# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef 'submit.cif' _audit_creation_method 'SHELXL-97 plus manual editing' _publ_contact_author_name 'Andrew D. Bond' _publ_contact_author_address ; University of Southern Denmark Department of Physics and Chemistry Campusvej 55 5230 Odense Denmark ; _publ_contact_author_email adb@chem.sdu.dk _publ_contact_author_fax '+45 6615 8780' _publ_contact_author_phone '+45 6650 2545' loop_ _publ_author_name K.Solanko A.Bond #============================================================================= data_5-Cl-A _database_code_depnum_ccdc_archive 'CCDC 823448' #TrackingRef 'submit.cif' _chemical_name_systematic '2-acetyloxy-5-chlorobenzoic acid' _chemical_name_common '5-chloro-aspirin (form II)' _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 Cl O4' _chemical_formula_sum 'C9 H7 Cl O4' _chemical_formula_weight 214.60 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.0838(4) _cell_length_b 17.9622(15) _cell_length_c 10.4409(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.445(3) _cell_angle_gamma 90.00 _cell_volume 943.09(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5535 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.388 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 12316 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 25.06 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 1659 _reflns_number_gt 1425 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0435P)^2^+0.5114P] 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 1659 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.289 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.045 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 Cl1 Cl 0.84727(10) 0.41267(3) 1.05692(4) 0.03965(19) Uani 1 1 d . . . O1 O 0.1829(2) 0.50428(7) 0.66743(12) 0.0247(3) Uani 1 1 d . . . H1 H 0.052(5) 0.5228(14) 0.619(2) 0.050(7) Uiso 1 1 d . . . O2 O 0.2415(2) 0.44394(7) 0.48676(11) 0.0245(3) Uani 1 1 d . . . O3 O 0.6832(2) 0.36020(7) 0.49567(11) 0.0238(3) Uani 1 1 d . . . O4 O 0.3672(3) 0.27380(8) 0.50337(13) 0.0369(4) Uani 1 1 d . . . C1 C 0.5359(3) 0.41889(9) 0.68242(17) 0.0202(4) Uani 1 1 d . . . C2 C 0.7044(3) 0.37007(10) 0.62909(16) 0.0207(4) Uani 1 1 d . . . C3 C 0.9107(3) 0.33444(10) 0.70556(17) 0.0254(4) Uani 1 1 d . . . H3A H 1.0226 0.3014 0.6673 0.030 Uiso 1 1 calc R . . C4 C 0.9556(4) 0.34664(11) 0.83812(18) 0.0274(4) Uani 1 1 d . . . H4A H 1.0965 0.3220 0.8914 0.033 Uiso 1 1 calc R . . C5 C 0.7911(4) 0.39544(10) 0.89097(17) 0.0259(4) Uani 1 1 d . . . C6 C 0.5830(3) 0.43127(10) 0.81541(17) 0.0239(4) Uani 1 1 d . . . H6A H 0.4721 0.4643 0.8543 0.029 Uiso 1 1 calc R . . C7 C 0.3083(3) 0.45647(9) 0.60157(17) 0.0199(4) Uani 1 1 d . . . C8 C 0.4906(4) 0.31234(10) 0.44034(18) 0.0271(4) Uani 1 1 d . . . C9 C 0.4638(5) 0.31621(13) 0.29648(19) 0.0411(5) Uani 1 1 d . . . H9A H 0.4212 0.2667 0.2599 0.062 Uiso 1 1 calc R . . H9B H 0.6315 0.3335 0.2711 0.062 Uiso 1 1 calc R . . H9C H 0.3211 0.3510 0.2639 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0456(3) 0.0516(4) 0.0189(3) 0.0012(2) -0.0049(2) 0.0105(2) O1 0.0260(7) 0.0262(7) 0.0203(6) -0.0005(5) -0.0016(5) 0.0071(5) O2 0.0246(6) 0.0281(7) 0.0194(7) -0.0013(5) -0.0018(5) 0.0040(5) O3 0.0244(6) 0.0274(7) 0.0198(6) -0.0003(5) 0.0041(5) -0.0013(5) O4 0.0476(8) 0.0327(8) 0.0307(7) -0.0035(6) 0.0062(6) -0.0171(7) C1 0.0192(8) 0.0185(9) 0.0222(9) 0.0025(7) 0.0006(7) -0.0034(7) C2 0.0207(9) 0.0210(9) 0.0204(9) 0.0009(7) 0.0032(7) -0.0053(7) C3 0.0215(9) 0.0241(10) 0.0304(10) 0.0020(8) 0.0035(7) 0.0015(7) C4 0.0229(9) 0.0286(10) 0.0287(10) 0.0069(8) -0.0026(7) 0.0024(7) C5 0.0286(9) 0.0284(10) 0.0194(9) 0.0026(7) -0.0007(7) -0.0008(8) C6 0.0245(9) 0.0241(10) 0.0228(9) 0.0010(7) 0.0024(7) 0.0008(7) C7 0.0199(9) 0.0181(9) 0.0219(9) 0.0023(7) 0.0033(7) -0.0028(7) C8 0.0325(10) 0.0221(10) 0.0263(10) -0.0047(8) 0.0028(8) 0.0001(8) C9 0.0530(13) 0.0447(13) 0.0252(11) -0.0074(9) 0.0041(9) -0.0054(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 Cl1 C5 1.7419(18) . ? O1 C7 1.321(2) . ? O1 H1 0.85(3) . ? O2 C7 1.218(2) . ? O3 C8 1.366(2) . ? O3 C2 1.393(2) . ? O4 C8 1.195(2) . ? C1 C6 1.392(2) . ? C1 C2 1.397(2) . ? C1 C7 1.490(2) . ? C2 C3 1.379(2) . ? C3 C4 1.387(3) . ? C3 H3A 0.950 . ? C4 C5 1.381(3) . ? C4 H4A 0.950 . ? C5 C6 1.382(2) . ? C6 H6A 0.950 . ? C8 C9 1.490(3) . ? C9 H9A 0.980 . ? C9 H9B 0.980 . ? C9 H9C 0.980 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 109.8(16) . . ? C8 O3 C2 116.63(13) . . ? C6 C1 C2 118.17(15) . . ? C6 C1 C7 119.89(15) . . ? C2 C1 C7 121.93(15) . . ? C3 C2 O3 117.42(15) . . ? C3 C2 C1 121.28(16) . . ? O3 C2 C1 121.11(15) . . ? C2 C3 C4 120.29(17) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C5 C4 C3 118.57(16) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? C4 C5 C6 121.68(17) . . ? C4 C5 Cl1 119.32(14) . . ? C6 C5 Cl1 119.00(14) . . ? C5 C6 C1 120.00(17) . . ? C5 C6 H6A 120.0 . . ? C1 C6 H6A 120.0 . . ? O2 C7 O1 123.11(15) . . ? O2 C7 C1 123.71(16) . . ? O1 C7 C1 113.17(15) . . ? O4 C8 O3 122.25(17) . . ? O4 C8 C9 127.22(18) . . ? O3 C8 C9 110.53(16) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 C8 O3 C2 C3 103.37(18) . . . . ? C8 O3 C2 C1 -81.6(2) . . . . ? C6 C1 C2 C3 0.5(2) . . . . ? C7 C1 C2 C3 -178.57(16) . . . . ? C6 C1 C2 O3 -174.29(15) . . . . ? C7 C1 C2 O3 6.6(2) . . . . ? O3 C2 C3 C4 174.86(15) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C3 C4 C5 Cl1 -179.01(14) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? Cl1 C5 C6 C1 179.40(13) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C7 C1 C6 C5 178.85(16) . . . . ? C6 C1 C7 O2 -173.88(16) . . . . ? C2 C1 C7 O2 5.2(3) . . . . ? C6 C1 C7 O1 5.2(2) . . . . ? C2 C1 C7 O1 -175.71(15) . . . . ? C2 O3 C8 O4 -8.9(2) . . . . ? C2 O3 C8 C9 171.33(15) . . . . ? #============================================================================= data_5-Br-A _database_code_depnum_ccdc_archive 'CCDC 823449' #TrackingRef 'submit.cif' _chemical_name_systematic '2-acetyloxy-5-bromobenzoic acid' _chemical_name_common '5-bromo-aspirin (form II)' _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 Br O4' _chemical_formula_sum 'C9 H7 Br O4' _chemical_formula_weight 259.06 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.0940(2) _cell_length_b 17.8642(7) _cell_length_c 10.6736(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.935(2) _cell_angle_gamma 90.00 _cell_volume 959.51(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4190 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 25.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.793 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 4.268 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.378 _exptl_absorpt_correction_T_max 0.848 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7302 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 25.05 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 1666 _reflns_number_gt 1505 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0227P)^2^+0.6958P] 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 1666 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0242 _refine_ls_R_factor_gt 0.0203 _refine_ls_wR_factor_ref 0.0516 _refine_ls_wR_factor_gt 0.0498 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.332 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.050 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 Br1 Br 0.84669(5) 0.410261(13) 1.06165(2) 0.03457(10) Uani 1 1 d . . . O1 O 0.1846(3) 0.50405(8) 0.66394(14) 0.0226(3) Uani 1 1 d . . . H1 H 0.064(5) 0.5215(13) 0.620(2) 0.027(7) Uiso 1 1 d . . . O2 O 0.2407(3) 0.44367(8) 0.48752(13) 0.0226(3) Uani 1 1 d . . . O3 O 0.6826(3) 0.35938(8) 0.49691(12) 0.0209(3) Uani 1 1 d . . . O4 O 0.3657(3) 0.27287(9) 0.50456(15) 0.0341(4) Uani 1 1 d . . . C1 C 0.5359(4) 0.41798(10) 0.67944(19) 0.0185(4) Uani 1 1 d . . . C2 C 0.7050(4) 0.36943(10) 0.62763(19) 0.0183(4) Uani 1 1 d . . . C3 C 0.9117(4) 0.33344(11) 0.7025(2) 0.0230(5) Uani 1 1 d . . . H3A H 1.0242 0.3007 0.6650 0.028 Uiso 1 1 calc R . . C4 C 0.9557(4) 0.34501(11) 0.8325(2) 0.0242(5) Uani 1 1 d . . . H4A H 1.0971 0.3203 0.8851 0.029 Uiso 1 1 calc R . . C5 C 0.7892(4) 0.39328(11) 0.88388(19) 0.0227(5) Uani 1 1 d . . . C6 C 0.5817(4) 0.42967(11) 0.8099(2) 0.0212(4) Uani 1 1 d . . . H6A H 0.4704 0.4626 0.8479 0.025 Uiso 1 1 calc R . . C7 C 0.3086(4) 0.45609(10) 0.60004(19) 0.0182(4) Uani 1 1 d . . . C8 C 0.4899(4) 0.31101(11) 0.4430(2) 0.0246(5) Uani 1 1 d . . . C9 C 0.4633(5) 0.31402(14) 0.3024(2) 0.0382(6) Uani 1 1 d . . . H9A H 0.4059 0.2650 0.2669 0.057 Uiso 1 1 calc R . . H9B H 0.6352 0.3270 0.2779 0.057 Uiso 1 1 calc R . . H9C H 0.3313 0.3520 0.2698 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.04064(16) 0.04439(16) 0.01603(14) 0.00137(9) -0.00395(10) 0.00851(10) O1 0.0234(8) 0.0245(8) 0.0178(8) 0.0004(6) -0.0035(7) 0.0084(6) O2 0.0217(7) 0.0268(7) 0.0173(8) -0.0018(6) -0.0037(6) 0.0040(6) O3 0.0212(7) 0.0254(7) 0.0158(7) -0.0003(6) 0.0019(6) -0.0015(6) O4 0.0445(10) 0.0315(8) 