#------------------------------------------------------------------------------ #$Date: 2025-09-04 15:44:29 +0100 (Thu, 04 Sep 2025) $ #$Revision: 302010 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/95/4519501.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_4519501 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 '0.47(C8 H7 F N2 O S), 0.53(C8 H8 N2 O S)' _chemical_formula_sum 'C8 H7.53 F0.47 N2 O S' _chemical_formula_weight 188.63 _chemical_name_systematic ; 6-methoxy-1,3-benzothiazol-2-amine : 6-(fluoromethoxy)-1,3-benzothiazol-2-amine 0.53:0.47 ; _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 2025-01-15 _cell_angle_alpha 90 _cell_angle_beta 94.322(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.1007(9) _cell_length_b 4.0084(2) _cell_length_c 11.4184(6) _cell_measurement_reflns_used 9214 _cell_measurement_temperature 150 _cell_measurement_theta_max 63.411 _cell_measurement_theta_min 3.378 _cell_volume 826.10(7) _computing_cell_refinement ; SAINT (2013) V8.41; 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 (2013) V8.41; 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 0.993 _diffrn_measured_fraction_theta_max 0.988 _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 0.0439 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 19531 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 63.434 _diffrn_reflns_theta_min 4.262 _diffrn_source 'Metal Jet' _diffrn_source_current 3.58 _diffrn_source_power 0.2495618 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.71 _exptl_absorpt_coefficient_mu 2.091 _exptl_absorpt_correction_T_max 0.2147 _exptl_absorpt_correction_T_min 0.1006 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1382 before and 0.0815 after correction. The Ratio of minimum to maximum transmission is 0.4686. 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 1.517 _exptl_crystal_description platelet _exptl_crystal_F_000 391 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.429 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 2033 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0360 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.2534P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1007 _refine_ls_wR_factor_ref 0.1014 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1955 _reflns_number_total 2033 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 06-1c_1d_047RZ1F_053TZ_jw27471.cif _cod_data_source_block jw27471 _cod_database_code 4519501 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 0.36055(2) 0.81567(9) 0.71376(2) 0.03540(14) Uani 1 1 d . . . . . O1 O 0.09082(6) 0.4886(3) 0.55187(10) 0.0518(3) Uani 1 1 d . . . . . N2 N 0.39613(6) 0.5112(3) 0.52357(9) 0.0349(3) Uani 1 1 d . . . . . N1 N 0.49748(6) 0.7274(4) 0.64211(10) 0.0392(3) Uani 1 1 d D . . . . C3 C 0.31913(7) 0.4909(3) 0.52564(11) 0.0337(3) Uani 1 1 d . . . . . C1 C 0.42395(7) 0.6762(3) 0.61443(11) 0.0337(3) Uani 1 1 d . . . . . C6 C 0.16719(7) 0.4999(4) 0.54994(13) 0.0405(3) Uani 1 1 d . . . . . C2 C 0.28925(7) 0.6434(3) 0.62196(11) 0.0342(3) Uani 1 1 d . . . . . C7 C 0.21367(8) 0.6499(4) 0.63713(12) 0.0382(3) Uani 1 1 d . . . . . H7 H 0.194768 0.751919 0.703771 0.046 Uiso 1 1 calc R U . . . C4 C 0.27077(8) 0.3352(4) 0.44094(12) 0.0379(3) Uani 1 1 d . . . . . H4 H 0.289543 0.225221 0.375717 0.045 Uiso 1 1 calc R U . . . C5 C 0.19547(8) 0.3435(4) 0.45339(12) 0.0408(3) Uani 1 1 d . . . . . H5 H 0.162413 0.241454 0.395512 0.049 Uiso 1 1 calc R U . . . C8 C 0.05802(9) 0.6775(5) 0.63720(17) 0.0556(4) Uani 1 1 d . . . A 1 H8A H 0.004124 0.678608 0.620326 0.083 Uiso 1 1 calc R U . A 1 H8B H 0.076730 0.906859 0.636129 0.083 