(8) 0.0107(8) 0.0018(8) C21 0.0240(9) 0.0220(9) 0.0255(8) -0.0009(7) 0.0060(6) 0.0008(7) C28 0.0319(9) 0.0244(9) 0.0291(9) 0.0032(7) 0.0050(7) -0.0059(8) C22 0.0251(8) 0.0247(9) 0.0228(8) -0.0011(7) 0.0066(6) 0.0059(7) C24 0.0371(10) 0.0247(9) 0.0292(9) 0.0023(7) 0.0074(7) -0.0057(8) C26 0.0235(8) 0.0284(9) 0.0261(8) -0.0018(7) 0.0042(7) 0.0037(7) C25 0.0260(9) 0.0245(9) 0.0302(9) -0.0020(7) 0.0066(7) -0.0027(7) O3 0.0503(8) 0.0245(7) 0.0337(7) 0.0022(5) 0.0166(6) 0.0082(6) C223 0.0285(9) 0.0278(9) 0.0196(8) -0.0003(7) 0.0019(6) 0.0049(7) C27 0.0345(10) 0.0289(10) 0.0256(9) 0.0066(7) 0.0042(7) -0.0010(8) C222 0.0277(9) 0.0265(10) 0.0238(8) 0.0019(7) 0.0047(7) 0.0052(7) C261 0.0305(10) 0.0359(11) 0.0388(11) -0.0062(9) 0.0006(8) -0.0031(8) C221 0.0298(10) 0.0465(13) 0.0316(10) -0.0009(9) 0.0045(8) -0.0011(9) O2 0.0506(8) 0.0242(7) 0.0385(7) -0.0002(6) 0.0213(6) 0.0043(6) C19 0.0281(8) 0.0240(8) 0.0261(8) 0.0042(7) 0.0084(7) 0.0045(7) C12 0.0318(9) 0.0267(9) 0.0258(8) -0.0024(7) 0.0095(7) 0.0065(8) C14 0.0464(11) 0.0218(9) 0.0319(10) 0.0029(7) 0.0107(8) -0.0010(9) C11 0.0303(9) 0.0227(8) 0.0288(9) 0.0014(7) 0.0093(7) 0.0012(8) C15 0.0342(10) 0.0265(10) 0.0338(10) 0.0002(7) 0.0064(8) -0.0028(8) O161 0.0445(8) 0.0531(10) 0.0316(7) 0.0033(7) -0.0053(6) -0.0114(7) C13 0.0497(12) 0.0259(9) 0.0233(9) 0.0033(8) 0.0092(8) 0.0030(9) C17 0.0363(10) 0.0409(12) 0.0292(9) 0.0108(8) 0.0024(8) -0.0006(9) O1 0.0666(10) 0.0273(7) 0.0342(8) 0.0036(6) 0.0196(7) 0.0105(7) C16 0.0305(9) 0.0390(11) 0.0296(9) -0.0001(8) 0.0027(7) -0.0002(8) C123 0.0338(10) 0.0287(10) 0.0195(8) -0.0014(7) 0.0036(7) 0.0039(7) C122 0.0337(10) 0.0323(10) 0.0278(9) -0.0033(7) 0.0092(7) 0.0036(8) C18 0.0345(10) 0.0288(10) 0.0325(9) 0.0068(8) 0.0064(8) -0.0058(8) C110 0.0331(9) 0.0231(9) 0.0289(9) -0.0008(7) 0.0082(7) 0.0021(7) C121 0.0393(11) 0.0587(15) 0.0357(11) -0.0081(10) 0.0046(9) 0.0179(11) C161 0.0424(12) 0.0450(13) 0.0418(12) -0.0067(10) -0.0029(10) -0.0066(11) O6 0.0506(9) 0.0593(10) 0.0419(9) -0.0050(8) -0.0003(7) 0.0073(8) O5 0.0492(9) 0.0751(13) 0.0553(10) -0.0253(9) -0.0096(7) 0.0197(9) C100 0.0488(13) 0.085(2) 0.0451(12) -0.0044(13) 0.0047(10) 0.0034(13) C200 0.0519(13) 0.0811(19) 0.0437(12) 0.0046(12) 0.0011(10) 0.0157(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 Na1 O1 2.2889(16) . ? Na1 O3 2.3136(15) 1_565 ? Na1 O5 2.3605(18) . ? Na1 O6 2.3881(18) . ? Na1 O4 2.5799(17) . ? Na1 O2 2.6122(18) 1_565 ? C210 C24 1.418(2) . ? C210 C29 1.422(2) . ? C210 C25 1.423(2) . ? O261 C26 1.374(2) . ? O261 C261 1.434(2) . ? O4 C223 1.286(2) . ? O4 H2 1.30(3) . ? C29 C28 1.415(2) . ? C29 C21 1.419(2) . ? C23 C24 1.364(3) . ? C23 C22 1.417(3) . ? C23 H23 0.98(2) . ? C21 C22 1.375(2) . ? C21 H21 0.98(2) . ? C28 C27 1.365(3) . ? C28 H28 0.91(2) . ? C22 C222 