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_7131715
_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         'C14 H16 B N O5, C3 H6 O'
_chemical_formula_sum            'C17 H22 B N O6'
_chemical_formula_weight         347.16
_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     direct
_audit_creation_date             2022-06-07
_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                 91.771(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1060(4)
_cell_length_b                   9.9589(3)
_cell_length_c                   13.1775(5)
_cell_measurement_reflns_used    4252
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.5240
_cell_measurement_theta_min      2.5670
_cell_volume                     1719.12(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       '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    'SIR2011  (Burla et al.,  2007)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.855
_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    -83.00  63.00   0.50   80.00    --  -12.80  21.00  90.00  292
  2  \w    -97.00 -71.00   0.50   80.00    --  -12.80  42.00  60.00   52
  3  \w    -16.00  65.00   0.50   80.00    --  -12.80  42.00  60.00  162
  4  \w   -101.00 -14.00   0.50   80.00    --  -12.80  31.00  30.00  174
;
_diffrn_measurement_device       'AFC11: 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      -0.0313842000
_diffrn_orient_matrix_UB_12      0.0467162000
_diffrn_orient_matrix_UB_13      -0.0269450000
_diffrn_orient_matrix_UB_21      -0.0017213000
_diffrn_orient_matrix_UB_22      -0.0434268000
_diffrn_orient_matrix_UB_23      -0.0426713000
_diffrn_orient_matrix_UB_31      -0.0440728000
_diffrn_orient_matrix_UB_32      -0.0317109000
_diffrn_orient_matrix_UB_33      0.0188129000
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11853
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.118
_diffrn_reflns_theta_min         2.564
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74014
_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    1.341
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone/diethyl ether'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_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     230
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0457P)^2^+0.4839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3057
_reflns_number_total             3951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00761h2.cif
_cod_data_source_block           25
_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_cell_volume        1719.14(10)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7131715
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.993
_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.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C11(H11A,H11B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_shelx_res_checksum              50365
_shelx_hkl_checksum              68683