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#$Date: 2022-11-10 12:33:07 +0200 (Thu, 10 Nov 2022) $
#$Revision: 279204 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106064.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_8106064
loop_
_publ_author_name
'Chen, Hong'
'Jia, Hui-Xia'
_publ_section_title
;
 Crystal structure of
 2-(4-(2-(4-(2-fluorophenyl)piperazin-1-yl)ethyl)benzyl)benzo[d]isothiazol-3(2H)-one
 1,1-dioxide, C26H26FN3O3S -- a saccharin dervative
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              111
_journal_page_last               113
_journal_paper_doi               10.1515/ncrs-2017-0197
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C26 H26 F N3 O3 S'
_chemical_formula_sum            'C26 H26 F N3 O3 S'
_chemical_formula_weight         479.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                97.80(3)
_cell_angle_beta                 97.77(3)
_cell_angle_gamma                106.84(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0252(14)
_cell_length_b                   9.3017(19)
_cell_length_c                   19.388(4)
_cell_measurement_reflns_used    4252
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.54
_cell_measurement_theta_min      2.15
_cell_volume                     1180.9(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1491
_diffrn_reflns_av_unetI/netI     0.1083
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19521
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         2.157
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   none
_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    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.150
_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     307
_refine_ls_number_reflns         4252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0729
_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)+(0.0970P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1854
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3291
_reflns_number_total             4252
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0197_suppl.cif
_cod_data_source_block           a
_cod_database_code               8106064
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C19(H19A,H19B), C11(H11A,H11B), C12(H12A,H12B),
 C10(H10A,H10B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C22(H22), C15(H15), C17(H17), C4(H4), C2(H2), C14(H14), C3(H3),
 C18(H18), C25(H25), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 1.12276(11) 0.18097(7) 0.92905(3) 0.0463(2) Uani 1 1 d . . . . .
F1 F -0.0029(2) 0.13890(19) 0.24270(8) 0.0577(4) Uani 1 1 d . . . . .
O1 O 1.3174(3) 0.5703(2) 0.88626(10) 0.0589(5) Uani 1 1 d . . . . .
O2 O 1.2623(3) 0.0968(2) 0.93180(11) 0.0710(6) Uani 1 1 d . . . . .
O3 O 0.9126(3) 0.0962(2) 0.90818(11) 0.0687(6) Uani 1 1 d . . . . .
N1 N 0.0003(3) 0.2318(2) 0.38308(10) 0.0345(5) Uani 1 1 d . . . . .
N2 N 0.2411(3) 0.1984(2) 0.50894(10) 0.0357(5) Uani 1 1 d . . . . .
N3 N 1.1891(3) 0.3122(2) 0.87851(10) 0.0410(5) Uani 1 1 d . . . . .
C1 C -0.1682(4) 0.1746(3) 0.25980(13) 0.0389(6) Uani 1 1 d . . . . .
C2 C -0.3220(4) 0.1643(3) 0.20618(14) 0.0505(7) Uani 1 1 d . . . . .
H2 H -0.3166 0.1294 0.1594 0.061 Uiso 1 1 calc R . . . .
C3 C -0.4855(4) 0.2068(3) 0.22270(15) 0.0525(7) Uani 1 1 d . . . . .
H3 H -0.5924 0.2000 0.1871 0.063 Uiso 1 1 calc R . . . .
C4 C -0.4891(4) 0.2593(3) 0.29206(15) 0.0491(7) Uani 1 1 d . . . . .
H4 H -0.5978 0.2902 0.3031 0.059 Uiso 1 1 calc R . . . .
C5 C -0.3335(4) 0.2669(3) 0.34581(13) 0.0429(6) Uani 1 1 d . . . . .
H5 H -0.3403 0.3013 0.3925 0.051 Uiso 1 1 calc R . . . .
C6 C -0.1664(3) 0.2237(2) 0.33124(12) 0.0353(5) Uani 1 1 d . . . . .
C7 C 0.0161(4) 0.0815(2) 0.39356(12) 0.0390(6) Uani 1 1 d . . . . .
H7A H 0.0067 0.0194 0.3480 0.047 Uiso 1 1 calc R . . . .
H7B H -0.0953 0.0298 0.4150 0.047 Uiso 1 1 calc R . . . .
C8 C 0.2145(4) 0.0991(3) 0.44063(12) 0.0408(6) Uani 1 1 d . . . . .
H8A H 0.2189 -0.0007 0.4486 0.049 Uiso 1 1 calc R . . . .
H8B H 0.3252 0.1417 0.4169 0.049 Uiso 1 1 calc R . . . .
C9 C 0.2222(4) 0.3456(3) 0.49653(13) 0.0465(7) Uani 1 1 d . . . . .
H9A H 0.3299 0.3948 0.4729 0.056 Uiso 1 1 calc R . . . .
H9B H 0.2367 0.4111 0.5416 0.056 Uiso 1 1 calc R . . . .
C10 C 0.0206(4) 0.3265(3) 0.45172(13) 0.0466(6) Uani 1 1 d . . . . .
