Formation of hydrazones and stabilized boron-nitrogen heterocycles in aqueous solution from carbohydrazides and ortho-formylphenylboronic acids
Gu, Han; Chio, Tak Ian; Lei, Zhen; Staples, Richard J.; Hirschi, Jennifer S.; Bane, Susan; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01708A

data_7155807
_publ_section_title
;
 Formation of hydrazones and stabilized boron-nitrogen heterocycles in
 aqueous solution from carbohydrazides and ortho-formylphenylboronic acids
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01708A
_journal_year                    2017
_chemical_formula_moiety         'C18 H16 B2 N4 O3'
_chemical_formula_sum            'C18 H16 B2 N4 O3'
_chemical_formula_weight         357.97
_chemical_name_systematic        'acetyl diazaborine'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-09-22
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5097)
;
_audit_update_record
;
2016-11-20 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                95.9130(10)
_cell_angle_beta                 94.5590(10)
_cell_angle_gamma                110.0140(10)
_cell_formula_units_Z            2
_cell_length_a                   7.35750(10)
_cell_length_b                   8.05570(10)
_cell_length_c                   15.1438(2)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.27
_cell_measurement_theta_min      5.90
_cell_volume                     832.53(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12241
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.259
_diffrn_reflns_theta_min         5.903
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0450 before and 0.0368 after correction. The Ratio of minimum to maximum transmission is 0.9213. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       chunk
_exptl_crystal_F_000             372
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.238
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0113(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0469P)^2^+0.3059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2997
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01708a2.cif
_cod_data_source_block           sbbu915a
_cod_database_code               7155807
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.833
_shelx_estimated_absorpt_t_min   0.746
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C11(H11A,H11B,H11C)
;
_contact_crystallographer_email  staples@chemistry.msu.com
_contact_crystallographer_name   'Richard Staples'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id Sample
_olex2_submission_special_instructions 'No special instructions were received'