1.521(2) . ? C24 H24 0.97(2) . ? C26 C25 1.369(2) . ? C26 C27 1.415(3) . ? C25 H25 0.95(2) . ? O3 C223 1.227(2) . ? O3 Na1 2.3137(15) 1_545 ? C223 C222 1.542(2) . ? C27 H27 0.940(19) . ? C222 C221 1.517(3) . ? C222 H22D 0.96(2) . ? C261 H26C 0.94(2) . ? C261 H26B 1.00(2) . ? C261 H26A 0.99(3) . ? C221 H22C 0.998(19) . ? C221 H22B 0.90(3) . ? C221 H22A 1.00(2) . ? O2 C123 1.289(2) . ? O2 Na1 2.6122(17) 1_545 ? O2 H2 1.18(3) . ? C19 C110 1.415(2) . ? C19 C11 1.415(3) . ? C19 C18 1.428(2) . ? C12 C11 1.372(3) . ? C12 C13 1.416(3) . ? C12 C122 1.519(3) . ? C14 C13 1.364(3) . ? C14 C110 1.421(3) . ? C14 H14 0.99(2) . ? C11 H11 0.97(2) . ? C15 C16 1.364(3) . ? C15 C110 1.424(3) . ? C15 H15 0.95(2) . ? O161 C16 1.382(2) . ? O161 C161 1.425(3) . ? C13 H13 0.99(2) . ? C17 C18 1.356(3) . ? C17 C16 1.408(3) . ? C17 H17 1.01(2) . ? O1 C123 1.220(2) . ? C123 C122 1.530(2) . ? C122 C121 1.528(3) . ? C122 H12D 1.03(2) . ? C18 H18 0.94(2) . ? C121 H12C 1.07(3) . ? C121 H12B 1.04(2) . ? C121 H12A 0.96(2) . ? C161 H16C 0.97(2) . ? C161 H16B 0.97(3) . ? C161 H16A 0.98(2) . ? O6 C200 1.402(3) . ? O6 H6 0.87(3) . ? O5 C100 1.375(3) . ? O5 H5A 0.99(4) . ? C100 H10A 0.9800 . ? C100 H10B 0.9800 . ? C100 H10C 0.9800 . ? C200 H20A 0.9800 . ? C200 H20B 0.9800 . ? C200 H20C 0.9800 . ? 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 Na1 O3 178.39(7) . 1_565 ? O1 Na1 O5 88.31(6) . . ? O3 Na1 O5 93.22(6) 1_565 . ? O1 Na1 O6 87.59(6) . . ? O3 Na1 O6 90.82(6) 1_565 . ? O5 Na1 O6 170.19(8) . . ? O1 Na1 O4 77.50(5) . . ? O3 Na1 O4 102.18(6) 1_565 . ? O5 Na1 O4 83.04(6) . . ? O6 Na1 O4 87.38(6) . . ? O1 Na1 O2 100.31(6) . 1_565 ? O3 Na1 O2 80.06(5) 1_565 1_565 ? O5 Na1 O2 95.01(7) . 1_565 ? O6 Na1 O2 94.49(6) . 1_565 ? O4 Na1 O2 177.07(6) . 1_565 ? C24 C210 C29 118.05(15) . . ? C24 C210 C25 121.79(16) . . ? C29 C210 C25 120.16(15) . . ? C26 O261 C261 117.15(15) . . ? C223 O4 Na1 155.38(11) . . ? C223 O4 H2 112.8(18) . . ? Na1 O4 H2 91.6(18) . . ? C28 C29 C21 122.53(16) . . ? C28 C29 C210 118.00(15) . . ? C21 C29 C210 119.48(15) . . ? C24 C23 C22 121.29(17) . . ? C24 C23 H23 118.7(13) . . ? C22 C23 H23 120.0(13) . . ? C22 C21 C29 121.23(16) . . ? C22 C21 H21 120.3(10) . . ? C29 C21 H21 118.3(10) . . ? C27 C28 C29 121.18(17) . . ? C27 C28 H28 117.0(13) . . ? C29 C28 H28 121.8(13) . . ? C21 C22 C23 118.79(16) . . ? C21 C22 C222 122.83(16) . . ? C23 C22 C222 118.38(15) . . ? C23 C24 C210 121.14(17) . . ? C23 C24 H24 121.0(12) . . ? C210 C24 H24 117.9(12) . . ? C25 C26 O261 124.79(17) . . ? C25 C26 C27 120.36(16) . . ? O261 C26 C27 114.84(15) . . ? C26 C25 C210 119.73(17) . . ? C26 C25 H25 121.1(10) . . ? C210 C25 H25 119.2(10) . . ? C223 O3 Na1 132.68(12) . 