Novel keto-enol tautomerism in 1,3,5-trihydroxybenzene systems.
Ruaysap, Makabodee; Kennedy, Stuart R.; Mayhan, Collin M.; Kelley, Steven P.; Kumari, Harshita; Deakyne, Carol A.; Atwood, Jerry L.; Chemical communications (Cambridge, England) 56 (2020) 12985–12988; doi:10.1039/d0cc03639k

data_7127334
_publ_section_title
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 Novel keto-enol tautomerism in 1,3,5-trihydroxybenzene systems.
;
_journal_issue                   85
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12985
_journal_page_last               12988
_journal_paper_doi               10.1039/d0cc03639k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety
'C9.25 H18.75 O17 S3 Sm, 0.35(C1 H4 O1), 0.65(O)'
_chemical_formula_sum            'C9.6 H19.5 O18 S3 Sm'
_chemical_formula_weight         669.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-05-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
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2020-05-18 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.340(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9342(15)
_cell_length_b                   8.8762(15)
_cell_length_c                   25.291(4)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      2.42
_cell_volume                     2005.6(6)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.705
_diffrn_reflns_theta_min         1.610
_diffrn_source                   'Sealed Source Mo with TRIUMPH optics'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.331
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1135 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.7522.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             1324
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.081
_refine_diff_density_min         -1.627
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.254
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4866
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.253
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+12.4473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4729
_reflns_number_total             4866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03639k2.cif
_cod_data_source_block           abs_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7127333--7127334.cif.'
_cod_original_cell_volume        2005.5(6)
_cod_original_formula_sum        'C9.60 H19.50 O18 S3 Sm'
_cod_database_code               7127334
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.618
_shelx_estimated_absorpt_t_min   0.435
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H6S of O6S, H2 of O2, H1 of O1
 At 1.5 times of:
  All C(H,H,H) groups, H3 of O3, All O(H,H,H,H,H,H,H,H,H) groups
2. Restrained distances
 O2W-H2WB = O2W-H2WA = O1W-H1WA = O1W-H1WB = O4W-H4WB = O4W-H4WA = O3W-H3WA =
 O3W-H3WB = O5S-H5W = O5W-H5W
 0.9 with sigma of 0.02
3. Others
 Fixed Sof: O5W(0.75) C1S(0.25) H1SA(0.25) H1SB(0.25) H1SC(0.25) O5S(0.25)
 O6S(0.35) H6S(0.35) C2S(0.35) H2SA(0.35) H2SB(0.35) H2SC(0.35) O6WC(0.25)
 O6WB(0.25) O6WA(0.15)
4.a Riding coordinates:
 C2S(H2SA,H2SB,H2SC)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
4.c Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2)
4.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6S(H6S)
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_shelx_res_checksum              71029
_shelx_hkl_checksum              8756
_olex2_submission_special_instructions 'No special instructions were received'