#------------------------------------------------------------------------------
#$Date: 2025-09-04 16:45:02 +0200 (Thu 04 de Sep de 2025) $
#$Revision: 302012 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/95/4519503.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_4519503
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         '0.69(C8 H6 F2 N2 O S), 0.31(C8 H8 N2 O S)'
_chemical_formula_sum            'C8 H6.61 F1.39 N2 O S'
_chemical_formula_weight         205.28
_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                 102.4296(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.4448(4)
_cell_length_b                   7.9586(2)
_cell_length_c                   11.9812(3)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    150
_cell_measurement_theta_max      58.898
_cell_measurement_theta_min      4.290
_cell_volume                     1717.55(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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_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 0.969
_diffrn_measured_fraction_theta_max 0.929
_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  0.0296
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14930
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.893
_diffrn_reflns_theta_min         5.286
_diffrn_source                   'Metal Jet'
_diffrn_source_current           3.57
_diffrn_source_power             0.2488647
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    2.148
_exptl_absorpt_correction_T_max  0.2075
_exptl_absorpt_correction_T_min  0.1128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1108 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.5436.
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    1.588
_exptl_crystal_description       block
_exptl_crystal_F_000             841
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0999P)²+1.9197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1693
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3398
_reflns_number_total             3482
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            09-1b_1d_069RZ2F_031TZ_jw27321.cif
_cod_data_source_block           jw27321
_cod_database_code               4519503
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 0.38721(3) 0.18077(8) 0.38459(5) 0.0314(2) Uani 1 1 d . . . . .
O1A O 0.13318(12) 0.4208(3) 0.4352(2) 0.0532(6) Uani 1 1 d . U . . .
N1A N 0.52963(13) 0.2091(3) 0.4946(2) 0.0368(5) Uani 1 1 d . . . . .
H1AA H 0.566380 0.243846 0.549289 0.044 Uiso 1 1 calc R U . . .
H1AB H 0.538637 0.142251 0.440647 0.044 Uiso 1 1 calc R U . . .
N2A N 0.44033(12) 0.3563(3) 0.56890(18) 0.0306(5) Uani 1 1 d . . . . .
C1A C 0.45997(14) 0.2578(3) 0.4935(2) 0.0295(5) Uani 1 1 d . . . . .
C2A C 0.32497(14) 0.2971(3) 0.4440(2) 0.0302(5) Uani 1 1 d . . . . .
C3A C 0.36362(14) 0.3830(3) 0.5410(2) 0.0299(5) Uani 1 1 d . . . . .
C4A C 0.32428(16) 0.4851(3) 0.6022(2) 0.0354(6) Uani 1 1 d . . . . .
H4A H 0.349701 0.546106 0.667075 0.043 Uiso 1 1 calc R U . . .
C5A C 0.24757(17) 0.4964(4) 0.5671(3) 0.0400(6) Uani 1 1 d . . . . .
H5A H 0.220169 0.566095 0.607528 0.048 Uiso 1 1 calc R U . . .
C6A C 0.21115(15) 0.4054(4) 0.4727(3) 0.0392(6) Uani 1 1 d . . . . .
C7A C 0.24810(15) 0.3061(3) 0.4080(2) 0.0353(6) Uani 1 1 d . . . . .
H7A H 0.222327 0.247149 0.342451 0.042 Uiso 1 1 calc R U . . .
C8A C 0.0904(2) 0.3382(5) 0.4940(3) 0.0561(8) Uani 1 1 d . U . A 1
H8AA H 0.039761 0.383075 0.474332 0.084 Uiso 1 1 calc R U . A 1
H8AB H 0.110435 0.352507 0.576105 0.084 Uiso 0.108(8) 1 calc R U P B 1
H8AC H 0.089616 0.218417 0.474719 0.084 Uiso 0.108(8) 1 calc R U P B 1
F1A F 0.10751(14) 0.1751(3) 0.5000(3) 0.0751(11) Uani 0.892(8) 1 d . U P B 2
F2A F 0.0989(2) 0.3896(7) 0.6011(3) 0.140(2) Uani 0.892(8) 1 d . U P B 2
S1B S 0.70782(4) 0.52804(8) 0.85342(5) 0.0321(2) Uani 1 1 d . . . . .