1_545 ? O3 C223 O4 123.50(17) . . ? O3 C223 C222 120.71(16) . . ? O4 C223 C222 115.78(15) . . ? C28 C27 C26 120.56(17) . . ? C28 C27 H27 120.1(12) . . ? C26 C27 H27 119.3(12) . . ? C221 C222 C22 114.16(15) . . ? C221 C222 C223 110.15(16) . . ? C22 C222 C223 109.09(14) . . ? C221 C222 H22D 110.0(12) . . ? C22 C222 H22D 109.7(12) . . ? C223 C222 H22D 103.1(12) . . ? O261 C261 H26C 105.1(13) . . ? O261 C261 H26B 107.4(14) . . ? H26C C261 H26B 111.1(17) . . ? O261 C261 H26A 109.6(14) . . ? H26C C261 H26A 108.9(18) . . ? H26B C261 H26A 114.3(19) . . ? C222 C221 H22C 111.4(11) . . ? C222 C221 H22B 109.4(15) . . ? H22C C221 H22B 104.6(18) . . ? C222 C221 H22A 108.5(13) . . ? H22C C221 H22A 108.4(16) . . ? H22B C221 H22A 115(2) . . ? C123 O2 Na1 160.04(12) . 1_545 ? C123 O2 H2 108.2(19) . . ? Na1 O2 H2 89.6(19) 1_545 . ? C110 C19 C11 119.75(15) . . ? C110 C19 C18 118.07(16) . . ? C11 C19 C18 122.18(17) . . ? C11 C12 C13 118.29(17) . . ? C11 C12 C122 120.73(18) . . ? C13 C12 C122 120.96(16) . . ? C13 C14 C110 120.96(18) . . ? C13 C14 H14 120.5(10) . . ? C110 C14 H14 118.6(10) . . ? C12 C11 C19 121.58(18) . . ? C12 C11 H11 122.0(11) . . ? C19 C11 H11 116.5(11) . . ? C16 C15 C110 119.41(18) . . ? C16 C15 H15 122.0(12) . . ? C110 C15 H15 118.5(12) . . ? C16 O161 C161 117.64(16) . . ? C14 C13 C12 121.54(17) . . ? C14 C13 H13 118.0(12) . . ? C12 C13 H13 120.4(12) . . ? C18 C17 C16 120.68(17) . . ? C18 C17 H17 119.6(12) . . ? C16 C17 H17 119.7(12) . . ? C123 O1 Na1 135.76(13) . . ? C15 C16 O161 124.71(18) . . ? C15 C16 C17 120.96(17) . . ? O161 C16 C17 114.32(17) . . ? O1 C123 O2 123.22(17) . . ? O1 C123 C122 119.41(17) . . ? O2 C123 C122 117.36(16) . . ? C12 C122 C121 113.32(17) . . ? C12 C122 C123 110.05(15) . . ? C121 C122 C123 111.22(16) . . ? C12 C122 H12D 109.8(11) . . ? C121 C122 H12D 107.2(11) . . ? C123 C122 H12D 104.8(11) . . ? C17 C18 C19 120.71(18) . . ? C17 C18 H18 123.8(12) . . ? C19 C18 H18 115.4(12) . . ? C19 C110 C14 117.81(16) . . ? C19 C110 C15 120.11(16) . . ? C14 C110 C15 122.08(18) . . ? C122 C121 H12C 109.3(12) . . ? C122 C121 H12B 111.7(13) . . ? H12C C121 H12B 110.5(17) . . ? C122 C121 H12A 106.9(14) . . ? H12C C121 H12A 106.2(19) . . ? H12B C121 H12A 112.0(18) . . ? O161 C161 H16C 109.4(16) . . ? O161 C161 H16B 107.2(15) . . ? H16C C161 H16B 110(2) . . ? O161 C161 H16A 104.7(14) . . ? H16C C161 H16A 112.7(18) . . ? H16B C161 H16A 113(2) . . ? C200 O6 Na1 111.09(13) . . ? C200 O6 H6 104.4(18) . . ? Na1 O6 H6 123.7(17) . . ? C100 O5 Na1 125.15(14) . . ? C100 O5 H5A 107(2) . . ? Na1 O5 H5A 123(2) . . ? O5 C100 H10A 109.5 . . ? O5 C100 H10B 109.5 . . ? H10A C100 H10B 109.5 . . ? O5 C100 H10C 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? O6 C200 H20A 109.5 . . ? O6 C200 H20B 109.5 . . ? H20A C200 H20B 109.5 . . ? O6 C200 H20C 109.5 . . ? H20A C200 H20C 109.5 . . ? H20B C200 H20C 109.5 . . ? 