0.0261(8) -0.0038(7) 0.0054(7) -0.0152(7) C1 0.0169(10) 0.0187(10) 0.0188(11) 0.0011(8) -0.0003(8) -0.0033(8) C2 0.0173(10) 0.0193(10) 0.0182(10) 0.0000(8) 0.0017(8) -0.0039(8) C3 0.0201(10) 0.0225(10) 0.0263(12) 0.0022(9) 0.0035(9) 0.0020(8) C4 0.0194(10) 0.0257(11) 0.0251(12) 0.0053(9) -0.0038(9) 0.0023(8) C5 0.0247(11) 0.0270(11) 0.0152(10) 0.0016(8) -0.0011(9) -0.0022(9) C6 0.0222(11) 0.0203(10) 0.0202(11) 0.0002(8) 0.0004(9) 0.0019(8) C7 0.0175(10) 0.0165(10) 0.0200(11) 0.0016(8) 0.0014(8) -0.0036(8) C8 0.0272(11) 0.0220(10) 0.0237(11) -0.0037(9) 0.0012(9) 0.0016(9) C9 0.0517(15) 0.0417(14) 0.0205(12) -0.0051(10) 0.0031(11) -0.0061(12) _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 Br1 C5 1.899(2) . ? O1 C7 1.316(2) . ? O1 H1 0.78(3) . ? O2 C7 1.217(2) . ? O3 C8 1.366(2) . ? O3 C2 1.394(2) . ? O4 C8 1.194(3) . ? C1 C6 1.391(3) . ? C1 C2 1.396(3) . ? C1 C7 1.489(3) . ? C2 C3 1.378(3) . ? C3 C4 1.386(3) . ? C3 H3A 0.950 . ? C4 C5 1.381(3) . ? C4 H4A 0.950 . ? C5 C6 1.380(3) . ? C6 H6A 0.950 . ? C8 C9 1.487(3) . ? C9 H9A 0.980 . ? C9 H9B 0.980 . ? C9 H9C 0.980 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 110.3(18) . . ? C8 O3 C2 116.41(15) . . ? C6 C1 C2 118.17(18) . . ? C6 C1 C7 119.70(18) . . ? C2 C1 C7 122.13(18) . . ? C3 C2 O3 117.18(17) . . ? C3 C2 C1 121.54(19) . . ? O3 C2 C1 121.14(17) . . ? C2 C3 C4 120.06(19) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 118.48(19) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? C6 C5 C4 122.00(19) . . ? C6 C5 Br1 118.82(16) . . ? C4 C5 Br1 119.18(16) . . ? C5 C6 C1 119.76(19) . . ? C5 C6 H6A 120.1 . . ? C1 C6 H6A 120.1 . . ? O2 C7 O1 122.99(18) . . ? O2 C7 C1 123.68(18) . . ? O1 C7 C1 113.32(17) . . ? O4 C8 O3 122.47(19) . . ? O4 C8 C9 127.1(2) . . ? O3 C8 C9 110.43(18) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 C8 O3 C2 C3 103.1(2) . . . . ? C8 O3 C2 C1 -81.2(2) . . . . ? C6 C1 C2 C3 0.2(3) . . . . ? C7 C1 C2 C3 -178.77(17) . . . . ? C6 C1 C2 O3 -175.29(17) . . . . ? C7 C1 C2 O3 5.7(3) . . . . ? O3 C2 C3 C4 175.75(17) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C3 C4 C5 Br1 -179.75(15) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? Br1 C5 C6 C1 -179.95(15) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C7 C1 C6 C5 178.77(18) . . . . ? C6 C1 C7 O2 -173.09(18) . . . . ? C2 C1 C7 O2 5.9(3) . . . . ? C6 C1 C7 O1 6.0(2) . . . . ? C2 C1 C7 O1 -175.02(17) . . . . ? C2 O3 C8 O4 -8.0(3) . . . . ? C2 O3 C8 C9 171.97(17) . . . . ? #============================================================================= data_5-Cl-A_A_I _database_code_depnum_ccdc_archive 'CCDC 823451' #TrackingRef 'submit.cif' _chemical_name_systematic ? _chemical_name_common '5-Cl-aspirin anhydride (form I)' _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 Cl2 O7' _chemical_formula_sum 'C18 H12 Cl2 O7' _chemical_formula_weight 411.18 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.5412(7) _cell_length_b 12.4530(8) _cell_length_c 13.5129(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1773.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5560 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 25.30 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.405 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.800 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 18370 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 25.72 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.72 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 3363 _reflns_number_gt 2943 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0258P)^2^+0.5289P] 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 (1983), 1436 Friedel pairs' _refine_ls_abs_structure_Flack -0.01(5) _refine_ls_number_reflns 3363 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0647 _refine_ls_wR_factor_gt 0.0611 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.161 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.040 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 Cl1 Cl 0.17391(6) 0.62449(5) 0.21130(5) 0.03512(16) Uani 1 1 d . . . Cl2 Cl 0.84916(6) 0.33884(5) 0.07462(4) 0.03936(17) Uani 1 1 d . . . O1 O 0.65617(14) 0.66563(11) 0.24143(11) 0.0272(3) Uani 1 1 d . . . O2 O 0.71927(16) 0.82229(15) 0.17675(13) 0.0441(5) Uani 1 1 d . . . O3 O 0.56241(14) 0.89829(12) 0.02943(11) 0.0243(3) Uani 1 1 d . . . O4 O 0.5236(2) 1.02736(16) 0.13924(16) 0.0578(6) Uani 1 1 d . . . O5 O 0.77680(15) 0.72529(13) 0.36793(11) 0.0295(4) Uani 1 1 d . . . O6 O 0.96886(14) 0.59212(11) 0.42945(11) 0.0248(4) Uani 1 1 d . . . O7 O 0.91120(16) 0.46025(14) 0.53350(12) 0.0333(4) Uani 1 1 d . . . C1 C 0.5055(2) 0.76364(16) 0.15060(16) 0.0203(5) Uani 1 1 d . . . C2 C 0.47104(19) 0.83544(17) 0.07636(15) 0.0214(5) Uani 1 1 d . . . C3 C 0.3476(2) 0.84162(19) 0.04353(15) 0.0268(5) Uani 1 1 d . . . H3A H 0.3260 0.8908 -0.0075 0.032 Uiso 1 1 calc R . . C4 C 0.2555(2) 0.77704(18) 0.08418(17) 0.0272(5) Uani 1 1 d . . . H4A H 0.1702 0.7811 0.0618 0.033 Uiso 1 1 calc R . . C5 C 0.2894(2) 0.70643(17) 0.15803(16) 0.0230(5) Uani 1 1 d . . . C6 C 0.4120(2) 0.69737(17) 0.19125(15) 0.0221(5) Uani 1 1 d . . . H6A H 0.4331 0.6467 0.2412 0.027 Uiso 1 1 calc R . . C7 C 0.6374(2) 0.75879(17) 0.18911(16) 0.0246(5) Uani 1 1 d . . . C8 C 0.5837(2) 0.99615(19) 0.07051(18) 0.0321(6) Uani 1 1 d . . . C9 C 0.6871(3) 1.0537(2) 0.01762(19) 0.0405(7) Uani 1 1 d . . . H9A H 0.7302 1.1024 0.0636 0.061 Uiso 1 1 calc R . . H9B H 0.6510 1.0951 -0.0372 0.061 Uiso 1 1 calc R . . H9C H 0.7481 1.0014 -0.0084 0.061 Uiso 1 1 calc R . . C10 C 0.7593(2) 0.65858(18) 0.30655(15) 0.0224(5) Uani 1 1 d . . . C11 C 0.8335(2) 0.55982(16) 0.28796(15) 0.0195(4) Uani 1 1 d . . . C12 C 0.8078(2) 0.49818(17) 0.20458(16) 0.0221(5) Uani 1 1 d . . . H12A H 0.7386 0.5168 0.1629 0.027 Uiso 1 1 calc R . . C13 C 0.8817(2) 0.41030(17) 0.18187(16) 0.0243(5) Uani 1 1 d . . . C14 C 0.9819(2) 0.38077(19) 0.24146(16) 0.0270(5) Uani 1 1 d . . . H14A H 1.0329 0.3204 0.2251 0.032 Uiso 1 1 calc R . . C15 C 1.0070(2) 0.44047(18) 0.32543(17) 0.0258(5) Uani 1 1 d . . . H15A H 1.0750 0.4202 0.3676 0.031 Uiso 1 1 calc R . . C16 C 0.9349(2) 0.52871(17) 0.34868(15) 0.0209(5) Uani 1 1 d . . . C17 C 0.9540(2) 0.5482(2) 0.52126(17) 0.0242(5) Uani 1 1 d . . . C18 C 0.9979(2) 0.6242(2) 0.59938(16) 0.0354(6) Uani 1 1 d . . . H18A H 0.9850 0.5918 0.6647 0.053 Uiso 1 1 calc R . . H18B H 0.9493 0.6911 0.5949 0.053 Uiso 1 1 calc R . . H18C H 1.0882 0.6396 0.5899 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0268(3) 0.0422(3) 0.0364(3) 0.0074(3) 0.0008(3) -0.0109(3) Cl2 0.0471(4) 0.0413(3) 0.0297(3) -0.0146(3) -0.0027(3) 0.0066(3) O1 0.0243(8) 0.0195(7) 0.0379(9) 0.0023(7) -0.0104(7) 0.0026(7) O2 0.0251(9) 0.0503(11) 0.0568(12) 0.0260(10) -0.0079(8) -0.0145(9) O3 0.0282(9) 0.0214(8) 0.0232(8) 0.0030(7) 0.0036(7) -0.0027(7) O4 0.0673(14) 0.0472(12) 0.0590(13) -0.0309(11) 0.0205(11) -0.0216(11) O5 0.0333(9) 0.0287(9) 0.0265(9) -0.0068(8) -0.0025(7) 0.0020(8) O6 0.0273(8) 0.0257(8) 0.0213(8) 0.0006(7) -0.0061(7) -0.0047(7) O7 0.0419(10) 0.0343(10) 0.0237(8) -0.0004(8) 0.0039(8) -0.0087(9) C1 0.0201(11) 0.0187(11) 0.0221(11) -0.0034(9) 0.0014(9) 0.0026(10) C2 0.0270(11) 0.0179(11) 0.0192(10) -0.0009(10) 0.0028(9) 0.0000(10) C3 0.0312(13) 0.0273(12) 0.0218(11) 0.0036(10) -0.0050(9) 0.0032(12) C4 0.0243(11) 0.0308(13) 0.0266(12) -0.0005(11) -0.0025(10) -0.0009(11) C5 0.0222(12) 0.0234(12) 0.0232(11) -0.0024(10) 0.0020(9) -0.0063(10) C6 0.0265(12) 0.0196(11) 0.0201(11) 0.0014(9) 0.0014(9) -0.0007(9) C7 0.0249(12) 0.0252(12) 0.0238(12) 0.0010(10) 0.0044(9) 0.0018(11) C8 0.0344(13) 0.0324(14) 0.0295(13) -0.0042(12) -0.0013(12) -0.0077(12) C9 0.0461(16) 0.0338(14) 0.0417(15) 0.0054(12) -0.0022(13) -0.0156(13) C10 0.0188(10) 0.0255(12) 0.0229(11) 0.0042(11) 0.0022(9) -0.0034(10) C11 0.0185(10) 0.0207(11) 0.0192(10) 0.0028(9) 0.0012(9) -0.0026(9) C12 0.0201(11) 0.0274(12) 0.0187(11) 0.0020(10) -0.0007(9) -0.0020(10) C13 0.0276(12) 0.0252(12) 0.0201(11) -0.0043(10) 0.0033(9) -0.0021(10) C14 0.0235(12) 0.0271(12) 0.0302(12) 0.0000(11) 0.0056(10) 0.0056(10) C15 0.0196(11) 0.0299(13) 0.0279(12) 0.0023(10) -0.0024(9) 0.0011(10) C16 0.0211(12) 0.0228(12) 0.0187(11) 0.0021(9) -0.0012(9) -0.0059(10) C17 0.0189(12) 0.0305(14) 0.0232(12) -0.0007(10) -0.0001(9) 0.0017(11) C18 0.0339(13) 0.0469(16) 0.0255(12) -0.0068(12) -0.0034(11) -0.0073(12) _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 Cl1 C5 1.744(2) . ? Cl2 C13 1.735(2) . ? O1 C7 1.373(3) . ? O1 C10 1.401(2) . ? O2 C7 1.182(2) . ? O3 C8 1.358(3) . ? O3 C2 1.394(2) . ? O4 C8 1.189(3) . ? O5 C10 1.188(2) . ? O6 C17 1.365(3) . ? O6 C16 1.394(2) . ? O7 C17 1.195(3) . ? C1 C2 1.392(3) . ? C1 C6 1.397(3) . ? C1 C7 1.486(3) . ? C2 C3 1.377(3) . ? C3 C4 1.375(3) . ? C3 H3A 0.950 . ? C4 C5 1.377(3) . ? C4 H4A 0.950 . ? C5 C6 1.373(3) . ? C6 H6A 0.950 . ? C8 C9 1.487(3) . ? C9 H9A 0.980 . ? C9 H9B 0.980 . ? C9 H9C 0.980 . ? C10 C11 1.480(3) . ? C11 C12 1.390(3) . ? C11 C16 1.401(3) . ? C12 C13 1.378(3) . ? C12 H12A 0.950 . ? C13 C14 1.378(3) . ? C14 C15 1.382(3) . ? C14 H14A 0.950 . ? C15 C16 1.373(3) . ? C15 H15A 0.950 . ? C17 C18 1.492(3) . ? C18 H18A 0.980 . ? C18 H18B 0.980 . ? C18 H18C 0.980 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 C10 119.22(17) . . ? C8 O3 C2 115.61(17) . . ? C17 O6 C16 117.05(16) . . ? C2 C1 C6 118.61(19) . . ? C2 C1 C7 121.49(19) . . ? C6 C1 C7 119.86(19) . . ? C3 C2 C1 121.0(2) . . ? C3 C2 O3 118.36(19) . . ? C1 C2 O3 120.57(18) . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 118.7(2) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? C6 C5 C4 122.2(2) . . ? C6 C5 Cl1 118.30(17) . . ? C4 C5 Cl1 119.45(17) . . ? C5 C6 C1 119.11(19) . . ? C5 C6 H6A 120.4 . . ? C1 C6 H6A 120.4 . . ? O2 C7 O1 122.2(2) . . ? O2 C7 C1 127.3(2) . . ? O1 C7 C1 110.46(18) . . ? O4 C8 O3 121.6(2) . . ? O4 C8 C9 127.5(2) . . ? O3 C8 C9 110.9(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 O1 121.0(2) . . ? O5 C10 C11 128.11(19) . . ? O1 C10 C11 110.86(18) . . ? C12 C11 C16 118.10(19) . . ? C12 C11 C10 119.54(19) . . ? C16 C11 C10 122.26(19) . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C12 C13 C14 121.0(2) . . ? C12 C13 Cl2 118.77(17) . . ? C14 C13 Cl2 120.18(17) . . ? C13 C14 C15 118.9(2) . . ? C13 C14 H14A 120.6 . . ? C15 C14 H14A 120.6 . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C15 C16 O6 119.36(19) . . ? C15 C16 C11 120.6(2) . . ? O6 C16 C11 119.85(18) . . ? O7 C17 O6 122.4(2) . . ? O7 C17 C18 126.9(2) . . ? O6 C17 C18 110.7(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C6 C1 C2 C3 0.2(3) . . . . ? C7 C1 C2 C3 -177.9(2) . . . . ? C6 C1 C2 O3 -176.00(18) . . . . ? C7 C1 C2 O3 6.0(3) . . . . ? C8 O3 C2 C3 92.3(2) . . . . ? C8 O3 C2 C1 -91.4(2) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? O3 C2 C3 C4 176.65(18) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C3 C4 C5 Cl1 179.52(17) . . . . ? C4 C5 C6 C1 1.5(3) . . . . ? Cl1 C5 C6 C1 -178.94(16) . . . . ? C2 C1 C6 C5 -1.1(3) . . . . ? C7 C1 C6 C5 177.0(2) . . . . ? C10 O1 C7 O2 19.7(3) . . . . ? C10 O1 C7 C1 -162.00(17) . . . . ? C2 C1 C7 O2 14.0(4) . . . . ? C6 C1 C7 O2 -164.0(2) . . . . ? C2 C1 C7 O1 -164.24(18) . . . . ? C6 C1 C7 O1 17.8(3) . . . . ? C2 O3 C8 O4 -3.3(3) . . . . ? C2 O3 C8 C9 177.17(19) . . . . ? C7 O1 C10 O5 52.0(3) . . . . ? C7 O1 C10 C11 -129.39(19) . . . . ? O5 C10 C11 C12 -171.9(2) . . . . ? O1 C10 C11 C12 9.6(3) . . . . ? O5 C10 C11 C16 4.3(3) . . . . ? O1 C10 C11 C16 -174.16(18) . . . . ? C16 C11 C12 C13 -1.2(3) . . . . ? C10 C11 C12 C13 175.23(19) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? C11 C12 C13 Cl2 -177.71(16) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? Cl2 C13 C14 C15 178.79(17) . . . . ? C13 C14 C15 C16 -1.0(3) . . . . ? C14 C15 C16 O6 -174.89(19) . . . . ? C14 C15 C16 C11 0.4(3) . . . . ? C17 O6 C16 C15 -69.5(2) . . . . ? C17 O6 C16 C11 115.2(2) . . . . ? C12 C11 C16 C15 0.7(3) . . . . ? C10 C11 C16 C15 -175.6(2) . . . . ? C12 C11 C16 O6 175.96(18) . . . . ? C10 C11 C16 O6 -0.4(3) . . . . ? C16 O6 C17 O7 -1.6(3) . . . . ? C16 O6 C17 C18 178.28(19) . . . . ? #============================================================================= data_5-Cl-A_A_II _database_code_depnum_ccdc_archive 'CCDC 823452' #TrackingRef 'submit.cif' _chemical_name_systematic ? _chemical_name_common '5-Cl-aspirin anhydride (form II)' _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 Cl2 O7' _chemical_formula_sum 'C18 H12 Cl2 O7' _chemical_formula_weight 411.18 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7838(3) _cell_length_b 14.2206(4) _cell_length_c 12.3774(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.635(3) _cell_angle_gamma 90.00 _cell_volume 1808.90(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3170 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 25.02 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.398 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7319 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 28.38 _diffrn_measured_fraction_theta_max 0.830 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 3766 _reflns_number_gt 2966 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0373P)^2^+1.1537P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3766 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.320 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.050 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 Cl1 Cl 0.14604(5) 0.38352(4) 0.10810(6) 0.04885(19) Uani 1 1 d . . . Cl2 Cl 0.63347(6) 0.06025(4) 0.05654(6) 0.04768(18) Uani 1 1 d . . . O1 O 0.64565(13) 0.40049(9) 0.20248(12) 0.0313(3) Uani 1 1 d . . . O2 O 0.70919(14) 0.54847(10) 0.17712(14) 0.0369(4) Uani 1 1 d . . . O3 O 0.51846(14) 0.66898(10) 0.06441(12) 0.0320(3) Uani 1 1 d . . . O4 O 0.56025(17) 0.72797(12) 0.23977(16) 0.0527(5) Uani 1 1 d . . . O5 O 0.82667(18) 0.42409(11) 0.34876(15) 0.0556(5) Uani 1 1 d . . . O6 O 1.02103(12) 0.29654(10) 0.37643(11) 0.0286(3) Uani 1 1 d . . . O7 O 0.93593(14) 0.26771(11) 0.51763(12) 0.0350(4) Uani 1 1 d . . . C1 C 0.48139(18) 0.51509(14) 0.13366(17) 0.0260(4) Uani 1 1 d . . . C2 C 0.43511(19) 0.60215(14) 0.08622(17) 0.0263(4) Uani 1 1 d . . . C3 C 0.3040(2) 0.62247(15) 0.05002(17) 0.0302(5) Uani 1 1 d . . . H3A H 0.2750 0.6829 0.0204 0.036 Uiso 1 1 calc R . . C4 C 0.2153(2) 0.55512(15) 0.05687(18) 0.0316(5) Uani 1 1 d . . . H4A H 0.1246 0.5682 0.0310 0.038 Uiso 1 1 calc R . . C5 C 0.25981(19) 0.46838(15) 0.10184(18) 0.0315(5) Uani 1 1 d . . . C6 C 0.39111(19) 0.44719(14) 0.14085(17) 0.0287(4) Uani 1 1 d . . . H6A H 0.4194 0.3871 0.1722 0.034 Uiso 1 1 calc R . . C7 C 0.62333(19) 0.49488(14) 0.17356(17) 0.0274(4) Uani 1 1 d . . . C8 C 0.5790(2) 0.72886(15) 0.1494(2) 0.0361(5) Uani 1 1 d . . . C9 C 0.6676(2) 0.7920(2) 0.1109(3) 0.0544(7) Uani 1 1 d . . . H9A H 0.6790 0.8512 0.1534 0.082 Uiso 1 1 calc R . . H9B H 0.6298 0.8051 0.0298 0.082 Uiso 1 1 calc R . . H9C H 0.7523 0.7614 0.1242 0.082 Uiso 1 1 calc R . . C10 C 0.7659(2) 0.37400(15) 0.27551(18) 0.0316(5) Uani 1 1 d . . . C11 C 0.80024(18) 0.27647(13) 0.25198(16) 0.0246(4) Uani 1 1 d . . . C12 C 0.71025(19) 0.21908(14) 0.17614(17) 0.0265(4) Uani 1 1 d . . . H12A H 0.6246 0.2412 0.1401 0.032 Uiso 1 1 calc R . . C13 C 0.7461(2) 0.12989(14) 0.15358(17) 0.0285(4) Uani 1 1 d . . . C14 C 0.8693(2) 0.09533(14) 0.20451(18) 0.0303(5) Uani 1 1 d . . . H14A H 0.8922 0.0338 0.1877 0.036 Uiso 1 1 calc R . . C15 C 0.95915(19) 0.15172(14) 0.28066(17) 0.0284(4) Uani 1 1 d . . . H15A H 1.0445 0.1290 0.3167 0.034 Uiso 1 1 calc R . . C16 C 0.92447(18) 0.24097(14) 0.30406(16) 0.0245(4) Uani 1 1 d . . . C17 C 1.01419(19) 0.30800(14) 0.48462(17) 0.0264(4) Uani 1 1 d . . . C18 C 1.1174(2) 0.37322(17) 0.5498(2) 0.0386(5) Uani 1 1 d . . . H18A H 1.0877 0.4058 0.6072 0.058 Uiso 1 1 calc R . . H18B H 1.1362 0.4195 0.4982 0.058 Uiso 1 1 calc R . . H18C H 1.1965 0.3374 0.5871 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0285(3) 0.0357(3) 0.0746(5) -0.0009(3) 0.0040(3) -0.0074(2) Cl2 0.0444(3) 0.0330(3) 0.0546(4) -0.0156(3) -0.0015(3) -0.0074(2) O1 0.0252(7) 0.0225(7) 0.0397(9) -0.0004(6) -0.0001(6) 0.0047(6) O2 0.0249(8) 0.0286(8) 0.0531(10) 0.0017(7) 0.0058(7) 0.0009(6) O3 0.0318(8) 0.0269(7) 0.0380(8) 0.0058(7) 0.0114(7) 0.0018(6) O4 0.0590(11) 0.0466(10) 0.0604(12) -0.0228(9) 0.0300(10) -0.0222(9) O5 0.0585(11) 0.0301(9) 0.0528(11) -0.0139(8) -0.0213(9) 0.0138(8) O6 0.0219(7) 0.0314(7) 0.0296(8) -0.0025(6) 0.0037(6) -0.0036(6) O7 0.0308(8) 0.0397(9) 0.0345(8) -0.0068(7) 0.0099(7) -0.0072(7) C1 0.0248(10) 0.0238(10) 0.0274(10) -0.0044(9) 0.0050(8) 0.0033(8) C2 0.0280(10) 0.0249(10) 0.0258(10) -0.0019(9) 0.0078(8) 0.0017(8) C3 0.0315(11) 0.0286(10) 0.0294(11) 0.0030(9) 0.0077(9) 0.0089(9) C4 0.0252(10) 0.0343(11) 0.0327(11) -0.0036(10) 0.0047(9) 0.0063(9) C5 0.0265(10) 0.0288(11) 0.0354(12) -0.0064(9) 0.0038(9) -0.0026(8) C6 0.0287(10) 0.0219(9) 0.0314(11) -0.0023(9) 0.0031(8) 0.0028(8) C7 0.0281(10) 0.0222(9) 0.0291(11) -0.0023(9) 0.0046(8) 0.0038(8) C8 0.0296(11) 0.0283(11) 0.0519(15) -0.0030(11) 0.0147(10) 0.0011(9) C9 0.0414(14) 0.0493(15) 0.075(2) 0.0070(14) 0.0217(13) -0.0105(12) C10 0.0297(11) 0.0250(10) 0.0336(12) -0.0011(10) -0.0003(9) 0.0059(8) C11 0.0260(10) 0.0214(9) 0.0254(10) 0.0010(8) 0.0064(8) 0.0006(8) C12 0.0226(10) 0.0257(10) 0.0285(10) 0.0002(9) 0.0039(8) 0.0001(8) C13 0.0308(11) 0.0252(10) 0.0274(11) -0.0025(9) 0.0059(8) -0.0060(8) C14 0.0370(12) 0.0224(10) 0.0323(11) 0.0001(9) 0.0119(9) 0.0046(8) C15 0.0252(10) 0.0291(10) 0.0299(11) 0.0025(9) 0.0069(8) 0.0070(8) C16 0.0222(9) 0.0257(10) 0.0240(10) -0.0001(8) 0.0048(8) -0.0027(8) C17 0.0232(10) 0.0243(10) 0.0284(11) -0.0025(9) 0.0028(8) 0.0035(8) C18 0.0349(12) 0.0393(12) 0.0398(13) -0.0118(11) 0.0085(10) -0.0102(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 Cl1 C5 1.739(2) . ? Cl2 C13 1.736(2) . ? O1 C10 1.389(2) . ? O1 C7 1.391(2) . ? O2 C7 1.190(2) . ? O3 C8 1.357(3) . ? O3 C2 1.390(2) . ? O4 C8 1.196(3) . ? O5 C10 1.183(3) . ? O6 C17 1.373(2) . ? O6 C16 1.395(2) . ? O7 C17 1.190(2) . ? C1 C6 1.393(3) . ? C1 C2 1.396(3) . ? C1 C7 1.487(3) . ? C2 C3 1.378(3) . ? C3 C4 1.375(3) . ? C3 H3A 0.950 . ? C4 C5 1.378(3) . ? C4 H4A 0.950 . ? C5 C6 1.384(3) . ? C6 H6A 0.950 . ? C8 C9 1.491(3) . ? C9 H9A 0.980 . ? C9 H9B 0.980 . ? C9 H9C 0.980 . ? C10 C11 1.487(3) . ? C11 C12 1.392(3) . ? C11 C16 1.394(3) . ? C12 C13 1.379(3) . ? C12 H12A 0.950 . ? C13 C14 1.377(3) . ? C14 C15 1.385(3) . ? C14 H14A 0.950 . ? C15 C16 1.378(3) . ? C15 H15A 0.950 . ? C17 C18 1.485(3) . ? C18 H18A 0.980 . ? C18 H18B 0.980 . ? C18 H18C 0.980 . ? 