O1B O 0.94146(12) 0.2408(3) 0.7658(2) 0.0530(6) Uani 1 1 d D U . . .
N1B N 0.55784(13) 0.4970(3) 0.77781(19) 0.0337(5) Uani 1 1 d . . . . .
H1BA H 0.517628 0.451156 0.736022 0.040 Uiso 1 1 calc R U . . .
H1BB H 0.553929 0.576157 0.827493 0.040 Uiso 1 1 calc R U . . .
N2B N 0.63646(12) 0.3296(3) 0.69409(18) 0.0314(5) Uani 1 1 d . . . . .
C1B C 0.62682(14) 0.4451(3) 0.7655(2) 0.0297(5) Uani 1 1 d . . . . .
C2B C 0.75997(14) 0.3919(3) 0.7879(2) 0.0306(5) Uani 1 1 d . . . . .
C3B C 0.71205(14) 0.2966(3) 0.7048(2) 0.0305(5) Uani 1 1 d . . . . .
C4B C 0.74131(16) 0.1812(3) 0.6395(2) 0.0365(6) Uani 1 1 d . . . . .
H4B H 0.709403 0.116732 0.582522 0.044 Uiso 1 1 calc R U . . .
C5B C 0.81772(17) 0.1613(4) 0.6584(3) 0.0408(6) Uani 1 1 d . . . . .
H5B H 0.838371 0.082543 0.614383 0.049 Uiso 1 1 calc R U . . .
C6B C 0.86430(16) 0.2567(4) 0.7420(3) 0.0393(6) Uani 1 1 d . . . . .
C7B C 0.83682(15) 0.3731(3) 0.8080(2) 0.0352(6) Uani 1 1 d . . . . .
H7B H 0.868980 0.437583 0.864648 0.042 Uiso 1 1 calc R U . . .
C8B C 0.9721(2) 0.1346(7) 0.6946(4) 0.0474(13) Uani 0.653(8) 1 d D U P C 3
H8BA H 1.026276 0.133931 0.719865 0.071 Uiso 0.327(4) 1 calc R U P C 3
H8BB H 0.952993 0.020338 0.698626 0.071 Uiso 0.5 1 calc R U P C 3
H8BC H 0.958385 0.175352 0.615722 0.071 Uiso 0.327(4) 1 calc R U P C 3
F1B F 0.9638(8) 0.1511(17) 0.5922(14) 0.087(3) Uani 0.327(4) 1 d . U P C 4
F2B F 1.0406(5) 0.1524(16) 0.7384(9) 0.099(3) Uani 0.327(4) 1 d . U P C 4
C8C C 0.9833(7) 0.280(3) 0.6846(11) 0.097(4) Uani 0.347(8) 1 d D U P C 5
H8CA H 1.036025 0.260404 0.717494 0.145 Uiso 0.173(4) 1 calc R U P C 5
H8CB H 0.967499 0.208042 0.617212 0.145 Uiso 0.173(4) 1 calc R U P C 5
H8CC H 0.975576 0.397883 0.662215 0.145 Uiso 0.5 1 calc R U P C 5
F1C F 0.9546(16) 0.221(3) 0.592(3) 0.087(3) Uani 0.173(4) 1 d . U P C 6
F2C F 1.0531(9) 0.302(3) 0.7448(16) 0.097(3) Uani 0.173(4) 1 d . U P C 6
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 88.66(12) . .
C8A O1A C6A 117.6(3) . .
H1AA N1A H1AB 120.0 . .
C1A N1A H1AA 120.0 . .
C1A N1A H1AB 120.0 . .
C1A N2A C3A 110.1(2) . .
N1A C1A S1A 118.77(19) . .
N2A C1A S1A 116.07(19) . .
N2A C1A N1A 125.1(2) . .
C3A C2A S1A 109.60(19) . .
C7A C2A S1A 128.2(2) . .
C7A C2A C3A 122.2(2) . .