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 O1 Na1 O4 C223 -179.4(3) . . . . ? O3 Na1 O4 C223 -1.1(3) 1_565 . . . ? O5 Na1 O4 C223 90.8(3) . . . . ? O6 Na1 O4 C223 -91.3(3) . . . . ? C24 C210 C29 C28 -178.20(17) . . . . ? C25 C210 C29 C28 1.8(2) . . . . ? C24 C210 C29 C21 1.4(2) . . . . ? C25 C210 C29 C21 -178.62(16) . . . . ? C28 C29 C21 C22 179.05(16) . . . . ? C210 C29 C21 C22 -0.5(3) . . . . ? C21 C29 C28 C27 179.21(18) . . . . ? C210 C29 C28 C27 -1.2(3) . . . . ? C29 C21 C22 C23 -0.9(2) . . . . ? C29 C21 C22 C222 178.41(15) . . . . ? C24 C23 C22 C21 1.5(2) . . . . ? C24 C23 C22 C222 -177.86(17) . . . . ? C22 C23 C24 C210 -0.6(3) . . . . ? C29 C210 C24 C23 -0.8(3) . . . . ? C25 C210 C24 C23 179.17(17) . . . . ? C261 O261 C26 C25 3.9(2) . . . . ? C261 O261 C26 C27 -176.24(15) . . . . ? O261 C26 C25 C210 179.77(16) . . . . ? C27 C26 C25 C210 -0.1(3) . . . . ? C24 C210 C25 C26 178.84(17) . . . . ? C29 C210 C25 C26 -1.2(2) . . . . ? Na1 O3 C223 O4 -15.9(3) 1_545 . . . ? Na1 O3 C223 C222 164.71(12) 1_545 . . . ? Na1 O4 C223 O3 -167.0(2) . . . . ? Na1 O4 C223 C222 12.4(4) . . . . ? C29 C28 C27 C26 0.0(3) . . . . ? C25 C26 C27 C28 0.7(3) . . . . ? O261 C26 C27 C28 -179.19(17) . . . . ? C21 C22 C222 C221 22.9(2) . . . . ? C23 C22 C222 C221 -157.75(16) . . . . ? C21 C22 C222 C223 -100.79(19) . . . . ? C23 C22 C222 C223 78.56(19) . . . . ? O3 C223 C222 C221 -36.6(2) . . . . ? O4 C223 C222 C221 144.01(16) . . . . ? O3 C223 C222 C22 89.4(2) . . . . ? O4 C223 C222 C22 -89.95(18) . . . . ? C13 C12 C11 C19 1.7(3) . . . . ? C122 C12 C11 C19 -176.94(16) . . . . ? C110 C19 C11 C12 0.5(3) . . . . ? C18 C19 C11 C12 -179.18(17) . . . . ? C110 C14 C13 C12 0.5(3) . . . . ? C11 C12 C13 C14 -2.2(3) . . . . ? C122 C12 C13 C14 176.43(18) . . . . ? O5 Na1 O1 C123 62.4(2) . . . . ? O6 Na1 O1 C123 -108.7(2) . . . . ? O4 Na1 O1 C123 -20.9(2) . . . . ? O2 Na1 O1 C123 157.2(2) 1_565 . . . ? C110 C15 C16 O161 -179.81(18) . . . . ? C110 C15 C16 C17 0.5(3) . . . . ? C161 O161 C16 C15 1.6(3) . . . . ? C161 O161 C16 C17 -178.74(18) . . . . ? C18 C17 C16 C15 -1.8(3) . . . . ? C18 C17 C16 O161 178.47(19) . . . . ? Na1 O1 C123 O2 20.5(3) . . . . ? Na1 O1 C123 C122 -158.70(14) . . . . ? Na1 O2 C123 O1 149.4(3) 1_545 . . . ? Na1 O2 C123 C122 -31.4(4) 1_545 . . . ? C11 C12 C122 C121 -125.0(2) . . . . ? C13 C12 C122 C121 56.4(2) . . . . ? C11 C12 C122 C123 109.73(19) . . . . ? C13 C12 C122 C123 -68.8(2) . . . . ? O1 C123 C122 C12 -97.4(2) . . . . ? O2 C123 C122 C12 83.3(2) . . . . ? O1 C123 C122 C121 136.2(2) . . . . ? O2 C123 C122 C121 -43.1(2) . . . . ? C16 C17 C18 C19 1.0(3) . . . . ? C110 C19 C18 C17 1.1(3) . . . . ? C11 C19 C18 C17 -179.22(18) . . . . ? C11 C19 C110 C14 -2.2(2) . . . . ? C18 C19 C110 C14 177.51(17) . . . . ? C11 C19 C110 C15 