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_7131713
_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_absolute_configuration ad
_chemical_formula_moiety         'C22 H26 B N O6'
_chemical_formula_sum            'C22 H26 B N O6'
_chemical_formula_weight         411.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
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;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-17 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
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'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
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_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
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_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
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_diffrn_measured_fraction_theta_max 0.991
_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   -115.00  65.00   0.50    5.00    --  -25.00  60.00  36.00  360
  2  \w   -115.00  32.00   0.50    5.00    --  -25.00  60.00   0.00  294
  3  \w    -22.00  23.00   0.50    5.00    --  -25.00  40.00 -72.00   90
  4  \w   -193.00 -13.00   0.50   10.00    -- -103.00  46.00-144.00  360
  5  \w   -162.00 -13.00   0.50   10.00    -- -103.00  60.00  36.00  298
  6  \w   -193.00 -29.50   0.50   10.00    -- -103.00  60.00 -36.00  327
  7  \w   -167.00 -13.00   0.50   10.00    -- -103.00  60.00 108.00  308
  8  \w   -167.00 -43.00   0.50   10.00    -- -103.00  26.00 144.00  248
  9  \w   -175.50 -13.00   0.50   10.00    -- -103.00  60.00-108.00  325
 10  \w   -193.00 -17.00   0.50   10.00    -- -103.00  60.00-180.00  352
 11  \w   -153.00 -15.00   0.50   10.00    -- -103.00  40.00  36.00  276
 12  \w   -114.50 -44.50   0.50   10.00    -- -103.00  40.00 -36.00  140
 13  \w   -137.00 -22.00   0.50   10.00    -- -103.00  53.00 108.00  230
 14  \w    -69.00 -24.00   0.50   10.00    -- -103.00  60.00 -72.00   90
 15  \w    -60.00 -15.00   0.50   10.00    -- -103.00  46.00-108.00   90
 16  \w    -60.00 -14.00   0.50   10.00    -- -103.00  40.00-108.00   92
 17  \w    -60.00 -13.00   0.50   10.00    -- -103.00  53.00-108.00   94
;
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_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Loop
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'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0945135000
_diffrn_orient_matrix_UB_12      0.0331922000
_diffrn_orient_matrix_UB_13      0.0570129000
_diffrn_orient_matrix_UB_21      0.0308744000
_diffrn_orient_matrix_UB_22      -0.1409698000
_diffrn_orient_matrix_UB_23      -0.0207988000
_diffrn_orient_matrix_UB_31      0.0247905000
_diffrn_orient_matrix_UB_32      0.0492455000
_diffrn_orient_matrix_UB_33      -0.0980769000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29685
_diffrn_reflns_point_group_measured_fraction_full 0.858
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.955
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_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/diethyl ether'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 2593 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
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_refine_ls_number_reflns         7388
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_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0900P)^2^+0.1076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.715
_reflns_Friedel_fraction_max     0.702
_reflns_number_gt                6742
_reflns_number_total             7388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00761h2.cif
_cod_data_source_block           18
_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        2062.35(5)
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               7131713
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.892
_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), C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C18(H18A,H18B),
 C21(H21A,H21B), C35(H35A,H35B), C38(H38A,H38B), C40(H40A,H40B), C42(H42A,H42B),
  C48(H48A,H48B), C51(H51A,H51B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C33(H33), C44(H44)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,
 H24C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C54(H54A,
 H54B,H54C)
;
_shelx_res_checksum              12443
_shelx_hkl_checksum              80534