H10A H -0.0877 0.2788 0.4754 0.056 Uiso 1 1 calc R . . . .
H10B H 0.0106 0.4258 0.4452 0.056 Uiso 1 1 calc R . . . .
C11 C 0.4338(4) 0.2146(3) 0.55249(12) 0.0429(6) Uani 1 1 d . . . . .
H11A H 0.5420 0.2706 0.5309 0.051 Uiso 1 1 calc R . . . .
H11B H 0.4467 0.1137 0.5534 0.051 Uiso 1 1 calc R . . . .
C12 C 0.4600(4) 0.2967(3) 0.62846(13) 0.0466(6) Uani 1 1 d . . . . .
H12A H 0.4675 0.4025 0.6285 0.056 Uiso 1 1 calc R . . . .
H12B H 0.3433 0.2493 0.6485 0.056 Uiso 1 1 calc R . . . .
C13 C 0.6492(4) 0.2908(3) 0.67369(12) 0.0396(6) Uani 1 1 d . . . . .
C14 C 0.6484(4) 0.1641(3) 0.70453(13) 0.0446(6) Uani 1 1 d . . . . .
H14 H 0.5292 0.0830 0.6977 0.053 Uiso 1 1 calc R . . . .
C15 C 0.8211(4) 0.1563(3) 0.74506(13) 0.0425(6) Uani 1 1 d . . . . .
H15 H 0.8166 0.0705 0.7653 0.051 Uiso 1 1 calc R . . . .
C16 C 1.0018(4) 0.2753(3) 0.75603(12) 0.0389(6) Uani 1 1 d . . . . .
C17 C 1.0044(4) 0.4013(3) 0.72511(13) 0.0472(6) Uani 1 1 d . . . . .
H17 H 1.1242 0.4816 0.7313 0.057 Uiso 1 1 calc R . . . .
C18 C 0.8300(4) 0.4089(3) 0.68496(13) 0.0483(7) Uani 1 1 d . . . . .
H18 H 0.8345 0.4951 0.6651 0.058 Uiso 1 1 calc R . . . .
C19 C 1.1901(4) 0.2701(3) 0.80278(12) 0.0453(6) Uani 1 1 d . . . . .
H19A H 1.2002 0.1677 0.7934 0.054 Uiso 1 1 calc R . . . .
H19B H 1.3083 0.3394 0.7909 0.054 Uiso 1 1 calc R . . . .
C20 C 1.2566(3) 0.4619(3) 0.91420(13) 0.0411(6) Uani 1 1 d . . . . .
C21 C 1.2405(3) 0.4644(3) 0.98975(13) 0.0408(6) Uani 1 1 d . . . . .
C22 C 1.2841(4) 0.5915(3) 1.04280(15) 0.0520(7) Uani 1 1 d . . . . .
H22 H 1.3319 0.6900 1.0337 0.062 Uiso 1 1 calc R . . . .
C23 C 1.2536(4) 0.5658(4) 1.11023(15) 0.0618(8) Uani 1 1 d . . . . .
H23 H 1.2831 0.6493 1.1467 0.074 Uiso 1 1 calc R . . . .
C24 C 1.1816(5) 0.4221(4) 1.12440(15) 0.0647(8) Uani 1 1 d . . . . .
H24 H 1.1625 0.4099 1.1700 0.078 Uiso 1 1 calc R . . . .
C25 C 1.1367(4) 0.2942(4) 1.07184(14) 0.0581(8) Uani 1 1 d . . . . .
H25 H 1.0871 0.1958 1.0809 0.070 Uiso 1 1 calc R . . . .
C26 C 1.1695(4) 0.3201(3) 1.00528(13) 0.0430(6) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
O2 S1 O3 117.44(14) . .
O2 S1 N3 109.18(12) . .
O2 S1 C26 112.60(13) . .
O3 S1 N3 110.43(11) . .
O3 S1 C26 111.86(14) . .
N3 S1 C26 92.51(11) . .
C6 N1 C7 113.86(18) . .
C6 N1 C10 116.07(19) . .
C10 N1 C7 109.36(18) . .
C11 N2 C8 110.44(18) . .
C11 N2 C9 112.20(19) . .
C9 N2 C8 109.01(18) . .
C20 N3 S1 115.06(17) . .
C20 N3 C19 122.8(2) . .
C19 N3 S1 121.97(17) . .
C1 C6 N1 120.1(2) . .
C1 C6 C5 115.5(2) . .
C5 C6 N1 124.4(2) . .
O1 C20 N3 123.6(2) . .
O1 C20 C21 127.2(2) . .
N3 C20 C21 109.2(2) . .
C26 C21 C20 112.9(2) . .
C26 C21 C22 119.6(2) . .
C22 C21 C20 127.5(2) . .
C15 C16 C19 120.9(2) . .
C17 C16 C19 120.6(2) . .
C17 C16 C15 118.4(2) . .
F1 C1 C6 117.6(2) . .