177.94(17) . . . . ? C18 C19 C110 C15 -2.4(2) . . . . ? C13 C14 C110 C19 1.7(3) . . . . ? C13 C14 C110 C15 -178.42(19) . . . . ? C16 C15 C110 C19 1.6(3) . . . . ? C16 C15 C110 C14 -178.27(18) . . . . ? O1 Na1 O6 C200 120.94(17) . . . . ? O3 Na1 O6 C200 -58.80(17) 1_565 . . . ? O4 Na1 O6 C200 43.36(17) . . . . ? O2 Na1 O6 C200 -138.90(17) 1_565 . . . ? O1 Na1 O5 C100 18.4(2) . . . . ? O3 Na1 O5 C100 -162.1(2) 1_565 . . . ? O4 Na1 O5 C100 96.0(2) . . . . ? O2 Na1 O5 C100 -81.8(2) 1_565 . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.204 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.036 # Attachment '- 3.cif' data_80b _database_code_depnum_ccdc_archive 'CCDC 856966' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Naproxen sodium mono salt DMF solvate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 N Na O4' _chemical_formula_weight 325.33 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' O O 0.0106 0.0060 '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' Na Na 0.0362 0.0249 '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(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.5777(12) _cell_length_b 5.8968(8) _cell_length_c 16.506(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.350(2) _cell_angle_gamma 90.00 _cell_volume 834.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3769 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 26.39 _chemical_absolute_configuration rm _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9581 _exptl_absorpt_correction_T_max 0.9787 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _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 'Siemens Platform CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9218 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3395 _reflns_number_gt 3140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0461P)^2^+0.1523P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_number_reflns 3395 _refine_ls_number_parameters 216 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.001 _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 Na22 Na -0.41273(7) -0.07771(11) 1.03002(3) 0.02683(15) Uani 1 1 d . . . O125 O -0.49782(15) 0.6094(2) 1.09273(7) 0.0326(3) Uani 1 1 d . . . O124 O -0.47683(15) 0.2366(2) 1.09871(8) 0.0364(3) Uani 1 1 d . . . O161 O -0.86841(14) 0.4551(2) 1.60822(7) 0.0364(3) Uani 1 1 d . . . C19 C -0.61263(19) 0.3432(3) 1.40207(9) 0.0232(3) Uani 1 1 d . . . C16 C -0.79178(17) 0.4326(3) 1.53739(9) 0.0270(3) Uani 1 1 d . . . C122 C -0.37669(18) 0.4486(3) 1.21340(9) 0.0264(3) Uani 1 1 d . . . C11 C -0.51163(18) 0.3122(3) 1.33688(9) 0.0247(3) Uani 1 1 d . . . H11 H -0.4523 0.1765 1.3343 0.030 Uiso 1 1 calc R . . C123 C -0.45641(16) 0.4298(3) 1.12816(8) 0.0239(3) Uani 1 1 d . . . C12 C -0.49757(18) 