# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Hursthouse, Mike' 'Montis, Riccardo' 'Leusen, Frank' 'Kendrick, John' _publ_contact_author_name 'Dr Mike Hursthouse' _publ_contact_author_email mbh@soton.ac.uk _publ_section_title ; Experimental and theoretical investigations of the polymorphism of 5-chloroacetoxybenzoic acid (5-chloroaspirin) ; # Attachment '- ESI_5ClAsp_2.cif' data_2-acetyloxy-5-chlorobenzoic_acid _database_code_depnum_ccdc_archive 'CCDC 846937' #TrackingRef '- ESI_5ClAsp_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-5-chlorobenzoic acid' ; _chemical_name_common '5-Chloroaspirin beta form' _chemical_melting_point 147 _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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.0853(2) _cell_length_b 17.8953(10) _cell_length_c 10.4472(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.267(3) _cell_angle_gamma 90.00 _cell_volume 940.85(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6451 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.389 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9262 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10972 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2150 _reflns_number_gt 1671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.7309P] 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 2150 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0361(4) 0.41890(11) -0.31788(18) 0.0156(4) Uani 1 1 d . . . C2 C 0.2060(4) 0.36999(11) -0.37107(18) 0.0166(4) Uani 1 1 d . . . C3 C 0.4123(4) 0.33433(11) -0.2948(2) 0.0202(4) Uani 1 1 d . . . H3 H 0.5246 0.3013 -0.3332 0.024 Uiso 1 1 calc R . . C4 C 0.4566(4) 0.34646(12) -0.1621(2) 0.0214(4) Uani 1 1 d . . . H4 H 0.5972 0.3217 -0.1089 0.026 Uiso 1 1 calc R . . C5 C 0.2915(4) 0.39545(11) -0.10920(19) 0.0202(4) Uani 1 1 d . . . C6 C 0.0828(4) 0.43146(11) -0.18436(19) 0.0193(4) Uani 1 1 d . . . H6 H -0.0282 0.4646 -0.1454 0.023 Uiso 1 1 calc R . . C7 C -0.1915(4) 0.45678(11) -0.39831(19) 0.0164(4) Uani 1 1 d . . . C8 C -0.0083(4) 0.31195(11) -0.5602(2) 0.0212(4) Uani 1 1 d . . . C9 C -0.0357(5) 0.31579(14) -0.7035(2) 0.0341(6) Uani 1 1 d . . . H9A H -0.0807 0.2662 -0.7400 0.051 Uiso 1 1 calc R . . H9B H 0.1325 0.3325 -0.7294 0.051 Uiso 1 1 calc R . . H9C H -0.1769 0.3512 -0.7357 0.051 Uiso 1 1 calc R . . O1 O -0.3174(3) 0.50447(8) -0.33233(13) 0.0200(3) Uani 1 1 d . . . H1 H -0.4485 0.5223 -0.3808 0.030 Uiso 1 1 calc R . . O2 O -0.2579(3) 0.44389(8) -0.51332(13) 0.0202(3) Uani 1 1 d . . . O3 O 0.1850(3) 0.35994(8) -0.50466(13) 0.0188(3) Uani 1 1 d . . . O4 O -0.1322(3) 0.27328(9) -0.49609(15) 0.0299(4) Uani 1 1 d . . . Cl1 Cl 0.34707(11) 0.41281(3) 0.05667(5) 0.03136(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0143(9) 0.0160(10) 0.0161(10) 0.0011(8) 0.0004(7) -0.0018(7) C2 0.0173(9) 0.0186(10) 0.0142(10) 0.0005(8) 0.0030(7) -0.0037(7) C3 0.0182(10) 0.0198(11) 