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_7131692
_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         'C14 H17 B Cl N3 O6 S, C4 H8 O2'
_chemical_formula_sum            'C18 H25 B Cl N3 O8 S'
_chemical_formula_weight         489.73
_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             2022-10-21
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2023-04-20 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.823(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2505(2)
_cell_length_b                   15.1794(2)
_cell_length_c                   11.4864(2)
_cell_measurement_reflns_used    7933
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.4350
_cell_measurement_theta_min      3.3280
_cell_volume                     2310.07(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.966
_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    -39.00  35.00   0.50    1.79    --  -42.99  37.00 -49.00  148
  2  \w   -104.00 -30.00   0.50    1.79    --  -42.99 -37.00 155.00  148
  3  \w     61.00  86.00   0.50    1.79    --   42.99-159.00 141.00   50
  4  \w   -170.00 -79.00   0.50    7.17    --  -96.00 -37.00 155.00  182
  5  \w    -83.00 -42.00   0.50    7.17    --  -96.00 119.00  20.00   82
  6  \w     67.00 134.00   0.50    7.17    --  108.01-159.00 141.00  134
  7  \w    109.00 154.00   0.50    7.17    --  108.01  86.00 130.00   90
  8  \w     85.00 114.00   0.50    7.17    --  108.01  37.00 -49.00   58
  9  \w     37.00 109.00   0.50    7.17    --  108.01-119.00 -65.00  144
 10  \w     75.00 121.00   0.50    1.79    --   42.99 178.00  60.00   92
 11  \w    -71.00 -28.00   0.50    7.17    --  -96.00 125.00  60.00   86
 12  \w    -50.00 -24.00   0.50    7.17    --  -96.00  45.00 120.00   52
 13  \w    -86.00 -61.00   0.50    7.17    --  -96.00 125.00 -30.00   50
 14  \w    -55.00 -24.00   0.50    7.17    --  -96.00  61.00  30.00   62
 15  \w   -138.00 -88.00   0.50    7.17    --  -96.00-125.00  90.00  100
 16  \w     84.00 172.00   0.50    7.17    --  108.01  30.00  60.00  176
 17  \w     36.00  88.00   0.50    7.17    --  108.01 -77.00  90.00  104
 18  \w     41.00  97.00   0.50    7.17    --  108.01 -77.00 150.00  112
 19  \w     49.00 106.00   0.50    7.17    --  108.01 -95.00 150.00  114
 20  \w     80.00 112.00   0.50    7.17    --  108.01-125.00   0.00   64
 21  \w     99.00 164.00   0.50    7.17    --  108.01 125.00 -30.00  130
 22  \w     48.00  74.00   0.50    7.17    --  108.01-125.00   0.00   52
 23  \w     92.00 118.00   0.50    7.17    --  108.01 -83.00  10.00   52
 24  \w    -51.00 -26.00   0.50    7.17    --  -96.00  45.00 -30.00   50
 25  \w   -132.00 -97.00   0.50    7.17    --  -96.00 -30.00-180.00   70
 26  \w   -160.00-134.00   0.50    7.17    --  -96.00 -30.00-180.00   52
 27  \w    -51.00 -25.00   0.50    7.17    --  -96.00  45.00  60.00   52
 28  \w    -51.00 -26.00   0.50    7.17    --  -96.00  45.00  30.00   50
 29  \w    -51.00 -26.00   0.50    7.17    --  -96.00  45.00  90.00   50
 30  \w     48.00  74.00   0.50    7.17    --  108.01 -95.00-120.00   52
 31  \w     79.00 105.00   0.50    7.17    --  108.01 -95.00 -30.00   52
;
_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      -0.0325367000
_diffrn_orient_matrix_UB_12      -0.0930720000
_diffrn_orient_matrix_UB_13      0.0377560000
_diffrn_orient_matrix_UB_21      -0.0431904000
_diffrn_orient_matrix_UB_22      0.0382586000
_diffrn_orient_matrix_UB_23      0.1131102000
_diffrn_orient_matrix_UB_31      -0.1028918000
_diffrn_orient_matrix_UB_32      0.0133501000
_diffrn_orient_matrix_UB_33      -0.0614383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19672
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.175
_diffrn_reflns_theta_min         3.336
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.742
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.366
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0725P)^2^+1.2179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3990
_reflns_number_total             4601
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02086j2.cif
_cod_data_source_block           CMBT
_cod_depositor_comments
'Adding full bibliography for 7131691--7131692.cif.'
_cod_database_code               7131692
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H17 B Cl N3 O6 S'
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.514
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C4(H4A,H4B), C2(H2A,H2B), C17(H17A,H17B)
1.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C13(H13), C9(H9), C10(H10), C12(H12)
1.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              32287
_shelx_hkl_checksum              69692
_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 1.906
_oxdiff_exptl_absorpt_empirical_full_min 0.537