#------------------------------------------------------------------------------
#$Date: 2025-09-04 16:44:17 +0200 (Thu 04 de Sep de 2025) $
#$Revision: 302009 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/95/4519500.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_4519500
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         '0.36(C8 H5 F3 N2 O S), 0.64(C8 H6 F2 N2 O S)'
_chemical_formula_sum            'C8 H5.64 F2.36 N2 O S'
_chemical_formula_weight         222.71
_chemical_name_systematic
;
6-(difluoromethoxy)-1,3-benzothiazol-2-amine :
6-(trifluoromethoxy)-1,3-benzothiazol-2-amine 
0.64:0.36'
;
_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             2024-12-02
_cell_angle_alpha                90
_cell_angle_beta                 100.160(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.0364(8)
_cell_length_b                   8.0701(3)
_cell_length_c                   11.8481(5)
_cell_measurement_reflns_used    9728
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.694
_cell_measurement_theta_min      3.298
_cell_volume                     1791.63(13)
_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    '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 0.995
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ 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  0.0416
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            43188
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.663
_diffrn_reflns_theta_min         4.105
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.1994564
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.74
_exptl_absorpt_coefficient_mu    2.196
_exptl_absorpt_correction_T_max  0.2103
_exptl_absorpt_correction_T_min  0.0935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1603 before and 0.0792 after correction.
The Ratio of minimum to maximum transmission is 0.4446.
The λ/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    1.651
_exptl_crystal_description       plate
_exptl_crystal_F_000             903
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0480
_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/[σ²(Fo²)+(0.0818P)²+1.2468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3998
_reflns_number_total             4104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            05-1a_1b_036RZ_064RZ2F_jw26912.cif
_cod_data_source_block           jw26912
_cod_database_code               4519500
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
S1A S -0.10817(2) 0.17905(6) 0.39458(4) 0.03368(15) Uani 1 1 d . . . . .
N1A N 0.02957(9) 0.2065(2) 0.49353(16) 0.0393(4) Uani 1 1 d . . . . .
H1AA H 0.065291 0.242397 0.545216 0.047 Uiso 1 1 calc R U . . .
H1AB H 0.037677 0.138194 0.439384 0.047 Uiso 1 1 calc R U . . .
N2A N -0.05471(9) 0.3569(2) 0.57406(14) 0.0332(3) Uani 1 1 d . . . . .
C1A C -0.03703(10) 0.2558(2) 0.49726(16) 0.0322(4) Uani 1 1 d . . . . .
C2A C -0.16672(10) 0.2982(2) 0.45857(16) 0.0322(4) Uani 1 1 d . . . . .
C3A C -0.12807(10) 0.3842(2) 0.55239(16) 0.0321(4) Uani 1 1 d . . . . .
C4A C -0.16467(11) 0.4892(2) 0.61605(18) 0.0369(4) Uani 1 1 d . . . . .
H4A H -0.139338 0.551243 0.678341 0.044 Uiso 1 1 calc R U . . .
C5A C -0.23823(12) 0.5018(3) 0.58730(19) 0.0400(4) Uani 1 1 d . . . . .
H5A H -0.263689 0.572345 0.630050 0.048 Uiso 1 1 calc R U . . .
C6A C -0.27476(11) 0.4106(3) 0.49556(19) 0.0393(4) Uani 1 1 d . . . . .
C7A C -0.24060(11) 0.3091(2) 0.42866(18) 0.0364(4) Uani 1 1 d . . . . .
H7A H -0.266253 0.249563 0.365352 0.044 Uiso 1 1 calc R U . . .
O1A O -0.34941(8) 0.4297(2) 0.46615(16) 0.0507(4) Uani 1 1 d . . . . .
C8A C -0.38927(15) 0.3342(4) 0.5220(3) 0.0589(7) Uani 1 1 d . . . . .
H8A H -0.440911 0.361865 0.497465 0.071 Uiso 0.574(8) 1 calc R U P A -1
F1A F -0.37077(15) 0.3499(5) 0.6361(2) 0.1333(13) Uani 1 1 d . . . . .
F2A F -0.37856(11) 0.1731(2) 0.5052(2) 0.0832(6) Uani 1 1 d . . . . .
