# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Tomislav Friscic' _publ_contact_author_email tf253@cam.ac.uk loop_ _publ_author_name Friscic Strobridge Halasz Dinnebier Stein Fabian data_2 _database_code_depnum_ccdc_archive 'CCDC 801659' #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; magnesium naproxen monohydrate ; _chemical_name_common 2 _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 Mg O7' _chemical_formula_sum 'C28 H28 Mg O7' _chemical_formula_weight 500.81 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mg Mg 0.0486 0.0363 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.0543(3) _cell_length_b 6.1624(2) _cell_length_c 15.0156(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.7970(10) _cell_angle_gamma 90.00 _cell_volume 1207.50(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6753 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 10263 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3931 _reflns_number_gt 3358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Non-hydrogen atoms were refined using the anisotropic model. Hydrogen atoms of hydrocarbon groups were placed in positions calculated based on the stereochemical properties of corresponding carbon atoms. Hydrogen atoms of OH groups were located from the Fourier difference map of electron density and their coordinates and Uiso were locked during the final least-squares calculations. ; _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^)+(0.0250P)^2^+0.5581P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_number_reflns 3931 _refine_ls_number_parameters 329 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.005 _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 Mg1 Mg 0.49261(7) 0.55360(17) 0.48795(6) 0.0182(2) Uani 1 1 d . . . O1 O 0.34776(14) 0.4743(3) 0.46507(15) 0.0259(5) Uani 1 1 d . . . O2 O 0.35751(14) 0.1163(3) 0.48658(13) 0.0223(5) Uani 1 1 d . . . O3 O 0.04219(16) 0.3406(4) 0.89707(15) 0.0378(6) Uani 1 1 d . . . O4 O 0.44830(13) 0.8171(3) 0.39479(13) 0.0201(4) Uani 1 1 d . . . O5 O 0.38064(17) 1.0680(4) 0.28379(14) 0.0376(6) Uani 1 1 d . . . O6 O 0.40389(16) 0.9099(3) -0.25485(15) 0.0292(5) Uani 1 1 d . . . O7 O 0.49287(13) 0.7904(3) 0.59192(13) 0.0215(4) Uani 1 1 d . . . C1 C 0.30816(19) 0.2913(5) 0.46469(18) 0.0208(6) Uani 1 1 d . . . C2 C 0.19162(19) 0.2846(5) 0.4368(2) 0.0222(6) Uani 1 1 d . . . H2 H 0.1624 0.4079 0.3916 0.027 Uiso 1 1 calc R . . C3 C 0.1465(2) 0.0769(6) 0.3827(2) 0.0309(7) Uani 1 1 d . . . H3A H 0.1754 -0.0486 0.4239 0.046 Uiso 1 