# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. # 1. SUBMISSION DETAILS _journal_coden_Cambridge 0182 #============================================================================== loop_ _audit_conform.dict_name _audit_conform.dict_version _audit_conform.dict_location cif_core.dic . ftp://ftp.iucr.org/pub/cif_core.dic cif_pd.dic . ftp://ftp.iucr.org/pub/cif_pd.dic _publ_contact_author_name 'Maryjane Tremayne' _publ_contact_author_address ; School of Chemistry University of Birmingham Edgbaston Birmingham, B15 2TT UK ; _publ_contact_author_email m.tremayne@bham.ac.uk _publ_contact_author_fax 44-121-414-3808 _publ_contact_author_phone 44-121-414-3201 _publ_contact_letter ; ? ; # 3. TITLE AND AUTHOR LIST _publ_section_title ; Combined optimization using Cultural and Differential Evolution: Application to crystal structure solution from powder diffraction data. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address M.Tremayne ; School of Chemistry University of Birmingham Edgbaston Birmingham, B15 2TT UK ; S.Y.Chong ; School of Chemistry University of Birmingham Edgbaston Birmingham, B15 2TT UK ; #============================================================================== # If more than one structure is reported, sections 5-10 should be completed # per structure. For each data set, replace the '?' in the data_? line below # by a unique identifier. #============================================================================== data_mprs _database_code_depnum_ccdc_archive 'CCDC 613003' loop_ _audit_conform.dict_name _audit_conform.dict_version _audit_conform.dict_location cif_core.dic . ftp://ftp.iucr.org/pub/cif_core.dic cif_pd.dic . ftp://ftp.iucr.org/pub/cif_pd.dic # 5. CHEMICAL DATA _chemical_name_systematic ; 3-Methyl-3-propylpyrrolidine-2,5-dione ; _chemical_name_common 3-Methyl-3-propylpyrrolidine-2,5-dione _chemical_formula_moiety 'C8 H13 N O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H13 N O2' _chemical_formula_weight 155.19 _chemical_melting_point ? _chemical_compound_source ? 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz #<--must include 'x,y,z' 1 +x,+y,+z 2 -x,+y+1/2,-z+1/2 -1 -x,-y,-z -2 +x,-y+1/2,+z+1/2 _cell_length_a 12.301(2) _cell_length_b 6.0698(4) _cell_length_c 11.6656(4) _cell_angle_alpha 90.0 _cell_angle_beta 100.958(4) _cell_angle_gamma 90.0 _cell_volume 855.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_special_details ; ? ; # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; 'disc' ; _pd_spec_mount_mode transmission # options are 'reflection' # or 'transmission' _pd_spec_shape ? # options are 'cylinder' # 'flat_sheet' or 'irregular' # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.706 #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; ? ; _pd_calibration_special_details # description of the method used # to calibrate the instrument ; ? ; _diffrn_ambient_temperature 293 _diffrn_source 'sealed X-ray tube' _diffrn_source_target Cu _diffrn_source_type ? _diffrn_radiation_type 'Cu K\a~1~' _diffrn_measurement_device_type 'Bruker AXS D5000' _diffrn_detector ? _diffrn_detector_type 'position sensitive detector' _pd_meas_scan_method step # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 1.54056 _diffrn_radiation_monochromator