Simple and versatile electrochemical synthesis of highly substituted 2,1-benzisoxazoles.
Lenhard, Marola S.; Winter, Johannes; Sandvoß, Alexander; Gálvez-Vázquez, María de Jesús; Schollmeyer, Dieter; Waldvogel, Siegfried R.; Organic & biomolecular chemistry 23 (2025) 2391–2399; doi:10.1039/d4ob01875c

data_7160272
_publ_section_title
;
 Simple and versatile electrochemical synthesis of highly substituted
 2,1-benzisoxazoles.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2391
_journal_page_last               2399
_journal_paper_doi               10.1039/d4ob01875c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C10 H9 Br N2 O2'
_chemical_formula_sum            'C10 H9 Br N2 O2'
_chemical_formula_weight         269.10
_chemical_name_systematic
;
3-(N-Acetylaminomethyl)-5-bromo-benzo[c]isoxazol
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-10-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                72.973(5)
_cell_angle_beta                 80.305(5)
_cell_angle_gamma                82.117(5)
_cell_formula_units_Z            4
_cell_length_a                   8.6341(5)
_cell_length_b                   9.4095(6)
_cell_length_c                   13.5968(8)
_cell_measurement_reflns_used    13360
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      3.07
_cell_volume                     1036.60(11)
_computing_cell_refinement       'X-Area Recipe 1.36.0.0 (STOE, 2020)'
_computing_data_collection       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_data_reduction        'X-Area Integrate 1.77.0.0 (STOE, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2014 (Shelxdrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9184
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.894
_diffrn_reflns_theta_min         3.069
_diffrn_source                   'sealed X-ray tube, 12x0.4mm long-fine focus'
_exptl_absorpt_coefficient_mu    3.946
_exptl_absorpt_correction_T_max  0.4233
_exptl_absorpt_correction_T_min  0.0989
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in F. R. Ahmed (Editor), 
"Crystallographic Computing", Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.690
_exptl_crystal_size_mid          0.490
_exptl_crystal_size_min          0.210
_refine_diff_density_max         1.174
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0504P)^2^+1.7947P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4329
_reflns_number_total             4937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01875c2.cif
_cod_data_source_block           5ac
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Dual' was changed to
'dual' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160272.cif.
;
_cod_database_code               7160272
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.172
_shelx_estimated_absorpt_t_max   0.491
_shelx_res_checksum              54707