Uiso 1 1 calc R U . A 1 H8C H 0.070249 0.579340 0.714847 0.083 Uiso 0.533(5) 1 calc R U P B 1 F1 F 0.06776(12) 0.5605(8) 0.7441(2) 0.0651(10) Uani 0.467(5) 1 d . . P B 2 H1A H 0.5290(10) 0.678(5) 0.5917(16) 0.052(5) Uiso 1 1 d D . . . . H1B H 0.5072(11) 0.894(4) 0.6887(17) 0.056(5) Uiso 1 1 d 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 0.03133(19) 0.0498(2) 0.02487(18) -0.00298(11) 0.00067(12) 0.00200(11) O1 0.0299(5) 0.0744(8) 0.0508(6) -0.0087(5) 0.0024(4) -0.0035(5) N2 0.0318(5) 0.0488(6) 0.0239(5) 0.0006(4) 0.0009(4) -0.0003(4) N1 0.0300(5) 0.0589(7) 0.0283(5) -0.0058(5) -0.0005(4) 0.0001(5) C3 0.0319(6) 0.0449(7) 0.0241(5) 0.0030(5) 0.0009(4) -0.0001(5) C1 0.0314(6) 0.0462(7) 0.0234(5) 0.0015(4) 0.0012(4) 0.0019(5) C6 0.0301(6) 0.0542(8) 0.0370(7) 0.0027(6) 0.0013(5) -0.0014(5) C2 0.0327(6) 0.0436(7) 0.0258(6) 0.0016(5) -0.0006(4) 0.0007(5) C7 0.0344(6) 0.0486(8) 0.0317(6) 0.0002(5) 0.0038(5) 0.0015(5) C4 0.0374(7) 0.0499(8) 0.0263(6) -0.0005(5) 0.0015(5) -0.0037(5) C5 0.0364(7) 0.0537(8) 0.0314(6) -0.0002(5) -0.0027(5) -0.0052(6) C8 0.0334(7) 0.0756(12) 0.0583(10) -0.0060(8) 0.0063(7) 0.0022(7) F1 0.0454(12) 0.103(2) 0.0485(13) 0.0075(12) 0.0105(9) -0.0008(12) 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' F F 0.0583 0.0400 '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 0.0412 0.0250 '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 88.62(6) . . C6 O1 C8 117.98(12) . . C1 N2 C3 110.06(11) . . C1 N1 H1A 119.7(14) . . C1 N1 H1B 114.3(14) . . H1A N1 H1B 118.2(19) . . N2 C3 C2 115.58(11) . . N2 C3 C4 125.87(12) . . C4 C3 C2 118.54(12) . . N2 C1 S1 116.28(10) . . N2 C1 N1 125.17(12) . . N1 C1 S1 118.38(10) . . O1 C6 C7 123.60(13) . . O1 C6 C5 115.02(13) . . C7 C6 C5 121.37(13) . . C3 C2 S1 109.43(9) . . C7 C2 S1 127.43(11) . . C7 C2 C3 123.14(12) . . C6 C7 C2 116.74(13) . . C6 C7 H7 121.6 . . C2 C7 H7 121.6 . . C3 C4 H4 120.4 . . C5 C4 C3 119.22(13) . . C5 C4 H4 120.4 . . C6 C5 H5 119.5 . . C4 C5 C6 120.97(13) . . C4 C5 H5 119.5 . . O1 C8 H8A 109.5 . . O1 C8 H8B 109.5 . . O1 C8 H8C 109.5 . . H8A C8 H8B 109.5 . . H8A C8 H8C 109.5 . . H8B C8 H8C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.7641(13) . S1 C2 1.7428(13) . O1 C6 1.3849(16) . O1 C8 1.401(2) . N2 C3 1.3980(16) . N2 C1 1.2996(17) . N1 C1 1.3600(17) . N1 H1A 0.864(15) . N1 H1B 0.864(15) . C3 C2 1.4020(18) . C3 C4 1.4013(18) . C6 C7 1.391(2) . C6 C5 1.398(2) . C2 C7 1.3921(19) . C7 H7 0.9500 . C4 H4 0.9500 . C4 C5 1.381(2) . C5 H5 0.9500 . C8 H8A 0.9800 . C8 H8B 0.9800 . C8 H8C 0.9800 . 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 C7 H7 F1 0.95 2.50 3.014(3) 114.1 . yes C4 H4 S1 0.95 2.97 3.4589(14) 113.4 4_575 yes C5 H5 F1 0.95 2.63 3.584(3) 176.9 4_565 yes C8 H8A O1 0.98 2.60 3.389(2) 137.6 3_566 yes N1 H1A N2 0.864(15) 2.100(15) 2.9583(16) 172.0(18) 3_666 yes N1 H1B N1 0.864(15) 2.356(16) 3.1720(18) 157.7(19) 2_656 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 C7 C6 178.69(11) . . . . O1 C6 C7 C2 -179.40(14) . . . . O1 C6 C5 C4 -179.71(14) . . . . N2 C3 C2 S1 -0.46(15) . . . . N2 C3 C2 C7 179.26(12) . . . . N2 C3 C4 C5 -178.23(13) . . . . C3 N2 C1 S1 1.47(15) . . . . C3 N2 C1 N1 176.62(13) . . . . C3 C2 C7 C6 -1.0(2) . . . . C3 C4 C5 C6 -1.0(2) . . . . C1 S1 C2 C3 1.01(10) . . . . C1 S1 C2 C7 -178.69(13) . . . . C1 N2 C3 C2 -0.63(16) . . . . C1 N2 C3 C4 179.12(13) . . . . C2 S1 C1 N2 -1.50(11) . . . . C2 S1 C1 N1 -176.99(12) . . . . C2 C3 C4 C5 1.5(2) . . . . C7 C6 C5 C4 -0.5(2) . . . . C4 C3 C2 S1 179.77(10) . . . . C4 C3 C2 C7 -0.5(2) . . . . C5 C6 C7 C2 1.5(2) . . . . C8 O1 C6 C7 9.2(2) . . . . C8 O1 C6 C5 -171.64(15) . . . . _cod_database_fobs_code 4519501