#------------------------------------------------------------------------------
#$Date: 2025-07-06 16:31:31 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300636 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/41/1574140.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_1574140
loop_
_publ_author_name
'Krammer, Leo'
'Darnhofer, Barbara'
'Kljajic, Marko'
'Liesinger, Laura'
'Schittmayer, Matthias'
'Neshchadin, Dmytro'
'Gescheidt, Georg'
'Kollau, Alexander'
'Mayer, Bernd'
'Fischer, Roland C.'
'Wallner, Silvia'
'Macheroux, Peter'
'Birner-Gruenberger, Ruth'
'Breinbauer, Rolf'
_publ_section_title
;
 A general approach for activity-based protein profiling of
 oxidoreductases with redox-differentiated diarylhalonium warheads
;
_journal_issue                   15
_journal_name_full               'Chemical Science'
_journal_page_first              6240
_journal_page_last               6256
_journal_paper_doi               10.1039/D4SC08454C
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C13 H8 Cl O2, C F3 O3 S'
_chemical_formula_sum            'C14 H8 Cl F3 O5 S'
_chemical_formula_weight         380.71
_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
_audit_creation_date             2021-10-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-31 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                95.756(2)
_cell_angle_beta                 99.723(2)
_cell_angle_gamma                97.231(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6746(4)
_cell_length_b                   8.0822(6)
_cell_length_c                   13.7840(10)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      30.16
_cell_measurement_theta_min      2.81
_cell_volume                     721.43(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39301
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.189
_diffrn_reflns_theta_min         1.511
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.89
_diffrn_source_power             0.0445
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6209
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1574 before and 0.0783 after correction.
The Ratio of minimum to maximum transmission is 0.8323.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       Block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4150
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0349
_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)+(0.0324P)²+0.9578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3895
_reflns_number_total             4150
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc08454c2.cif
_cod_data_source_block           rf2357_0m_a
_cod_depositor_comments
'Adding full bibliography for 1574140--1574142.cif.'
_cod_database_code               1574140
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C11(H11), C10(H10), C9(H9), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O2(H2)
;
_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
Cl1 Cl 0.26279(6) 0.81039(4) 0.30416(3) 0.01238(9) Uani 1 1 d . . . . .
S1 S 0.30411(6) -0.13422(4) 0.75893(3) 0.01095(9) Uani 1 1 d . . . . .
F1 F 0.00202(16) -0.03527(15) 0.83869(9) 0.0258(2) Uani 1 1 d . . . . .
F2 F 0.23641(17) 0.16510(12) 0.82530(8) 0.0193(2) Uani 1 1 d . . . . .
F3 F 0.29386(19) 0.00403(15) 0.93918(8) 0.0250(2) Uani 1 1 d . . . . .
O1 O 0.2526(2) 0.05771(15) 0.45883(9) 0.0198(3) Uani 1 1 d . . . . .
O2 O 0.2175(2) 0.20731(15) 0.59890(9) 0.0174(2) Uani 1 1 d . . . . .
H2 H 0.214(4) 0.113(3) 0.6201(9) 0.026 Uiso 1 1 calc R U . . .
C1 C 0.2543(2) 0.63733(18) 0.37396(11) 0.0103(3) Uani 1 1 d . . . . .
O3 O 0.52270(18) -0.07773(15) 0.78179(10) 0.0173(2) Uani 1 1 d . . . . .
O4 O 0.2029(2) -0.09556(15) 0.66389(9) 0.0175(2) Uani 1 1 d . . . . .
O5 O 0.23804(19) -0.29991(15) 0.78119(9) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.2559(2) 0.48886(18) 0.31370(11) 0.0097(3) Uani 1 1 d . . . . .
C3 C 0.2515(2) 0.34251(18) 0.35902(11) 0.0104(3) Uani 1 1 d . . . . .
H3 H 0.2535 0.2376 0.3217 0.012 Uiso 1 1 calc R U . . .
C4 C 0.2440(2) 0.35160(18) 0.45984(11) 0.0100(3) Uani 1 1 d . . . . .
C5 C 0.2441(2) 0.50518(19) 0.51674(11) 0.0103(3) Uani 1 1 d . . . . .
H5 H 0.2402 0.5077 0.5854 0.012 Uiso 1 1 calc R U . . .
C6 C 0.2497(2) 0.65494(19) 0.47390(11) 0.0107(3) Uani 1 1 d . . . . .
H6 H 0.2503 0.7607 0.5109 0.013 Uiso 1 1 calc R U . . .
C7 C 0.2608(2) 0.51200(19) 0.21081(11) 0.0103(3) Uani 1 1 d . . . . .
C12 C 0.2618(2) 0.67792(19) 0.19258(11) 0.0111(3) Uani 1 1 d . . . . .
C11 C 0.2625(2) 0.7374(2) 0.10253(12) 0.0128(3) Uani 1 1 d . . . . .
H11 H 0.2621 0.8529 0.0949 0.015 Uiso 1 1 calc R U . . .
C10 C 0.2639(2) 0.6164(2) 0.02338(12) 0.0137(3) Uani 1 1 d . . . . .
H10 H 0.2635 0.6488 -0.0410 0.016 Uiso 1 1 calc R U . . .
C9 C 0.2660(2) 0.4478(2) 0.03772(12) 0.0140(3) Uani 1 1 d . . . . .
H9 H 0.2682 0.3677 -0.0174 0.017 Uiso 1 1 calc R U . . .
C8 C 0.2649(2) 0.39415(19) 0.13006(12) 0.0129(3) Uani 1 1 d . . . . .
H8 H 0.2669 0.2790 0.1383 0.015 Uiso 1 1 calc R U . . .
C13 C 0.2382(2) 0.19007(19) 0.50424(11) 0.0114(3) Uani 1 1 d . . . . .