F1 C1 C2 118.4(2) . .
C2 C1 C6 124.0(2) . .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
N1 C7 C8 110.71(19) . .
H7A C7 H7B 108.1 . .
C8 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
C6 C5 H5 119.4 . .
C4 C5 C6 121.2(2) . .
C4 C5 H5 119.4 . .
C21 C26 S1 110.29(18) . .
C21 C26 C25 123.2(3) . .
C25 C26 S1 126.5(2) . .
N2 C8 C7 111.78(19) . .
N2 C8 H8A 109.3 . .
N2 C8 H8B 109.3 . .
C7 C8 H8A 109.3 . .
C7 C8 H8B 109.3 . .
H8A C8 H8B 107.9 . .
C21 C22 H22 121.3 . .
C21 C22 C23 117.4(3) . .
C23 C22 H22 121.3 . .
N3 C19 C16 112.5(2) . .
N3 C19 H19A 109.1 . .
N3 C19 H19B 109.1 . .
C16 C19 H19A 109.1 . .
C16 C19 H19B 109.1 . .
H19A C19 H19B 107.8 . .
C16 C15 H15 119.6 . .
C14 C15 C16 120.7(2) . .
C14 C15 H15 119.6 . .
C16 C17 H17 119.7 . .
C16 C17 C18 120.6(2) . .
C18 C17 H17 119.7 . .
C5 C4 H4 119.5 . .
C3 C4 C5 120.9(3) . .
C3 C4 H4 119.5 . .
N2 C11 H11A 108.8 . .
N2 C11 H11B 108.8 . .
N2 C11 C12 113.7(2) . .
H11A C11 H11B 107.7 . .
C12 C11 H11A 108.8 . .
C12 C11 H11B 108.8 . .
C1 C2 H2 120.6 . .
C1 C2 C3 118.8(3) . .
C3 C2 H2 120.6 . .
C14 C13 C12 120.8(2) . .
C18 C13 C14 117.5(2) . .
C18 C13 C12 121.7(2) . .
C15 C14 C13 121.3(2) . .
C15 C14 H14 119.4 . .
C13 C14 H14 119.4 . .
C11 C12 H12A 109.4 . .
C11 C12 H12B 109.4 . .
C13 C12 C11 111.3(2) . .
C13 C12 H12A 109.4 . .
C13 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
C4 C3 C2 119.5(2) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C17 C18 C13 121.5(2) . .
C17 C18 H18 119.3 . .
C13 C18 H18 119.3 . .
C26 C25 H25 121.7 . .
C26 C25 C24 116.6(3) . .
C24 C25 H25 121.7 . .
N1 C10 H10A 109.7 . .
N1 C10 H10B 109.7 . .
N1 C10 C9 109.6(2) . .
H10A C10 H10B 108.2 . .
C9 C10 H10A 109.7 . .
C9 C10 H10B 109.7 . .
N2 C9 C10 111.4(2) . .
N2 C9 H9A 109.4 . .
N2 C9 H9B 109.4 . .
C10 C9 H9A 109.4 . .
C10 C9 H9B 109.4 . .
H9A C9 H9B 108.0 . .
C22 C23 H23 118.9 . .
C24 C23 C22 122.1(3) . .
C24 C23 H23 118.9 . .
C25 C24 H24 119.5 . .
C23 C24 C25 121.0(3) . .
C23 C24 H24 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.421(2) .
S1 O3 1.429(2) .
S1 N3 1.669(2) .
S1 C26 1.752(3) .
F1 C1 1.365(3) .
O1 C20 1.206(3) .
N1 C6 1.413(3) .
N1 C7 1.472(3) .
N1 C10 1.458(3) .
N2 C8 1.464(3) .
N2 C11 1.452(3) .
N2 C9 1.461(3) .
N3 C20 1.382(3) .
N3 C19 1.469(3) .
C6 C1 1.396(3) .
C6 C5 1.397(3) .
C20 C21 1.482(3) .
C21 C26 1.380(3) .
C21 C22 1.387(3) .
C16 C19 1.516(3) .
C16 C15 1.390(3) .
C16 C17 1.383(3) .
C1 C2 1.367(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C8 1.512(3) .
C5 H5 0.9300 .
C5 C4 1.383(3) .
C26 C25 1.382(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C22 H22 0.9300 .
C22 C23 1.394(4) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C15 H15 0.9300 .
C15 C14 1.379(3) .
C17 H17 0.9300 .
C17 C18 1.385(3) .
C4 H4 0.9300 .
C4 C3 1.373(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.525(3) .
C2 H2 0.9300 .
C2 C3 1.381(4) .
C13 C14 1.392(3) .
C13 C12 1.509(3) .
C13 C18 1.385(3) .
C14 H14 0.9300 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C3 H3 0.9300 .
C18 H18 0.9300 .
C25 H25 0.9300 .
C25 C24 1.386(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 C9 1.507(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C23 H23 0.9300 .
C23 C24 1.365(4) .
C24 H24 0.9300 .