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 C10 O1 C7 118.92(16) . . ? C8 O3 C2 117.79(16) . . ? C17 O6 C16 116.31(15) . . ? C6 C1 C2 118.29(18) . . ? C6 C1 C7 120.91(18) . . ? C2 C1 C7 120.79(18) . . ? C3 C2 O3 116.99(18) . . ? C3 C2 C1 121.56(19) . . ? O3 C2 C1 121.22(17) . . ? C4 C3 C2 119.92(19) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 118.97(19) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C4 C5 C6 122.04(19) . . ? C4 C5 Cl1 118.33(16) . . ? C6 C5 Cl1 119.63(16) . . ? C5 C6 C1 119.19(19) . . ? C5 C6 H6A 120.4 . . ? C1 C6 H6A 120.4 . . ? O2 C7 O1 122.45(18) . . ? O2 C7 C1 126.85(18) . . ? O1 C7 C1 110.63(16) . . ? O4 C8 O3 122.7(2) . . ? O4 C8 C9 127.7(2) . . ? O3 C8 C9 109.6(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 O1 121.79(18) . . ? O5 C10 C11 126.79(19) . . ? O1 C10 C11 111.35(17) . . ? C12 C11 C16 118.40(18) . . ? C12 C11 C10 121.00(17) . . ? C16 C11 C10 120.59(17) . . ? C13 C12 C11 119.67(18) . . ? C13 C12 H12A 120.2 . . ? C11 C12 H12A 120.2 . . ? C14 C13 C12 121.76(19) . . ? C14 C13 Cl2 119.25(16) . . ? C12 C13 Cl2 118.98(16) . . ? C13 C14 C15 118.96(19) . . ? C13 C14 H14A 120.5 . . ? C15 C14 H14A 120.5 . . ? C16 C15 C14 119.84(18) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C15 C16 C11 121.36(18) . . ? C15 C16 O6 117.34(17) . . ? C11 C16 O6 121.18(17) . . ? O7 C17 O6 122.07(18) . . ? O7 C17 C18 127.36(19) . . ? O6 C17 C18 110.56(17) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C8 O3 C2 C3 98.3(2) . . . . ? C8 O3 C2 C1 -87.1(2) . . . . ? C6 C1 C2 C3 1.8(3) . . . . ? C7 C1 C2 C3 -179.23(18) . . . . ? C6 C1 C2 O3 -172.44(18) . . . . ? C7 C1 C2 O3 6.5(3) . . . . ? O3 C2 C3 C4 172.39(18) . . . . ? C1 C2 C3 C4 -2.1(3) . . . . ? C2 C3 C4 C5 1.0(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C3 C4 C5 Cl1 -179.16(16) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? Cl1 C5 C6 C1 178.89(16) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? C7 C1 C6 C5 -179.39(19) . . . . ? C10 O1 C7 O2 24.5(3) . . . . ? C10 O1 C7 C1 -158.46(17) . . . . ? C6 C1 C7 O2 -175.8(2) . . . . ? C2 C1 C7 O2 5.3(3) . . . . ? C6 C1 C7 O1 7.3(3) . . . . ? C2 C1 C7 O1 -171.62(17) . . . . ? C2 O3 C8 O4 -2.4(3) . . . . ? C2 O3 C8 C9 177.72(18) . . . . ? C7 O1 C10 O5 32.7(3) . . . . ? C7 O1 C10 C11 -150.20(17) . . . . ? O5 C10 C11 C12 168.6(2) . . . . ? O1 C10 C11 C12 -8.3(3) . . . . ? O5 C10 C11 C16 -12.5(4) . . . . ? O1 C10 C11 C16 170.55(17) . . . . ? C16 C11 C12 C13 -0.7(3) . . . . ? C10 C11 C12 C13 178.15(19) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C11 C12 C13 Cl2 -178.70(15) . . . . ? C12 C13 C14 C15 0.2(3) . . . . ? Cl2 C13 C14 C15 179.12(16) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C11 -0.4(3) . . . . ? C14 C15 C16 O6 -176.44(17) . . . . ? C12 C11 C16 C15 0.8(3) . . . . ? C10 C11 C16 C15 -178.04(19) . . . . ? C12 C11 C16 O6 176.71(17) . . . . ? C10 C11 C16 O6 -2.2(3) . . . . ? C17 O6 C16 C15 -105.2(2) . . . . ? C17 O6 C16 C11 78.8(2) . . . . ? C16 O6 C17 O7 5.1(3) . . . . ? C16 O6 C17 C18 -176.45(17) . . . . ? #============================================================================= data_5-Br-AA_I _database_code_depnum_ccdc_archive 'CCDC 823453' #TrackingRef 'submit.cif' _chemical_name_systematic ? _chemical_name_common '5-Br-aspirin anhydride (form I)' _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 Br2 O7' _chemical_formula_sum 'C18 H12 Br2 O7' _chemical_formula_weight 500.10 _chemical_absolute_configuration ad 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.5579(5) _cell_length_b 12.5176(7) _cell_length_c 13.7487(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1817.02(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9496 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 25.67 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.828 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 4.500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.254 _exptl_absorpt_correction_T_max 0.662 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 17330 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.69 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 3427 _reflns_number_gt 3211 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0131P)^2^] 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 (1983), 1464 Friedel pairs' _refine_ls_abs_structure_Flack 0.005(5) _refine_ls_number_reflns 3427 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0181 _refine_ls_wR_factor_ref 0.0391 _refine_ls_wR_factor_gt 0.0387 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.218 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.045 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 Br1 Br 0.16973(2) 0.61534(2) 0.209946(18) 0.03024(7) Uani 1 1 d . . . Br2 Br 0.85501(2) 0.340269(19) 0.072010(17) 0.03107(7) Uani 1 1 d . . . O1 O 0.65815(14) 0.66928(12) 0.24662(11) 0.0240(3) Uani 1 1 d . . . O2 O 0.72563(15) 0.82205(14) 0.17935(13) 0.0410(5) Uani 1 1 d . . . O3 O 0.57045(13) 0.89910(12) 0.03400(10) 0.0219(3) Uani 1 1 d . . . O4 O 0.52801(18) 1.02668(14) 0.14339(14) 0.0460(5) Uani 1 1 d . . . O5 O 0.77902(15) 0.72947(12) 0.37042(11) 0.0281(4) Uani 1 1 d . . . O6 O 0.95961(13) 0.58942(11) 0.43913(11) 0.0215(3) Uani 1 1 d . . . O7 O 0.90576(15) 0.45447(13) 0.53904(11) 0.0285(4) Uani 1 1 d . . . C1 C 0.5114(2) 0.76502(16) 0.15268(16) 0.0175(5) Uani 1 1 d . . . C2 C 0.47841(19) 0.83553(17) 0.07823(15) 0.0194(5) Uani 1 1 d . . . C3 C 0.3564(2) 0.84026(18) 0.04316(15) 0.0237(5) Uani 1 1 d . . . H3A H 0.3363 0.8885 -0.0079 0.028 Uiso 1 1 calc R . . C4 C 0.2628(2) 0.77543(17) 0.08154(16) 0.0240(5) Uani 1 1 d . . . H4A H 0.1783 0.7790 0.0580 0.029 Uiso 1 1 calc R . . C5 C 0.2953(2) 0.70538(18) 0.15490(16) 0.0213(5) Uani 1 1 d . . . C6 C 0.41676(19) 0.69823(17) 0.19068(15) 0.0186(5) Uani 1 1 d . . . H6A H 0.4364 0.6485 0.2407 0.022 Uiso 1 1 calc R . . C7 C 0.6414(2) 0.75966(17) 0.19232(15) 0.0216(5) Uani 1 1 d . . . C8 C 0.5894(2) 0.99685(19) 0.07591(19) 0.0285(5) Uani 1 1 d . . . C9 C 0.6914(2) 1.0559(2) 0.02434(19) 0.0364(7) Uani 1 1 d . . . H9A H 0.7412 1.0968 0.0715 0.055 Uiso 1 1 calc R . . H9B H 0.6536 1.1047 -0.0232 0.055 Uiso 1 1 calc R . . H9C H 0.7466 1.0049 -0.0093 0.055 Uiso 1 1 calc R . . C10 C 0.76058(19) 0.66226(18) 0.31129(15) 0.0196(5) Uani 1 1 d . . . C11 C 0.83363(19) 0.56250(15) 0.29479(15) 0.0166(4) Uani 1 1 d . . . C12 C 0.81152(19) 0.50326(17) 0.21042(16) 0.0197(5) Uani 1 1 d . . . H12A H 0.7460 0.5241 0.1671 0.024 Uiso 1 1 calc R . . C13 C 0.8842(2) 0.41483(16) 0.18972(15) 0.0205(5) Uani 1 1 d . . . C14 C 0.9799(2) 0.38212(18) 0.25158(16) 0.0224(5) Uani 1 1 d . . . H14A H 1.0306 0.3217 0.2362 0.027 Uiso 1 1 calc R . . C15 C 1.0002(2) 0.43929(18) 0.33638(17) 0.0221(5) Uani 1 1 d . . . H15A H 1.0642 0.4167 0.3804 0.027 Uiso 1 1 calc R . . C16 C 0.9290(2) 0.52857(17) 0.35797(15) 0.0180(5) Uani 1 1 d . . . C17 C 0.9486(2) 0.54217(19) 0.52854(16) 0.0215(5) Uani 1 1 d . . . C18 C 0.9948(2) 0.6153(2) 0.60660(16) 0.0307(6) Uani 1 1 d . . . H18A H 0.9794 0.5826 0.6703 0.046 Uiso 1 1 calc R . . H18B H 0.9495 0.6834 0.6025 0.046 Uiso 1 1 calc R . . H18C H 1.0858 0.6277 0.5982 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02402(12) 0.03747(14) 0.02924(13) 0.00526(11) 0.00039(11) -0.01105(11) Br2 0.03721(15) 0.03181(13) 0.02420(12) -0.01023(11) -0.00171(11) 0.00362(11) O1 0.0214(8) 0.0182(8) 0.0324(8) 0.0037(7) -0.0087(7) 0.0011(7) O2 0.0259(9) 0.0464(11) 0.0506(12) 0.0238(9) -0.0102(8) -0.0145(9) O3 0.0261(9) 0.0181(8) 0.0214(8) 0.0021(7) 0.0031(6) -0.0036(7) O4 0.0586(13) 0.0378(12) 0.0416(12) -0.0207(10) 0.0158(11) -0.0184(10) O5 0.0331(10) 0.0255(10) 0.0257(9) -0.0062(8) -0.0056(7) 0.0040(7) O6 0.0247(8) 0.0219(9) 0.0178(8) 0.0012(7) -0.0042(7) -0.0046(6) O7 0.0353(10) 0.0279(10) 0.0223(9) 0.0020(7) 0.0024(7) -0.0049(8) C1 0.0192(12) 0.0160(12) 0.0174(11) -0.0029(9) 0.0021(9) 0.0017(9) C2 0.0240(11) 0.0160(11) 0.0183(11) -0.0031(10) 0.0034(9) -0.0007(10) C3 0.0293(13) 0.0218(11) 0.0200(11) 0.0046(10) -0.0031(9) 0.0040(11) C4 0.0202(11) 0.0303(13) 0.0215(12) -0.0016(11) -0.0053(10) 0.0020(10) C5 0.0235(13) 0.0203(12) 0.0200(12) -0.0015(10) 0.0047(9) -0.0074(9) C6 0.0214(12) 0.0170(11) 0.0173(12) 0.0007(9) -0.0002(9) -0.0010(9) C7 0.0221(12) 0.0221(12) 0.0206(12) 0.0005(9) 0.0039(10) 0.0008(10) C8 0.0319(14) 0.0270(13) 0.0266(14) -0.0015(12) -0.0065(12) -0.0055(11) C9 0.0404(16) 0.0328(15) 0.0360(16) 0.0042(12) -0.0035(12) -0.0146(12) C10 0.0185(11) 0.0217(11) 0.0186(12) 0.0031(10) 0.0035(9) -0.0034(10) C11 0.0162(10) 