0.4728(3) 1.27772(9) 0.0255(3) Uani 1 1 d . . . C13 C -0.5932(2) 0.6698(3) 1.28017(9) 0.0287(3) Uani 1 1 d . . . H13 H -0.5874 0.7803 1.2385 0.034 Uiso 1 1 calc R . . C17 C -0.70412(19) 0.2296(3) 1.53280(10) 0.0286(3) Uani 1 1 d . . . H17 H -0.7050 0.1234 1.5761 0.034 Uiso 1 1 calc R . . C15 C -0.79461(19) 0.5851(3) 1.47497(9) 0.0265(3) Uani 1 1 d . . . H15 H -0.8568 0.7180 1.4775 0.032 Uiso 1 1 calc R . . C110 C -0.70355(18) 0.5438(3) 1.40582(9) 0.0244(3) Uani 1 1 d . . . C18 C -0.61861(18) 0.1856(3) 1.46684(9) 0.0260(3) Uani 1 1 d . . . H18 H -0.5622 0.0473 1.4642 0.031 Uiso 1 1 calc R . . C14 C -0.6938(2) 0.7028(3) 1.34180(10) 0.0288(3) Uani 1 1 d . . . H14 H -0.7578 0.8343 1.3415 0.035 Uiso 1 1 calc R . . C121 C -0.2595(2) 0.6447(3) 1.21717(11) 0.0373(4) Uani 1 1 d . . . H12C H -0.2100 0.6529 1.2717 0.056 Uiso 1 1 calc R . . H12B H -0.3140 0.7875 1.2049 0.056 Uiso 1 1 calc R . . H12A H -0.1796 0.6193 1.1774 0.056 Uiso 1 1 calc R . . C161 C -0.9486(2) 0.6621(4) 1.62112(12) 0.0390(4) Uani 1 1 d . . . H16C H -0.9983 0.6564 1.6735 0.058 Uiso 1 1 calc R . . H16B H -1.0285 0.6844 1.5777 0.058 Uiso 1 1 calc R . . H16A H -0.8743 0.7884 1.6211 0.058 Uiso 1 1 calc R . . O103 O -0.14405(14) -0.0555(3) 1.04743(8) 0.0465(3) Uani 1 1 d . . . N1 N 0.07017(17) 0.0931(3) 1.11318(9) 0.0386(4) Uani 1 1 d . . . C102 C -0.0802(2) 0.0853(4) 1.09267(12) 0.0424(4) Uani 1 1 d . . . C101 C 0.1759(3) -0.0658(5) 1.07534(18) 0.0704(7) Uani 1 1 d . . . H10F H 0.1150 -0.1802 1.0448 0.106 Uiso 1 1 calc R . . H10E H 0.2414 -0.1405 1.1174 0.106 Uiso 1 1 calc R . . H10D H 0.2422 0.0168 1.0384 0.106 Uiso 1 1 calc R . . C100 C 0.1379(2) 0.2771(4) 1.16069(14) 0.0512(6) Uani 1 1 d . . . H10C H 0.0545 0.3693 1.1827 0.077 Uiso 1 1 calc R . . H10B H 0.2017 0.3717 1.1262 0.077 Uiso 1 1 calc R . . H10A H 0.2035 0.2151 1.2054 0.077 Uiso 1 1 calc R . . H122 H -0.326(2) 0.308(4) 1.2203(11) 0.027(5) Uiso 1 1 d . . . H102 H -0.142(3) 0.204(5) 1.1213(15) 0.060(7) Uiso 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 Na22 0.0323(3) 0.0220(3) 0.0258(3) 0.0000(3) -0.0032(2) -0.0002(3) O125 0.0448(7) 0.0263(6) 0.0262(6) 0.0040(5) -0.0056(5) -0.0016(5) O124 0.0510(8) 0.0254(6) 0.0324(7) -0.0072(5) -0.0033(6) 0.0018(6) O161 0.0401(6) 0.0415(7) 0.0281(6) 0.0068(6) 0.0094(5) 0.0079(6) C19 0.0263(7) 0.0218(7) 0.0212(7) -0.0012(6) -0.0033(6) -0.0022(6) C16 0.0270(7) 0.0309(8) 0.0231(7) -0.0003(7) -0.0008(5) -0.0016(7) C122 0.0306(7) 0.0270(9) 0.0215(7) 0.0000(7) -0.0002(6) 0.0025(7) C11 0.0274(8) 0.0222(8) 0.0242(8) -0.0023(6) -0.0038(6) 0.0008(6) C123 0.0269(7) 0.0248(7) 0.0200(6) -0.0005(7) 0.0026(5) -0.0021(7) C12 0.0312(8) 0.0271(9) 0.0178(7) -0.0031(6) -0.0022(6) 0.0002(6) C13 0.0404(9) 0.0252(8) 0.0202(7) 0.0036(6) -0.0002(6) 0.0028(7) C17 0.0316(8) 0.0272(8) 