KMnO4/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids
Yuan, Jinwei; Yang, Liangru; Yin, Qiuyue; Mao, Pu; Qu, Ling-Bo; RSC Adv.  (2016) –; doi:10.1039/C6RA04787D

data_7224824
_publ_section_title
;
 KMnO4/AcOH-mediated C3-selective direct arylation of coumarins with
 arylboronic acids
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA04787D
_journal_year                    2016
_chemical_formula_moiety         'C15 H9 Br O2'
_chemical_formula_sum            'C15 H9 Br O2'
_chemical_formula_weight         301.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1904(13)
_cell_length_b                   3.9703(3)
_cell_length_c                   25.5341(19)
_cell_measurement_reflns_used    1278
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      22.9620
_cell_measurement_theta_min      4.0980
_cell_volume                     1235.84(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -58.00 -33.00   0.50    7.50    --  -14.59 127.00   5.00   50
  2  \w    -67.00 -42.00   0.50    7.50    --  -14.59 142.00 176.00   50
  3  \w     20.00  45.00   0.50    7.50    --   17.71-142.00 120.00   50
  4  \w     11.00  36.00   0.50    7.50    --   17.71-127.00 -69.00   50
  5  \w    -69.00 -42.00   0.50    7.50    --  -14.59-178.00  30.00   54
  6  \w      3.00  73.00   0.50    7.50    --   17.71  57.00-120.00  140
  7  \w      6.00  71.00   0.50    7.50    --   17.71  57.00 -60.00  130
  8  \w      5.00  85.00   0.50    7.50    --   17.71  57.00 150.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0300850000
_diffrn_orient_matrix_UB_12      -0.0197876000
_diffrn_orient_matrix_UB_13      -0.0235776000
_diffrn_orient_matrix_UB_21      0.0492317000
_diffrn_orient_matrix_UB_22      -0.0142137000
_diffrn_orient_matrix_UB_23      0.0146084000
_diffrn_orient_matrix_UB_31      -0.0073315000
_diffrn_orient_matrix_UB_32      -0.1770810000
_diffrn_orient_matrix_UB_33      0.0014631000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7951
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.342
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.618
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0392P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                1694
_reflns_number_total             2420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra04787d2.cif
_cod_data_source_block           201512164
_cod_original_cell_volume        1235.85(18)
_cod_database_code               7224824
_chemical_oxdiff_formula         C20H20N3O2Br1
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
;
_shelx_res_checksum              51053
_shelx_shelxl_version_number     2014/7
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.813