Ge # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 2865 _pd_meas_2theta_range_min 4 _pd_meas_2theta_range_max 61 _pd_meas_2theta_range_inc 0.02 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function ? _pd_proc_ls_background_function ? _pd_proc_ls_pref_orient_corr ; ? ; _pd_proc_ls_prof_R_factor 0.0508 _pd_proc_ls_prof_wR_factor 0.0633 _pd_proc_ls_prof_wR_expected ? _refine_ls_R_I_factor ? _refine_ls_R_Fsqd_factor 0.198 _refine_ls_R_factor_all ? _refine_special_details ; ? ; _refine_ls_matrix_type ? _refine_ls_weighting_scheme ? # options are 'sigma' (based on measured su's) # or 'calc' (calculated weights) _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_number_parameters 105 _refine_ls_number_restraints 69 _refine_ls_number_constraints ? # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 1.04 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max 0.0 _refine_ls_shift/su_mean ? # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 4 _pd_proc_2theta_range_max 61 _pd_proc_2theta_range_inc 0.02 _pd_proc_wavelength 1.54056 # Each refinement must be accompanied by a listing of the powder data # in CIF format. Each listing should be sent as a separate file consisting # of one data block containing a single powder profile. The value of # _pd_block_diffractogram_id is used to associate each refinement with # its corresponding powder profile, since it must match the value # of _pd_block_id in the file containing the powder data. A template # for supplying powder data in CIF format is available by ftp at # ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given # at ftp://ftp.iucr.org/pub/rietdataxmpl.cif. _pd_block_diffractogram_id mprsprofile # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # The following items are used to identify the programs used. _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'POSSUM (Tremayne, Seaton 2002)' _computing_structure_refinement 'GSAS (Larson et al. 1994)' _computing_molecular_graphics ? _computing_publication_material ? #============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv N1 0.5177(12) 0.7552(27) 0.0857(14) 1.0 4 0.013(22) H1 0.4539(0) 0.8117(0) 0.0435(0) 1.0 4 0.05(0) C1 0.5295(12) 0.5752(35) 0.1617(21) 1.0 4 0.014(26) O1 0.4476(15) 0.4728(26) 0.1801(15) 1.0 4 0.022(11) C2 0.6441(14) 0.5131(20) 0.2066(14) 1.0 4 0.044(11) H2A 0.6587(22) 0.3443(21) 0.181(4) 1.0 4 0.05(0) H2B 0.6624(21) 0.528(6) 0.3016(14) 1.0 4 0.05(0) C3 0.7141(11) 0.6679(20) 0.1541(10) 1.0 4 0.044(11) C4 0.6311(12) 0.8327(23) 0.0893(13) 1.0 4 0.014(26) O4 0.6561(17) 0.9778(23) 0.0263(11) 1.0 4 0.022(11) C5 0.7699(15) 0.5531(28) 0.0604(9) 1.0 4 0.023(19) H5A 0.7073(19) 0.463(5) -0.0011(16) 1.0 4 0.05(0) H5B 0.8083(25) 0.677(4) 0.0133(24) 1.0 4 0.05(0) C6 0.8585(18) 0.3920(28) 0.1203(10) 1.0 4 0.023(19) H6A 0.8235(32) 0.286(6) 0.1800(28) 1.0 4 0.05(0) H6B 0.9285(23) 0.484(5) 0.1693(28) 1.0 4 0.05(0) C7 0.8975(23) 0.2506(23) 0.0283(13) 1.0 4 0.023(19) H7A 0.842(7) 0.267(22) -0.052(4) 1.0 4 0.05(0) H7B 0.977(6) 0.302(16) 0.018(11) 1.0 4 0.05(0) H7C 0.901(12) 0.084(5) 0.055(10) 1.0 4 0.05(0) C8 0.7993(15) 0.7892(31) 0.2477(14) 1.0 4 0.035(36) H8A 0.7572(30) 0.898(20) 0.295(8) 1.0 4 0.05(0) H8B 0.844(10) 0.673(5) 0.306(8) 1.0 4 0.05(0) H8C 0.855(9) 0.880(21) 0.2064(34) 1.0 4 0.05(0) # Note: if the displacement parameters were refined anisotropically # the U matrices should be given as for single-crystal studies. loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol ? ? ? ? ? ? ? ? #============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.40(3) . 