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#$Date: 2025-09-04 18:02:51 +0300 (Thu, 04 Sep 2025) $
#$Revision: 302016 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/95/4519507.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_4519507
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 H6 F2 N2 O S'
_chemical_formula_sum            'C8 H6 F2 N2 O S'
_chemical_formula_weight         216.21
_chemical_name_systematic        6-(difluoromethoxy)-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   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             2024-11-26
_cell_angle_alpha                90
_cell_angle_beta                 101.366(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7483(10)
_cell_length_b                   7.9725(4)
_cell_length_c                   11.9698(6)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.584
_cell_measurement_theta_min      3.524
_cell_volume                     1754.05(16)
_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 0.975
_diffrn_measured_fraction_theta_max 0.957
_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  0.0524
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       22
_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       -15
_diffrn_reflns_number            49845
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.790
_diffrn_reflns_theta_min         4.185
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    2.191
_exptl_absorpt_correction_T_max  0.2103
_exptl_absorpt_correction_T_min  0.0913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1728 before and 0.0967 after correction.
The Ratio of minimum to maximum transmission is 0.4341.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_recrystallization_method 'crystallized from Acetone'
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0745
_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)+(0.0953P)²+3.1881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2136
_refine_ls_wR_factor_ref         0.2153
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3622
_reflns_number_total             3874
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            02-1b_RZ2F_P21c_jw26931_150K.cif
_cod_data_source_block           jw26931
_cod_database_code               4519507
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 0.61040(6) 0.18047(12) 0.61033(8) 0.0524(3) Uani 1 1 d . . . . .
N1A N 0.4701(2) 0.2076(4) 0.5059(3) 0.0563(8) Uani 1 1 d . . . . .
H1AA H 0.433878 0.243003 0.452845 0.068 Uiso 1 1 calc R U . . .
H1AB H 0.461609 0.140108 0.559918 0.068 Uiso 1 1 calc R U . . .
N2A N 0.55687(19) 0.3561(4) 0.4282(3) 0.0490(7) Uani 1 1 d . . . . .
C1A C 0.5382(2) 0.2564(5) 0.5043(3) 0.0496(8) Uani 1 1 d . . . . .
C2A C 0.6710(2) 0.2990(5) 0.5489(3) 0.0503(8) Uani 1 1 d . . . . .
C3A C 0.6315(2) 0.3843(4) 0.4525(3) 0.0485(8) Uani 1 1 d . . . . .
C4A C 0.6697(2) 0.4879(5) 0.3907(3) 0.0538(9) Uani 1 1 d . . . . .
H4A H 0.644336 0.549653 0.327256 0.065 Uiso 1 1 calc R U . . .
C5A C 0.7442(2) 0.5000(5) 0.4219(4) 0.0570(10) Uani 1 1 d . . . . .
H5A H 0.770381 0.569824 0.379821 0.068 Uiso 1 1 calc R U . . .
C6A C 0.7812(2) 0.4100(5) 0.5152(4) 0.0569(9) Uani 1 1 d . . . . .
C7A C 0.7457(2) 0.3098(5) 0.5813(3) 0.0545(9) Uani 1 1 d . . . . .
H7A H 0.771552 0.251257 0.645936 0.065 Uiso 1 1 calc R U . . .
O1A O 0.85717(17) 0.4295(4) 0.5492(3) 0.0665(8) Uani 1 1 d . . . . .
C8A C 0.8988(3) 0.3390(6) 0.4933(5) 0.0718(12) Uani 1 1 d . . . . .
H8A H 0.951233 0.359161 0.526965 0.086 Uiso 1 1 calc R U . . .
F1A F 0.8862(3) 0.3714(7) 0.3800(4) 0.1371(18) Uani 1 1 d . . . . .
F2A F 0.88406(18) 0.1739(4) 0.4967(4) 0.0981(11) Uani 1 1 d . . . . .
S1B S 0.29612(6) 0.52971(12) 0.15369(8) 0.0529(3) Uani 1 1 d . . . . .