0.0172(10) 0.0166(11) 0.0036(9) 0.0033(10) -0.0024(9) C12 0.0181(11) 0.0249(12) 0.0161(11) 0.0017(10) -0.0006(10) -0.0026(9) C13 0.0216(12) 0.0215(12) 0.0185(12) -0.0028(9) 0.0035(9) -0.0052(9) C14 0.0195(12) 0.0206(12) 0.0272(12) -0.0016(11) 0.0017(9) 0.0025(10) C15 0.0168(12) 0.0258(13) 0.0237(13) 0.0043(10) -0.0041(9) 0.0003(10) C16 0.0178(12) 0.0221(13) 0.0143(12) 0.0032(9) 0.0009(9) -0.0049(10) C17 0.0164(12) 0.0299(14) 0.0183(12) -0.0001(10) -0.0016(9) 0.0045(11) C18 0.0304(14) 0.0392(14) 0.0225(13) -0.0026(12) -0.0050(10) -0.0043(12) _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 Br1 C5 1.898(2) . ? Br2 C13 1.894(2) . ? O1 C7 1.367(2) . ? O1 C10 1.403(2) . ? O2 C7 1.197(3) . ? O3 C8 1.367(3) . ? O3 C2 1.395(2) . ? O4 C8 1.191(3) . ? O5 C10 1.186(2) . ? O6 C17 1.369(3) . ? O6 C16 1.389(3) . ? O7 C17 1.196(3) . ? C1 C2 1.396(3) . ? C1 C6 1.404(3) . ? C1 C7 1.478(3) . ? C2 C3 1.377(3) . ? C3 C4 1.383(3) . ? C3 H3A 0.950 . ? C4 C5 1.380(3) . ? C4 H4A 0.950 . ? C5 C6 1.376(3) . ? C6 H6A 0.950 . ? C8 C9 1.486(3) . ? C9 H9A 0.980 . ? C9 H9B 0.980 . ? C9 H9C 0.980 . ? C10 C11 1.485(3) . ? C11 C16 1.396(3) . ? C11 C12 1.396(3) . ? C12 C13 1.377(3) . ? C12 H12A 0.950 . ? C13 C14 1.383(3) . ? C14 C15 1.385(3) . ? C14 H14A 0.950 . ? C15 C16 1.379(3) . ? C15 H15A 0.950 . ? C17 C18 1.492(3) . ? C18 H18A 0.980 . ? C18 H18B 0.980 . ? C18 H18C 0.980 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 C10 119.86(17) . . ? C8 O3 C2 115.37(17) . . ? C17 O6 C16 117.69(16) . . ? C2 C1 C6 118.1(2) . . ? C2 C1 C7 122.07(19) . . ? C6 C1 C7 119.78(19) . . ? C3 C2 O3 118.33(19) . . ? C3 C2 C1 121.2(2) . . ? O3 C2 C1 120.41(19) . . ? C2 C3 C4 120.6(2) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? C5 C4 C3 118.3(2) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? C6 C5 C4 122.3(2) . . ? C6 C5 Br1 118.02(17) . . ? C4 C5 Br1 119.67(17) . . ? C5 C6 C1 119.4(2) . . ? C5 C6 H6A 120.3 . . ? C1 C6 H6A 120.3 . . ? O2 C7 O1 121.7(2) . . ? O2 C7 C1 127.3(2) . . ? O1 C7 C1 111.05(18) . . ? O4 C8 O3 122.0(2) . . ? O4 C8 C9 127.6(2) . . ? O3 C8 C9 110.5(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 O1 121.1(2) . . ? O5 C10 C11 128.0(2) . . ? O1 C10 C11 110.87(18) . . ? C16 C11 C12 118.41(18) . . ? C16 C11 C10 122.37(19) . . ? C12 C11 C10 119.12(19) . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C14 121.2(2) . . ? C12 C13 Br2 118.83(16) . . ? C14 C13 Br2 119.91(17) . . ? C13 C14 C15 118.6(2) . . ? C13 C14 H14A 120.7 . . ? C15 C14 H14A 120.7 . . ? C16 C15 C14 121.0(2) . . ? C16 C15 H15A 119.5 . . ? C14 C15 H15A 119.5 . . ? C15 C16 O6 119.39(19) . . ? C15 C16 C11 120.4(2) . . ? O6 C16 C11 120.04(18) . . ? O7 C17 O6 122.5(2) . . ? O7 C17 C18 126.8(2) . . ? O6 C17 C18 110.7(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C8 O3 C2 C3 93.0(2) . . . . ? C8 O3 C2 C1 -90.3(2) . . . . ? C6 C1 C2 C3 0.4(3) . . . . ? C7 C1 C2 C3 -179.1(2) . . . . ? C6 C1 C2 O3 -176.19(18) . . . . ? C7 C1 C2 O3 4.3(3) . . . . ? O3 C2 C3 C4 177.12(19) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C3 C4 C5 Br1 179.77(16) . . . . ? C4 C5 C6 C1 0.8(3) . . . . ? Br1 C5 C6 C1 -178.91(15) . . . . ? C2 C1 C6 C5 -1.0(3) . . . . ? C7 C1 C6 C5 178.5(2) . . . . ? C10 O1 C7 O2 18.7(3) . . . . ? C10 O1 C7 C1 -162.87(18) . . . . ? C2 C1 C7 O2 12.8(4) . . . . ? C6 C1 C7 O2 -166.7(2) . . . . ? C2 C1 C7 O1 -165.44(18) . . . . ? C6 C1 C7 O1 15.0(3) . . . . ? C2 O3 C8 O4 -2.5(3) . . . . ? C2 O3 C8 C9 178.54(18) . . . . ? C7 O1 C10 O5 52.8(3) . . . . ? C7 O1 C10 C11 -128.32(18) . . . . ? O5 C10 C11 C16 8.1(3) . . . . ? O1 C10 C11 C16 -170.70(18) . . . . ? O5 C10 C11 C12 -168.3(2) . . . . ? O1 C10 C11 C12 13.0(3) . . . . ? C16 C11 C12 C13 -1.2(3) . . . . ? C10 C11 C12 C13 175.22(19) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C11 C12 C13 Br2 -177.60(15) . . . . ? C12 C13 C14 C15 1.1(3) . . . . ? Br2 C13 C14 C15 178.99(16) . . . . ? C13 C14 C15 C16 -1.6(3) . . . . ? C14 C15 C16 O6 -174.20(19) . . . . ? C14 C15 C16 C11 0.7(3) . . . . ? C17 O6 C16 C15 -64.0(3) . . . . ? C17 O6 C16 C11 121.1(2) . . . . ? C12 C11 C16 C15 0.7(3) . . . . ? C10 C11 C16 C15 -175.61(19) . . . . ? C12 C11 C16 O6 175.59(18) . . . . ? C10 C11 C16 O6 -0.7(3) . . . . ? C16 O6 C17 O7 -5.4(3) . . . . ? C16 O6 C17 C18 175.44(18) . . . . ? #============================================================================= data_5-Br-AA_I_I _database_code_depnum_ccdc_archive 'CCDC 823454' #TrackingRef 'submit.cif' _chemical_name_systematic ? _chemical_name_common '5-Br-aspirin anhydride (form II)' _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 Br2 O7' _chemical_formula_sum 'C18 H12 Br2 O7' _chemical_formula_weight 500.10 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.9944(7) _cell_length_b 7.9432(4) _cell_length_c 14.0330(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.825(2) _cell_angle_gamma 90.00 _cell_volume 1822.52(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8311 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 24.76 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.823 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 4.487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.404 _exptl_absorpt_correction_T_max 0.663 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 24574 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 25.01 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 3205 _reflns_number_gt 2629 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0228P)^2^+0.5739P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3205 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0495 _refine_ls_wR_factor_gt 0.0466 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.257 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.058 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 Br1 Br 0.556357(13) 0.78037(3) 0.514404(18) 0.03059(8) Uani 1 1 d . . . Br2 Br 0.291671(15) 0.48026(3) 0.074357(18) 0.03686(9) Uani 1 1 d . . . O1 O 0.24952(8) 0.5710(2) 0.43496(10) 0.0244(4) Uani 1 1 d . . . O2 O 0.21460(9) 0.5356(3) 0.57840(12) 0.0424(5) Uani 1 1 d . . . O3 O 0.34155(9) 0.41099(19) 0.72437(11) 0.0255(4) Uani 1 1 d . . . O4 O 0.31768(10) 0.6376(2) 0.80861(12) 0.0359(4) Uani 1 1 d . . . O5 O 0.12629(9) 0.7002(2) 0.40853(12) 0.0335(4) Uani 1 1 d . . . O6 O 0.01406(8) 0.48829(19) 0.26578(11) 0.0269(4) Uani 1 1 d . . . O7 O 0.07832(10) 0.3044(2) 0.38289(13) 0.0376(4) Uani 1 1 d . . . C1 C 0.35534(13) 0.5735(3) 0.58470(16) 0.0214(5) Uani 1 1 d . . . C2 C 0.39014(13) 0.5067(3) 0.67860(16) 0.0219(5) Uani 1 1 d . . . C3 C 0.47248(14) 0.5211(3) 0.72328(18) 0.0290(6) Uani 1 1 d . . . H3A H 0.4951 0.4746 0.7873 0.035 Uiso 1 1 calc R . . C4 C 0.52249(14) 0.6030(3) 0.67536(17) 0.0282(6) Uani 1 1 d . . . H4A H 0.5794 0.6136 0.7061 0.034 Uiso 1 1 calc R . . C5 C 0.48851(13) 0.6693(3) 0.58190(17) 0.0240(5) Uani 1 1 d . . . C6 C 0.40601(13) 0.6549(3) 0.53584(16) 0.0218(5) Uani 1 1 d . . . H6A H 0.3838 0.7000 0.4714 0.026 Uiso 1 1 calc R . . C7 C 0.26637(14) 0.5591(3) 0.53785(17) 0.0258(5) Uani 1 1 d . . . C8 C 0.30112(14) 0.4949(3) 0.78259(16) 0.0251(5) Uani 1 1 d . . . C9 C 0.23767(14) 0.3864(3) 0.80534(18) 0.0323(6) Uani 1 1 d . . . H9A H 0.2064 0.4519 0.8417 0.048 Uiso 1 1 calc R . . H9B H 0.2639 0.2909 0.8459 0.048 Uiso 1 1 calc R . . H9C H 0.2007 0.3448 0.7435 0.048 Uiso 1 1 calc R . . C10 C 0.17180(13) 0.6142(3) 0.37872(16) 0.0227(5) Uani 1 1 d . . . C11 C 0.15701(12) 0.5454(3) 0.27664(16) 0.0200(5) Uani 1 1 d . . . C12 C 0.22006(13) 0.5413(3) 0.23110(16) 0.0218(5) Uani 1 1 d . . . H12A H 0.2733 0.5787 0.2657 0.026 Uiso 1 1 calc R . . C13 C 0.20494(14) 0.4826(3) 0.13545(17) 0.0247(5) Uani 1 1 d . . . C14 C 0.12846(14) 0.4238(3) 0.08362(17) 0.0306(6) Uani 1 1 d . . . H14A H 0.1190 0.3836 0.0177 0.037 Uiso 1 1 calc R . . C15 C 0.06607(14) 0.4249(3) 0.12966(17) 0.0296(6) Uani 1 1 d . . . H15A H 0.0135 0.3831 0.0957 0.035 Uiso 1 1 calc R . . C16 C 0.07998(13) 0.4865(3) 0.22458(16) 0.0237(5) Uani 1 1 d . . . C17 C 0.01956(14) 0.3882(3) 0.34689(17) 0.0268(5) Uani 1 1 d . . . C18 C -0.05649(14) 0.4031(3) 0.37949(19) 0.0352(6) Uani 1 1 d . . . H18A H -0.0519 0.3322 0.4379 0.053 Uiso 1 1 calc R . . H18B H -0.1034 0.3663 0.3259 0.053 Uiso 1 1 calc R . . H18C H -0.0642 0.5207 0.3961 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02621(13) 0.02900(15) 0.03759(16) -0.00259(11) 0.01047(11) -0.00434(10) Br2 0.04130(15) 0.04485(18) 0.03040(15) -0.00242(12) 0.01993(12) -0.00207(12) O1 0.0176(8) 0.0398(10) 0.0143(8) -0.0004(7) 0.0022(6) 0.0013(7) O2 0.0232(9) 0.0824(15) 0.0238(9) 0.0078(9) 0.0098(8) 0.0010(9) O3 0.0338(9) 0.0216(9) 0.0215(9) -0.0026(7) 0.0079(7) -0.0025(7) O4 0.0535(11) 0.0247(10) 0.0313(10) -0.0044(8) 0.0147(8) 0.0017(8) O5 0.0287(9) 0.0427(11) 0.0275(9) -0.0062(8) 0.0049(8) 0.0099(8) O6 0.0175(8) 0.0370(10) 0.0251(9) 0.0067(8) 0.0038(7) 0.0014(7) O7 0.0303(9) 0.0450(11) 0.0372(10) 0.0167(9) 0.0087(8) 0.0085(9) C1 0.0226(12) 0.0219(13) 0.0194(12) -0.0052(10) 0.0053(10) 0.0023(10) C2 0.0265(12) 0.0185(13) 0.0202(12) -0.0051(10) 