0.0225(11) 0.0024(9) 0.0028(8) 0.0010(8) C4 0.0190(10) 0.0240(11) 0.0200(11) 0.0055(9) -0.0012(8) 0.0028(8) C5 0.0222(10) 0.0227(11) 0.0146(10) 0.0026(8) -0.0007(7) -0.0013(8) C6 0.0199(10) 0.0206(11) 0.0173(10) 0.0007(8) 0.0017(8) 0.0021(8) C7 0.0156(9) 0.0174(10) 0.0164(10) 0.0010(8) 0.0023(7) -0.0027(7) C8 0.0251(11) 0.0198(11) 0.0188(11) -0.0034(8) 0.0033(8) 0.0002(8) C9 0.0447(14) 0.0387(14) 0.0186(12) -0.0063(10) 0.0037(10) -0.0048(11) O1 0.0200(7) 0.0222(8) 0.0166(7) -0.0008(6) -0.0015(5) 0.0063(6) O2 0.0198(7) 0.0237(8) 0.0159(8) -0.0018(6) -0.0017(5) 0.0025(6) O3 0.0184(7) 0.0231(8) 0.0151(7) -0.0005(6) 0.0026(5) -0.0008(5) O4 0.0387(9) 0.0285(9) 0.0223(8) -0.0032(7) 0.0046(7) -0.0126(7) Cl1 0.0351(3) 0.0425(4) 0.0144(3) 0.0006(2) -0.0038(2) 0.0082(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.399(3) . ? C1 C2 1.400(3) . ? C1 C7 1.492(3) . ? C2 C3 1.379(3) . ? C2 O3 1.396(2) . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 Cl1 1.743(2) . ? C6 H6 0.9500 . ? C7 O2 1.222(2) . ? C7 O1 1.319(2) . ? C8 O4 1.203(2) . ? C8 O3 1.370(2) . ? C8 C9 1.485(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O1 H1 0.8400 . ? 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 C6 C1 C2 118.04(17) . . ? C6 C1 C7 119.70(17) . . ? C2 C1 C7 122.25(17) . . ? C3 C2 O3 117.41(17) . . ? C3 C2 C1 121.44(18) . . ? O3 C2 C1 120.97(17) . . ? C2 C3 C4 120.34(18) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 118.51(18) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 121.86(19) . . ? C4 C5 Cl1 119.31(15) . . ? C6 C5 Cl1 118.83(16) . . ? C5 C6 C1 119.81(18) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O2 C7 O1 123.34(17) . . ? O2 C7 C1 123.37(17) . . ? O1 C7 C1 113.28(16) . . ? O4 C8 O3 121.75(19) . . ? O4 C8 C9 127.4(2) . . ? O3 C8 C9 110.84(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 . . ? C7 O1 H1 109.5 . . ? C8 O3 C2 116.84(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.84 1.83 2.6676(18) 176.9 3_464 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.318 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.071 # Attachment '- ESI_5ClAsp_3.cif' # # Structure prediction using Avant-garde Materials Simulation Software # GRACE # Calculations by: # Stephen Chan, John Kendrick and Frank Leusen # # Rank: 1 # Energy: -152.0931685 kcals/mol/atom # Relative energy: 0.0 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank01 _database_code_depnum_ccdc_archive 'CCDC 846938' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.698131 _cell_length_b 7.668607 _cell_length_c 11.265813 _cell_angle_alpha 96.807403 _cell_angle_beta 94.343552 _cell_angle_gamma 72.652214 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C 0.566370 0.372364 0.674696 C2_0 C 0.436679 0.448203 0.779169 C6_0 C 0.722007 0.464022 0.636137 C7_0 C 0.538144 0.205381 0.601054 C3_0 C 0.463214 0.608597 0.842560 O3_0 O 0.261436 0.377418 0.818839 C5_0 