N2A C3A C2A 115.6(2) . .
C4A C3A N2A 125.1(2) . .
C4A C3A C2A 119.3(2) . .
C3A C4A H4A 120.4 . .
C5A C4A C3A 119.3(3) . .
C5A C4A H4A 120.4 . .
C4A C5A H5A 120.2 . .
C6A C5A C4A 119.7(3) . .
C6A C5A H5A 120.2 . .
C5A C6A O1A 119.6(3) . .
C7A C6A O1A 117.4(3) . .
C7A C6A C5A 122.9(3) . .
C2A C7A H7A 121.7 . .
C6A C7A C2A 116.6(3) . .
C6A C7A H7A 121.7 . .
O1A C8A H8AA 109.5 . .
O1A C8A H8AB 109.5 . .
O1A C8A H8AC 109.5 . .
H8AA C8A H8AB 109.5 . .
H8AA C8A H8AC 109.5 . .
H8AB C8A H8AC 109.5 . .
C2B S1B C1B 88.68(12) . .
C6B O1B C8B 117.2(3) . .
C6B O1B C8C 121.9(7) . .
H1BA N1B H1BB 120.0 . .
C1B N1B H1BA 120.0 . .
C1B N1B H1BB 120.0 . .
C1B N2B C3B 110.4(2) . .
N1B C1B S1B 120.56(19) . .
N2B C1B S1B 116.25(19) . .
N2B C1B N1B 123.1(2) . .
C3B C2B S1B 109.33(19) . .
C7B C2B S1B 128.9(2) . .
C7B C2B C3B 121.8(2) . .
N2B C3B C2B 115.3(2) . .
C4B C3B N2B 125.0(2) . .
C4B C3B C2B 119.7(2) . .
C3B C4B H4B 120.4 . .
C5B C4B C3B 119.2(2) . .
C5B C4B H4B 120.4 . .
C4B C5B H5B 119.9 . .
C4B C5B C6B 120.1(3) . .
C6B C5B H5B 119.9 . .
C5B C6B O1B 122.7(3) . .
C7B C6B O1B 115.3(3) . .
C7B C6B C5B 122.0(3) . .
C2B C7B H7B 121.4 . .
C6B C7B C2B 117.2(2) . .
C6B C7B H7B 121.4 . .
O1B C8B H8BA 109.5 . .
O1B C8B H8BB 109.5 . .
O1B C8B H8BC 109.5 . .
H8BA C8B H8BB 109.5 . .
H8BA C8B H8BC 109.5 . .
H8BB C8B H8BC 109.5 . .
O1B C8C H8CA 109.5 . .
O1B C8C H8CB 109.5 . .
O1B C8C H8CC 109.5 . .
H8CA C8C H8CB 109.5 . .
H8CA C8C H8CC 109.5 . .
H8CB C8C H8CC 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1A C1A 1.768(3) .
S1A C2A 1.742(3) .
O1A C6A 1.417(3) .
O1A C8A 1.339(4) .
N1A H1AA 0.8800 .
N1A H1AB 0.8800 .
N1A C1A 1.339(3) .
N2A C1A 1.305(3) .
N2A C3A 1.398(3) .
C2A C3A 1.403(4) .
C2A C7A 1.392(4) .
C3A C4A 1.398(4) .
C4A H4A 0.9500 .
C4A C5A 1.389(4) .
C5A H5A 0.9500 .
C5A C6A 1.389(4) .
C6A C7A 1.385(4) .
C7A H7A 0.9500 .
C8A H8AA 0.9800 .
C8A H8AB 0.9800 .
C8A H8AC 0.9800 .
S1B C1B 1.761(3) .
S1B C2B 1.744(3) .
O1B C6B 1.396(3) .
O1B C8B 1.403(5) .
O1B C8C 1.401(5) .
N1B H1BA 0.8800 .
N1B H1BB 0.8800 .
N1B C1B 1.376(3) .
N2B C1B 1.294(3) .
N2B C3B 1.397(3) .
C2B C3B 1.403(4) .
C2B C7B 1.394(4) .
C3B C4B 1.389(4) .