1 calc R . . H3B H 0.1632 0.0675 0.3250 0.046 Uiso 1 1 calc R . . H3C H 0.0719 0.0782 0.3643 0.046 Uiso 1 1 calc R . . C4 C 0.16640(19) 0.3273(5) 0.5254(2) 0.0223(7) Uani 1 1 d . . . C5 C 0.1974(2) 0.5279(5) 0.5742(2) 0.0248(7) Uani 1 1 d . . . H5 H 0.2299 0.6332 0.5489 0.030 Uiso 1 1 calc R . . C6 C 0.1815(2) 0.5730(6) 0.6568(2) 0.0267(7) Uani 1 1 d . . . H6 H 0.2038 0.7082 0.6880 0.032 Uiso 1 1 calc R . . C7 C 0.1326(2) 0.4223(5) 0.6965(2) 0.0238(7) Uani 1 1 d . . . C8 C 0.1162(2) 0.4651(5) 0.7828(2) 0.0273(7) Uani 1 1 d . . . H8 H 0.1401 0.5966 0.8169 0.033 Uiso 1 1 calc R . . C9 C 0.0655(2) 0.3144(6) 0.8167(2) 0.0279(7) Uani 1 1 d . . . C10 C 0.0318(2) 0.1180(5) 0.7677(2) 0.0312(8) Uani 1 1 d . . . H10 H -0.0024 0.0148 0.7923 0.037 Uiso 1 1 calc R . . C11 C 0.0476(2) 0.0739(6) 0.6857(2) 0.0280(7) Uani 1 1 d . . . H11 H 0.0243 -0.0601 0.6537 0.034 Uiso 1 1 calc R . . C12 C 0.0981(2) 0.2239(5) 0.6468(2) 0.0240(7) Uani 1 1 d . . . C13 C 0.1164(2) 0.1812(5) 0.5616(2) 0.0239(7) Uani 1 1 d . . . H13 H 0.0935 0.0480 0.5289 0.029 Uiso 1 1 calc R . . C14 C 0.0701(3) 0.5413(7) 0.9475(3) 0.0533(10) Uani 1 1 d . . . H14A H 0.1447 0.5593 0.9706 0.080 Uiso 1 1 calc R . . H14B H 0.0480 0.5411 1.0022 0.080 Uiso 1 1 calc R . . H14C H 0.0369 0.6613 0.9043 0.080 Uiso 1 1 calc R . . C15 C 0.3913(2) 0.8735(5) 0.3095(2) 0.0229(7) Uani 1 1 d . . . C16 C 0.3346(2) 0.6997(5) 0.2364(2) 0.0249(7) Uani 1 1 d . . . H16 H 0.3743 0.5613 0.2546 0.030 Uiso 1 1 calc R . . C17 C 0.2290(2) 0.6630(6) 0.2417(2) 0.0343(8) Uani 1 1 d . . . H17A H 0.2363 0.6482 0.3089 0.052 Uiso 1 1 calc R . . H17B H 0.1986 0.5303 0.2067 0.052 Uiso 1 1 calc R . . H17C H 0.1845 0.7869 0.2129 0.052 Uiso 1 1 calc R . . C18 C 0.3260(2) 0.7603(5) 0.13555(19) 0.0208(7) Uani 1 1 d . . . C19 C 0.2734(2) 0.9507(5) 0.0900(2) 0.0253(7) Uani 1 1 d . . . H19 H 0.2389 1.0365 0.1212 0.030 Uiso 1 1 calc R . . C20 C 0.2716(2) 1.0126(5) 0.0019(2) 0.0254(7) Uani 1 1 d . . . H20 H 0.2354 1.1400 -0.0273 0.030 Uiso 1 1 calc R . . C21 C 0.3227(2) 0.8901(5) -0.0466(2) 0.0222(7) Uani 1 1 d . . . C22 C 0.3309(2) 0.9654(5) -0.1330(2) 0.0235(7) Uani 1 1 d . . . H22 H 0.2986 1.0969 -0.1616 0.028 Uiso 1 1 calc R . . C23 C 0.3858(2) 0.8462(5) -0.1746(2) 0.0247(7) Uani 1 1 d . . . C24 C 0.4300(2) 0.6460(5) -0.1352(2) 0.0267(7) Uani 1 1 d . . . H24 H 0.4667 0.5639 -0.1655 0.032 Uiso 1 1 calc R . . C25 C 0.4204(2) 0.5696(5) -0.0537(2) 0.0258(7) Uani 1 1 d . . . H25 H 0.4483 0.4319 -0.0292 0.031 Uiso 1 1 calc R . . C26 C 0.3694(2) 0.6923(5) -0.0049(2) 0.0222(7) Uani 1 1 d . . . C27 C 0.3695(2) 0.6318(5) 0.0867(2) 0.0230(7) Uani 1 1 d . . . H27 H 0.4006 0.4988 0.1146 0.028 Uiso 1 1 calc R . . C28 C 0.3826(2) 1.1329(5) -0.2812(2) 0.0300(8) Uani 1 1 d . . . H28A H 0.3086 1.1582 -0.3034 0.045 Uiso 1 1 calc R . . H28B H 0.4069 1.1683 -0.3328 0.045 Uiso 1 1 calc R . . H28C H 0.4177 1.2251 -0.2254 0.045 Uiso 1 1 calc R . . H1O H 0.4331 0.7806 0.6077 0.040 Uiso 1 1 d . . . H2O H 0.5461 0.7151 0.6512 0.040 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 Mg1 0.0192(4) 0.0156(5) 0.0195(5) 0.0001(4) 0.0068(4) -0.0005(4) O1 0.0213(10) 0.0209(13) 0.0352(12) 0.0003(9) 0.0101(9) -0.0016(9) O2 0.0195(10) 0.0200(13) 0.0273(11) -0.0004(8) 0.0084(8) 0.0017(8) O3 0.0391(12) 0.0512(17) 0.0279(12) -0.0024(12) 0.0179(10) -0.0029(12) O4 0.0199(10) 0.0180(11) 0.0204(11) 0.0012(9) 0.0053(8) 0.0011(9) O5 0.0566(14) 0.0203(13) 0.0218(11) 0.0027(11) -0.0017(10) -0.0047(12) O6 0.0394(13) 0.0275(13) 0.0265(12) -0.0006(10) 0.0189(10) 0.0005(10) O7 0.0256(10) 0.0204(11) 0.0208(10) 0.0021(9) 0.0115(8) 0.0029(10) C1 0.0212(14) 0.0242(17) 0.0184(15) 0.0001(13) 0.0089(11) 0.0024(15) C2 0.0177(14) 0.0239(16) 0.0238(16) 0.0020(14) 0.0062(11) 0.0028(14) C3 0.0246(15) 0.038(2) 0.0299(16) -0.0039(17) 0.0102(13) -0.0042(16) C4 0.0147(13) 0.0248(18) 0.0259(16) 0.0015(14) 0.0058(11) 0.0007(13) C5 0.0229(14) 0.0216(18) 0.0310(17) 0.0008(14) 0.0111(12) -0.0043(13) C6 0.0234(15) 0.0223(17) 0.0330(17) -0.0023(16) 0.0088(13) -0.0020(14) C7 0.0133(14) 0.0280(19) 0.0271(16) -0.0008(14) 0.0040(12) 0.0026(13) C8 0.0250(16) 0.0298(18) 0.0249(17) -0.0054(14) 0.0065(13) 0.0021(14) C9 0.0211(14) 0.039(2) 0.0233(16) 0.0040(16) 0.0080(12) 0.0069(16) C10 0.0241(16) 0.037(2) 0.0355(19) 0.0046(15) 0.0149(14) -0.0035(14) C11 0.0222(15) 0.0270(18) 0.0352(17) -0.0005(16) 0.0113(13) -0.0032(15) C12 0.0154(14) 0.0273(18) 0.0278(16) 0.0004(14) 0.0065(12) 0.0008(12) C13 0.0179(14) 0.0227(17) 0.0294(16) -0.0046(14) 0.0067(12) -0.0007(13) C14 0.067(3) 0.064(3) 0.037(2) -0.010(2) 0.0284(18) -0.003(2) C15 0.0257(15) 0.0206(18) 0.0225(17) 0.0009(13) 0.0091(13) 0.0004(13) C16 0.0285(16) 0.0238(17) 0.0191(15) 0.0014(13) 0.0049(12) -0.0014(13) C17 0.0326(18) 0.040(2) 0.0288(18) -0.0032(16) 0.0097(14) -0.0107(16) C18 0.0216(14) 0.0210(18) 0.0180(15) -0.0013(12) 0.0052(11) -0.0031(12) C19 0.0228(15) 0.0305(18) 0.0206(16) 0.0004(14) 0.0058(12) 0.0050(14) C20 0.0260(15) 0.026(2) 0.0217(16) 0.0015(13) 0.0056(12) 0.0070(14) C21 0.0204(15) 0.0247(17) 0.0205(16) -0.0018(13) 0.0064(12) -0.0010(13) C22 0.0257(15) 0.0220(16) 0.0205(16) 