1_555 N N1 H1 0.91 . 1_555 N C1 C2 1.46(2) . 1_555 N C1 O1 1.23(3) . 1_555 N C2 C3 1.48(2) . 1_555 N C2 H2A 1.09(2) . 1_555 N C2 H2B 1.09(2) . 1_555 N H2A H2B 1.79(4) . 1_555 N C3 C4 1.524(19) . 1_555 N C3 C8 1.55(2) . 1_555 N C3 C5 1.56(2) . 1_555 N C4 N1 1.47(2) . 1_555 N C4 O4 1.223(19) . 1_555 N O4 H1 1.92544(13) . -1_675 N C5 C6 1.53(3) . 1_555 N C5 H5B 1.09(3) . 1_555 N C5 H5A 1.09(3) . 1_555 N H5A H5B 1.78(4) . 1_555 N C6 C7 1.52(2) . 1_555 N C6 H6A 1.09(4) . 1_555 N C6 H6B 1.10(4) . 1_555 N H6A H6B 1.79(5) . 1_555 N C7 H7C 1.06(5) . 1_555 N C7 H7A 1.06(6) . 1_555 N C7 H7B 1.05(8) . 1_555 N H7A H7C 1.74(13) . 1_555 N H7A H7B 1.72(12) . 1_555 N H7B H7C 1.72(13) . 1_555 N C8 H8A 1.07(10) . 1_555 N C8 H8B 1.06(9) . 1_555 N C8 H8C 1.07(11) . 1_555 N H8A H8B 1.73(13) . 1_555 N H8A H8C 1.74(11) . 1_555 N H8B H8C 1.74(12) . 1_555 N 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 104.5(13) 1_555 . 1_555 N C1 N1 H1 127.00 1_555 . 1_555 N C4 N1 H1 127.00 1_555 . 1_555 N C2 C1 N1 113.9(15) 1_555 . 1_555 N C2 C1 O1 125(2) 1_555 . 1_555 N N1 C1 O1 120.7(17) 1_555 . 1_555 N C1 C2 C3 106.7(13) 1_555 . 1_555 N C1 C2 H2A 110(2) 1_555 . 1_555 N C1 C2 H2B 110(2) 1_555 . 1_555 N C3 C2 H2A 110(2) 1_555 . 1_555 N C3 C2 H2B 110(2) 1_555 . 1_555 N H2A C2 H2B 110(3) 1_555 . 1_555 N C2 C3 C4 103.6(12) 1_555 . 1_555 N C2 C3 C8 112.2(11) 1_555 . 1_555 N C2 C3 C5 111.9(11) 1_555 . 1_555 N C4 C3 C8 109.8(11) 1_555 . 1_555 N C4 C3 C5 106.8(10) 1_555 . 1_555 N C8 C3 C5 112.2(12) 1_555 . 1_555 N C3 C4 N1 110.2(12) 1_555 . 1_555 N C3 C4 O4 123.4(15) 1_555 . 1_555 N N1 C4 O4 124.2(16) 1_555 . 1_555 N C3 C5 C6 109.6(9) 1_555 . 1_555 N C3 C5 H5B 110(2) 1_555 . 1_555 N C3 C5 H5A 109.5(19) 1_555 . 1_555 N C6 C5 H5B 110(2) 1_555 . 1_555 N C6 C5 H5A 109(2) 1_555 . 1_555 N H5B C5 H5A 109(2) 1_555 . 1_555 N C5 C6 C7 109.4(11) 1_555 . 1_555 N C5 C6 H6A 110(3) 1_555 . 1_555 N C5 C6 H6B 110(2) 1_555 . 1_555 N C7 C6 H6A 110(2) 1_555 . 1_555 N C7 C6 H6B 109(2) 1_555 . 1_555 N H6A C6 H6B 110(3) 1_555 . 1_555 N C6 C7 H7C 109(6) 1_555 . 1_555 N C6 C7 H7A 109(6) 1_555 . 1_555 N C6 C7 H7B 110(6) 1_555 . 1_555 N H7C C7 H7A 110(9) 1_555 . 1_555 N H7C C7 H7B 110(10) 1_555 . 1_555 N H7A C7 H7B 109(8) 1_555 . 1_555 N C3 C8 H8A 110(4) 1_555 . 1_555 N C3 C8 H8B 110(4) 1_555 . 1_555 N C3 C8 H8C 109(3) 1_555 . 1_555 N H8A C8 H8B 109(7) 1_555 . 1_555 N H8A C8 H8C 109(8) 1_555 . 1_555 N H8B C8 H8C 110(8) 1_555 . 1_555 N loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1 O4 3_675 0.91 1.93 2.80(1) 161(1) C8 H8A O1 2_655 1.07(8) 2.63(5) 3.49(3) 138(1) C5 H5A O1 3_665 1.09(3) 2.58(3) 3.49(1) 141(1) #============================================================================== # Additional structures (sections 5-10 and associated data_? identifiers) # may be added at this point. #============================================================================== # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./