0.0266(8) 0.0066(7) -0.0019(6) -0.0023(7) C15 0.0282(7) 0.0250(8) 0.0260(8) 0.0000(7) -0.0011(6) 0.0035(6) C110 0.0288(8) 0.0230(8) 0.0211(7) 0.0008(6) -0.0026(6) 0.0004(6) C18 0.0290(8) 0.0207(8) 0.0278(8) 0.0025(6) -0.0031(6) -0.0003(6) C14 0.0382(9) 0.0235(8) 0.0246(8) 0.0020(7) -0.0007(6) 0.0058(7) C121 0.0381(9) 0.0462(11) 0.0275(8) -0.0044(8) -0.0002(7) -0.0092(8) C161 0.0403(9) 0.0430(11) 0.0342(9) -0.0034(8) 0.0093(7) 0.0052(8) O103 0.0360(6) 0.0535(8) 0.0495(7) -0.0013(8) -0.0031(6) -0.0047(7) N1 0.0304(7) 0.0428(9) 0.0427(8) 0.0018(7) 0.0011(6) -0.0024(7) C102 0.0311(9) 0.0522(12) 0.0443(10) -0.0035(10) 0.0057(8) 0.0002(9) C101 0.0428(11) 0.0535(14) 0.114(2) -0.0252(17) -0.0063(12) 0.0102(12) C100 0.0428(11) 0.0607(15) 0.0503(12) -0.0096(10) 0.0058(9) -0.0097(10) _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 Na22 O125 2.2518(14) 1_545 ? Na22 O124 2.2524(14) . ? Na22 O103 2.3145(14) . ? Na22 O125 2.4048(13) 2_447 ? Na22 O124 2.5391(14) 2_447 ? Na22 C123 2.7997(15) 2_447 ? Na22 Na22 3.4344(7) 2_447 ? Na22 Na22 3.4344(7) 2_457 ? O125 C123 1.254(2) . ? O125 Na22 2.2518(14) 1_565 ? O125 Na22 2.4049(13) 2_457 ? O124 C123 1.248(2) . ? O124 Na22 2.5391(14) 2_457 ? O161 C16 1.3709(18) . ? O161 C161 1.422(2) . ? C19 C18 1.419(2) . ? C19 C110 1.419(2) . ? C19 C11 1.421(2) . ? C16 C15 1.367(2) . ? C16 C17 1.417(3) . ? C122 C12 1.521(2) . ? C122 C121 1.532(2) . ? C122 C123 1.543(2) . ? C122 H122 0.94(2) . ? C11 C12 1.369(2) . ? C11 H11 0.9500 . ? C123 Na22 2.7997(15) 2_457 ? C12 C13 1.424(2) . ? C13 C14 1.374(2) . ? C13 H13 0.9500 . ? C17 C18 1.362(2) . ? C17 H17 0.9500 . ? C15 C110 1.430(2) . ? C15 H15 0.9500 . ? C110 C14 1.418(2) . ? C18 H18 0.9500 . ? C14 H14 0.9500 . ? C121 H12C 0.9800 . ? C121 H12B 0.9800 . ? C121 H12A 0.9800 . ? C161 H16C 0.9800 . ? C161 H16B 0.9800 . ? C161 H16A 0.9800 . ? O103 C102 1.230(3) . ? N1 C102 1.321(2) . ? N1 C100 1.447(3) . ? N1 C101 1.462(3) . ? C102 H102 1.01(3) . ? C101 H10F 0.9800 . ? C101 H10E 0.9800 . ? C101 H10D 0.9800 . ? C100 H10C 0.9800 . ? C100 H10B 0.9800 . ? C100 H10A 0.9800 . ? 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 O125 Na22 O124 110.64(5) 1_545 . ? O125 Na22 O103 109.22(6) 1_545 . ? O124 Na22 O103 98.82(6) . . ? O125 Na22 O125 131.67(4) 1_545 2_447 ? O124 Na22 O125 88.32(5) . 2_447 ? O103 Na22 O125 111.12(5) . 2_447 ? O125 Na22 O124 85.09(5) 1_545 2_447 ? O124 Na22 O124 133.29(4) . 2_447 ? O103 Na22 O124 117.63(5) . 2_447 ? O125 Na22 O124 52.95(4) 2_447 2_447 ? O125 Na22 C123 108.45(5) 1_545 2_447 ? O124 Na22 C123 111.08(5) . 2_447 ? O103 Na22 C123 118.29(5) . 2_447 ? O125 Na22 C123 26.52(5) 2_447 2_447 ? O124 Na22 C123 26.46(5) 2_447 2_447 ? O125 Na22 Na22 44.23(3) 1_545 2_447 ? O124 Na22 Na22 137.66(5) . 2_447 ? O103 Na22 Na22 120.29(5) . 