0.0030(13) 0.0058(12) 0.0035(13) C23 0.0250(15) 0.0275(19) 0.0199(16) -0.0028(13) 0.0063(12) -0.0047(13) C24 0.0308(17) 0.0249(17) 0.0254(17) -0.0075(13) 0.0117(13) 0.0001(14) C25 0.0267(15) 0.0194(16) 0.0291(16) -0.0025(15) 0.0078(12) 0.0044(14) C26 0.0224(15) 0.0207(17) 0.0217(15) -0.0012(13) 0.0061(12) -0.0017(13) C27 0.0231(15) 0.0194(16) 0.0222(15) 0.0005(12) 0.0034(12) -0.0019(12) C28 0.0327(17) 0.032(2) 0.0280(17) 0.0080(15) 0.0143(14) 0.0057(14) _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 Mg1 O1 1.995(2) . ? Mg1 O2 2.033(2) 2_656 ? Mg1 O7 2.072(2) 2_646 ? Mg1 O4 2.082(2) . ? Mg1 O7 2.136(2) . ? Mg1 O4 2.197(2) 2_646 ? Mg1 Mg1 3.1003(2) 2_656 ? Mg1 Mg1 3.1003(2) 2_646 ? O1 C1 1.257(4) . ? O2 C1 1.258(4) . ? O2 Mg1 2.033(2) 2_646 ? O3 C9 1.372(3) . ? O3 C14 1.427(5) . ? O4 C15 1.281(3) . ? O4 Mg1 2.197(2) 2_656 ? O5 C15 1.251(4) . ? O6 C23 1.377(4) . ? O6 C28 1.431(4) . ? O7 Mg1 2.072(2) 2_656 ? O7 H1O 0.9557(17) . ? O7 H2O 1.0359(18) . ? C1 C2 1.533(4) . ? C2 C4 1.521(4) . ? C2 C3 1.522(4) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C13 1.373(4) . ? C4 C5 1.421(4) . ? C5 C6 1.367(4) . ? C5 H5 0.9500 . ? C6 C7 1.412(4) . ? C6 H6 0.9500 . ? C7 C12 1.420(4) . ? C7 C8 1.424(4) . ? C8 C9 1.378(4) . ? C8 H8 0.9500 . ? C9 C10 1.404(5) . ? C10 C11 1.358(4) . ? C10 H10 0.9500 . ? C11 C12 1.416(4) . ? C11 H11 0.9500 . ? C12 C13 1.420(4) . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.529(4) . ? C16 C18 1.520(4) . ? C16 C17 1.533(4) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C27 1.368(4) . ? C18 C19 1.420(4) . ? C19 C20 1.368(4) . ? C19 H19 0.9500 . ? C20 C21 1.416(4) . ? C20 H20 0.9500 . ? C21 C26 1.415(4) . ? C21 C22 1.422(4) . ? C22 C23 1.373(4) . ? C22 H22 0.9500 . ? C23 C24 1.409(5) . ? C24 C25 1.363(4) . ? C24 H24 0.9500 . ? C25 C26 1.419(4) . ? C25 H25 0.9500 . ? C26 C27 1.425(4) . ? C27 H27 0.9500 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 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 Mg1 O2 176.69(11) . 2_656 ? O1 Mg1 O7 91.26(9) . 2_646 ? O2 Mg1 O7 86.55(8) 2_656 2_646 ? O1 Mg1 O4 92.51(8) . . ? O2 Mg1 O4 90.50(8) 2_656 . ? O7 Mg1 O4 106.90(9) 2_646 . ? O1 Mg1 O7 91.03(9) . . ? O2 Mg1 O7 90.70(8) 2_656 . ? O7 Mg1 O7 169.78(8) 2_646 . ? O4 Mg1 O7 82.94(8) . . ? O1 Mg1 O4 91.91(8) . 2_646 ? O2 Mg1 O4 85.32(8) 2_656 2_646 ? O7 Mg1 O4 81.69(8) 2_646 2_646 ? O4 Mg1 O4 170.24(9) . 2_646 ? O7 Mg1 O4 88.28(8) . 2_646 ? O1 Mg1 Mg1 106.46(8) . 2_656 ? O2 Mg1 Mg1 76.67(7) 2_656 2_656 ? O7 Mg1 Mg1 145.98(8) 2_646 2_656 ? O4 Mg1 Mg1 45.06(6) . 