Chloroacetyl boronate <i>N</i>-tosylhydrazone as a versatile synthetic building block.
Miyazaki, Ryuya; Muto, Kei; Yamaguchi, Junichiro; Chemical communications (Cambridge, England) 59 (2023) 7419–7422; doi:10.1039/d3cc02086j

data_7131691
_publ_section_title
;
 Chloroacetyl boronate <i>N</i>-tosylhydrazone as a versatile synthetic
 building block.
;
_journal_issue                   48
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7419
_journal_page_last               7422
_journal_paper_doi               10.1039/d3cc02086j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C21 H24 B N3 O6 S'
_chemical_formula_sum            'C21 H24 B N3 O6 S'
_chemical_formula_weight         457.30
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-04-20 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.3367(14)
_cell_length_b                   26.3367(14)
_cell_length_c                   6.5069(6)
_cell_measurement_reflns_used    1126
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      63.0010
_cell_measurement_theta_min      3.3520
_cell_volume                     4513.3(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_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     34.00  64.00   0.50    0.05    --  108.01 -61.00   0.00   60
  2  \w     36.00  89.00   0.50    0.05    --  108.01 -77.00  60.00  106
  3  \w     37.00  68.00   0.50    0.05    --  108.01 -61.00 120.00   62
  4  \w     37.00  63.00   0.50    0.05    --  108.01 -61.00  60.00   52
  5  \w    112.00 169.00   0.50    0.05    --  108.01  54.00  60.00  114
  6  \w     35.00  60.00   0.50    0.05    --  108.01 -54.00 -82.00   50
  7  \w     34.00  59.00   0.50    0.05    --  108.01 -61.00-120.00   50
  8  \w      1.00  33.00   0.50    0.05    --   43.05 -19.00-180.00   64
  9  \w     73.00 100.00   0.50    0.05    --  108.01 -95.00  60.00   54
 10  \w     44.00  95.00   0.50    0.05    --   43.05-133.00  45.00  102
 11  \w     81.00 117.00   0.50    0.05    --  108.01-133.00  45.00   72
 12  \w     35.00  60.00   0.50    0.05    --  108.01 -95.00  60.00   50
 13  \w     34.00  60.00   0.50    0.05    --  108.01 -95.00-150.00   52
 14  \w     63.00 104.00   0.50    0.05    --  108.01 -95.00-150.00   82
 15  \w     -4.00  34.00   0.50    0.05    --  -43.05  38.00 120.00   76
 16  \w    -43.00  -8.00   0.50    0.05    --  -43.05  38.00 120.00   70
 17  \w    -86.00 -28.00   0.50    0.05    --  -96.00 137.00 -68.00  116
 18  \w    -67.00 -40.00   0.50    0.05    --  -43.05 125.00-150.00   54
 19  \w    -92.00 -27.00   0.50    0.05    --  -96.00  77.00 -60.00  130
 20  \w   -164.00-115.00   0.50    0.05    --  -96.00 -54.00 -82.00   98
 21  \w   -112.00 -66.00   0.50    0.05    --  -43.05-137.00-131.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0371914000
_diffrn_orient_matrix_UB_12      -0.0439127000
_diffrn_orient_matrix_UB_13      0.0414942000
_diffrn_orient_matrix_UB_21      -0.0071980000
_diffrn_orient_matrix_UB_22      0.0072541000
_diffrn_orient_matrix_UB_23      0.2334433000
_diffrn_orient_matrix_UB_31      -0.0445273000
_diffrn_orient_matrix_UB_32      -0.0378655000
_diffrn_orient_matrix_UB_33      -0.0031977000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1468
_diffrn_reflns_av_unetI/netI     0.1417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11055
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.107
_diffrn_reflns_theta_min         3.356
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.346
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.1006
_refine_ls_shift/su_max          0.306
_refine_ls_shift/su_mean         0.055
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1640P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2509
_refine_ls_wR_factor_ref         0.3332
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                2087
_reflns_number_total             4368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02086j2.cif
_cod_data_source_block           4a
_cod_depositor_comments
'Adding full bibliography for 7131691--7131692.cif.'
_cod_original_cell_volume        4513.3(6)
_cod_database_code               7131691
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.243
_diffrn_oxdiff_digest_frames
;
011ee156908676283d01c48753d983e65201606345a
;
_diffrn_oxdiff_digest_hkl
;
01a6c3d58342d63a1793c850bbdf658920f0be
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C17(H17), C3(H3), C20(H20), C19(H19), C21(H21),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              97037
_shelx_hkl_checksum              45005
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.432
_oxdiff_exptl_absorpt_empirical_full_min 0.441