#------------------------------------------------------------------------------ #$Date: 2025-09-04 15:43:58 +0100 (Thu, 04 Sep 2025) $ #$Revision: 302006 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519499.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4519499 loop_ _publ_author_name 'Abdel Rahman Al Ahmad' 'Thierry Maris' 'James D. Wuest' _publ_contact_author_id_orcid 0000-0001-9731-4046 _publ_section_title ; ArOCF3, ArOCHF2, ArOCH2F, and ArOCH3: What the F Does to Control the Crystallization of Riluzole and Analogous Fluoromethyl Ethers ; _journal_name_full 'Crystal growth & Design' _journal_page_first 6408 _journal_page_last 6420 _journal_paper_doi 10.1021/acs.cgd.5c00831 _journal_volume 25 _journal_year 2025 _chemical_formula_moiety 'C8 H8 N2 O S' _chemical_formula_sum 'C8 H8 N2 O S' _chemical_formula_weight 180.22 _chemical_name_systematic 6-methoxy-1,3-benzothiazol-2-amine _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_contact_author_email thierry.maris@umontreal.ca _audit_contact_author_name 'Thierry Maris' _audit_contact_author_phone '+1 514 340 4711 2579' _audit_creation_date 2024-11-26 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.1046(6) _cell_length_b 6.7053(2) _cell_length_c 16.6877(6) _cell_measurement_reflns_used 9911 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.720 _cell_measurement_theta_min 4.612 _cell_volume 1690.14(10) _computing_cell_refinement ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.42 _diffrn_detector_type 'Bruker CMOS Photon III ' _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Ga K\a' _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_unetI/netI 0.0329 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 13058 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.816 _diffrn_reflns_theta_min 4.611 _diffrn_source 'Metal Jet' _diffrn_source_current 2.86 _diffrn_source_power 0.1993706 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.71 _exptl_absorpt_coefficient_mu 1.973 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_correction_T_min 0.4506 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1675 before and 0.0874 after correction. The Ratio of minimum to maximum transmission is 0.6002. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.417 _exptl_crystal_description Block _exptl_crystal_F_000 752 _exptl_crystal_recrystallization_method 'crystallized in EtOAc' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.277 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.073 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 141 _refine_ls_number_reflns 1594 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.139 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0407 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+0.6820P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1161 _refine_ls_wR_factor_ref 0.1185 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1462 _reflns_number_total 1594 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 04-1d_TZ_Pbca_jw24681.cif _cod_data_source_block jw24681 _cod_database_code 4519499 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z+1/2' 4 'x+1/2, -y+1/2, -z' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z-1/2' 8 '-x-1/2, y-1/2, z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.67054(3) 0.78241(7) 0.37058(3) 0.0311(2) Uani 1 1 d . . . . . O1 O 0.68040(8) 0.45007(19) 0.09136(7) 0.0299(3) Uani 1 1 d . . . . . N1 N 0.56170(10) 0.4921(2) 0.40563(8) 0.0273(4) Uani 1 1 d . . . . . N2 N 0.58819(13) 0.7122(3) 0.51178(10) 0.0375(4) Uani 1 1 d . . . . . H2A H 0.6208(16) 0.807(4) 0.5327(14) 0.041(6) Uiso 1 1 d . . . . . H2B H 0.5515(16) 0.650(4) 0.5412(13) 0.038(6) Uiso 1 1 d . . . . . C1 C 0.60007(12) 0.6486(3) 0.43622(10) 0.0279(4) Uani 1 1 d . . . . . C2 C 0.64617(12) 0.6087(3) 0.29591(10) 0.0253(4) Uani 1 1 d . . . . . C3 C 0.58750(11) 0.4652(3) 0.32624(10) 0.0240(4) Uani 1 1 d . . . . . C4 