#------------------------------------------------------------------------------ #$Date: 2025-09-04 15:43:44 +0100 (Thu, 04 Sep 2025) $ #$Revision: 302005 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519498.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_4519498 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 H7 F N2 O S' _chemical_formula_sum 'C8 H7 F N2 O S' _chemical_formula_weight 198.22 _chemical_name_systematic 6-(fluoromethoxy)-1,3-benzothiazol-2-amine _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _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 2024-11-08 _cell_angle_alpha 90 _cell_angle_beta 93.845(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.0784(6) _cell_length_b 4.0461(1) _cell_length_c 11.4161(4) _cell_measurement_reflns_used 9926 _cell_measurement_temperature 150 _cell_measurement_theta_max 60.636 _cell_measurement_theta_min 4.266 _cell_volume 833.17(5) _computing_cell_refinement ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 4 (2022) 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 'XT (Sheldrick, 2015)' _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 0.999 _diffrn_measured_fraction_theta_max 0.996 _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 0.0408 _diffrn_reflns_av_unetI/netI 0.0236 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 18276 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.655 _diffrn_reflns_theta_min 2.131 _diffrn_source 'Metal Jet' _diffrn_source_current 3.57 _diffrn_source_power 0.2488647 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.71 _exptl_absorpt_coefficient_mu 2.154 _exptl_absorpt_correction_T_max 0.3107 _exptl_absorpt_correction_T_min 0.2053 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1619 before and 0.0761 after correction. The Ratio of minimum to maximum transmission is 0.6608. 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 1.580 _exptl_crystal_description plate _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.386 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.059 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 134 _refine_ls_number_reflns 1921 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.094 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0427 _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^)+(0.0440P)^2^+1.0054P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1137 _refine_ls_wR_factor_ref 0.1158 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1763 _reflns_number_total 1921 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 03-1c_RZ1F_P21c_jw27092_150K.cif _cod_data_source_block jw27092 _cod_database_code 4519498 loop_ _space_group_symop_id _space_group_symop_operation_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' 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 0.36033(3) 0.81368(15) 0.71557(4) 0.03332(18) Uani 1 1 d . . . . . C1 C 0.42405(11) 0.6768(6) 0.61567(18) 0.0325(5) Uani 1 1 d . . . . . N1 N 0.49787(10) 0.7307(6) 0.64187(18) 0.0393(5) Uani 1 1 d . . . . . F1 F 0.06923(8) 0.5415(5) 0.75224(14) 0.0568(5) Uani 1 1 d . . . . . O1 O 0.09131(8) 0.4591(5) 0.56123(16) 0.0439(4) Uani 1 1 d . . . . . C2 C 0.28964(11) 0.6392(6) 0.62501(18) 0.0311(4) Uani 1 1 d . . . . . N2 N 0.39671(9) 0.5125(5) 0.52522(15) 0.0323(4) Uani 1 1 d . . . . . C3 C 0.31938(11) 0.4886(6) 0.52809(18) 0.0304(4) Uani 1 1 d . . . . . C4 C 0.27185(12) 0.3299(6) 0.44483(19) 0.0339(5) Uani 1 1 d . . . . . H4 H 0.291020 0.222654 0.379313 0.041 Uiso 1 1 calc R U . . . C5 C 0.19628(12) 0.3305(6) 0.4588(2) 0.0359(5) Uani 1 1 d . . . . . H5 H 0.163422 0.226237 0.401840 0.043 Uiso 1 1 calc R U . . . C6 C 0.16805(11) 0.4831(6) 0.5561(2) 0.0346(5) Uani 1 1 d . . . . . C7 C 0.21378(11) 0.6360(6) 