# 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 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author 'Martins, Felipe Terra' _publ_contact_author_email felipe@quimica.ufg.br _publ_contact_author_name 'Felipe Terra Martins' loop_ _publ_author_name 'Felipe Terra Martins' 'de Lima, P.' 'Azarias, Lilian' 'de Abreu, Polyana' 'Neves, Person' 'Legendre, Alexandre' 'de Andrade, Fabiano' 'de Oliveira, Guilherme' 'Ellena, Javier' 'Doriguetto, Antonio' data_TiclopidineHCl_FormII _database_code_depnum_ccdc_archive 'CCDC 804556' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-[(2-Chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride ; _chemical_name_common 'ticlopidine hydrochloride form II' _chemical_melting_point ? _chemical_formula_sum 'C14 H15 Cl2 N S' _chemical_formula_weight 300.23 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 5.4410(2) _cell_length_b 12.2260(4) _cell_length_c 21.7050(7) _cell_angle_alpha 90 _cell_angle_beta 101.040(2) _cell_angle_gamma 90 _cell_volume 1417.13(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2647 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.103 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_size_max 0.548 _exptl_crystal_size_mid 0.091 _exptl_crystal_size_min 0.072 _exptl_crystal_F_000 624 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.033 0 -1 0 0.039 -1 0 0 0.257 1 0 0 0.291 0 0 -1 0.045 0 0 1 0.046 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.587 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.0037711 _diffrn_orient_matrix_ub_12 -0.0149656 _diffrn_orient_matrix_ub_13 0.0461128 _diffrn_orient_matrix_ub_21 -0.1840327 _diffrn_orient_matrix_ub_22 -0.0022847 _diffrn_orient_matrix_ub_23 -0.0020919 _diffrn_orient_matrix_ub_31 0.0045288 _diffrn_orient_matrix_ub_32 -0.0803776 _diffrn_orient_matrix_ub_33 -0.0085263 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_unetI/netI 0.0379 _diffrn_reflns_number 4993 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.95 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.934 _reflns_number_total 2592 _reflns_number_gt 2051 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0849P)^2^+0.8919P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2592 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1436 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.297 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.086 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' S S 0.1246 0.1234 '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' 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 0.63676(17) -0.05328(7) 0.89079(4) 0.0581(3) Uani 1 1 d . . . Cl2 Cl 0.84134(15) -0.08474(6) 0.74151(4) 0.0525(3) Uani 1 1 d . . . S1 S 0.6070(2) 0.12804(9) 0.53632(5) 0.0737(4) Uani 1 1 d . . . N1 N 0.5338(5) 0.1240(2) 0.73950(13) 0.0448(6) Uani 1 1 d . . . C2 C 0.6721(5) 0.2041(2) 0.64747(15) 0.0424(7) Uani 1 1 d . . . C9 C 0.7152(7) 0.1538(3) 0.85269(16) 0.0499(8) Uani 1 1 d . . . C10 C 0.8096(6) 0.0656(3) 0.89022(16) 0.0470(8) Uani 1 1 d . . . C7 C 0.6572(6) 0.2199(3) 0.71452(16) 0.0457(7) Uani 1 1 d . . . H7B H 0.5627 0.2858 0.7188 0.055 Uiso 1 1 calc R . . H7A H 0.8247 0.2292 0.7391 0.055 Uiso 1 1 calc R . . C1 C 0.5374(6) 0.1269(3) 0.61020(17) 0.0523(8) Uani 1 1 d . . . C14 C 0.8549(8) 0.2507(3) 0.86075(18) 0.0629(10) Uani 1 1 d . . . H14 H 0.7931 0.3125 0.8379 0.076 Uiso 1 1 calc R . . C8 C 0.4801(6) 0.1467(3) 0.80398(18) 