Salicylate Metal-Binding Isosteres as Fragments for Metalloenzyme Inhibition
Jackl, Moritz K.; Seo, Hyeonglim; Karges, Johannes; Kalaj, Mark; Cohen, Seth M.; Chemical Science  (2022) –; doi:10.1039/D1SC06011B

data_1566101
_publ_section_title
;
 Salicylate Metal-Binding Isosteres as Fragments for Metalloenzyme
 Inhibition
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06011B
_journal_year                    2022
_chemical_formula_moiety
'C39 H39 B N8 O4 S Zn, 0.77(C6 H6), 0.191(C5)'
_chemical_formula_sum            'C44.58 H43.62 B N8 O4 S Zn'
_chemical_formula_weight         863.69
_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     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc292q9f
_audit_creation_date             2021-08-27
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-22 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.3670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.9170(10)
_cell_length_b                   12.6257(7)
_cell_length_c                   27.9346(11)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.32
_cell_volume                     8644.6(7)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution
'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            170610
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.061
_diffrn_reflns_theta_min         2.016
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.7357
_exptl_absorpt_correction_T_min  0.7018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0938 before and 0.0669 after correction.
The Ratio of minimum to maximum transmission is 0.9539.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             3601
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.979
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1109
_refine_ls_number_reflns         17087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0449
_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/[\s^2^(Fo^2^)+(0.0363P)^2^+11.3344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12756
_reflns_number_total             17087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06011b4.cif
_cod_data_source_block           mkj2_17
_cod_database_code               1566101
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.936
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C1)=Sof(C2)=Sof(C6)=Sof(C7)=Sof(C5)=1-FVAR(1)
 Sof(C036)=Sof(H036)=Sof(C037)=Sof(H037)=Sof(C038)=Sof(H038)=Sof(C039)=
 Sof(H039)=Sof(C03A)=Sof(H03E)=Sof(C03B)=Sof(H03F)=FVAR(1)
 Sof(C3)=Sof(C4)=1-FVAR(2)
 Sof(C02Z)=Sof(H3)=Sof(C033)=Sof(H033)=Sof(C030)=Sof(H030)=Sof(C031)=Sof(H031)=
 Sof(C03C)=Sof(H03D)=Sof(C035)=Sof(H035)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 B02A(H02A), B032(H032)
3.b Aromatic/amide H refined with riding coordinates:
 N00M(H00M), C00Y(H00Y), C010(H010), C013(H013), C015(H015), C018(H018),
 C019(H019), C01D(H01G), C01F(H01H), C01H(H01Y), C01J(H01L), C01K(H01M),
 C01L(H01N), C01M(H01O), C01N(H01P), C01O(H01), C01P(H01Q), C01R(H01U),
 C01S(H01V), C01T(H01W), C01U(H01X), C01V(H1), C01Y(H2), C01Z(H01Z), C022(H022),
  N024(H024), C025(H025), C026(H026), C027(H027), C028(H028), C029(H029),
 C02B(H02I), C02D(H02J), C02F(H02F), C02G(H02K), C02H(H02L), C02J(H02M),
 C02K(H02N), C02L(H02O), C02M(H02P), C02P(H02Q), C02Q(H02R), C02S(H02S),
 C02U(H02W), C02V(H02X), C02X(H02Z), C02Z(H3), C033(H033), C030(H030),
 C031(H031), C03C(H03D), C035(H035), C036(H036), C037(H037), C038(H038),
 C039(H039), C03A(H03E), C03B(H03F)
3.c Fitted hexagon refined as free rotating group:
 C02Z(C033,C030,C031,C03C,C035)
3.d Idealised Me refined as rotating group:
 C01B(H01A,H01B,H01C), C01C(H01D,H01E,H01F), C01G(H01I,H01J,H01K), C01Q(H01R,
 H01S,H01T), C021(H02E,H02G,H02H), C02R(H02B,H02C,H02D), C02T(H02T,H02U,H02V),
 C02W(H02Y,H,HA), C02Y(H02,HB,HC), C034(H03A,H03B,H03C)
;
_shelx_res_checksum              66469
_shelx_hkl_checksum              47788
_olex2_submission_special_instructions 'No special instructions were received'