0.64242(19) 0.0329(5) Uani 1 1 d . . . . . H7 H 0.194565 0.733287 0.709756 0.039 Uiso 1 1 calc R U . . . C8 C 0.05749(13) 0.6641(7) 0.6387(2) 0.0429(6) Uani 1 1 d . . . . . H1A H 0.530(2) 0.675(9) 0.587(3) 0.067(10) Uiso 1 1 d . . . . . H1B H 0.5068(17) 0.919(8) 0.689(3) 0.055(9) Uiso 1 1 d . . . . . H8A H 0.0797(16) 0.897(8) 0.639(3) 0.047(8) Uiso 1 1 d . . . . . H8B H 0.0047(15) 0.657(7) 0.617(2) 0.041(7) 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 0.0268(3) 0.0411(3) 0.0322(3) -0.0034(2) 0.00299(19) 0.0017(2) C1 0.0270(10) 0.0398(12) 0.0308(10) 0.0018(9) 0.0031(8) 0.0021(9) N1 0.0246(9) 0.0554(13) 0.0379(10) -0.0092(9) 0.0024(7) -0.0011(9) F1 0.0358(7) 0.0846(13) 0.0509(8) 0.0131(9) 0.0110(6) -0.0006(8) O1 0.0233(7) 0.0535(11) 0.0555(10) -0.0061(9) 0.0080(7) -0.0013(7) C2 0.0267(9) 0.0329(11) 0.0340(10) 0.0031(9) 0.0029(8) 0.0016(8) N2 0.0247(8) 0.0407(10) 0.0318(9) 0.0005(8) 0.0038(6) -0.0001(7) C3 0.0247(9) 0.0350(11) 0.0317(10) 0.0041(8) 0.0038(7) 0.0015(8) C4 0.0314(10) 0.0373(12) 0.0334(10) -0.0016(9) 0.0053(8) -0.0018(9) C5 0.0289(10) 0.0403(12) 0.0382(11) 0.0002(10) -0.0002(8) -0.0039(9) C6 0.0234(9) 0.0371(12) 0.0434(11) 0.0043(9) 0.0031(8) 0.0002(8) C7 0.0286(10) 0.0353(11) 0.0353(10) 0.0005(9) 0.0062(8) 0.0033(9) C8 0.0285(11) 0.0513(15) 0.0494(13) 0.0030(12) 0.0056(9) 0.0054(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 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' F F 0.0583 0.0400 '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 88.51(10) . . N1 C1 S1 118.64(17) . . N2 C1 S1 116.42(16) . . N2 C1 N1 124.8(2) . . C1 N1 H1A 118(2) . . C1 N1 H1B 112.5(19) . . H1A N1 H1B 120(3) . . C8 O1 C6 117.89(19) . . C3 C2 S1 109.90(15) . . C7 C2 S1 127.43(17) . . C7 C2 C3 122.7(2) . . C1 N2 C3 110.09(18) . . C2 C3 N2 115.07(19) . . C4 C3 C2 119.14(19) . . C4 C3 N2 125.80(19) . . C3 C4 H4 120.4 . . C5 C4 C3 119.2(2) . . C5 C4 H4 120.4 . . C4 C5 H5 119.7 . . C4 C5 C6 120.5(2) . . C6 C5 H5 119.7 . . O1 C6 C5 114.8(2) . . C7 C6 O1 123.2(2) . . C7 C6 C5 121.95(19) . . C2 C7 H7 121.8 . . C6 C7 C2 116.5(2) . . C6 C7 H7 121.8 . . F1 C8 H8A 107.0(16) . . F1 C8 H8B 108.4(16) . . O1 C8 F1 109.6(2) . . O1 C8 H8A 111.2(16) . . O1 C8 H8B 106.6(17) . . H8A C8 H8B 114(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.764(2) . S1 C2 1.739(2) . C1 N1 1.365(3) . C1 N2 1.298(3) . N1 H1A 0.92(4) . N1 H1B 0.94(3) . F1 C8 1.390(3) . O1 C6 1.396(2) . O1 C8 1.385(3) . C2 C3 1.402(3) . C2 C7 1.399(3) . N2 C3 1.404(2) . C3 C4 1.394(3) . C4 H4 0.9500 . C4 C5 1.386(3) . C5 H5 0.9500 . C5 C6 1.397(3) . C6 C7 1.388(3) . C7 H7 0.9500 . C8 H8A 1.02(3) . C8 H8B 0.97(3) . 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 C5 H5 F1 0.95 2.57 3.518(3) 177.2 4_565 yes C7 H7 F1 0.95 2.47 2.998(3) 114.7 . yes N1 H1A N2 0.92(4) 2.04(4) 2.954(3) 172(3) 3_666 yes N1 H1B N1 0.94(3) 2.31(3) 3.189(3) 155(3) 2_656 yes C8 H8B F1 0.97(3) 2.59(3) 3.084(3) 111.6(19) 2_556 yes C8 H8B O1 0.97(3) 2.62(3) 3.446(3) 142(2) 3_566 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 C1 N2 C3 1.2(3) . . . . S1 C2 C3 N2 -0.3(2) . . . . S1 C2 C3 C4 179.31(17) . . . . S1 C2 C7 C6 179.26(17) . . . . C1 S1 C2 C3 0.79(17) . . . . C1 S1 C2 C7 179.7(2) . . . . C1 N2 C3 C2 -0.5(3) . . . . C1 N2 C3 C4 179.8(2) . . . . N1 C1 N2 C3 176.8(2) . . . . O1 C6 C7 C2 179.8(2) . . . . C2 S1 C1 N1 -177.1(2) . . . . C2 S1 C1 N2 -1.21(19) . . . . C2 C3 C4 C5 1.2(3) . . . . N2 C3 C4 C5 -179.2(2) . . . . C3 C2 C7 C6 -1.9(3) . . . . C3 C4 C5 C6 -1.1(3) . . . . C4 C5 C6 O1 -178.5(2) . . . . C4 C5 C6 C7 -0.6(4) . . . . C5 C6 C7 C2 2.1(3) . . . . C6 O1 C8 F1 -77.3(3) . . . . C7 C2 C3 N2 -179.3(2) . . . . C7 C2 C3 C4 0.3(3) . . . . C8 O1 C6 C5 -165.6(2) . . . . C8 O1 C6 C7 16.5(3) . . . . _cod_database_fobs_code 4519498