#------------------------------------------------------------------------------ #$Date: 2025-09-04 15:44:40 +0100 (Thu, 04 Sep 2025) $ #$Revision: 302011 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/95/4519502.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_4519502 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 '0.44(C8 H6 F2 N2 O S), 0.56(C8 H8 N2 O S)' _chemical_formula_sum 'C8 H7.12 F0.88 N2 O S' _chemical_formula_weight 196.06 _chemical_name_systematic ; 6-methoxy-1,3-benzothiazol-2-amine : 6-(difluoromethoxy)-1,3-benzothiazol-2-amine 0.56:0.44 ; _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 geom _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 2024-12-05 _cell_angle_alpha 90 _cell_angle_beta 93.014(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.3651(11) _cell_length_b 4.0703(2) _cell_length_c 11.4599(6) _cell_measurement_reflns_used 9866 _cell_measurement_temperature 150 _cell_measurement_theta_max 63.342 _cell_measurement_theta_min 4.196 _cell_volume 855.46(8) _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 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (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 0.996 _diffrn_measured_fraction_theta_max 0.990 _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 0.0503 _diffrn_reflns_av_unetI/netI 0.0405 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 12188 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 63.486 _diffrn_reflns_theta_min 4.194 _diffrn_source 'Metal Jet' _diffrn_source_current 3.57 _diffrn_source_power 0.24886469999999997 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.71 _exptl_absorpt_coefficient_mu 2.080 _exptl_absorpt_correction_T_max 0.2667 _exptl_absorpt_correction_T_min 0.1206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1582 before and 0.0951 after correction. The Ratio of minimum to maximum transmission is 0.4522. 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 1.522 _exptl_crystal_description plate _exptl_crystal_F_000 404 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.451 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.069 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 2119 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.118 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0619 _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^)+(0.0988P)^2^+0.5113P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1794 _refine_ls_wR_factor_ref 0.1853 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1875 _reflns_number_total 2119 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 07-1b_1d_044RZ2F_056TZ_jw27311.cif _cod_data_source_block jw27311 _cod_database_code 4519502 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 0.13667(3) 0.81614(15) 0.28132(5) 0.0485(3) Uani 1 1 d . . . . . O1 O 0.39971(13) 0.4454(10) 0.4243(3) 0.1138(12) Uani 1 1 d . . . . . N1 N 0.00219(11) 0.7351(6) 0.35870(18) 0.0493(5) Uani 1 1 d . . . . . H1A H -0.030124 0.655514 0.405204 0.059 Uiso 1 1 calc R U . . . H1B H -0.012275 0.850565 0.296824 0.059 Uiso 1 1 calc R U . . . N2 N 0.10109(10) 0.5130(5) 0.47131(16) 0.0433(4) Uani 1 1 d . . . . . C1 C 0.07420(13) 0.6799(5) 0.38237(19) 0.0432(5) Uani 1 1 d . . . . . C2 C 0.20604(14) 0.6367(6) 0.3685(2) 0.0474(5) Uani 1 1 d . . . . . C3 C 0.17660(13) 0.4856(6) 0.4660(2) 0.0447(5) Uani 1 1 d . . . . . C4 C 0.22304(14) 0.3268(6) 0.5469(2) 0.0507(6) Uani 1 1 d . . . . . H4 H 0.204222 0.220626 0.612746 0.061 Uiso 1 1 calc R U . . . C5 C 0.29724(16) 