F3A F -0.4564(2) 0.3772(7) 0.4863(5) 0.091(2) Uani 0.426(8) 1 d . . P A -2
S1B S 0.20172(3) 0.53199(6) 0.83829(4) 0.03520(15) Uani 1 1 d . . . . .
N1B N 0.05784(9) 0.4965(2) 0.77283(14) 0.0358(3) Uani 1 1 d . . . . .
H1BA H 0.019344 0.449377 0.734023 0.043 Uiso 1 1 calc R U . . .
H1BB H 0.053822 0.575898 0.822215 0.043 Uiso 1 1 calc R U . . .
N2B N 0.13405(9) 0.3301(2) 0.68498(14) 0.0332(3) Uani 1 1 d . . . . .
C1B C 0.12414(10) 0.4463(2) 0.75633(16) 0.0326(4) Uani 1 1 d . . . . .
C2B C 0.25249(11) 0.3978(2) 0.77005(16) 0.0338(4) Uani 1 1 d . . . . .
C3B C 0.20670(10) 0.3002(2) 0.69059(16) 0.0331(4) Uani 1 1 d . . . . .
C4B C 0.23560(12) 0.1857(2) 0.62407(19) 0.0395(4) Uani 1 1 d . . . . .
H4B H 0.205166 0.119036 0.570141 0.047 Uiso 1 1 calc R U . . .
C5B C 0.30887(13) 0.1692(3) 0.6368(2) 0.0465(5) Uani 1 1 d . . . . .
H5B H 0.329152 0.091882 0.591273 0.056 Uiso 1 1 calc R U . . .
C6B C 0.35294(12) 0.2677(3) 0.7174(2) 0.0473(5) Uani 1 1 d . . . . .
C7B C 0.32621(12) 0.3825(3) 0.7847(2) 0.0417(4) Uani 1 1 d . . . . .
H7B H 0.356876 0.448284 0.838886 0.050 Uiso 1 1 calc R U . . .
O1B O 0.42748(10) 0.2617(3) 0.7320(2) 0.0789(7) Uani 1 1 d D . . . .
C8B C 0.46172(17) 0.1442(5) 0.6921(3) 0.0615(10) Uani 0.713(3) 1 d D U P B 1
H8B H 0.442288 0.033834 0.709472 0.074 Uiso 0.713(3) 1 calc R U P B 1
F1B F 0.53003(9) 0.1576(3) 0.7410(2) 0.0905(7) Uani 1 1 d D U . B 1
F2B F 0.45637(17) 0.1646(5) 0.5798(3) 0.1000(12) Uani 0.713(3) 1 d D U P B 1
C8C C 0.4630(5) 0.1306(8) 0.7621(6) 0.083(2) Uani 0.287(3) 1 d D U P B 2
F1C F 0.4516(13) 0.0195(18) 0.6777(13) 0.070(2) Uani 0.1435(17) 1 d D U P B 2
F2C F 0.4411(5) -0.0085(7) 0.7070(7) 0.070(2) Uani 0.287(3) 1 d D U P B 2
F3C F 0.4590(6) 0.1002(16) 0.8713(8) 0.096(4) Uani 0.1435(17) 1 d D U P B 2
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
C2A S1A C1A 88.76(9) . .
H1AA N1A H1AB 120.0 . .
C1A N1A H1AA 120.0 . .
C1A N1A H1AB 120.0 . .
C1A N2A C3A 110.04(16) . .
N1A C1A S1A 119.30(14) . .
N2A C1A S1A 115.95(14) . .
N2A C1A N1A 124.75(18) . .
C3A C2A S1A 109.33(14) . .
C7A C2A S1A 128.26(15) . .
C7A C2A C3A 122.38(18) . .
N2A C3A C2A 115.88(16) . .
N2A C3A C4A 125.10(18) . .
C4A C3A C2A 119.01(18) . .
C3A C4A H4A 120.3 . .
C5A C4A C3A 119.3(2) . .
C5A C4A H4A 120.3 . .
C4A C5A H5A 120.1 . .
C4A C5A C6A 119.82(19) . .
C6A C5A H5A 120.1 . .