C14 C 0.2042(2) 0.0065(2) 0.84536(12) 0.0137(3) 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'
Cl Cl 0.1484 0.1585 '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'
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'
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
_geom_angle_publ_flag
C1 Cl1 C12 92.12(7) . . ?
O3 S1 O4 114.38(8) . . ?
O3 S1 C14 103.07(7) . . ?
O4 S1 C14 101.56(7) . . ?
O5 S1 O3 116.06(7) . . ?
O5 S1 O4 114.59(7) . . ?
O5 S1 C14 104.67(7) . . ?
C13 O2 H2 109.5 . . ?
C2 C1 Cl1 110.40(11) . . ?
C6 C1 Cl1 122.72(11) . . ?
C6 C1 C2 126.88(14) . . ?
C1 C2 C7 113.62(13) . . ?
C3 C2 C1 116.65(13) . . ?
C3 C2 C7 129.72(13) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.26(13) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 121.39(14) . . ?
C3 C4 C13 116.82(13) . . ?
C5 C4 C13 121.79(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.95(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 114.85(13) . . ?
C1 C6 H6 122.6 . . ?
C5 C6 H6 122.6 . . ?
C12 C7 C2 113.35(13) . . ?
C12 C7 C8 116.75(14) . . ?
C8 C7 C2 129.89(14) . . ?
C7 C12 Cl1 110.48(11) . . ?
C11 C12 Cl1 123.02(12) . . ?
C11 C12 C7 126.50(14) . . ?
C12 C11 H11 122.4 . . ?
C12 C11 C10 115.27(14) . . ?
C10 C11 H11 122.4 . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.68(14) . . ?
C9 C10 H10 119.7 . . ?
C10 C9 H9 119.1 . . ?
C8 C9 C10 121.81(15) . . ?
C8 C9 H9 119.1 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.97(14) . . ?
C9 C8 H8 120.5 . . ?
O1 C13 O2 123.50(14) . . ?
O1 C13 C4 123.26(14) . . ?
O2 C13 C4 113.24(13) . . ?
F1 C14 S1 111.20(11) . . ?
F1 C14 F2 107.20(13) . . ?
F2 C14 S1 110.75(11) . . ?
F3 C14 S1 111.96(11) . . ?
F3 C14 F1 108.00(13) . . ?
F3 C14 F2 107.53(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7759(15) . ?
Cl1 C12 1.7823(15) . ?
S1 O3 1.4438(12) . ?
S1 O4 1.4513(12) . ?
S1 O5 1.4357(12) . ?
S1 C14 1.8289(16) . ?
F1 C14 1.3346(19) . ?
F2 C14 1.3369(19) . ?
F3 C14 1.3333(19) . ?
O1 C13 1.2073(19) . ?
O2 H2 0.84(3) . ?
O2 C13 1.3305(19) . ?
C1 C2 1.392(2) . ?
C1 C6 1.376(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.454(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C4 C5 1.400(2) . ?
C4 C13 1.495(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(2) . ?
C6 H6 0.9500 . ?
C7 C12 1.388(2) . ?
C7 C8 1.397(2) . ?
C12 C11 1.376(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.398(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.386(2) . ?
C8 H8 0.9500 . ?
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
_geom_torsion_publ_flag
Cl1 C1 C2 C3 179.48(11) . . . . ?
Cl1 C1 C2 C7 -0.92(16) . . . . ?
Cl1 C1 C6 C5 -179.74(11) . . . . ?
Cl1 C12 C11 C10 179.32(11) . . . . ?
C1 Cl1 C12 C7 -1.57(12) . . . . ?
C1 Cl1 C12 C11 178.55(14) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C2 C7 C12 -0.27(19) . . . . ?
C1 C2 C7 C8 179.55(15) . . . . ?
O3 S1 C14 F1 -176.05(11) . . . . ?
O3 S1 C14 F2 64.86(12) . . . . ?
O3 S1 C14 F3 -55.14(13) . . . . ?
O4 S1 C14 F1 65.26(13) . . . . ?
O4 S1 C14 F2 -53.83(12) . . . . ?
O4 S1 C14 F3 -173.83(12) . . . . ?
O5 S1 C14 F1 -54.25(13) . . . . ?
O5 S1 C14 F2 -173.34(11) . . . . ?
O5 S1 C14 F3 66.66(13) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C2 C3 C4 C13 179.63(13) . . . . ?
C2 C7 C12 Cl1 1.33(16) . . . . ?
C2 C7 C12 C11 -178.79(15) . . . . ?
C2 C7 C8 C9 179.02(15) . . . . ?
C3 C2 C7 C12 179.26(15) . . . . ?
C3 C2 C7 C8 -0.9(3) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C13 O1 4.8(2) . . . . ?
C3 C4 C13 O2 -175.80(13) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C5 C4 C13 O1 -174.60(15) . . . . ?
C5 C4 C13 O2 4.8(2) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C6 C1 C2 C7 179.94(14) . . . . ?
C7 C2 C3 C4 -179.00(14) . . . . ?
C7 C12 C11 C10 -0.5(2) . . . . ?
C12 Cl1 C1 C2 1.41(11) . . . . ?
C12 Cl1 C1 C6 -179.41(13) . . . . ?
C12 C7 C8 C9 -1.2(2) . . . . ?
C12 C11 C10 C9 -0.4(2) . . . . ?
C11 C10 C9 C8 0.6(2) . . . . ?
C10 C9 C8 C7 0.3(2) . . . . ?
C8 C7 C12 Cl1 -178.52(11) . . . . ?
C8 C7 C12 C11 1.4(2) . . . . ?
C13 C4 C5 C6 179.96(13) . . . . ?