C 0.743014 0.625972 0.699003 H6_0 H 0.823761 0.407528 0.555823 O2_0 O 0.390352 0.123693 0.624374 O1_0 O 0.679797 0.153033 0.508163 H3_0 H 0.359597 0.664120 0.922619 C4_0 C 0.615636 0.699574 0.802878 C8_0 C 0.340326 0.212421 0.867660 Cl1_0 Cl 0.928558 0.740460 0.645861 H2_0 H 0.647450 0.039533 0.457810 H4_0 H 0.631231 0.827984 0.850478 C9_0 C 0.128414 0.143771 0.886292 O4_0 O 0.556997 0.138711 0.891765 H9A_0 H 0.176650 0.052935 0.957772 H9B_0 H 0.090430 0.065001 0.802886 H9C_0 H -0.038830 0.256346 0.905026 #END # # Rank: 2 # Energy: -152.089305 kcals/mol/atom # Relative energy: 0.0038635 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank02 _database_code_depnum_ccdc_archive 'CCDC 846939' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2_1/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y+1/2,-z+1/2 3 -x,-y,-z 4 x,-y+1/2,z+1/2 _cell_length_a 10.215715 _cell_length_b 4.755658 _cell_length_c 20.698040 _cell_angle_alpha 90.000000 _cell_angle_beta 112.235745 _cell_angle_gamma 90.000000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C -0.203269 0.130985 0.081299 C2_0 C -0.183604 -0.088384 0.129613 C6_0 C -0.085065 0.230059 0.069319 C7_0 C -0.339017 0.276836 0.042871 C3_0 C -0.049285 -0.196562 0.166479 O3_0 O -0.297659 -0.224875 0.137190 C5_0 C 0.048122 0.118394 0.105760 H6_0 H -0.100378 0.397174 0.031328 O2_0 O -0.346354 0.454394 -0.002928 O1_0 O -0.446248 0.215570 0.060740 H3_0 H -0.037071 -0.365976 0.203654 C4_0 C 0.067928 -0.093022 0.155290 C8_0 C -0.354765 -0.116378 0.182536 Cl1_0 Cl 0.191355 0.248005 0.089275 H2_0 H -0.530230 0.350276 0.034975 H4_0 H 0.172172 -0.179164 0.184601 C9_0 C -0.482945 -0.279576 0.177516 O4_0 O -0.303567 0.085147 0.219778 H9A_0 H -0.460969 -0.505308 0.178442 H9B_0 H -0.568257 -0.232753 0.127249 H9C_0 H -0.516756 -0.222949 0.219884 #END # # Rank: 3 # Energy: -152.0810178 kcals/mol/atom # Relative energy: 0.0121507 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank03 _database_code_depnum_ccdc_archive 'CCDC 846940' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.636700 _cell_length_b 7.569624 _cell_length_c 11.502712 _cell_angle_alpha 96.704352 _cell_angle_beta 94.264441 _cell_angle_gamma 73.325119 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C 0.561165 1.375567 -0.326088 C2_0 C 0.436080 1.450750 -0.222360 C6_0 C 0.718189 1.468362 -0.365235 C7_0 C 0.535261 1.207951 -0.401304 C3_0 C 0.468890 1.611575 -0.160266 O3_0 O 0.258939 1.379328 -0.181782 C5_0 C 0.745723 1.630617 -0.303736 H6_0 H 0.815147 1.411106 -0.445326 O2_0 O 0.658282 1.151992 -0.491029 O1_0 O 0.376493 1.127036 -0.368923 H3_0 H 0.368673 1.666822 -0.080719 C4_0 C 0.623045 1.703500 -0.200482 C8_0 C 0.338607 1.217146 -0.129240 Cl1_0 Cl 0.933076 1.746272 -0.357674 H2_0 H 0.367367 1.014066 -0.428536 H4_0 H 0.643196 1.832179 -0.153571 C9_0 C 0.125489 1.147475 -0.107720 O4_0 O 0.557093 1.145611 -0.105228 H9A_0 H -0.040927 1.261046 -0.087762 H9B_0 H 0.081221 1.068391 -0.188620 H9C_0 H 0.177066 1.055627 -0.037830 #END # # Rank: 4 # Energy: -152.080154 kcals/mol/atom # Relative energy: 0.0130145 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank04 _database_code_depnum_ccdc_archive 'CCDC 846941' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2_1/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y+1/2,-z+1/2 3 -x,-y,-z 4 x,-y+1/2,z+1/2 _cell_length_a 10.389333 _cell_length_b 4.743047 _cell_length_c 20.497275 _cell_angle_alpha 90.000000 _cell_angle_beta 111.766082 _cell_angle_gamma 90.000000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C 0.795116 -0.646511 0.583616 C2_0 C 0.812303 -0.426598 0.632158 C6_0 C 0.912507 -0.743625 0.572026 C7_0 C 0.660191 -0.785975 0.545540 C3_0 C 0.942974 -0.315078 0.669311 O3_0 O 0.699477 -0.293076 0.639807 C5_0 C 1.042154 -0.628877 0.608979 H6_0 H 0.900547 -0.911135 0.534089 O2_0 O 0.553330 -0.733532 0.557565 O1_0 O 0.664355 -0.973509 0.498861 H3_0 H 0.952677 -0.145284 0.706527 C4_0 C 1.059413 -0.416263 0.658538 C8_0 C 0.635927 -0.416498 0.681058 Cl1_0 Cl 1.184316 -0.757155 0.592981 H2_0 H 0.571935 -1.085967 0.477143 H4_0 H 1.161133 -0.328803 0.688332 C9_0 C 0.506368 -0.260997 0.673516 O4_0 O 0.683581 -0.622893 0.717204 H9A_0 H 0.521252 -0.034006 0.669771 H9B_0 H 0.473877 -0.308361 0.717241 H9C_0 H 0.424513 -0.329122 0.624409 #END # # Rank: 5 # Energy: -152.0800849 kcals/mol/atom # Relative energy: 0.0130836 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank05 _database_code_depnum_ccdc_archive 'CCDC 846942' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2_1/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y+1/2,-z+1/2 3 -x,-y,-z 4 x,-y+1/2,z+1/2 _cell_length_a 5.087961 _cell_length_b 18.234094 _cell_length_c 10.287294 _cell_angle_alpha 90.000000 _cell_angle_beta 98.030769 _cell_angle_gamma 90.000000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C 0.027179 0.581249 0.678984 C2_0 C 0.193592 0.630875 0.624621 C6_0 C 0.079123 0.567179 0.814288 C7_0 C -0.199754 0.543983 0.599236 C3_0 C 0.399052 0.666636 0.702893 O3_0 O 0.173253 0.641911 0.489661 C5_0 C 0.287221 0.602582 0.891228 H6_0 H -0.045230 0.528406 0.857874 O2_0 O -0.265155 0.556973 0.480006 O1_0 O -0.328179 0.496982 0.664998 H3_0 H 0.522859 0.704294 0.656092 C4_0 C 0.447098 0.653171 0.837312 C8_0 C -0.020720 0.688846 0.432201 Cl1_0 Cl 0.350299 0.582593 1.057948 H2_0 H -0.487282 0.475275 0.603631 H4_0 H 0.605351 0.682099 0.899076 C9_0 C -0.042110 0.685995 0.286293 O4_0 O -0.152611 0.726504 0.496686 H9A_0 H -0.209931 0.650145 0.250000 H9B_0 H 0.136039 0.663067 0.253859 H9C_0 H -0.082215 0.740411 0.243686 #END # # Rank: 6 # Energy: -152.0787923 kcals/mol/atom # Relative energy: 0.0143762 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank06 _database_code_depnum_ccdc_archive 'CCDC 846943' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2_1/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y+1/2,-z+1/2 