0.0055(10) -0.0007(10) C3 0.0326(14) 0.0238(14) 0.0242(13) 0.0035(11) -0.0033(11) -0.0002(11) C4 0.0220(12) 0.0244(14) 0.0315(15) -0.0023(11) -0.0039(11) -0.0018(10) C5 0.0249(12) 0.0173(12) 0.0301(14) -0.0056(11) 0.0079(11) -0.0017(10) C6 0.0226(12) 0.0224(12) 0.0188(12) -0.0027(10) 0.0033(9) 0.0052(10) C7 0.0268(13) 0.0310(14) 0.0193(13) -0.0011(11) 0.0057(10) 0.0013(11) C8 0.0310(13) 0.0271(15) 0.0141(12) 0.0006(11) 0.0008(10) 0.0063(11) C9 0.0346(14) 0.0366(16) 0.0255(14) 0.0015(12) 0.0079(11) -0.0018(12) C10 0.0207(12) 0.0252(14) 0.0214(12) 0.0022(11) 0.0047(10) -0.0022(10) C11 0.0204(11) 0.0196(12) 0.0187(12) 0.0031(10) 0.0032(10) 0.0012(9) C12 0.0231(12) 0.0200(12) 0.0203(12) 0.0011(10) 0.0028(10) -0.0026(10) C13 0.0299(13) 0.0229(13) 0.0234(13) 0.0010(11) 0.0106(11) -0.0018(10) C14 0.0390(14) 0.0323(15) 0.0176(13) -0.0034(11) 0.0028(11) -0.0031(12) C15 0.0273(13) 0.0329(15) 0.0239(14) -0.0009(11) -0.0009(10) -0.0045(11) C16 0.0225(12) 0.0247(14) 0.0234(13) 0.0071(11) 0.0054(10) 0.0026(10) C17 0.0252(13) 0.0292(14) 0.0246(13) -0.0021(12) 0.0044(11) -0.0063(11) C18 0.0272(13) 0.0444(17) 0.0360(15) -0.0037(13) 0.0118(11) -0.0055(12) _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 Br1 C5 1.898(2) . ? Br2 C13 1.897(2) . ? O1 C10 1.384(3) . ? O1 C7 1.396(3) . ? O2 C7 1.186(3) . ? O3 C8 1.375(3) . ? O3 C2 1.400(3) . ? O4 C8 1.200(3) . ? O5 C10 1.190(3) . ? O6 C17 1.371(3) . ? O6 C16 1.394(3) . ? O7 C17 1.192(3) . ? C1 C2 1.394(3) . ? C1 C6 1.397(3) . ? C1 C7 1.480(3) . ? C2 C3 1.373(3) . ? C3 C4 1.382(3) . ? C3 H3A 0.9500 . ? C4 C5 1.385(3) . ? C4 H4A 0.950 . ? C5 C6 1.379(3) . ? C6 H6A 0.950 . ? C8 C9 1.482(3) . ? C9 H9A 0.980 . ? C9 H9B 0.980 . ? C9 H9C 0.980 . ? C10 C11 1.489(3) . ? C11 C12 1.390(3) . ? C11 C16 1.394(3) . ? C12 C13 1.377(3) . ? C12 H12A 0.950 . ? C13 C14 1.386(3) . ? C14 C15 1.384(3) . ? C14 H14A 0.950 . ? C15 C16 1.378(3) . ? C15 H15A 0.950 . ? C17 C18 1.489(3) . ? C18 H18A 0.980 . ? C18 H18B 0.980 . ? C18 H18C 0.980 . ? 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 C10 O1 C7 120.07(16) . . ? C8 O3 C2 117.52(17) . . ? C17 O6 C16 117.26(16) . . ? C2 C1 C6 118.7(2) . . ? C2 C1 C7 120.6(2) . . ? C6 C1 C7 120.6(2) . . ? C3 C2 C1 121.1(2) . . ? C3 C2 O3 119.4(2) . . ? C1 C2 O3 119.28(19) . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C6 C5 C4 121.4(2) . . ? C6 C5 Br1 118.88(17) . . ? C4 C5 Br1 119.76(17) . . ? C5 C6 C1 119.5(2) . . ? C5 C6 H6A 120.3 . . ? C1 C6 H6A 120.3 . . ? O2 C7 O1 122.5(2) . . ? O2 C7 C1 126.9(2) . . ? O1 C7 C1 110.54(18) . . ? O4 C8 O3 121.7(2) . . ? O4 C8 C9 127.4(2) . . ? O3 C8 C9 110.9(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 O1 123.5(2) . . ? O5 C10 C11 126.4(2) . . ? O1 C10 C11 110.00(18) . . ? C12 C11 C16 118.8(2) . . ? C12 C11 C10 120.14(18) . . ? C16 C11 C10 121.01(19) . . ? C13 C12 C11 119.6(2) . . ? C13 C12 H12A 120.2 . . ? C11 C12 H12A 120.2 . . ? C12 C13 C14 121.6(2) . . ? C12 C13 Br2 118.84(16) . . ? C14 C13 Br2 119.52(17) . . ? C15 C14 C13 118.8(2) . . ? C15 C14 H14A 120.6 . . ? C13 C14 H14A 120.6 . . ? C16 C15 C14 120.1(2) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C15 C16 O6 117.34(19) . . ? C15 C16 C11 121.0(2) . . ? O6 C16 C11 121.7(2) . . ? O7 C17 O6 122.4(2) . . ? O7 C17 C18 127.7(2) . . ? O6 C17 C18 109.9(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C6 C1 C2 C3 0.5(3) . . . . ? C7 C1 C2 C3 -179.2(2) . . . . ? C6 C1 C2 O3 -173.97(19) . . . . ? C7 C1 C2 O3 6.3(3) . . . . ? C8 O3 C2 C3 95.5(2) . . . . ? C8 O3 C2 C1 -89.9(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? O3 C2 C3 C4 174.6(2) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C3 C4 C5 Br1 -179.41(17) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? Br1 C5 C6 C1 -179.98(16) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? C7 C1 C6 C5 178.8(2) . . . . ? C10 O1 C7 O2 22.6(3) . . . . ? C10 O1 C7 C1 -159.45(19) . . . . ? C2 C1 C7 O2 21.3(4) . . . . ? C6 C1 C7 O2 -158.4(3) . . . . ? C2 C1 C7 O1 -156.5(2) . . . . ? C6 C1 C7 O1 23.8(3) . . . . ? C2 O3 C8 O4 -13.5(3) . . . . ? C2 O3 C8 C9 166.16(18) . . . . ? C7 O1 C10 O5 28.9(3) . . . . ? C7 O1 C10 C11 -154.14(19) . . . . ? O5 C10 C11 C12 140.1(2) . . . . ? O1 C10 C11 C12 -36.8(3) . . . . ? O5 C10 C11 C16 -39.0(3) . . . . ? O1 C10 C11 C16 144.1(2) . . . . ? C16 C11 C12 C13 1.3(3) . . . . ? C10 C11 C12 C13 -177.9(2) . . . . ? C11 C12 C13 C14 -1.3(3) . . . . ? C11 C12 C13 Br2 179.35(16) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? Br2 C13 C14 C15 179.38(18) . . . . ? C13 C14 C15 C16 1.2(4) . . . . ? C14 C15 C16 O6 178.3(2) . . . . ? C14 C15 C16 C11 -1.3(4) . . . . ? C17 O6 C16 C15 115.6(2) . . . . ? C17 O6 C16 C11 -64.8(3) . . . . ? C12 C11 C16 C15 0.0(3) . . . . ? C10 C11 C16 C15 179.2(2) . . . . ? C12 C11 C16 O6 -179.56(19) . . . . ? C10 C11 C16 O6 -0.5(3) . . . . ? C16 O6 C17 O7 1.3(3) . . . . ? C16 O6 C17 C18 -178.84(19) . . . . ? #============================================================================= data_5-Me-AA_I _database_code_depnum_ccdc_archive 'CCDC 823456' #TrackingRef 'submit.cif' _chemical_name_systematic ? _chemical_name_common '5-Me-aspirin anhydride (form I)' _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 O7' _chemical_formula_sum 'C20 H18 O7' _chemical_formula_weight 370.34 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9176(9) _cell_length_b 9.9757(10) _cell_length_c 11.5419(17) _cell_angle_alpha 95.485(7) _cell_angle_beta 109.352(7) _cell_angle_gamma 117.882(4) _cell_volume 908.32(18) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2144 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 24.63 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.857 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 10529 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 25.23 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 0.972 _reflns_number_total 3189 _reflns_number_gt 1997 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0443P)^2^+0.3120P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3189 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1132 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.219 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.046 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 O1 O 0.41766(19) 0.48960(19) 0.25136(15) 0.0287(4) Uani 1 1 d . . . O2 O 0.2675(2) 0.5788(2) 0.13242(16) 0.0361(5) Uani 1 1 d . . . O3 O 0.37898(19) 0.71817(18) -0.03741(14) 0.0311(4) Uani 1 1 d . . . O4 O 0.4566(2) 0.9277(2) 0.11909(17) 0.0403(5) Uani 1 1 d . . . O5 O 0.1859(2) 0.2823(2) 0.24750(15) 0.0337(4) Uani 1 1 d . . . O6 O 0.04442(18) 0.34045(18) 0.39865(15) 0.0274(4) Uani 1 1 d . . . O7 O 0.1573(2) 0.2153(2) 0.50521(17) 0.0396(5) Uani 1 1 d . . . C1 C 0.5324(3) 0.6440(3) 0.1286(2) 0.0245(6) Uani 1 1 d . . . C2 C 0.5248(3) 0.7180(3) 0.0318(2) 0.0274(6) Uani 1 1 d . . . C3 C 0.6526(3) 0.7800(3) -0.0062(2) 0.0334(6) Uani 1 1 d . . . H3A H 0.6458 0.8305 -0.0718 0.040 Uiso 1 1 calc R . . C4 C 0.7921(3) 0.7688(3) 0.0515(2) 0.0355(7) Uani 1 1 d . . . H4A H 0.8807 0.8126 0.0250 0.043 Uiso 1 1 calc R . . C5 C 0.8054(3) 0.6949(3) 0.1475(2) 0.0305(6) Uani 1 1 d . . . C6 C 0.6738(3) 0.6344(3) 0.1845(2) 0.0277(6) Uani 1 1 d . . . H6A H 0.6808 0.5845 0.2505 0.033 Uiso 1 1 calc R . . C7 C 0.3921(3) 0.5722(3) 0.1672(2) 0.0273(6) Uani 1 1 d . . . C8 C 0.3511(3) 0.8220(3) 0.0217(2) 0.0314(6) Uani 1 1 d . . . C9 C 0.1767(3) 0.7824(3) -0.0530(3) 0.0412(7) Uani 1 1 d . . . H9A H 0.1679 0.8734 -0.0270 0.062 Uiso 1 1 calc R . . H9B H 0.0974 0.6901 -0.0363 0.062 Uiso 1 1 calc R . . H9C H 0.1494 0.7575 -0.1451 0.062 Uiso 1 1 calc R . . C10 C 0.2924(3) 0.4200(3) 0.2971(2) 0.0264(6) Uani 1 1 d . . . C11 C 0.3194(3) 0.5286(3) 0.4101(2) 0.0247(6) Uani 1 1 d . . . C12 C 0.4672(3) 0.6799(3) 0.4704(2) 0.0300(6) Uani 1 1 d . . . H12A H 0.5490 0.7125 0.4366 0.036 Uiso 1 1 calc R . . C13 C 0.4972(3) 0.7837(3) 0.5785(2) 0.0331(6) Uani 1 1 d . . . C14 C 0.3776(3) 0.7327(3) 0.6276(2) 0.0345(6) Uani 1 1 d . . . H14A H 0.3973 0.8009 0.7027 0.041 Uiso 1 1 calc R . . C15 C 0.2296(3) 0.5840(3) 0.5689(2) 0.0312(6) Uani 1 1 d . . . H15A H 0.1482 0.5514 0.6030 0.037 Uiso 1 1 calc R . . C16 C 0.2014(3) 0.4840(3) 0.4610(2) 0.0258(6) Uani 1 1 d . . . C17 C 0.0380(3) 0.2078(3) 0.4264(2) 0.0284(6) Uani 1 1 d . . . C18 C -0.1306(3) 0.0625(3) 0.3468(3) 0.0404(7) Uani 1 1 d . . . H18A H -0.1455 -0.0220 0.3877 0.061 Uiso 1 1 calc R . . H18B H -0.1394 0.0277 0.2609 0.061 Uiso 1 1 calc R . . H18C H -0.2183 0.0858 0.3394 0.061 Uiso 1 1 calc R . . C19 C 0.9537(3) 0.6769(3) 0.2080(3) 0.0433(7) Uani 1 1 d . . . H19A H 1.0366 0.7312 0.1741 0.065 Uiso 1 1 calc R . . H19B H 0.9149 0.5637 0.1877 0.065 Uiso 1 1 calc R . . H19C H 1.0058 0.7239 0.3016 0.065 Uiso 1 1 calc R . . C20 C 0.6567(3) 0.9461(3) 0.6406(3) 0.0467(8) Uani 1 1 d . . . H20A H 0.6376 1.0182 0.6869 0.070 Uiso 1 1 calc R . . H20B H 0.6889 0.9872 0.5740 0.070 Uiso 1 1 calc R . . H20C H 0.7474 0.9385 0.7012 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0293(9) 0.0340(10) 0.0292(9) 0.0132(8) 0.0169(8) 0.0179(8) O2 