C5A C6A O1A 118.55(19) . .
C7A C6A C5A 122.74(19) . .
C7A C6A O1A 118.6(2) . .
C2A C7A H7A 121.7 . .
C6A C7A C2A 116.67(19) . .
C6A C7A H7A 121.7 . .
C8A O1A C6A 116.8(2) . .
O1A C8A H8A 110.0 . .
O1A C8A F1A 111.9(2) . .
F1A C8A H8A 110.0 . .
F2A C8A O1A 111.8(2) . .
F2A C8A H8A 110.0 . .
F2A C8A F1A 102.9(3) . .
F3A C8A O1A 107.0(3) . .
F3A C8A F1A 111.4(4) . .
F3A C8A F2A 111.9(3) . .
C2B S1B C1B 88.84(9) . .
H1BA N1B H1BB 120.0 . .
C1B N1B H1BA 120.0 . .
C1B N1B H1BB 120.0 . .
C1B N2B C3B 110.56(16) . .
N1B C1B S1B 120.58(14) . .
N2B C1B S1B 116.04(15) . .
N2B C1B N1B 123.32(18) . .
C3B C2B S1B 109.26(15) . .
C7B C2B S1B 128.90(16) . .
C7B C2B C3B 121.83(18) . .
N2B C3B C2B 115.31(17) . .
C4B C3B N2B 125.24(18) . .
C4B C3B C2B 119.44(18) . .
C3B C4B H4B 120.2 . .
C5B C4B C3B 119.7(2) . .
C5B C4B H4B 120.2 . .
C4B C5B H5B 120.3 . .
C4B C5B C6B 119.4(2) . .
C6B C5B H5B 120.3 . .
C7B C6B C5B 122.6(2) . .
C7B C6B O1B 114.9(2) . .
O1B C6B C5B 122.5(2) . .
C2B C7B H7B 121.4 . .
C6B C7B C2B 117.10(19) . .
C6B C7B H7B 121.4 . .
C8B O1B C6B 123.2(2) . .
C8C O1B C6B 122.7(5) . .
O1B C8B H8B 110.5 . .
O1B C8B F1B 107.5(3) . .
O1B C8B F2B 108.8(3) . .
F1B C8B H8B 110.5 . .
F2B C8B H8B 110.5 . .
F2B C8B F1B 108.8(3) . .
O1B C8C F1C 110.0(11) . .
O1B C8C F2C 117.4(7) . .
O1B C8C F3C 107.9(4) . .
F1C C8C F3C 125.1(13) . .
F2C C8C F1C 21.0(9) . .
F2C C8C F3C 104.8(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1A C1A 1.7654(19) .
S1A C2A 1.7434(19) .
N1A H1AA 0.8800 .
N1A H1AB 0.8800 .
N1A C1A 1.337(2) .
N2A C1A 1.310(2) .
N2A C3A 1.392(3) .
C2A C3A 1.404(3) .
C2A C7A 1.391(3) .
C3A C4A 1.399(3) .
C4A H4A 0.9500 .
C4A C5A 1.385(3) .
C5A H5A 0.9500 .
C5A C6A 1.392(3) .
C6A C7A 1.380(3) .
C6A O1A 1.410(2) .
C7A H7A 0.9500 .
O1A C8A 1.336(3) .
C8A H8A 1.0000 .
C8A F1A 1.341(4) .
C8A F2A 1.336(3) .
C8A F3A 1.320(5) .
S1B C1B 1.760(2) .
S1B C2B 1.7426(19) .
N1B H1BA 0.8800 .
N1B H1BB 0.8800 .
N1B C1B 1.372(2) .
N2B C1B 1.298(2) .
N2B C3B 1.394(2) .
C2B C3B 1.406(3) .
C2B C7B 1.389(3) .
C3B C4B 1.389(3) .
C4B H4B 0.9500 .
C4B C5B 1.383(3) .
C5B H5B 0.9500 .
C5B C6B 1.401(3) .
C6B C7B 1.377(3) .
C6B O1B 1.400(3) .
C7B H7B 0.9500 .
O1B C8B 1.286(4) .
O1B C8C 1.272(6) .
C8B H8B 1.0000 .