C 0.56024(13) 0.3106(3) 0.27627(11) 0.0278(4) Uani 1 1 d . . . . . H4 H 0.5248(16) 0.213(4) 0.2987(13) 0.044(7) Uiso 1 1 d . . . . . C5 C 0.58987(12) 0.3019(3) 0.19756(11) 0.0272(4) Uani 1 1 d . . . . . H5 H 0.5725(13) 0.195(3) 0.1638(12) 0.023(5) Uiso 1 1 d . . . . . C6 C 0.64719(12) 0.4483(3) 0.16873(10) 0.0250(4) Uani 1 1 d . . . . . C7 C 0.67646(11) 0.6032(3) 0.21739(11) 0.0262(4) Uani 1 1 d . . . . . H7 H 0.7171(14) 0.704(3) 0.1951(12) 0.031(5) Uiso 1 1 d . . . . . C8 C 0.65249(16) 0.2929(3) 0.03880(12) 0.0352(5) Uani 1 1 d . . . . . H8A H 0.6844(13) 0.329(3) -0.0118(13) 0.029(5) Uiso 1 1 d . . . . . H8B H 0.5820(14) 0.310(3) 0.0338(12) 0.029(5) Uiso 1 1 d . . . . . H8C H 0.6723(12) 0.152(3) 0.0625(12) 0.025(5) 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 S1 0.0384(4) 0.0290(3) 0.0260(3) -0.00188(16) 0.00110(18) -0.01238(18) O1 0.0359(7) 0.0290(7) 0.0246(7) -0.0009(5) 0.0053(5) -0.0002(5) N1 0.0331(8) 0.0269(8) 0.0220(7) 0.0022(6) -0.0017(6) -0.0053(6) N2 0.0488(11) 0.0390(10) 0.0248(8) -0.0044(7) 0.0019(8) -0.0188(8) C1 0.0322(10) 0.0269(9) 0.0247(9) 0.0032(7) -0.0025(7) -0.0045(7) C2 0.0272(9) 0.0224(9) 0.0263(9) 0.0016(7) -0.0041(7) -0.0011(7) C3 0.0257(9) 0.0239(9) 0.0224(8) 0.0039(6) -0.0031(7) -0.0012(6) C4 0.0307(10) 0.0253(9) 0.0275(9) 0.0019(7) -0.0004(7) -0.0062(7) C5 0.0299(10) 0.0243(9) 0.0275(9) -0.0010(7) -0.0018(8) -0.0011(7) C6 0.0264(9) 0.0256(9) 0.0229(9) 0.0016(7) 0.0002(7) 0.0049(7) C7 0.0262(9) 0.0254(9) 0.0269(9) 0.0025(7) 0.0008(7) -0.0023(7) C8 0.0462(12) 0.0328(11) 0.0266(10) -0.0056(8) 0.0060(9) 0.0007(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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' N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 S1 C1 88.66(9) . . C6 O1 C8 117.21(14) . . C1 N1 C3 110.64(15) . . H2A N2 H2B 120(2) . . C1 N2 H2A 121.9(15) . . C1 N2 H2B 118.1(15) . . N1 C1 S1 115.66(13) . . N1 C1 N2 124.35(17) . . N2 C1 S1 119.99(15) . . C3 C2 S1 109.48(13) . . C7 C2 S1 128.48(14) . . C7 C2 C3 122.03(16) . . N1 C3 C2 115.54(15) . . C4 C3 N1 125.69(16) . . C4 C3 C2 118.77(16) . . C3 C4 H4 117.0(14) . . C5 C4 C3 120.18(17) . . C5 C4 H4 122.7(14) . . C4 C5 H5 120.3(12) . . C4 C5 C6 119.76(17) . . C6 C5 H5 119.9(12) . . O1 C6 C5 123.52(16) . . O1 C6 C7 115.02(15) . . C7 C6 C5 121.45(16) . . C2 C7 C6 117.80(16) . . C2 C7 H7 122.9(12) . . C6 C7 H7 119.3(12) . . O1 C8 H8A 101.4(12) . . O1 C8 H8B 105.1(11) . . O1 C8 H8C 110.0(11) . . H8A C8 H8B 112.7(16) . . H8A C8 H8C 112.9(16) . . H8B C8 H8C 113.7(15) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.7714(18) . S1 C2 1.7450(18) . O1 C6 1.385(2) . O1 C8 1.435(2) . N1 C1 1.303(2) . N1 C3 1.393(2) . N2 H2A 0.88(3) . N2 H2B 0.85(2) . N2 C1 1.343(2) . C2 C3 1.403(2) . C2 C7 1.388(2) . C3 C4 1.392(2) . C4 H4 0.92(2) . C4 C5 1.389(3) . C5 H5 0.95(2) . C5 C6 1.395(3) . C6 C7 1.390(2) . C7 H7 0.98(2) . C8 H8A 1.00(2) . C8 H8B 1.07(2) . C8 H8C 1.07(2) . 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 _geom_hbond_publ_flag N2 H2A O1 0.88(3) 2.10(3) 2.972(2) 171(2) 7_576 yes N2 H2B N1 0.85(2) 2.15(3) 2.984(2) 167(2) 5_666 yes C8 H8C O1 1.07(2) 2.649(19) 3.525(3) 139.1(13) 8_755 yes 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 S1 C2 C3 N1 0.6(2) . . . . S1 C2 C3 C4 -179.28(13) . . . . S1 C2 C7 C6 -179.87(14) . . . . O1 C6 C7 C2 -179.42(15) . . . . N1 C3 C4 C5 179.10(17) . . . . C1 S1 C2 C3 -0.05(14) . . . . C1 S1 C2 C7 179.45(18) . . . . C1 N1 C3 C2 -1.1(2) . . . . C1 N1 C3 C4 178.84(17) . . . . C2 S1 C1 N1 -0.58(15) . . . . C2 S1 C1 N2 -179.66(18) . . . . C2 C3 C4 C5 -1.0(3) . . . . C3 N1 C1 S1 1.0(2) . . . . C3 N1 C1 N2 -179.94(18) . . . . C3 C2 C7 C6 -0.4(3) . . . . C3 C4 C5 C6 0.1(3) . . . . C4 C5 C6 O1 179.49(16) . . . . C4 C5 C6 C7 0.7(3) . . . . C5 C6 C7 C2 -0.5(3) . . . . C7 C2 C3 N1 -178.91(16) . . . . C7 C2 C3 C4 1.2(3) . . . . C8 O1 C6 C5 0.9(3) . . . . C8 O1 C6 C7 179.76(16) . . . . _cod_database_fobs_code 4519499