Synthesis of Novel Benzoxaborinin-4-ones and its Application in Indolin-2-ones Synthesis Using Suzuki-Miyaura Reaction Protocol
Iyer, Pravin S.; Nawaz Khan, Fazlur-Rahman; Kannan, Murugan; Chinnapattu, Murugan; RSC Adv.  (2015) –; doi:10.1039/C5RA05755H

data_7220159
_publ_section_title
;
 Synthesis of Novel Benzoxaborinin-4-ones and its Application in
 Indolin-2-ones Synthesis Using Suzuki-Miyaura Reaction Protocol
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA05755H
_journal_year                    2015
_chemical_formula_moiety         'C23 H15 Cl F N O2'
_chemical_formula_sum            'C23 H15 Cl F N O2'
_chemical_formula_weight         391.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-03-31 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.511(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.292(5)
_cell_length_b                   10.0001(19)
_cell_length_c                   15.408(3)
_cell_measurement_reflns_used    4280
_cell_measurement_temperature    298(2)
_cell_volume                     3763.0(13)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22200
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         1.668
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1062 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.9209.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear reddish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0011(3)
_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   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0678P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2151
_reflns_number_total             4218
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra05755h2.cif
_cod_data_source_block           red
_cod_depositor_comments
;

2018-01-23
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        3763.0(12)
_cod_original_formula_moiety     '0.25(C23 H15 Cl F N O2)'
_cod_original_formula_sum        'C5.75 H3.75 Cl0.25 F0.25 N0.25 O0.50'
_cod_original_formula_units_Z    32
_cod_original_formula_weight     97.95
_cod_database_code               7220159
_shelxl_version_number           2014-1
_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:
 C2(H2), C3(H3), C8(H8), C11(H11), C13(H13), C14(H14), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              84544
_shelx_hkl_checksum              44266
_olex2_submission_special_instructions 'No special instructions were received'