3 -x,-y,-z 4 x,-y+1/2,z+1/2 _cell_length_a 10.312932 _cell_length_b 4.794936 _cell_length_c 19.859244 _cell_angle_alpha 90.000000 _cell_angle_beta 69.295081 _cell_angle_gamma 90.000000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C -0.168250 0.171266 0.155295 C2_0 C -0.264198 -0.047979 0.167100 C6_0 C -0.148094 0.292905 0.215120 C7_0 C -0.088437 0.296234 0.084309 C3_0 C -0.340143 -0.136581 0.236662 O3_0 O -0.277100 -0.200979 0.110063 C5_0 C -0.224191 0.202852 0.284271 H6_0 H -0.072920 0.460624 0.205905 O2_0 O 0.004959 0.469454 0.079397 O1_0 O -0.123753 0.221555 0.029378 H3_0 H -0.413717 -0.306960 0.244620 C4_0 C -0.321501 -0.010846 0.295776 C8_0 C -0.367481 -0.107691 0.077811 Cl1_0 Cl -0.198803 0.361606 0.357061 H2_0 H -0.070751 0.344923 -0.014904 H4_0 H -0.381347 -0.082959 0.349673 C9_0 C -0.357893 -0.286277 0.014768 O4_0 O -0.443178 0.092235 0.100565 H9A_0 H -0.250620 -0.290583 -0.023143 H9B_0 H -0.426629 -0.207270 -0.011911 H9C_0 H -0.385207 -0.501613 0.033001 #END # # Rank: 7 # Energy: -152.0709785 kcals/mol/atom # Relative energy: 0.0221900 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank07 _database_code_depnum_ccdc_archive 'CCDC 846944' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2_1/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y+1/2,-z+1/2 3 -x,-y,-z 4 x,-y+1/2,z+1/2 _cell_length_a 10.206399 _cell_length_b 4.814215 _cell_length_c 20.192409 _cell_angle_alpha 90.000000 _cell_angle_beta 69.304793 _cell_angle_gamma 90.000000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C -1.169208 0.187348 0.655316 C2_0 C -1.264904 -0.033201 0.666632 C6_0 C -1.149866 0.308690 0.714432 C7_0 C -1.091650 0.305982 0.584392 C3_0 C -1.341258 -0.123711 0.734855 O3_0 O -1.277084 -0.185522 0.610387 C5_0 C -1.226362 0.216240 0.782285 H6_0 H -1.075325 0.477624 0.706323 O2_0 O -1.118204 0.244149 0.530449 O1_0 O -0.994434 0.486540 0.584350 H3_0 H -1.414584 -0.294956 0.742231 C4_0 C -1.323372 0.001196 0.793276 C8_0 C -1.366055 -0.090280 0.577489 Cl1_0 Cl -1.201577 0.373908 0.854173 H2_0 H -0.951626 0.590168 0.536248 H4_0 H -1.383588 -0.072302 0.846172 C9_0 C -1.355849 -0.269504 0.515620 O4_0 O -1.441475 0.110833 0.599026 H9A_0 H -1.377611 -0.485946 0.533037 H9B_0 H -1.248462 -0.263414 0.477275 H9C_0 H -1.428608 -0.198428 0.490499 #END # # Rank: 8 # Energy: -152.0679582 kcals/mol/atom # Relative energy: 0.0252103 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank08 _database_code_depnum_ccdc_archive 'CCDC 846945' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,-z+1/2 3 -x,-y,-z 4 x,-y,z+1/2 5 x+1/2,y+1/2,z 6 -x+1/2,y+1/2,-z+1/2 7 -x+1/2,-y+1/2,-z 8 x+1/2,-y+1/2,z+1/2 _cell_length_a 14.203804 _cell_length_b 5.679548 _cell_length_c 22.999630 _cell_angle_alpha 90.000000 _cell_angle_beta 96.719397 _cell_angle_gamma 90.000000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C -0.064495 0.020971 0.087047 C2_0 C -0.024366 0.122013 0.140152 C6_0 C -0.021396 -0.181203 0.066990 C7_0 C -0.147182 0.123702 0.050180 C3_0 C 0.054585 0.021824 0.172239 O3_0 O -0.055089 0.337048 0.160202 C5_0 C 0.058960 -0.275399 0.098644 H6_0 H -0.051065 -0.261578 0.026103 O2_0 O -0.184584 0.313539 0.062288 O1_0 O -0.176696 -0.002145 0.003255 H3_0 H 0.084367 0.103783 0.213012 C4_0 C 0.097173 -0.177230 0.151692 C8_0 C -0.139869 0.347399 0.183430 Cl1_0 Cl 0.113925 -0.518682 0.071578 H2_0 H -0.233040 0.079109 -0.021549 H4_0 H 0.160435 -0.252790 0.175856 C9_0 C -0.168652 0.596355 0.191778 O4_0 O -0.182442 0.170506 0.195396 H9A_0 H -0.107106 0.711035 0.201907 H9B_0 H -0.216189 0.607813 0.225766 H9C_0 H -0.206583 0.658841 0.150281 #END # # Rank: 9 # Energy: -152.0617212 kcals/mol/atom # Relative energy: 0.0314473 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank09 _database_code_depnum_ccdc_archive 'CCDC 846946' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.664365 _cell_length_b 7.633939 _cell_length_c 11.774226 _cell_angle_alpha 107.590760 _cell_angle_beta 91.793664 _cell_angle_gamma 74.749124 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C 0.434747 0.735695 0.673790 C2_0 C 0.565540 0.726287 0.776414 C6_0 C 0.277636 0.616820 0.635563 C7_0 C 0.462713 0.858399 0.601185 C3_0 C 0.539005 0.602861 0.838198 O3_0 O 0.741996 0.825132 0.815096 C5_0 C 0.256103 0.492196 0.696901 H6_0 H 0.175109 0.622533 0.556670 O2_0 O 0.609516 0.959545 0.624421 O1_0 O 0.322180 0.848391 0.509218 H3_0 H 0.642380 0.601490 0.917447 C4_0 C 0.385019 0.483998 0.798845 C8_0 C 0.666883 1.019944 0.865634 Cl1_0 Cl 0.067828 0.341657 0.643731 H2_0 H 0.354206 0.930780 0.458407 H4_0 H 0.368846 0.383285 0.844954 C9_0 C 0.880103 1.104138 0.881955 O4_0 O 0.452426 1.106293 0.891766 H9A_0 H 0.853062 1.221071 0.965662 H9B_0 H 0.888014 1.162864 0.808120 H9C_0 H 1.054442 0.999050 0.879440 #END # # Rank: 10 # Energy: -152.0578962 kcals/mol/atom # Relative energy: 0.0352723 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank10 _database_code_depnum_ccdc_archive 'CCDC 846947' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2_1/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y+1/2,-z+1/2 3 -x,-y,-z 4 x,-y+1/2,z+1/2 _cell_length_a 4.808232 _cell_length_b 19.470672 _cell_length_c 11.1683705837728 _cell_angle_alpha 90 _cell_angle_beta 115.216232749444 _cell_angle_gamma 90 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C 0.113663 0.923299 1.234651 C2_0 C 0.316054 0.876790 1.216735 C6_0 C 0.144333 0.934971 1.363646 C7_0 C -0.142348 0.959762 1.127225 C3_0 C 0.535030 0.841731 1.323955 O3_0 O 0.324180 0.868962 1.094162 C5_0 C 0.364028 0.899793 1.469919 H6_0 H -0.009984 0.971490 1.377802 O2_0 O -0.286197 1.005693 1.155349 O1_0 O -0.212487 0.939773 1.005248 H3_0 H 0.688532 0.805848 1.307568 C4_0 C 0.559786 0.852491 1.451282 C8_0 C 0.145417 0.818504 1.009709 Cl1_0 Cl 