Synthesis of complex aryl MIDA boronates by Rh-catalyzed [2+2+2] cycloaddition.
Halford-McGuff, John M; Cordes, David B.; Watson, Allan J. B.; Chemical communications (Cambridge, England) 59 (2023) 7759–7762; doi:10.1039/d3cc00761h

data_7131714
_publ_section_title
;
 Synthesis of complex aryl MIDA boronates by Rh-catalyzed [2+2+2]
 cycloaddition.
;
_journal_issue                   50
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7759
_journal_page_last               7762
_journal_paper_doi               10.1039/d3cc00761h
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C17 H17 N O3 S'
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.37
_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     dual
_audit_creation_date             2022-06-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-23 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.692(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1250(4)
_cell_length_b                   7.7985(2)
_cell_length_c                   12.6248(3)
_cell_measurement_reflns_used    7905
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5530
_cell_measurement_theta_min      2.7190
_cell_volume                     1481.78(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_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      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     63.00  89.00   0.50   10.00    --    0.00  42.00 -90.00   52
  2  \w    -35.00  76.00   0.50   10.00    --  -12.80  42.00 -30.00  222
  3  \w     51.00  76.00   0.50   10.00    --  -12.80  42.00   0.00   50
  4  \w     36.00  70.00   0.50   10.00    --  -12.80  42.00  30.00   68
  5  \w     39.00  64.00   0.50   10.00    --  -12.80  42.00 120.00   50
  6  \w    -39.00  74.00   0.50   10.00    --  -12.80  42.00 -90.00  226
  7  \w    -28.00  76.00   0.50   10.00    --  -12.80  42.00 150.00  208
  8  \w    -53.00 -26.00   0.50   10.00    --  -12.80  42.00-150.00   54
  9  \w    -11.00  74.00   0.50   10.00    --  -12.80  42.00-150.00  170
 10  \w     48.00  73.00   0.50   10.00    --  -12.80  42.00 -60.00   50
 11  \w     -8.00  74.00   0.50   10.00    --  -12.80  42.00  60.00  164
 12  \w    -83.00 -58.00   0.50   10.00    --  -12.80  42.00 -30.00   50
;
_diffrn_measurement_device       'AFC8: Quarter \c 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0470538000
_diffrn_orient_matrix_UB_12      -0.0036247000
_diffrn_orient_matrix_UB_13      -0.0035812000
_diffrn_orient_matrix_UB_21      0.0004018000
_diffrn_orient_matrix_UB_22      0.0504406000
_diffrn_orient_matrix_UB_23      0.0467968000
_diffrn_orient_matrix_UB_31      -0.0025116000
_diffrn_orient_matrix_UB_32      0.0756058000
_diffrn_orient_matrix_UB_33      -0.0313998000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19815
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.110
_diffrn_reflns_theta_min         2.707
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/diethyl ether'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3514
_refine_ls_number_restraints     380
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0475P)^2^+0.4636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2826
_reflns_number_total             3514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00761h2.cif
_cod_data_source_block           33
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7131713--7131715.cif.
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7131714
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.934
_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
2. Restrained distances
 O6-C5 = O6A-C9
 1.36 with sigma of 0.02
 C8-C9 = C8A-C5
 1.5 with sigma of 0.02
 O6A-C7A = O6-C7
 1.45 with sigma of 0.02
 C8-C7 = C7A-C8A
 1.51 with sigma of 0.02
 C4-C3 = C4-C5 = C9-C5 = C5A-C9A = C9-C10 = C4A-C5A = C4A-C3A = C10-C11 = C3-
 C11 = C11A-C3A = C10A-C11A = C9A-C10A
 1.39 with sigma of 0.02
 C11A-C12A = C2A-C3A
 1.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O6 \\sim O6A \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C7A
\\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
4. Others
 Sof(O6A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(C10A)=
 Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(1)
 Sof(O6)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(C7)=
 Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C2A(H2AA,H2AB),
 C7A(H7AA,H7AB), C8A(H8AA,H8AB), C12A(H12C,H12D)
5.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18), C4(H4), C10(H10), C4A(H4A), C10A(H10A)
5.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              46302
_shelx_hkl_checksum              86761