0.0304(10) 0.0442(11) 0.0410(11) 0.0211(9) 0.0174(9) 0.0221(9) O3 0.0334(10) 0.0285(10) 0.0238(9) 0.0041(8) 0.0079(8) 0.0144(8) O4 0.0402(11) 0.0314(11) 0.0344(11) -0.0022(9) 0.0077(9) 0.0160(9) O5 0.0329(10) 0.0286(10) 0.0289(10) 0.0022(8) 0.0123(8) 0.0104(9) O6 0.0227(9) 0.0230(9) 0.0311(10) 0.0064(8) 0.0094(8) 0.0101(8) O7 0.0332(10) 0.0368(11) 0.0376(11) 0.0141(9) 0.0064(9) 0.0158(9) C1 0.0268(14) 0.0180(13) 0.0205(13) 0.0009(11) 0.0100(11) 0.0068(11) C2 0.0285(14) 0.0213(13) 0.0213(13) -0.0008(11) 0.0074(11) 0.0087(11) C3 0.0374(16) 0.0247(14) 0.0265(14) 0.0026(11) 0.0150(13) 0.0082(13) C4 0.0299(15) 0.0253(14) 0.0364(16) -0.0021(12) 0.0194(13) 0.0025(12) C5 0.0277(14) 0.0235(14) 0.0294(14) -0.0011(12) 0.0127(12) 0.0070(12) C6 0.0286(14) 0.0202(13) 0.0228(13) -0.0006(11) 0.0076(12) 0.0083(11) C7 0.0315(15) 0.0220(13) 0.0210(13) 0.0033(11) 0.0079(12) 0.0117(12) C8 0.0369(16) 0.0256(14) 0.0299(15) 0.0113(13) 0.0149(13) 0.0145(13) C9 0.0422(16) 0.0390(16) 0.0385(16) 0.0129(13) 0.0118(14) 0.0221(14) C10 0.0234(13) 0.0300(15) 0.0257(14) 0.0122(12) 0.0106(12) 0.0134(13) C11 0.0244(13) 0.0243(14) 0.0247(13) 0.0072(11) 0.0092(11) 0.0132(12) C12 0.0262(14) 0.0280(14) 0.0328(15) 0.0088(12) 0.0114(12) 0.0130(12) C13 0.0277(14) 0.0262(14) 0.0328(15) 0.0011(12) 0.0052(12) 0.0116(12) C14 0.0331(15) 0.0332(15) 0.0305(15) -0.0019(12) 0.0081(13) 0.0185(13) C15 0.0282(14) 0.0345(15) 0.0321(15) 0.0072(12) 0.0138(12) 0.0175(13) C16 0.0228(13) 0.0221(13) 0.0266(13) 0.0050(11) 0.0065(11) 0.0108(11) C17 0.0321(15) 0.0293(15) 0.0242(14) 0.0072(11) 0.0142(12) 0.0153(12) C18 0.0360(15) 0.0270(15) 0.0382(16) 0.0064(13) 0.0067(13) 0.0090(13) C19 0.0280(15) 0.0380(16) 0.0507(18) 0.0026(14) 0.0168(14) 0.0100(13) C20 0.0386(16) 0.0289(15) 0.0531(19) -0.0011(13) 0.0143(15) 0.0098(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 O1 C7 1.368(3) . ? O1 C10 1.415(3) . ? O2 C7 1.201(3) . ? O3 C8 1.368(3) . ? O3 C2 1.402(3) . ? O4 C8 1.197(3) . ? O5 C10 1.193(3) . ? O6 C17 1.368(3) . ? O6 C16 1.402(3) . ? O7 C17 1.194(3) . ? C1 C6 1.389(3) . ? C1 C2 1.397(3) . ? C1 C7 1.480(3) . ? C2 C3 1.367(3) . ? C3 C4 1.385(4) . ? C3 H3A 0.950 . ? C4 C5 1.392(4) . ? C4 H4A 0.950 . ? C5 C6 1.390(3) . ? C5 C19 1.508(3) . ? C6 H6A 0.950 . ? C8 C9 1.483(3) . ? C9 H9A 0.980 . ? C9 H9B 0.980 . ? C9 H9C 0.980 . ? C10 C11 1.474(3) . ? C11 C16 1.390(3) . ? C11 C12 1.402(3) . ? C12 C13 1.392(3) . ? C12 H12A 0.950 . ? C13 C14 1.386(3) . ? C13 C20 1.507(3) . ? C14 C15 1.388(3) . ? C14 H14A 0.950 . ? C15 C16 1.377(3) . ? C15 H15A 0.950 . ? C17 C18 1.484(3) . ? C18 H18A 0.980 . ? C18 H18B 0.980 . ? C18 H18C 0.980 . ? C19 H19A 0.980 . ? C19 H19B 0.980 . ? C19 H19C 0.980 . ? C20 H20A 0.980 . ? C20 H20B 0.980 . ? C20 H20C 0.980 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 C10 115.53(17) . . ? C8 O3 C2 117.61(17) . . ? C17 O6 C16 116.61(17) . . ? C6 C1 C2 117.8(2) . . ? C6 C1 C7 120.7(2) . . ? C2 C1 C7 121.4(2) . . ? C3 C2 C1 121.2(2) . . ? C3 C2 O3 117.7(2) . . ? C1 C2 O3 120.8(2) . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C3 C4 C5 121.5(2) . . ? C3 C4 H4A 119.2 . . ? C5 C4 H4A 119.2 . . ? C6 C5 C4 117.3(2) . . ? C6 C5 C19 120.5(2) . . ? C4 C5 C19 122.2(2) . . ? C1 C6 C5 122.5(2) . . ? C1 C6 H6A 118.8 . . ? C5 C6 H6A 118.8 . . ? O2 C7 O1 121.1(2) . . ? O2 C7 C1 127.8(2) . . ? O1 C7 C1 111.2(2) . . ? O4 C8 O3 122.8(2) . . ? O4 C8 C9 127.3(2) . . ? O3 C8 C9 109.9(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 O1 118.4(2) . . ? O5 C10 C11 127.6(2) . . ? O1 C10 C11 113.8(2) . . ? C16 C11 C12 118.1(2) . . ? C16 C11 C10 121.4(2) . . ? C12 C11 C10 120.5(2) . . ? C13 C12 C11 121.7(2) . . ? C13 C12 H12A 119.2 . . ? C11 C12 H12A 119.2 . . ? C14 C13 C12 118.2(2) . . ? C14 C13 C20 121.4(2) . . ? C12 C13 C20 120.4(2) . . ? C13 C14 C15 121.2(2) . . ? C13 C14 H14A 119.4 . . ? C15 C14 H14A 119.4 . . ? C16 C15 C14 119.7(2) . . ? C16 C15 H15A 120.2 . . ? C14 C15 H15A 120.2 . . ? C15 C16 C11 121.2(2) . . ? C15 C16 O6 117.7(2) . . ? C11 C16 O6 121.0(2) . . ? O7 C17 O6 121.7(2) . . ? O7 C17 C18 126.9(2) . . ? O6 C17 C18 111.3(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C5 C19 H19A 109.5 . . ? C5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 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 C6 C1 C2 C3 -0.4(3) . . . . ? C7 C1 C2 C3 -178.0(2) . . . . ? C6 C1 C2 O3 173.71(19) . . . . ? C7 C1 C2 O3 -3.9(3) . . . . ? C8 O3 C2 C3 -108.4(2) . . . . ? C8 O3 C2 C1 77.3(3) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? O3 C2 C3 C4 -174.0(2) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C3 C4 C5 C19 177.9(2) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? C7 C1 C6 C5 177.5(2) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C19 C5 C6 C1 -178.0(2) . . . . ? C10 O1 C7 O2 -2.5(3) . . . . ? C10 O1 C7 C1 178.27(18) . . . . ? C6 C1 C7 O2 175.6(2) . . . . ? C2 C1 C7 O2 -6.8(4) . . . . ? C6 C1 C7 O1 -5.2(3) . . . . ? C2 C1 C7 O1 172.34(19) . . . . ? C2 O3 C8 O4 12.3(3) . . . . ? C2 O3 C8 C9 -168.0(2) . . . . ? C7 O1 C10 O5 98.9(3) . . . . ? C7 O1 C10 C11 -85.6(2) . . . . ? O5 C10 C11 C16 -10.3(4) . . . . ? O1 C10 C11 C16 174.69(19) . . . . ? O5 C10 C11 C12 168.8(2) . . . . ? O1 C10 C11 C12 -6.2(3) . . . . ? C16 C11 C12 C13 0.3(4) . . . . ? C10 C11 C12 C13 -178.9(2) . . . . ? C11 C12 C13 C14 1.1(4) . . . . ? C11 C12 C13 C20 -179.5(2) . . . . ? C12 C13 C14 C15 -1.6(4) . . . . ? C20 C13 C14 C15 178.9(2) . . . . ? C13 C14 C15 C16 0.8(4) . . . . ? C14 C15 C16 C11 0.6(4) . . . . ? C14 C15 C16 O6 -174.8(2) . . . . ? C12 C11 C16 C15 -1.1(3) . . . . ? C10 C11 C16 C15 178.0(2) . . . . ? C12 C11 C16 O6 174.1(2) . . . . ? C10 C11 C16 O6 -6.7(3) . . . . ? C17 O6 C16 C15 -98.5(2) . . . . ? C17 O6 C16 C11 86.1(3) . . . . ? C16 O6 C17 O7 4.3(3) . . . . ? C16 O6 C17 C18 -175.4(2) . . . . ? #============================================================================= data_5-Me-AA_II _database_code_depnum_ccdc_archive 'CCDC 823457' #TrackingRef 'submit.cif' _chemical_name_systematic ? _chemical_name_common '5-Me-aspirin anhydride (form II)' _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 O7' _chemical_formula_sum 'C20 H18 O7' _chemical_formula_weight 370.34 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.749(2) _cell_length_b 8.3818(8) _cell_length_c 10.6736(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.440(5) _cell_angle_gamma 90.00 _cell_volume 1840.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9317 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 22.75 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details 'TWINABS (Bruker, 2008)' _exptl_special_details ; The crystal was integrated as a two-component twin, with the two orientations related by a 180 deg. rotation around a*. Refinement using HKLF-5 format in SHELXL. Refined BASF parameter = 0.476(1). Twin Law: transforms h1.1(1)->h1.2(2) 1.00001 0.00004 0.49803 -0.00002 -1.00000 0.00017 -0.00003 -0.00028 -1.00001 Statistics for singles for twin component 1 #------------------------------------------- Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -12.0 0.0713 0.951 - 1.004 0.792 - 0.863 0.601 5060 2926 2 20.5 0.0865 0.927 - 1.004 0.799 - 0.894 0.597 1728 844 3 10.5 0.0617 0.941 - 1.005 0.792 - 0.865 0.577 3124 1896 4 -22.0 0.0867 0.957 - 1.033 0.792 - 0.856 0.616 5553 2975 Statistics for singles for twin component 2 #------------------------------------------- Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -12.0 0.0735 0.951 - 1.004 0.792 - 0.864 0.598 5084 2869 2 20.5 0.0916 0.927 - 1.004 0.800 - 0.894 0.598 1715 844 3 10.5 0.0638 0.941 - 1.005 0.792 - 0.865 0.574 3121 1879 4 -22.0 0.0925 0.957 - 1.033 0.792 - 0.856 0.621 5562 2912 Statistics for all composite reflections #--------------------------------------- Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -12.0 0.0522 0.951 - 1.004 0.792 - 0.861 0.652 5923 4437 2 20.5 0.0680 0.926 - 1.004 0.801 - 0.938 0.650 2078 1275 3 10.5 0.0420 0.941 - 1.005 0.792 - 0.865 0.604 3232 2590 4 -22.0 0.0549 0.957 - 1.034 0.792 - 0.856 0.664 5444 4142 Statistics for all single and composite reflections #-------------------------------------------------- Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -12.0 0.0611 0.951 - 1.004 0.792 - 0.864 0.619 16067 10214 2 20.5 0.0778 0.926 - 1.004 0.799 - 0.938 0.617 5521 2970 3 10.5 0.0516 0.941 - 1.005 0.792 - 0.865 0.585 9477 6350 4 -22.0 0.0699 0.957 - 1.034 0.792 - 0.856 0.634 16559 10027 ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 5172 # data are merged in TWINABS: statistics shown above _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0815 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.11 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 5172 _reflns_number_gt 3242 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0385P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5172 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0766 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.199 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.043 