0.389187 0.914715 1.627428 H2_0 H -0.414230 0.964111 0.941729 H4_0 H 0.730287 0.824142 1.533622 C9_0 C 0.176626 0.820875 0.882250 O4_0 O -0.011263 0.779357 1.040046 H9A_0 H 0.057120 0.777572 0.819218 H9B_0 H 0.420347 0.819889 0.902142 H9C_0 H 0.079964 0.869381 0.831519 #END # # Rank: 11 # Energy: -152.0569866 kcals/mol/atom # Relative energy: 0.0361819 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank11 _database_code_depnum_ccdc_archive 'CCDC 846948' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.617291 _cell_length_b 7.527219 _cell_length_c 12.0390782856 _cell_angle_alpha 107.864735239 _cell_angle_beta 91.6219891191 _cell_angle_gamma 75.717246 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C 0.439906 -1.263987 -0.326923 C2_0 C 0.565766 -1.270357 -0.224906 C6_0 C 0.280934 -1.385462 -0.365660 C7_0 C 0.466095 -1.143658 -0.401130 C3_0 C 0.532123 -1.393330 -0.164198 O3_0 O 0.744465 -1.169106 -0.185387 C5_0 C 0.252059 -1.509640 -0.305499 H6_0 H 0.183478 -1.380972 -0.444427 O2_0 O 0.344575 -1.150577 -0.490233 O1_0 O 0.623011 -1.035541 -0.368868 H3_0 H 0.631250 -1.392228 -0.085175 C4_0 C 0.375932 -1.514644 -0.204026 C8_0 C 0.670222 -0.973466 -0.131057 Cl1_0 Cl 0.061327 -1.663292 -0.359409 H2_0 H 0.631773 -0.961982 -0.428644 H4_0 H 0.354720 -1.614688 -0.158323 C9_0 C 0.884855 -0.885717 -0.111905 O4_0 O 0.455041 -0.888689 -0.104845 H9A_0 H 0.857953 -0.770716 -0.028149 H9B_0 H 1.059505 -0.991346 -0.116173 H9C_0 H 0.893455 -0.821451 -0.181811 #END # # Rank: 12 # Energy: -152.0561969 kcals/mol/atom # Relative energy: 0.0369716 kcals/mol/atom # ############################################## # Avant-garde Materials Simulation # ############################################## data_QM_rank12 _database_code_depnum_ccdc_archive 'CCDC 846949' #TrackingRef '- ESI_5ClAsp_3.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,-z+1/2 3 -x,-y,-z 4 x,-y,z+1/2 5 x+1/2,y+1/2,z 6 -x+1/2,y+1/2,-z+1/2 7 -x+1/2,-y+1/2,-z 8 x+1/2,-y+1/2,z+1/2 _cell_length_a 14.026615 _cell_length_b 5.666110 _cell_length_c 23.548281 _cell_angle_alpha 90.000000 _cell_angle_beta 96.987375 _cell_angle_gamma 90.000000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1_0 C 0.437008 0.524826 0.086839 C2_0 C 0.477630 0.620239 0.139477 C6_0 C 0.479812 0.322871 0.066457 C7_0 C 0.353949 0.624668 0.049143 C3_0 C 0.556790 0.514610 0.170734 O3_0 O 0.447578 0.835241 0.160091 C5_0 C 0.560244 0.222811 0.097287 H6_0 H 0.449210 0.248761 0.025754 O2_0 O 0.322149 0.521277 0.003945 O1_0 O 0.318265 0.824575 0.065850 H3_0 H 0.587050 0.592364 0.211183 C4_0 C 0.598961 0.315531 0.149867 C8_0 C 0.364507 0.843293 0.185465 Cl1_0 Cl 0.614780 -0.020413 0.069904 H2_0 H 0.261673 0.881287 0.036365 H4_0 H 0.662272 0.235755 0.173553 C9_0 C 0.336547 1.092200 0.195621 O4_0 O 0.322168 0.665050 0.197285 H9A_0 H 0.288527 1.100260 0.228801 H9B_0 H 0.298557 1.161883 0.155567 H9C_0 H 0.399582 1.204300 0.206513 #END