2_656 ? O7 Mg1 Mg1 41.74(6) . 2_656 ? O4 Mg1 Mg1 125.22(7) 2_646 2_656 ? O1 Mg1 Mg1 78.25(7) . 2_646 ? O2 Mg1 Mg1 98.46(7) 2_656 2_646 ? O7 Mg1 Mg1 43.35(6) 2_646 2_646 ? O4 Mg1 Mg1 147.55(8) . 2_646 ? O7 Mg1 Mg1 127.72(7) . 2_646 ? O4 Mg1 Mg1 42.12(6) 2_646 2_646 ? Mg1 Mg1 Mg1 167.26(6) 2_656 2_646 ? C1 O1 Mg1 129.97(19) . . ? C1 O2 Mg1 130.10(18) . 2_646 ? C9 O3 C14 117.4(3) . . ? C15 O4 Mg1 143.5(2) . . ? C15 O4 Mg1 122.08(19) . 2_656 ? Mg1 O4 Mg1 92.82(7) . 2_656 ? C23 O6 C28 115.3(2) . . ? Mg1 O7 Mg1 94.91(7) 2_656 . ? Mg1 O7 H1O 118.54(15) 2_656 . ? Mg1 O7 H1O 112.02(15) . . ? Mg1 O7 H2O 130.79(15) 2_656 . ? Mg1 O7 H2O 97.27(13) . . ? H1O O7 H2O 100.33(16) . . ? O1 C1 O2 124.6(2) . . ? O1 C1 C2 116.9(3) . . ? O2 C1 C2 118.5(3) . . ? C4 C2 C3 115.2(2) . . ? C4 C2 C1 109.2(2) . . ? C3 C2 C1 111.0(2) . . ? C4 C2 H2 107.0 . . ? C3 C2 H2 107.0 . . ? C1 C2 H2 107.0 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C13 C4 C5 118.0(3) . . ? C13 C4 C2 123.6(3) . . ? C5 C4 C2 118.4(3) . . ? C6 C5 C4 121.5(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 121.2(3) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C12 118.0(3) . . ? C6 C7 C8 122.1(3) . . ? C12 C7 C8 119.9(3) . . ? C9 C8 C7 119.5(3) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? O3 C9 C8 124.8(3) . . ? O3 C9 C10 114.7(3) . . ? C8 C9 C10 120.5(3) . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 121.2(3) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C12 C13 122.4(3) . . ? C11 C12 C7 118.2(3) . . ? C13 C12 C7 119.4(3) . . ? C4 C13 C12 121.8(3) . . ? C4 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O5 C15 O4 121.8(3) . . ? O5 C15 C16 118.6(3) . . ? O4 C15 C16 119.5(3) . . ? C18 C16 C15 111.7(2) . . ? C18 C16 C17 111.5(2) . . ? C15 C16 C17 108.8(3) . . ? C18 C16 H16 108.2 . . ? C15 C16 H16 108.2 . . ? C17 C16 H16 108.2 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C27 C18 C19 118.4(3) . . ? C27 C18 C16 120.4(3) . . ? C19 C18 C16 121.2(3) . . ? C20 C19 C18 121.0(3) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 121.2(3) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C26 C21 C20 118.2(3) . . ? C26 C21 C22 120.2(3) . . ? C20 C21 C22 121.5(3) . . ? C23 C22 C21 119.4(3) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 O6 124.3(3) . . ? C22 C23 C24 120.8(3) . . ? O6 C23 C24 114.9(3) . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 121.1(3) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C21 C26 C25 118.1(3) . . ? C21 C26 C27 119.1(3) . . ? C25 C26 C27 122.7(3) . . ? C18 C27 C26 121.7(3) . . ? C18 C27 H27 119.1 . . ? C26 C27 H27 119.1 . . ? O6 C28 H28A 109.5 . . ? O6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 O2 Mg1 O1 C1 -7.8(18) 2_656 . . . ? O7 Mg1 O1 C1 40.7(2) 2_646 . . . ? O4 Mg1 O1 C1 147.7(2) . . . . ? O7 Mg1 O1 C1 -129.3(2) . . . . ? O4 Mg1 O1 C1 -41.0(2) 2_646 . . . ? Mg1 Mg1 O1 C1 -168.7(2) 2_656 . . . ? Mg1 Mg1 O1 C1 -0.9(2) 2_646 . . . ? O1 Mg1 O4 C15 -52.7(3) . . . . ? O2 Mg1 O4 C15 125.9(3) 2_656 . . . ? O7 Mg1 O4 C15 39.3(3) 2_646 . . . ? O7 Mg1 O4 C15 -143.5(3) . . . . ? O4 Mg1 O4 C15 -169.6(4) 2_646 . . . ? Mg1 Mg1 O4 C15 -163.6(3) 2_656 . . . ? Mg1 Mg1 O4 C15 19.2(4) 2_646 . . . ? O1 Mg1 O4 Mg1 110.91(9) . . . 2_656 ? O2 Mg1 O4 Mg1 -70.46(8) 2_656 . . 2_656 ? O7 Mg1 O4 Mg1 -157.00(8) 2_646 . . 2_656 ? O7 Mg1 O4 Mg1 20.18(6) . . . 2_656 ? O4 Mg1 O4 Mg1 -5.9(3) 2_646 . . 2_656 ? Mg1 Mg1 O4 Mg1 -177.19(13) 2_646 . . 2_656 ? O1 Mg1 O7 Mg1 -113.93(9) . . . 2_656 ? O2 Mg1 O7 Mg1 68.89(8) 2_656 . . 2_656 ? O7 Mg1 O7 Mg1 143.1(4) 2_646 . . 2_656 ? O4 Mg1 O7 Mg1 -21.52(6) . . . 2_656 ? O4 Mg1 O7 Mg1 154.19(8) 2_646 . . 2_656 ? Mg1 Mg1 O7 Mg1 170.16(9) 2_646 . . 2_656 ? Mg1 O1 C1 O2 5.5(4) . . . . ? Mg1 O1 C1 C2 -175.45(17) . . . . ? Mg1 O2 C1 O1 -8.8(4) 2_646 . . . ? Mg1 O2 C1 C2 172.12(17) 2_646 . . . ? O1 C1 C2 C4 -85.8(3) . . . . ? O2 C1 C2 C4 93.3(3) . . . . ? O1 C1 C2 C3 146.0(3) . . . . ? O2 C1 C2 C3 -34.8(3) . . . . ? C3 C2 C4 C13 6.9(4) . . . . ? C1 C2 C4 C13 -118.9(3) . . . . ? C3 C2 C4 C5 -174.0(2) . . . . ? C1 C2 C4 C5 60.2(3) . . . . ? C13 C4 C5 C6 2.2(4) . . . . ? C2 C4 C5 C6 -176.9(3) . . . . ? C4 C5 C6 C7 -0.6(4) . . . . ? C5 C6 C7 C12 -1.5(4) . . . . ? C5 C6 C7 C8 179.4(3) . . . . ? C6 C7 C8 C9 178.2(3) . . . . ? C12 C7 C8 C9 -0.9(4) . . . . ? C14 O3 C9 C8 1.9(4) . . . . ? C14 O3 C9 C10 -177.2(3) . . . . ? C7 C8 C9 O3 -177.7(3) . . . . ? C7 C8 C9 C10 1.3(4) . . . . ? O3 C9 C10 C11 178.3(3) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C9 C10 C11 C12 -0.1(5) . . . . ? C10 C11 C12 C13 179.4(3) . . . . ? C10 C11 C12 C7 0.4(4) . . . . ? C6 C7 C12 C11 -179.0(3) . . . . ? C8 C7 C12 C11 0.1(4) . . . . ? C6 C7 C12 C13 2.0(4) . . . . ? C8 C7 C12 C13 -178.9(3) . . . . ? C5 C4 C13 C12 -1.7(4) . . . . ? C2 C4 C13 C12 177.4(3) . . . . ? C11 C12 C13 C4 -179.3(3) . . . . ? C7 C12 C13 C4 -0.3(4) . . . . ? Mg1 O4 C15 O5 173.4(2) . . . . ? Mg1 O4 C15 O5 12.8(4) 2_656 . . . ? Mg1 O4 C15 C16 -6.7(5) . . . . ? Mg1 O4 C15 C16 -167.35(19) 2_656 . . . ? O5 C15 C16 C18 33.9(4) . . . . ? O4 C15 C16 C18 -145.9(3) . . . . ? O5 C15 C16 