N1B N 0.44235(19) 0.4960(4) 0.2255(3) 0.0531(8) Uani 1 1 d . . . . .
H1BA H 0.481705 0.449882 0.266101 0.064 Uiso 1 1 calc R U . . .
H1BB H 0.446282 0.575202 0.175864 0.064 Uiso 1 1 calc R U . . .
C1B C 0.3753(2) 0.4448(5) 0.2396(3) 0.0503(8) Uani 1 1 d . . . . .
C2B C 0.2443(2) 0.3950(5) 0.2198(3) 0.0498(8) Uani 1 1 d . . . . .
N2B N 0.36471(19) 0.3297(4) 0.3104(3) 0.0506(7) Uani 1 1 d . . . . .
C3B C 0.2905(2) 0.2986(5) 0.3019(3) 0.0503(8) Uani 1 1 d . . . . .
C4B C 0.2607(2) 0.1831(5) 0.3668(4) 0.0559(9) Uani 1 1 d . . . . .
H4B H 0.291541 0.117165 0.422369 0.067 Uiso 1 1 calc R U . . .
C5B C 0.1868(3) 0.1647(5) 0.3503(4) 0.0635(11) Uani 1 1 d . . . . .
H5B H 0.166216 0.086174 0.394604 0.076 Uiso 1 1 calc R U . . .
C6B C 0.1418(2) 0.2618(5) 0.2683(4) 0.0613(10) Uani 1 1 d . . . . .
C7B C 0.1690(2) 0.3771(5) 0.2020(4) 0.0578(10) Uani 1 1 d . . . . .
H7B H 0.137612 0.441920 0.146313 0.069 Uiso 1 1 calc R U . . .
O1B O 0.06749(18) 0.2496(4) 0.2500(3) 0.0820(11) Uani 1 1 d D . . . .
C8B C 0.0348(3) 0.1318(9) 0.3051(4) 0.0770(16) Uani 0.817(4) 1 d D . P A 1
H8B H 0.056328 0.018650 0.296985 0.092 Uiso 0.817(4) 1 calc R U P A 1
F1B F -0.0347(2) 0.1324(6) 0.2586(4) 0.1017(14) Uani 0.817(4) 1 d D . P A 1
F2B F 0.0393(2) 0.1681(6) 0.4120(3) 0.0956(13) Uani 0.817(4) 1 d D . P A 1
C8C C 0.0212(5) 0.294(4) 0.2911(8) 0.0770(16) Uani 0.183(4) 1 d D . P A 2
H8C H 0.032185 0.416146 0.284239 0.092 Uiso 0.183(4) 1 calc R U P A 2
F1C F 0.0227(7) 0.301(3) 0.4006(8) 0.1017(14) Uani 0.183(4) 1 d D . P A 2
F2C F -0.0470(4) 0.308(3) 0.2407(12) 0.0956(13) Uani 0.183(4) 1 d D . P A 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 89.01(19) . .
H1AA N1A H1AB 120.0 . .
C1A N1A H1AA 120.0 . .
C1A N1A H1AB 120.0 . .
C1A N2A C3A 110.4(3) . .
N1A C1A S1A 119.2(3) . .
N2A C1A S1A 115.8(3) . .
N2A C1A N1A 125.0(4) . .
C3A C2A S1A 108.8(3) . .
C7A C2A S1A 128.6(3) . .
C7A C2A C3A 122.6(4) . .
N2A C3A C2A 115.9(3) . .
N2A C3A C4A 125.8(4) . .
C4A C3A C2A 118.3(4) . .
C3A C4A H4A 120.1 . .
C5A C4A C3A 119.8(4) . .
C5A C4A H4A 120.1 . .
C4A C5A H5A 120.0 . .
C4A C5A C6A 120.0(4) . .
C6A C5A H5A 120.0 . .
C5A C6A O1A 119.3(4) . .
C7A C6A C5A 122.5(4) . .
C7A C6A O1A 118.1(4) . .