0.0565(9) Uani 1 1 d . . . H8A H 0.3889 0.2151 0.8031 0.068 Uiso 1 1 calc R . . H8B H 0.3748 0.089 0.8153 0.068 Uiso 1 1 calc R . . C11 C 1.0408(7) 0.0708(3) 0.93016(17) 0.0572(9) Uani 1 1 d . . . H11 H 1.1037 0.0096 0.9534 0.069 Uiso 1 1 calc R . . C3 C 0.8281(6) 0.2663(3) 0.61556(16) 0.0502(8) Uani 1 1 d . . . H3 H 0.9298 0.3233 0.634 0.06 Uiso 1 1 calc R . . C6 C 0.2992(6) 0.0927(4) 0.6942(2) 0.0660(11) Uani 1 1 d . . . H6A H 0.1902 0.1559 0.6859 0.079 Uiso 1 1 calc R . . H6B H 0.2113 0.0365 0.7129 0.079 Uiso 1 1 calc R . . C12 C 1.1778(8) 0.1662(4) 0.93564(18) 0.0674(11) Uani 1 1 d . . . H12 H 1.334 0.1692 0.962 0.081 Uiso 1 1 calc R . . C5 C 0.3566(7) 0.0507(3) 0.6330(2) 0.0686(11) Uani 1 1 d . . . H5A H 0.4289 -0.0219 0.639 0.082 Uiso 1 1 calc R . . H5B H 0.2032 0.046 0.6018 0.082 Uiso 1 1 calc R . . C4 C 0.8130(8) 0.2339(3) 0.55536(18) 0.0620(10) Uani 1 1 d . . . H4 H 0.9036 0.2654 0.5277 0.074 Uiso 1 1 calc R . . C13 C 1.0831(9) 0.2567(4) 0.9020(2) 0.0731(12) Uani 1 1 d . . . H13 H 1.1718 0.3222 0.9068 0.088 Uiso 1 1 calc R . . H1 H 0.633(9) 0.065(4) 0.740(2) 0.088 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0662(6) 0.0431(5) 0.0685(6) 0.0107(4) 0.0219(4) -0.0016(4) Cl2 0.0541(5) 0.0376(4) 0.0698(6) 0.0047(4) 0.0217(4) 0.0079(3) S1 0.0999(8) 0.0622(7) 0.0530(6) -0.0009(4) -0.0005(5) -0.0095(6) N1 0.0364(13) 0.0358(14) 0.0638(17) 0.0107(12) 0.0133(12) 0.0030(11) C2 0.0407(15) 0.0350(16) 0.0509(17) 0.0037(13) 0.0071(13) 0.0040(12) C9 0.0598(19) 0.0399(17) 0.057(2) 0.0039(14) 0.0293(16) 0.0074(14) C10 0.0553(19) 0.0388(17) 0.0532(18) -0.0005(14) 0.0262(15) 0.0019(14) C7 0.0477(17) 0.0369(16) 0.0552(19) 0.0060(14) 0.0165(14) -0.0013(13) C1 0.0503(17) 0.0419(18) 0.060(2) 0.0090(15) -0.0003(15) -0.0030(15) C14 0.096(3) 0.0414(19) 0.061(2) 0.0015(16) 0.039(2) -0.0002(19) C8 0.0536(19) 0.051(2) 0.073(2) 0.0182(17) 0.0332(17) 0.0157(16) C11 0.070(2) 0.060(2) 0.0459(19) -0.0012(16) 0.0230(17) 0.0012(18) C3 0.0512(18) 0.0440(18) 0.057(2) 0.0061(15) 0.0138(15) -0.0032(14) C6 0.0369(17) 0.070(3) 0.087(3) 0.025(2) 0.0010(17) -0.0079(16) C12 0.076(3) 0.080(3) 0.050(2) -0.010(2) 0.0210(18) -0.013(2) C5 0.060(2) 0.058(2) 0.078(3) 0.012(2) -0.0103(19) -0.0197(18) C4 0.073(2) 0.062(2) 0.055(2) 0.0070(18) 0.0219(18) -0.0023(19) C13 0.105(3) 0.066(3) 0.057(2) -0.016(2) 0.037(2) -0.030(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C10 1.732(3) . ? S1 C4 1.711(4) . ? S1 C1 1.717(4) . ? N1 C7 1.503(4) . ? N1 C6 1.504(5) . ? N1 C8 1.509(5) . ? C2 C1 1.361(5) . ? C2 C3 1.416(4) . ? C2 C7 1.485(5) . ? C9 C10 1.389(5) . ? C9 C14 1.400(5) . ? C9 C8 1.498(5) . ? C10 C11 1.386(5) . ? C1 C5 1.505(5) . ? C14 C13 1.387(6) . ? C11 C12 1.378(6) . ? C3 C4 1.353(5) . ? C6 C5 1.511(6) . ? C12 C13 1.371(6) . ? 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 C4 S1 C1 91.81(17) . . ? C7 N1 C6 110.1(3) . . ? C7 N1 C8 111.7(3) . . ? C6 N1 C8 111.3(3) . . ? C1 C2 C3 112.7(3) . . ? C1 C2 C7 123.2(3) . . ? C3 C2 C7 124.0(3) . . ? C10 C9 C14 116.9(3) . . ? C10 C9 C8 122.6(3) . . ? C14 C9 C8 120.4(3) . . ? C11 C10 C9 121.4(3) . . ? C11 C10 Cl1 117.6(3) . . ? C9 C10 Cl1 121.0(3) . . ? C2 C7 N1 111.3(3) . . ? C2 C1 C5 123.0(4) . . ? C2 C1 S1 111.1(3) . . ? C5 C1 S1 125.9(3) . . ? C13 C14 C9 121.5(4) . . ? C9 C8 N1 112.0(3) . . ? C12 C11 C10 120.3(4) . . ? C4 C3 C2 112.6(3) . . ? N1 C6 C5 111.7(3) . . ? C13 C12 C11 119.7(4) . . ? C1 C5 C6 109.7(3) . . ? C3 C4 S1 111.8(3) . . ? C12 C13 C14 120.0(4) . . ?