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 O1 O 0.28535(5) 0.57326(13) 0.21292(11) 0.0278(3) Uani 1 1 d . . . O2 O 0.21632(5) 0.65160(14) 0.34712(12) 0.0328(3) Uani 1 1 d . . . O3 O 0.10472(5) 0.47283(13) 0.31148(11) 0.0271(3) Uani 1 1 d . . . O4 O 0.05669(6) 0.71286(16) 0.28389(13) 0.0411(4) Uani 1 1 d . . . O5 O 0.37448(6) 0.55373(14) 0.35295(14) 0.0472(4) Uani 1 1 d . . . O6 O 0.39803(5) 0.82199(15) 0.50263(11) 0.0357(3) Uani 1 1 d . . . O7 O 0.49302(6) 0.79793(18) 0.42407(13) 0.0469(4) Uani 1 1 d . . . C1 C 0.17426(8) 0.52539(18) 0.15131(16) 0.0211(4) Uani 1 1 d . . . C2 C 0.11515(8) 0.47080(18) 0.18446(16) 0.0227(4) Uani 1 1 d . . . C3 C 0.06888(8) 0.40590(19) 0.09627(16) 0.0268(4) Uani 1 1 d . . . H3A H 0.0290 0.3686 0.1201 0.032 Uiso 1 1 calc R . . C4 C 0.08074(8) 0.39502(19) -0.02812(17) 0.0291(4) Uani 1 1 d . . . H4A H 0.0485 0.3498 -0.0893 0.035 Uiso 1 1 calc R . . C5 C 0.13871(8) 0.44876(19) -0.06561(16) 0.0253(4) Uani 1 1 d . . . C6 C 0.18487(8) 0.51248(18) 0.02581(16) 0.0234(4) Uani 1 1 d . . . H6A H 0.2250 0.5485 0.0021 0.028 Uiso 1 1 calc R . . C7 C 0.22477(8) 0.59178(19) 0.24838(17) 0.0241(4) Uani 1 1 d . . . C8 C 0.07871(8) 0.6092(2) 0.35391(18) 0.0301(4) Uani 1 1 d . . . C9 C 0.08267(9) 0.6070(2) 0.49380(16) 0.0420(5) Uani 1 1 d . . . H9A H 0.0546 0.6905 0.5212 0.063 Uiso 1 1 calc R . . H9B H 0.1277 0.6262 0.5312 0.063 Uiso 1 1 calc R . . H9C H 0.0684 0.5027 0.5213 0.063 Uiso 1 1 calc R . . C10 C 0.33689(8) 0.6419(2) 0.29539(18) 0.0291(4) Uani 1 1 d . . . C11 C 0.33891(8) 0.8170(2) 0.29184(18) 0.0260(4) Uani 1 1 d . . . C12 C 0.30952(8) 0.9012(2) 0.18760(17) 0.0272(4) Uani 1 1 d . . . H12A H 0.2866 0.8443 0.1188 0.033 Uiso 1 1 calc R . . C13 C 0.31276(8) 1.0658(2) 0.18146(18) 0.0321(5) Uani 1 1 d . . . C14 C 0.34628(9) 1.1462(2) 0.2829(2) 0.0395(5) Uani 1 1 d . . . H14A H 0.3494 1.2592 0.2799 0.047 Uiso 1 1 calc R . . C15 C 0.37530(9) 1.0657(2) 0.38845(19) 0.0380(5) Uani 1 1 d . . . H15A H 0.3974 1.1231 0.4578 0.046 Uiso 1 1 calc R . . C16 C 0.37203(8) 0.9018(2) 0.39246(18) 0.0302(5) Uani 1 1 d . . . C17 C 0.46052(10) 0.7664(2) 0.5048(2) 0.0385(5) Uani 1 1 d . . . C18 C 0.47932(9) 0.6674(3) 0.61909(19) 0.0574(6) Uani 1 1 d . . . H18A H 0.5232 0.6249 0.6174 0.086 Uiso 1 1 calc R . . H18B H 0.4486 0.5788 0.6205 0.086 Uiso 1 1 calc R . . H18C H 0.4786 0.7331 0.6948 0.086 Uiso 1 1 calc R . . C19 C 0.15137(9) 0.4375(2) -0.20078(17) 0.0412(5) Uani 1 1 d . . . H19A H 0.1604 0.5441 -0.2319 0.062 Uiso 1 1 calc R . . H19D H 0.1131 0.3930 -0.2523 0.062 Uiso 1 1 calc R . . H19B H 0.1889 0.3680 -0.2062 0.062 Uiso 1 1 calc R . . C20 C 0.28064(10) 1.1538(2) 0.06686(19) 0.0456(5) Uani 1 1 d . . . H20D H 0.2995 1.1186 -0.0080 0.068 Uiso 1 1 calc R . . H20A H 0.2876 1.2687 0.0787 0.068 Uiso 1 1 calc R . . H20B H 0.2339 1.1313 0.0554 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0167(6) 0.0277(7) 0.0382(8) -0.0074(6) 0.0003(6) -0.0018(5) O2 0.0290(7) 0.0401(8) 0.0286(8) -0.0092(6) 0.0011(6) -0.0032(6) O3 0.0284(7) 0.0291(7) 0.0237(7) 0.0027(6) 0.0035(6) -0.0012(6) O4 0.0467(8) 0.0448(8) 0.0318(8) 0.0019(7) 0.0056(7) 0.0177(7) O5 0.0364(8) 0.0314(8) 0.0674(10) 0.0034(8) -0.0176(8) 0.0030(6) O6 0.0252(7) 0.0514(8) 0.0300(8) -0.0005(7) 0.0019(6) 0.0005(6) O7 0.0267(8) 0.0834(10) 0.0307(9) 0.0006(8) 0.0047(7) -0.0007(7) C1 0.0209(9) 0.0161(9) 0.0251(10) 0.0010(8) -0.0022(8) 0.0019(7) C2 0.0255(10) 0.0198(9) 0.0227(10) 0.0031(8) 0.0025(8) 0.0044(8) C3 0.0196(10) 0.0279(10) 0.0321(11) 0.0012(8) 0.0009(9) -0.0056(8) C4 0.0273(10) 0.0293(11) 0.0282(11) -0.0021(8) -0.0062(9) -0.0010(8) C5 0.0298(10) 0.0210(9) 0.0245(10) -0.0013(8) 0.0012(9) -0.0004(8) C6 0.0199(9) 0.0207(10) 0.0300(11) 0.0015(8) 0.0048(8) 0.0014(7) C7 0.0230(10) 0.0172(10) 0.0312(12) 0.0055(8) 0.0004(9) -0.0001(8) C8 0.0234(10) 0.0404(12) 0.0266(11) -0.0027(10) 0.0039(9) -0.0018(9) C9 0.0426(12) 0.0566(13) 0.0269(11) -0.0047(10) 0.0045(10) -0.0032(10) C10 0.0199(9) 0.0311(11) 0.0356(11) -0.0009(10) 0.0005(9) -0.0026(9) C11 0.0182(9) 0.0253(10) 0.0349(12) -0.0027(10) 0.0055(9) -0.0026(8) C12 0.0199(9) 0.0273(10) 0.0349(12) -0.0043(9) 0.0063(9) -0.0007(8) C13 0.0300(10) 0.0265(11) 0.0407(12) -0.0009(10) 0.0082(9) 0.0018(9) C14 0.0389(12) 0.0228(11) 0.0577(15) -0.0023(11) 0.0091(11) -0.0022(9) C15 0.0318(11) 0.0351(12) 0.0465(13) -0.0168(11) 0.0025(10) -0.0055(9) C16 0.0209(10) 0.0354(12) 0.0342(12) -0.0025(10) 0.0035(9) -0.0017(8) C17 0.0218(12) 0.0627(15) 0.0292(14) -0.0102(10) -0.0039(11) -0.0033(10) C18 0.0341(12) 0.1032(19) 0.0343(13) 0.0136(14) 0.0025(10) 0.0116(12) C19 0.0441(12) 0.0497(13) 0.0300(12) -0.0055(10) 0.0052(10) -0.0055(10) C20 0.0549(13) 0.0329(12) 0.0505(14) 0.0080(11) 0.0125(11) 0.0062(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 O1 C7 1.3677(19) . ? O1 C10 1.4162(19) . ? O2 C7 1.2003(19) . ? O3 C8 1.366(2) . ? O3 C2 1.4005(19) . ? O4 C8 1.197(2) . ? O5 C10 1.1866(19) . ? O6 C17 1.375(2) . ? O6 C16 1.399(2) . ? O7 C17 1.190(2) . ? C1 C6 1.390(2) . ? C1 C2 1.397(2) . ? C1 C7 1.483(2) . ? C2 C3 1.367(2) . ? C3 C4 1.384(2) . ? C3 H3A 0.950 . ? C4 C5 1.391(2) . ? C4 H4A 0.950 . ? C5 C6 1.383(2) . ? C5 C19 1.502(2) . ? C6 H6A 0.950 . ? C8 C9 1.485(2) . ? C9 H9A 0.980 . ? C9 H9B 0.980 . ? C9 H9C 0.980 . ? C10 C11 1.469(3) . ? C11 C12 1.390(2) . ? C11 C16 1.393(2) . ? C12 C13 1.383(2) . ? C12 H12A 0.950 . ? C13 C14 1.384(2) . ? C13 C20 1.508(2) . ? C14 C15 1.383(3) . ? C14 H14A 0.950 . ? C15 C16 1.376(2) . ? C15 H15A 0.950 . ? C17 C18 1.486(3) . ? C18 H18A 0.980 . ? C18 H18B 0.980 . ? C18 H18C 0.980 . ? C19 H19A 0.980 . ? C19 H19D 0.980 . ? C19 H19B 0.980 . ? C20 H20D 0.980 . ? C20 H20A 0.980 . ? C20 H20B 0.980 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 C10 115.40(13) . . ? C8 O3 C2 116.63(13) . . ? C17 O6 C16 115.85(15) . . ? C6 C1 C2 118.21(16) . . ? C6 C1 C7 121.11(16) . . ? C2 C1 C7 120.67(16) . . ? C3 C2 C1 121.15(16) . . ? C3 C2 O3 119.24(15) . . ? C1 C2 O3 119.48(15) . . ? C2 C3 C4 119.37(16) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 121.49(16) . . ? C3 C4 H4A 119.3 . . ? C5 C4 H4A 119.3 . . ? C6 C5 C4 117.89(17) . . ? C6 C5 C19 120.71(16) . . ? C4 C5 C19 121.40(16) . . ? C5 C6 C1 121.90(17) . . ? C5 C6 H6A 119.0 . . ? C1 C6 H6A 119.0 . . ? O2 C7 O1 122.30(15) . . ? O2 C7 C1 126.85(16) . . ? O1 C7 C1 110.83(15) . . ? O4 C8 O3 122.37(17) . . ? O4 C8 C9 127.16(18) . . ? O3 C8 C9 110.47(17) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 O1 117.49(16) . . ? O5 C10 C11 128.07(16) . . ? O1 C10 C11 114.31(14) . . ? C12 C11 C16 118.66(17) . . ? C12 C11 C10 121.13(15) . . ? C16 C11 C10 120.19(16) . . ? C13 C12 C11 121.70(17) . . ? C13 C12 H12A 119.2 . . ? C11 C12 H12A 119.2 . . ? C12 C13 C14 118.12(18) . . ? C12 C13 C20 120.48(17) . . ? C14 C13 C20 121.40(16) . . ? C15 C14 C13 121.42(18) . . ? C15 C14 H14A 119.3 . . ? C13 C14 H14A 119.3 . . ? C16 C15 C14 119.65(18) . . ? C16 C15 H15A 120.2 . . ? C14 C15 H15A 120.2 . . ? C15 C16 C11 120.44(18) . . ? C15 C16 O6 119.21(16) . . ? C11 C16 O6 120.16(16) . . ? O7 C17 O6 122.30(19) . . ? O7 C17 C18 127.24(18) . . ? O6 C17 C18 110.45(19) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C5 C19 H19A 109.5 . . ? C5 C19 H19D 109.5 . . ? H19A C19 H19D 109.5 . . ? C5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? H19D C19 H19B 109.5 . . ? C13 C20 H20D 109.5 . . ? C13 C20 H20A 109.5 . . ? H20D C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20D C20 H20B 109.5 . . ? H20A C20 H20B 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 C6 C1 C2 C3 0.2(2) . . . . ? C7 C1 C2 C3 -178.43(14) . . . . ? C6 C1 C2 O3 175.94(14) . . . . ? C7 C1 C2 O3 -2.7(2) . . . . ? C8 O3 C2 C3 -95.14(17) . . . . ? C8 O3 C2 C1 89.02(17) . . . . ? C1 C2 C3 C4 -0.4(2) . . . . ? O3 C2 C3 C4 -176.14(14) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C3 C4 C5 C19 -179.73(16) . . . . ? C4 C5 C6 C1 -0.8(2) . . . . ? C19 C5 C6 C1 179.53(16) . . . . ? C2 C1 C6 C5 0.4(2) . . . . ? C7 C1 C6 C5 179.04(14) . . . . ? C10 O1 C7 O2 -5.3(2) . . . . ? C10 O1 C7 C1 176.12(13) . . . . ? C6 C1 C7 O2 156.54(17) . . . . ? C2 C1 C7 O2 -24.9(2) . . . . ? C6 C1 C7 O1 -25.0(2) . . . . ? C2 C1 C7 O1 153.60(14) . . . . ? C2 O3 C8 O4 11.0(2) . . . . ? C2 O3 C8 C9 -168.69(14) . . . . ? C7 O1 C10 O5 111.64(18) . . . . ? C7 O1 C10 C11 -72.14(17) . . . . ? O5 C10 C11 C12 153.4(2) . . . . ? O1 C10 C11 C12 -22.3(2) . . . . ? O5 C10 C11 C16 -24.9(3) . . . . ? O1 C10 C11 C16 159.34(16) . . . . ? C16 C11 C12 C13 0.4(2) . . . . ? C10 C11 C12 C13 -178.00(15) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C11 C12 C13 C20 179.72(17) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C20 C13 C14 C15 179.46(17) . . . . ? C13 C14 C15 C16 1.3(3) . . . . ? C14 C15 C16 C11 -1.0(3) . . . . ? C14 C15 C16 O6 -176.11(16) . . . . ? C12 C11 C16 C15 0.2(3) . . . . ? C10 C11 C16 C15 178.56(15) . . . . ? C12 C11 C16 O6 175.27(14) . . . . ? C10 C11 C16 O6 -6.3(2) . . . . ? C17 O6 C16 C15 -95.51(18) . . . . ? C17 O6 C16 C11 89.33(19) . . . . ? C16 O6 C17 O7 7.5(2) . . . . ? C16 O6 C17 C18 -172.99(16) . . . . ? #===END