Synthesis of aryloxyacetamides from arylboronic acids and 2-bromoacetonitrile promoted by alkaline solutions of hydrogen peroxide
Guo, Mengping; Li, Yingmin; Wen, Yongju; Shen, Xiuli; RSC Advances 13 (2023) 2631–2634; doi:10.1039/D2RA07451F

data_7246162
_publ_section_title
;
 Synthesis of aryloxyacetamides from arylboronic acids and
 2-bromoacetonitrile promoted by alkaline solutions of hydrogen peroxide
;
_journal_issue                   4
_journal_name_full               'RSC Advances'
_journal_page_first              2631
_journal_page_last               2634
_journal_paper_doi               10.1039/D2RA07451F
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C9 H11 N O2 S'
_chemical_formula_sum            'C9 H11 N O2 S'
_chemical_formula_weight         197.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-21 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.2907(9)
_cell_length_b                   14.516(2)
_cell_length_c                   23.891(4)
_cell_measurement_reflns_used    1745
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.7820
_cell_measurement_theta_min      2.8070
_cell_volume                     1834.8(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -86.00 -33.00   1.00    6.00    --  -11.59 -37.00 120.00   53
  2  \w      5.00  85.00   1.00    6.00    --   11.74  37.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0345314000
_diffrn_orient_matrix_UB_12      0.0307732000
_diffrn_orient_matrix_UB_13      -0.0217693000
_diffrn_orient_matrix_UB_21      0.0313469000
_diffrn_orient_matrix_UB_22      -0.0379956000
_diffrn_orient_matrix_UB_23      -0.0173526000
_diffrn_orient_matrix_UB_31      -0.1256574000
_diffrn_orient_matrix_UB_32      -0.0009349000
_diffrn_orient_matrix_UB_33      -0.0102704000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5577
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.208
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0492P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                2801
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra07451f2.cif
_cod_data_source_block           25_3
_cod_original_cell_volume        1834.9(5)
_cod_database_code               7246162
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6AA(H6AA,H6AB), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C1AA(H1AA), C3(H3), C4AA(H4AA), C6(H6), C2AA(H2AA), C5AA(H5AA)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N0AA(H0AA,H0AB)
2.d Idealised Me refined as rotating group:
 C8AA(H8AA,H8AB,H8AC), C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 2018-12-12
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.583
_oxdiff_exptl_absorpt_empirical_full_min 0.539