C8B F1B 1.331(3) .
C8B F2B 1.327(4) .
C8C F1C 1.331(5) .
C8C F2C 1.328(5) .
C8C F3C 1.333(5) .
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
N1A H1AA N2B 0.88 2.05 2.916(2) 169.1 . yes
N1A H1AB N1B 0.88 2.34 3.211(2) 168.7 4_565 yes
N1B H1BA N2A 0.88 2.28 3.103(2) 155.8 . yes
N1B H1BB N2A 0.88 2.58 3.434(2) 164.4 2_556 yes
C4B H4B S1B 0.95 3.00 3.768(2) 139.4 4_565 yes
C5B H5B F2B 0.95 2.52 3.002(4) 111.6 . 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
S1A C2A C3A N2A -0.4(2) . . . .
S1A C2A C3A C4A 179.45(14) . . . .
S1A C2A C7A C6A 178.53(15) . . . .
N2A C3A C4A C5A -178.21(18) . . . .
C1A S1A C2A C3A -0.64(14) . . . .
C1A S1A C2A C7A -178.85(18) . . . .
C1A N2A C3A C2A 1.5(2) . . . .
C1A N2A C3A C4A -178.24(18) . . . .
C2A S1A C1A N1A -179.58(16) . . . .
C2A S1A C1A N2A 1.63(15) . . . .
C2A C3A C4A C5A 2.0(3) . . . .
C3A N2A C1A S1A -2.1(2) . . . .
C3A N2A C1A N1A 179.21(18) . . . .
C3A C2A C7A C6A 0.5(3) . . . .
C3A C4A C5A C6A -0.2(3) . . . .
C4A C5A C6A C7A -1.5(3) . . . .
C4A C5A C6A O1A -178.14(18) . . . .
C5A C6A C7A C2A 1.4(3) . . . .
C5A C6A O1A C8A -86.5(3) . . . .
C6A O1A C8A F1A 54.5(3) . . . .
C6A O1A C8A F2A -60.3(3) . . . .
C6A O1A C8A F3A 176.8(3) . . . .
C7A C2A C3A N2A 177.98(17) . . . .
C7A C2A C3A C4A -2.2(3) . . . .
C7A C6A O1A C8A 96.8(3) . . . .
O1A C6A C7A C2A 177.96(17) . . . .
S1B C2B C3B N2B -0.5(2) . . . .
S1B C2B C3B C4B 178.73(15) . . . .
S1B C2B C7B C6B -178.58(18) . . . .
N2B C3B C4B C5B 179.1(2) . . . .
C1B S1B C2B C3B 0.36(14) . . . .
C1B S1B C2B C7B 179.4(2) . . . .
C1B N2B C3B C2B 0.4(2) . . . .
C1B N2B C3B C4B -178.80(19) . . . .
C2B S1B C1B N1B 176.88(16) . . . .
C2B S1B C1B N2B -0.18(15) . . . .
C2B C3B C4B C5B 0.0(3) . . . .
C3B N2B C1B S1B -0.1(2) . . . .
C3B N2B C1B N1B -177.04(17) . . . .
C3B C2B C7B C6B 0.4(3) . . . .
C3B C4B C5B C6B 0.5(3) . . . .
C4B C5B C6B C7B -0.5(4) . . . .
C4B C5B C6B O1B -177.8(2) . . . .
C5B C6B C7B C2B 0.1(4) . . . .
C5B C6B O1B C8B -15.2(5) . . . .
C5B C6B O1B C8C -60.8(5) . . . .
C6B O1B C8B F1B -167.1(3) . . . .
C6B O1B C8B F2B 75.2(4) . . . .
C6B O1B C8C F1C 69.1(12) . . . .
C6B O1B C8C F2C 47.6(10) . . . .
C6B O1B C8C F3C -70.4(9) . . . .
C7B C2B C3B N2B -179.65(18) . . . .
C7B C2B C3B C4B -0.4(3) . . . .
C7B C6B O1B C8B 167.4(3) . . . .
C7B C6B O1B C8C 121.8(4) . . . .
O1B C6B C7B C2B 177.5(2) . . . .

_cod_database_fobs_code 4519500
