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_7155804
_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_absolute_configuration unk
_chemical_formula_moiety         'C9 H10 B N3 O2'
_chemical_formula_sum            'C9 H10 B N3 O2'
_chemical_formula_weight         203.01
_chemical_name_systematic        'glyzide diazaborine'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-19
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.10.10 svn.r3347 for OlexSys, GUI svn.r5252)
;
_audit_update_record
;
2016-11-20 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2080(8)
_cell_length_b                   5.9717(2)
_cell_length_c                   9.2902(4)
_cell_measurement_reflns_used    2420
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.14
_cell_measurement_theta_min      5.14
_cell_volume                     954.67(7)
_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 8.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0908
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.136
_diffrn_reflns_theta_min         5.140
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1182 before and 0.0848 after correction. The Ratio of minimum to maximum transmission is 0.7106. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1738
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0747
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1049P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.1781
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1512
_reflns_number_total             1738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01708a2.cif
_cod_data_source_block           jhbu1016d
_cod_database_code               7155804
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.907
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.1(7) -0.1(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9)
;
_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 1
_olex2_submission_special_instructions 'No special instructions were received'