NSPs: chromogenic linkers for fast, selective, and irreversible cysteine modification.
Hua, Yong; Zou, Zhi; Prescimone, Alessandro; Ward, Thomas R.; Mayor, Marcel; Köhler, Valentin; Chemical science 15 (2024) 10997–11004; doi:10.1039/d4sc01710b

data_1571895
_publ_section_title
;
 NSPs: chromogenic linkers for fast, selective, and irreversible cysteine
 modification.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              10997
_journal_page_last               11004
_journal_paper_doi               10.1039/d4sc01710b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C16 H16 N2 O4 S2, H2 O'
_chemical_formula_sum            'C16 H18 N2 O5 S2'
_chemical_formula_weight         382.44
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-17
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-30 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                113.735(2)
_cell_angle_beta                 92.388(2)
_cell_angle_gamma                99.774(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2197(2)
_cell_length_b                   9.7011(2)
_cell_length_c                   11.5746(2)
_cell_measurement_reflns_used    54727
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.32
_cell_measurement_theta_min      4.20
_cell_volume                     826.42(3)
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_data_reduction
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area LANA 2.6.2.0 (STOE, 2021)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'EIGER2 1M'
_diffrn_detector_area_resol_mean 13.33
_diffrn_detector_type            'DECTRIS EIGER2 1M'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
 5740 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22220
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         72.830
_diffrn_reflns_theta_min         5.076
_diffrn_source                   'Axo Cu'
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.208
_exptl_absorpt_correction_T_max  0.1331
_exptl_absorpt_correction_T_min  0.1022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens in: F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard,
Copenhagen (1970), 255 - 270. Afterwards scaling of reflection intensities was
performed within STOE LANA. J. Koziskova, F. Hahn, J. Richter, J. Kozisek, Acta
Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of water and acetone  by solvent layering'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.1
_exptl_crystal_size_rad          0.170
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0111(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0379
_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/[\s^2^(Fo^2^)+(0.0555P)^2^+0.6655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3191
_reflns_number_total             3201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01710b2.cif
_cod_data_source_block           yh20220106-1_150k
_cod_depositor_comments          'Adding full bibliography for 1571895.cif.'
_cod_database_code               1571895
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.740
_shelx_estimated_absorpt_t_min   0.566
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C10(H10), C6(H6), C8(H8), C13(H13), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              11886
_shelx_hkl_checksum              44752
_olex2_date_sample_data_collection 2022-01-15
_olex2_date_sample_submission    2022-01-10
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id YH20220106_1_150K
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '40.0 mm'
_stoe_detector_pixelsize_x       '0.075 mm'
_stoe_detector_pixelsize_y       '0.075 mm'
_stoe_detector_size_x            '8.0 cm'
_stoe_detector_size_y            '7.7 cm'
_stoe_evaluation_integration_a   7.2
_stoe_evaluation_integration_b   0.1
_stoe_evaluation_integration_ems 0.016
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max 4
_stoe_evaluation_lana_bos_l_odd_max 1
_stoe_evaluation_lana_completeness 97.4
_stoe_evaluation_lana_dxs_max_order 1
_stoe_evaluation_lana_dys_max_order 1
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 145.7
_stoe_evaluation_lana_max_2theta_desired 145.7
_stoe_evaluation_lana_mean_redundancy 6.9
_stoe_evaluation_lana_number_refls_after_or 22220
_stoe_evaluation_lana_number_refls_outliers 7089
_stoe_evaluation_lana_number_refls_total 29309
_stoe_evaluation_lana_number_refls_unique 3201
_stoe_evaluation_lana_number_refls_written 22220
_stoe_evaluation_lana_or_c1      0.035
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      0.7
_stoe_evaluation_lana_point_group -1
_stoe_evaluation_lana_table
;
2Theta          15.5   30.9   46.3   61.7   77.1   92.5  107.9  123.3  138.7
<Resolution>    4.47   2.77   1.94   1.49   1.23   1.07   0.95   0.88   0.83
N(total)         119   1089   2408   4210   6733   6576   3936   2931   1307
<Redundancy>     3.3    8.2    8.7    9.3   11.2    9.1    5.1    3.8    2.6
Complet. [perc] 90.3  100.0  100.0  100.0  100.0   99.6   99.1   98.4   84.2
<I/sigma>     1335.6  698.7  381.0  234.1  190.6  151.3  118.0  121.0  118.2
R(int)         0.009  0.011  0.013  0.015  0.015  0.015  0.019  0.020  0.053
;
_stoe_measurement_identifier     YH20220106-1_150K
_stoe_measurement_max_exposure_per_frame '15.0 s'
_stoe_measurement_mean_exposure_per_frame '15.0 s'
_stoe_measurement_min_exposure_per_frame '4.0 s'
_stoe_measurement_total_exposure_time '23.9 h'
_stoe_measurement_total_frame_number 5740
_stoe_measurement_total_run_number 99
_stoe_measurement_tube_power     '50.0 W'