Iridium(i)-catalyzed hydration/esterification of 2-alkynylphenols and carboxylic acids.
Zeng, Linwei; Chen, Renjie; Zhang, Chen; Xie, Hujun; Cui, Sunliang; Chemical communications (Cambridge, England) 56 (2020) 3093–3096; doi:10.1039/c9cc09984k

data_7125932
_publ_section_title
;
 Iridium(i)-catalyzed hydration/esterification of 2-alkynylphenols and
 carboxylic acids.
;
_journal_issue                   20
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3093
_journal_page_last               3096
_journal_paper_doi               10.1039/c9cc09984k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '2(C19 H12 O2 S), 0.5(H4 O2)'
_chemical_formula_sum            'C38 H26 O5 S2'
_chemical_formula_weight         626.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-08 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.2240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6651(5)
_cell_length_b                   9.1102(3)
_cell_length_c                   18.3035(5)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      32.55
_cell_measurement_theta_min      2.30
_cell_volume                     2956.26(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.99
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25186
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.606
_diffrn_reflns_theta_min         2.298
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1225 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.8663.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5380
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0694P)^2^+1.2980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4170
_reflns_number_total             5380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09984k2.cif
_cod_data_source_block           181127_zlw_8_97_7_0m
_cod_depositor_comments
'Adding full bibliography for 7125932--7125934.cif.'
_cod_database_code               7125932
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.911
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 S1-C10 \\sim S1A-C10A
 with sigma of 0.02
 S1-C13 \\sim S1A-C13A
 with sigma of 0.02
 C11-C10 \\sim C11A-C10A
 with sigma of 0.02
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 C9-C10 \\sim C9-C10A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 S1-C11 \\sim S1A-C11A
 with sigma of 0.04
 S1-C9 \\sim S1A-C9
 with sigma of 0.04
 S1-C12 \\sim S1A-C12A
 with sigma of 0.04
 C11-C9 \\sim C11A-C9
 with sigma of 0.04
 C11-C13 \\sim C11A-C13A
 with sigma of 0.04
 C10-C12 \\sim C10A-C12A
 with sigma of 0.04
 C10-C13 \\sim C10A-C13A
 with sigma of 0.04
3. Others
 Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(H12A)=Sof(C10A)=Sof(C11A)=Sof(H11A)=
 Sof(S1A)=1-FVAR(1)
 Sof(S1)=Sof(C11)=Sof(H11)=Sof(C10)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=FVAR(1)
 Fixed Sof: H3A(0.5) H3B(0.5)
4.a Free rotating group:
 O3(H3A,H3B)
4.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C1(H1), C4(H4), C15(H15), C19(H19), C3(H3), C2(H2), C12(H12),
 C16(H16), C17(H17), C18(H18), C13(H13), C13A(H13A), C12A(H12A), C11A(H11A)
;
_shelx_res_checksum              28246
_olex2_submission_special_instructions 'No special instructions were received'