C17 -89.7(3) . . . . ? O4 C15 C16 C17 90.5(3) . . . . ? C15 C16 C18 C27 118.8(3) . . . . ? C17 C16 C18 C27 -119.2(3) . . . . ? C15 C16 C18 C19 -60.9(3) . . . . ? C17 C16 C18 C19 61.1(4) . . . . ? C27 C18 C19 C20 -4.1(4) . . . . ? C16 C18 C19 C20 175.5(3) . . . . ? C18 C19 C20 C21 -0.5(4) . . . . ? C19 C20 C21 C26 4.8(4) . . . . ? C19 C20 C21 C22 -173.0(3) . . . . ? C26 C21 C22 C23 -1.1(4) . . . . ? C20 C21 C22 C23 176.6(3) . . . . ? C21 C22 C23 O6 -175.9(3) . . . . ? C21 C22 C23 C24 2.9(4) . . . . ? C28 O6 C23 C22 14.0(4) . . . . ? C28 O6 C23 C24 -164.9(3) . . . . ? C22 C23 C24 C25 -1.2(4) . . . . ? O6 C23 C24 C25 177.7(3) . . . . ? C23 C24 C25 C26 -2.4(4) . . . . ? C20 C21 C26 C25 179.9(3) . . . . ? C22 C21 C26 C25 -2.3(4) . . . . ? C20 C21 C26 C27 -4.4(4) . . . . ? C22 C21 C26 C27 173.4(3) . . . . ? C24 C25 C26 C21 4.1(4) . . . . ? C24 C25 C26 C27 -171.5(3) . . . . ? C19 C18 C27 C26 4.5(4) . . . . ? C16 C18 C27 C26 -175.2(3) . . . . ? C21 C26 C27 C18 -0.2(4) . . . . ? C25 C26 C27 C18 175.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.172 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.052 data_3 _database_code_depnum_ccdc_archive 'CCDC 801660' #TrackingRef 'deposit.cif' _chemical_formula_sum 'C28 H26 Mg1 O10' _chemical_formula_weight 546.82 _chemical_formula_moiety 'C28 H26 Mg1 O10' _symmetry_cell_setting orthorhombic _cell_formula_units_Z 2 _chemical_absolute_configuration syn _diffrn_measurement_device_type ; Bruker D8 Advance in Debye-Scherrer geometry ; _diffrn_ambient_temperature 291 _diffrn_radiation_type 'Cu K\a_1' _diffrn_radiation_wavelength 1.54059 _exptl_crystal_density_diffrn 1.372 _refine_ls_hydrogen_treatment constr _refine_ls_shift/su_max <0.01 _refine_ls_number_parameters 67 _pd_proc_ls_prof_R_factor 0.0486 _pd_proc_ls_prof_wR_factor 0.0641 _refine_ls_R_Fsqd_factor 0.0253 _refine_ls_goodness_of_fit_all 1.71 _cell_measurement_temperature 291 _exptl_crystal_colour white _refine_ls_structure_factor_coef Fsqd _exptl_special_details ; ; _pd_proc_ls_profile_function ; Calculated from fundamental parameters ; _cell_length_a 43.6732(37) _cell_length_b 5.88876(52) _cell_length_c 5.14629(39) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1323.53(19) _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 'x, y, z' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv O21 O 4 0.22079(11) 0.8410(10) 0.81818(73) 1 0.10(32) O22 O 4 0.24394(10) -0.71899(59) 0.82108(85) 1 0.10(32) Mg1 Mg 4 0.251000(95) 1.0035(12) 0.0759(14) 0.5 0.10(32) O1 O 4 0.7865563 -0.429964 