C2A C7A C6A 116.8(4) . .
C2A C7A H7A 121.6 . .
C6A C7A H7A 121.6 . .
C8A O1A C6A 116.9(4) . .
O1A C8A H8A 109.6 . .
O1A C8A F1A 113.3(4) . .
O1A C8A F2A 111.7(4) . .
F1A C8A H8A 109.6 . .
F2A C8A H8A 109.6 . .
F2A C8A F1A 102.8(5) . .
C2B S1B C1B 88.80(19) . .
H1BA N1B H1BB 120.0 . .
C1B N1B H1BA 120.0 . .
C1B N1B H1BB 120.0 . .
N1B C1B S1B 120.2(3) . .
N2B C1B S1B 115.8(3) . .
N2B C1B N1B 123.9(4) . .
C3B C2B S1B 109.4(3) . .
C7B C2B S1B 129.3(3) . .
C7B C2B C3B 121.2(4) . .
C1B N2B C3B 110.9(3) . .
N2B C3B C2B 115.0(3) . .
C4B C3B C2B 119.5(4) . .
C4B C3B N2B 125.5(4) . .
C3B C4B H4B 120.1 . .
C5B C4B C3B 119.9(4) . .
C5B C4B H4B 120.1 . .
C4B C5B H5B 120.1 . .
C4B C5B C6B 119.7(4) . .
C6B C5B H5B 120.1 . .
C7B C6B C5B 122.4(4) . .
O1B C6B C5B 121.8(4) . .
O1B C6B C7B 115.8(4) . .
C2B C7B H7B 121.3 . .
C6B C7B C2B 117.3(4) . .
C6B C7B H7B 121.3 . .
C8B O1B C6B 120.8(4) . .
C8C O1B C6B 138.4(10) . .
O1B C8B H8B 110.3 . .
F1B C8B O1B 107.2(4) . .
F1B C8B H8B 110.3 . .
F2B C8B O1B 112.1(5) . .
F2B C8B H8B 110.3 . .
F2B C8B F1B 106.4(6) . .
O1B C8C H8C 94.6 . .
O1B C8C F1C 125.4(9) . .
O1B C8C F2C 126.0(8) . .
F1C C8C H8C 94.6 . .
F2C C8C H8C 94.6 . .
F2C C8C F1C 106.7(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1A C1A 1.770(4) .
S1A C2A 1.748(4) .
N1A H1AA 0.8800 .
N1A H1AB 0.8800 .
N1A C1A 1.337(5) .
N2A C1A 1.308(5) .
N2A C3A 1.390(5) .
C2A C3A 1.417(5) .
C2A C7A 1.380(6) .
C3A C4A 1.397(5) .
C4A H4A 0.9500 .
C4A C5A 1.377(6) .
C5A H5A 0.9500 .
C5A C6A 1.392(6) .
C6A C7A 1.383(6) .
C6A O1A 1.410(5) .
C7A H7A 0.9500 .
O1A C8A 1.335(6) .
C8A H8A 1.0000 .
C8A F1A 1.354(6) .
C8A F2A 1.346(6) .
S1B C1B 1.765(4) .
S1B C2B 1.740(4) .
N1B H1BA 0.8800 .
N1B H1BB 0.8800 .
N1B C1B 1.364(5) .
C1B N2B 1.291(5) .
C2B C3B 1.404(6) .
C2B C7B 1.393(6) .
N2B C3B 1.396(5) .
C3B C4B 1.391(5) .
C4B H4B 0.9500 .
C4B C5B 1.368(6) .
C5B H5B 0.9500 .
C5B C6B 1.396(7) .
C6B C7B 1.375(6) .
C6B O1B 1.371(5) .
C7B H7B 0.9500 .
O1B C8B 1.361(7) .
O1B C8C 1.137(12) .
C8B H8B 1.0000 .
C8B F1B 1.312(5) .
C8B F2B 1.299(5) .
C8C H8C 1.0000 .