2_447 ? O125 Na22 Na22 91.74(4) 2_447 2_447 ? O124 Na22 Na22 40.97(3) 2_447 2_447 ? C123 Na22 Na22 65.86(4) 2_447 2_447 ? O125 Na22 Na22 133.67(5) 1_545 2_457 ? O124 Na22 Na22 47.65(3) . 2_457 ? O103 Na22 Na22 114.04(5) . 2_457 ? O125 Na22 Na22 40.78(3) 2_447 2_457 ? O124 Na22 Na22 89.17(4) 2_447 2_457 ? C123 Na22 Na22 64.15(4) 2_447 2_457 ? Na22 Na22 Na22 118.30(3) 2_447 2_457 ? C123 O125 Na22 144.63(11) . 1_565 ? C123 O125 Na22 94.59(9) . 2_457 ? Na22 O125 Na22 94.98(4) 1_565 2_457 ? C123 O124 Na22 156.03(12) . . ? C123 O124 Na22 88.50(9) . 2_457 ? Na22 O124 Na22 91.38(4) . 2_457 ? C16 O161 C161 117.57(14) . . ? C18 C19 C110 118.43(14) . . ? C18 C19 C11 121.88(15) . . ? C110 C19 C11 119.57(14) . . ? C15 C16 O161 125.77(16) . . ? C15 C16 C17 120.56(14) . . ? O161 C16 C17 113.67(15) . . ? C12 C122 C121 111.46(14) . . ? C12 C122 C123 110.73(12) . . ? C121 C122 C123 110.92(14) . . ? C12 C122 H122 109.0(12) . . ? C121 C122 H122 110.9(12) . . ? C123 C122 H122 103.5(12) . . ? C12 C11 C19 121.69(15) . . ? C12 C11 H11 119.2 . . ? C19 C11 H11 119.2 . . ? O124 C123 O125 123.83(13) . . ? O124 C123 C122 118.09(15) . . ? O125 C123 C122 118.08(15) . . ? O124 C123 Na22 65.04(8) . 2_457 ? O125 C123 Na22 58.89(7) . 2_457 ? C122 C123 Na22 175.76(12) . 2_457 ? C11 C12 C13 118.46(14) . . ? C11 C12 C122 121.03(14) . . ? C13 C12 C122 120.43(14) . . ? C14 C13 C12 121.09(15) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C18 C17 C16 120.52(15) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C16 C15 C110 119.74(15) . . ? C16 C15 H15 120.1 . . ? C110 C15 H15 120.1 . . ? C14 C110 C19 117.98(13) . . ? C14 C110 C15 122.21(15) . . ? C19 C110 C15 119.72(14) . . ? C17 C18 C19 120.95(15) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C13 C14 C110 121.07(15) . . ? C13 C14 H14 119.5 . . ? C110 C14 H14 119.5 . . ? C122 C121 H12C 109.5 . . ? C122 C121 H12B 109.5 . . ? H12C C121 H12B 109.5 . . ? C122 C121 H12A 109.5 . . ? H12C C121 H12A 109.5 . . ? H12B C121 H12A 109.5 . . ? O161 C161 H16C 109.5 . . ? O161 C161 H16B 109.5 . . ? H16C C161 H16B 109.5 . . ? O161 C161 H16A 109.5 . . ? H16C C161 H16A 109.5 . . ? H16B C161 H16A 109.5 . . ? C102 O103 Na22 121.99(13) . . ? C102 N1 C100 122.08(18) . . ? C102 N1 C101 119.00(18) . . ? C100 N1 C101 118.03(16) . . ? O103 C102 N1 125.8(2) . . ? O103 C102 H102 121.5(15) . . ? N1 C102 H102 112.6(15) . . ? N1 C101 H10F 109.5 . . ? N1 C101 H10E 109.5 . . ? H10F C101 H10E 109.5 . . ? N1 C101 H10D 109.5 . . ? H10F C101 H10D 109.5 . . ? H10E C101 H10D 109.5 . . ? N1 C100 H10C 109.5 . . ? N1 C100 H10B 109.5 . . ? H10C C100 H10B 109.5 . . ? N1 C100 H10A 109.5 . . ? H10C C100 H10A 109.5 . . ? H10B C100 H10A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.328 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.036