ArOCF3, ArOCHF2, ArOCH2F, and ArOCH3: What the F Does to Control the Crystallization of Riluzole and Analogous Fluoromethyl Ethers
Abdel Rahman Al Ahmad; Thierry Maris; James D. Wuest; Crystal growth & Design 25 (2025) 6408–6420; doi:10.1021/acs.cgd.5c00831

data_4519508
_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         '0.32(C8 H6 F2 N2 O S), 0.68(C8 H8 N2 O S)'
_chemical_formula_sum            'C8 H7.37 F0.63 N2 O S'
_chemical_formula_weight         191.60
_chemical_name_systematic
;
6-methoxy-1,3-benzothiazol-2-amine :
6-(difluoromethoxy)-1,3-benzothiazol-2-amine
0.68 : 0.32
;
_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             2024-12-06
_cell_angle_alpha                90
_cell_angle_beta                 92.806(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.269(3)
_cell_length_b                   4.0563(7)
_cell_length_c                   11.5914(18)
_cell_measurement_reflns_used    2145
_cell_measurement_temperature    150
_cell_measurement_theta_max      51.175
_cell_measurement_theta_min      4.217
_cell_volume                     857.9(2)
_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 0.941
_diffrn_measured_fraction_theta_max 0.925
_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  0.0862
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10330
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.248
_diffrn_reflns_theta_min         4.216
_diffrn_source                   'Metal Jet'
_diffrn_source_current           3.57
_diffrn_source_power             0.24897
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.74
_exptl_absorpt_coefficient_mu    2.038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1536 before and 0.0865 after correction.
 The Ratio of minimum to maximum transmission is 0.38.

Final HKLF 4 output contains 14901 reflections, Rint = 0.0862
 (4149 with I > 3sig(I), Rint = 0.0598)
;
_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    1.483
_exptl_crystal_description       platelet
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.611
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1510
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.617
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.1052
_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^)+(0.0821P)^2^+0.4139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2596
_refine_ls_wR_factor_ref         0.2729
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                982
_reflns_number_total             1510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            08-1b_1d_032RZ2F_068TZ_jw27293.cif
_cod_data_source_block           jw27293
_cod_database_code               4519508
_cod_database_fobs_code 4519508