0.3249(8) 0.5305(3) 0.0628(7) Uani 1 1 d . . . . . H5 H 0.329566 0.220263 0.586299 0.075 Uiso 1 1 calc R U . . . C6 C 0.32502(15) 0.4759(9) 0.4324(3) 0.0678(8) Uani 1 1 d . . . . . C7 C 0.28003(16) 0.6328(8) 0.3494(3) 0.0606(7) Uani 1 1 d . . . . . H7 H 0.298885 0.733205 0.282536 0.073 Uiso 1 1 calc R U . . . C8 C 0.4351(2) 0.6593(15) 0.3528(5) 0.1099(17) Uani 1 1 d . . . A 1 H8A H 0.487508 0.655870 0.373661 0.165 Uiso 0.560(8) 1 calc R U P B 1 H8B H 0.416207 0.882141 0.362911 0.165 Uiso 0.560(8) 1 calc R U P B 1 H8C H 0.426596 0.591615 0.271174 0.165 Uiso 1 1 calc R U . A 1 F1 F 0.5042(3) 0.596(2) 0.3726(6) 0.123(3) Uani 0.440(8) 1 d . . P B 2 F2 F 0.4221(3) 0.601(3) 0.2378(6) 0.148(4) Uani 0.440(8) 1 d . . P B 2 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 0.0568(4) 0.0426(4) 0.0467(4) 0.0016(2) 0.0088(3) -0.0079(2) O1 0.0492(13) 0.127(3) 0.168(3) 0.038(2) 0.0269(16) 0.0087(15) N1 0.0499(11) 0.0525(11) 0.0452(10) 0.0085(9) 0.0013(8) -0.0036(9) N2 0.0482(10) 0.0394(9) 0.0424(9) -0.0014(7) 0.0038(7) -0.0008(8) C1 0.0518(12) 0.0368(11) 0.0411(10) -0.0022(8) 0.0039(9) -0.0052(9) C2 0.0506(12) 0.0406(11) 0.0516(12) -0.0053(9) 0.0068(10) -0.0044(9) C3 0.0485(11) 0.0391(11) 0.0468(11) -0.0072(9) 0.0065(9) -0.0035(9) C4 0.0526(13) 0.0477(13) 0.0521(13) -0.0048(10) 0.0045(10) 0.0047(10) C5 0.0521(14) 0.0621(17) 0.0739(18) -0.0029(13) -0.0008(13) 0.0066(12) C6 0.0459(13) 0.0675(19) 0.091(2) -0.0002(16) 0.0127(13) 0.0001(13) C7 0.0572(15) 0.0560(15) 0.0701(17) -0.0021(13) 0.0161(13) -0.0075(12) C8 0.0501(17) 0.155(5) 0.127(4) -0.014(3) 0.026(2) -0.020(2) F1 0.047(2) 0.207(8) 0.114(4) 0.010(5) 0.001(2) -0.020(3) F2 0.051(3) 0.298(12) 0.095(4) 0.013(6) 0.015(3) 0.002(4) 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 0.0389 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 88.45(11) . . C8 O1 C6 118.8(3) . . H1A N1 H1B 120.0 . . C1 N1 H1A 120.0 . . C1 N1 H1B 120.0 . . C1 N2 C3 110.2(2) . . N1 C1 S1 118.60(17) . . N2 C1 S1 116.49(18) . . N2 C1 N1 124.7(2) . . C3 C2 S1 109.83(18) . . C7 C2 S1 127.5(2) . . C7 C2 C3 122.7(2) . . N2 C3 C2 115.1(2) . . C4 C3 N2 125.8(2) . . C4 C3 C2 119.1(2) . . C3 C4 H4 120.4 . . C5 C4 C3 119.1(3) . . C5 C4 H4 120.4 . . C4 C5 H5 119.7 . . C4 C5 C6 120.6(3) . . C6 C5 H5 119.7 . . O1 C6 C5 114.7(3) . . C7 C6 O1 123.6(3) . . C7 C6 C5 121.7(3) . . C2 C7 H7 121.6 . . C6 C7 C2 116.9(3) . . C6 C7 H7 121.6 . . 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 1.762(2) . S1 C2 1.738(3) . O1 C6 1.385(3) . O1 C8 1.381(6) . N1 H1A 0.8800 . N1 H1B 0.8800 . N1 C1 1.355(3) . N2 C1 1.301(3) . N2 C3 1.396(3) . C2 C3 1.408(3) . C2 C7 1.388(4) . C3 C4 1.386(4) . C4 H4 0.9500 . C4 C5 1.385(4) . C5 H5 0.9500 . C5 C6 1.401(5) . C6 C7 1.383(5) . C7 H7 0.9500 . C8 H8A 0.9800 . C8 H8B 0.9800 . C8 H8C 0.9800 . 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 N2 -0.2(2) . . . . S1 C2 C3 C4 179.89(18) . . . . S1 C2 C7 C6 179.4(2) . . . . O1 C6 C7 C2 178.6(3) . . . . N2 C3 C4 C5 -179.0(2) . . . . C1 S1 C2 C3 0.63(17) . . . . C1 S1 C2 C7 -179.7(2) . . . . C1 N2 C3 C2 -0.5(3) . . . . C1 N2 C3 C4 179.4(2) . . . . C2 S1 C1 N1 -176.60(19) . . . . C2 S1 C1 N2 -1.02(19) . . . . C2 C3 C4 C5 0.9(4) . . . . C3 N2 C1 S1 1.1(2) . . . . C3 N2 C1 N1 176.3(2) . . . . C3 C2 C7 C6 -1.0(4) . . . . C3 C4 C5 C6 -1.2(4) . . . . C4 C5 C6 O1 -177.7(3) . . . . C4 C5 C6 C7 0.4(5) . . . . C5 C6 C7 C2 0.6(5) . . . . C7 C2 C3 N2 -179.9(2) . . . . C7 C2 C3 C4 0.2(4) . . . . C8 O1 C6 C5 -161.3(4) . . . . C8 O1 C6 C7 20.7(6) . . . . _cod_database_fobs_code 4519502