C4B H4B 0.9500 .
C4B C5B 1.388(4) .
C5B H5B 0.9500 .
C5B C6B 1.395(4) .
C6B C7B 1.383(4) .
C7B H7B 0.9500 .
C8B H8BA 0.9800 .
C8B H8BB 0.9800 .
C8B H8BC 0.9800 .
C8C H8CA 0.9800 .
C8C H8CB 0.9800 .
C8C H8CC 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
N1A H1AA N2B 0.88 2.04 2.913(3) 169.0 . yes
N1A H1AB N1B 0.88 2.34 3.208(3) 170.6 4_565 yes
N1B H1BA N2A 0.88 2.32 3.144(3) 155.8 . yes
N1B H1BB N2A 0.88 2.54 3.395(3) 163.1 2_656 yes
C4B H4B S1B 0.95 2.97 3.740(3) 139.0 4_565 yes
C5B H5B F1B 0.95 2.45 2.970(13) 114.5 . yes
C7B H7B F1A 0.95 2.47 3.332(4) 151.4 2_656 yes
C8C H8CC O1A 0.98 2.54 3.321(17) 136.4 3_666 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 -0.8(3) . . . .
S1A C2A C3A C4A 179.82(19) . . . .
S1A C2A C7A C6A 178.3(2) . . . .
O1A C6A C7A C2A 177.9(2) . . . .
N2A C3A C4A C5A -177.9(2) . . . .
C1A S1A C2A C3A -0.47(18) . . . .
C1A S1A C2A C7A -178.7(2) . . . .
C1A N2A C3A C2A 2.1(3) . . . .
C1A N2A C3A C4A -178.5(2) . . . .
C2A S1A C1A N1A -179.8(2) . . . .
C2A S1A C1A N2A 1.8(2) . . . .
C2A C3A C4A C5A 1.4(4) . . . .
C3A N2A C1A S1A -2.5(3) . . . .
C3A N2A C1A N1A 179.2(2) . . . .
C3A C2A C7A C6A 0.3(4) . . . .
C3A C4A C5A C6A 0.5(4) . . . .
C4A C5A C6A O1A -178.2(2) . . . .
C4A C5A C6A C7A -2.2(4) . . . .
C5A C6A C7A C2A 1.8(4) . . . .
C7A C2A C3A N2A 177.6(2) . . . .
C7A C2A C3A C4A -1.8(4) . . . .
C8A O1A C6A C5A -77.6(4) . . . .
C8A O1A C6A C7A 106.1(3) . . . .
S1B C2B C3B N2B -0.4(3) . . . .
S1B C2B C3B C4B 178.7(2) . . . .
S1B C2B C7B C6B -178.9(2) . . . .
O1B C6B C7B C2B -179.4(2) . . . .
N2B C3B C4B C5B 179.6(3) . . . .
C1B S1B C2B C3B 0.46(19) . . . .
C1B S1B C2B C7B 179.8(3) . . . .
C1B N2B C3B C2B 0.1(3) . . . .
C1B N2B C3B C4B -179.0(2) . . . .
C2B S1B C1B N1B 176.6(2) . . . .
C2B S1B C1B N2B -0.4(2) . . . .
C2B C3B C4B C5B 0.6(4) . . . .
C3B N2B C1B S1B 0.2(3) . . . .
C3B N2B C1B N1B -176.7(2) . . . .
C3B C2B C7B C6B 0.3(4) . . . .
C3B C4B C5B C6B -0.2(4) . . . .
C4B C5B C6B O1B 179.2(3) . . . .
C4B C5B C6B C7B -0.2(5) . . . .
C5B C6B C7B C2B 0.1(4) . . . .
C7B C2B C3B N2B -179.8(2) . . . .
C7B C2B C3B C4B -0.7(4) . . . .
C8B O1B C6B C5B 5.8(5) . . . .
C8B O1B C6B C7B -174.8(3) . . . .
C8C O1B C6B C5B 63.6(11) . . . .
C8C O1B C6B C7B -116.9(10) . . . .

_cod_database_fobs_code 4519503