C8C F1C 1.306(6) .
C8C F2C 1.306(6) .
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(5) 168.8 . yes
N1A H1AB N1B 0.88 2.35 3.219(5) 169.5 4_566 yes
C8A H8A F1C 1.00 2.26 2.782(11) 111.3 1_655 yes
N1B H1BA N2A 0.88 2.29 3.112(5) 156.1 . yes
N1B H1BB N2A 0.88 2.56 3.411(5) 163.7 2_655 yes
C4B H4B S1B 0.95 2.99 3.771(4) 140.1 4_566 yes
C5B H5B F2B 0.95 2.52 3.000(6) 111.7 . yes
C7B H7B F2A 0.95 2.50 3.363(6) 151.4 2_655 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(4) . . . .
S1A C2A C3A C4A 179.6(3) . . . .
S1A C2A C7A C6A 178.1(3) . . . .
N2A C3A C4A C5A -177.7(4) . . . .
C1A S1A C2A C3A -0.7(3) . . . .
C1A S1A C2A C7A -178.6(4) . . . .
C1A N2A C3A C2A 1.8(4) . . . .
C1A N2A C3A C4A -178.3(3) . . . .
C2A S1A C1A N1A -179.2(3) . . . .
C2A S1A C1A N2A 1.8(3) . . . .
C2A C3A C4A C5A 2.2(5) . . . .
C3A N2A C1A S1A -2.4(4) . . . .
C3A N2A C1A N1A 178.8(3) . . . .
C3A C2A C7A C6A 0.4(6) . . . .
C3A C4A C5A C6A -0.3(6) . . . .
C4A C5A C6A C7A -1.7(6) . . . .
C4A C5A C6A O1A -177.2(4) . . . .
C5A C6A C7A C2A 1.6(6) . . . .
C5A C6A O1A C8A -82.8(5) . . . .
C6A O1A C8A F1A 59.8(6) . . . .
C6A O1A C8A F2A -55.7(6) . . . .
C7A C2A C3A N2A 177.6(3) . . . .
C7A C2A C3A C4A -2.3(5) . . . .
C7A C6A O1A C8A 101.4(5) . . . .
O1A C6A C7A C2A 177.2(3) . . . .
S1B C1B N2B C3B 0.0(4) . . . .
S1B C2B C3B N2B -0.9(4) . . . .
S1B C2B C3B C4B 179.2(3) . . . .
S1B C2B C7B C6B -178.8(3) . . . .
N1B C1B N2B C3B -177.1(3) . . . .
C1B S1B C2B C3B 0.7(3) . . . .
C1B S1B C2B C7B 179.8(4) . . . .
C1B N2B C3B C2B 0.6(5) . . . .
C1B N2B C3B C4B -179.5(4) . . . .
C2B S1B C1B N1B 176.8(3) . . . .
C2B S1B C1B N2B -0.4(3) . . . .
C2B C3B C4B C5B -0.2(6) . . . .
N2B C3B C4B C5B 179.9(4) . . . .
C3B C2B C7B C6B 0.2(6) . . . .
C3B C4B C5B C6B 0.2(7) . . . .
C4B C5B C6B C7B 0.0(7) . . . .
C4B C5B C6B O1B -179.0(4) . . . .
C5B C6B C7B C2B -0.2(7) . . . .
C5B C6B O1B C8B -5.5(7) . . . .
C5B C6B O1B C8C 78(2) . . . .
C6B O1B C8B F1B -170.5(5) . . . .
C6B O1B C8B F2B 73.1(7) . . . .
C6B O1B C8C F1C -40(5) . . . .
C6B O1B C8C F2C 158.6(18) . . . .
C7B C2B C3B N2B 180.0(3) . . . .
C7B C2B C3B C4B 0.0(6) . . . .
C7B C6B O1B C8B 175.4(4) . . . .
C7B C6B O1B C8C -101(2) . . . .
O1B C6B C7B C2B 178.8(4) . . . .

_cod_database_fobs_code 4519507