1.177609 1 2.39(31) O2 O 4 0.7961645 -0.07653124 1.307802 1 2.39(31) C1 C 4 0.8028612 -0.254419 1.184841 1 2.39(31) O3 O 4 0.9761092 -0.298074 1.988373 1 2.39(31) C2 C 4 0.8332101 -0.2618794 1.035132 1 2.39(31) H2 H 4 0.8323711 -0.3976305 0.9186933 1 2.39(31) C3 C 4 0.836668 -0.0544658 0.8609689 1 2.39(31) H3A H 4 0.8368038 0.0832696 0.9678284 1 2.39(31) H3B H 4 0.8194944 -0.04805804 0.7386791 1 2.39(31) H3C H 4 0.8559523 -0.06509286 0.7642401 1 2.39(31) C4 C 4 0.8593162 -0.3011277 1.225537 1 2.39(31) C5 C 4 0.8581777 -0.496113 1.387819 1 2.39(31) H5 H 4 0.8417858 -0.6007956 1.368282 1 2.39(31) C6 C 4 0.8801025 -0.5366447 1.57168 1 2.39(31) H6 H 4 0.8785573 -0.667956 1.678101 1 2.39(31) C7 C 4 0.9050208 -0.3866334 1.606205 1 2.39(31) C8 C 4 0.9279445 -0.4243038 1.79805 1 2.39(31) H8 H 4 0.9265533 -0.5510496 1.911526 1 2.39(31) C9 C 4 0.952207 -0.2752788 1.81764 1 2.39(31) C10 C 4 0.9540772 -0.08513539 1.653452 1 2.39(31) H10 H 4 0.970781 0.01708069 1.670446 1 2.39(31) C11 C 4 0.9322789 -0.04589343 1.471041 1 2.39(31) H11 H 4 0.9339387 0.08375619 1.362277 1 2.39(31) C12 C 4 0.907071 -0.1947706 1.439554 1 2.39(31) C13 C 4 0.8837879 -0.1566814 1.25181 1 2.39(31) H13 H 4 0.8851735 -0.02772622 1.141566 1 2.39(31) C14 C 4 0.9758026 -0.4901751 2.157575 1 2.39(31) H14A H 4 0.9575963 -0.4837917 2.268679 1 2.39(31) H14B H 4 0.9942278 -0.4887017 2.266252 1 2.39(31) H14C H 4 0.9753607 -0.6298462 2.054118 1 2.39(31) _vrf_ATOM006_3 ; PROBLEM: _atom_site_U_iso_or_equiv is missing RESPONSE: Displacement parameters are reported as Biso. ; _vrf_GEOM001_3 ; PROBLEM: _geom_bond_atom_site_label_1 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM003_3 ; PROBLEM: _geom_bond_distance is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM006_3 ; PROBLEM: _geom_angle_atom_site_label_2 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM007_3 ; PROBLEM: _geom_angle_atom_site_label_3 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_PLAT762_3 ; PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles RESPONSE: Bonds and angles not calculated. ; _vrf_PLAT161_3 ; PROBLEM: Missing or Zero su (esd) on x-coordinate for ... O1 RESPONSE: Atoms of the naproxene unit were refined as part of a rigid body. ; _vrf_PLAT162_3 ; PROBLEM: Missing or Zero su (esd) on x-coordinate for ... O1 RESPONSE: Atoms of the naproxene unit were refined as part of a rigid body. ; _vrf_PLAT163_3 ; PROBLEM: Missing or Zero su (esd) on x-coordinate for ... O1 RESPONSE: Atoms of the naproxene unit were refined as part of a rigid body. ;