Visible-Light-Promoted Oxidative Halogenation of Alkynes
Li, Yiming; Mou, Tao; Lu, Linglin; Jiang, Xuefeng; Chemical Communications  (2019) –; doi:10.1039/C9CC07655G

data_7124372
_publ_section_title
;
 Visible-Light-Promoted Oxidative Halogenation of Alkynes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07655G
_journal_year                    2019
_chemical_formula_moiety         'C9 H5 Br2 N O'
_chemical_formula_sum            'C9 H5 Br2 N O'
_chemical_formula_weight         302.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-11 deposited with the CCDC.    2019-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.1410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.40930(10)
_cell_length_b                   9.09290(10)
_cell_length_c                   13.3012(2)
_cell_measurement_reflns_used    14654
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1730
_cell_measurement_theta_min      4.8700
_cell_volume                     986.26(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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     19.00  79.00   1.00    1.00    --    0.00  82.00-120.00   60
  2  \w    -16.00  15.00   1.00    1.00    --    0.00  38.00  30.00   31
  3  \w     38.00  88.00   1.00    1.00    --    0.00  38.00 -30.00   50
  4  \w    -32.00  10.00   1.00    1.00    --    0.00  82.00-120.00   42
  5  \w    -32.00   1.00   1.00    1.00    --    0.00  82.00  30.00   33
  6  \w    -11.00  23.00   1.00    1.00    --    0.00  38.00-180.00   34
  7  \w     37.00  88.00   1.00    1.00    --    0.00  57.00-150.00   51
  8  \w     45.00  82.00   1.00    1.00    --    0.00  38.00 150.00   37
  9  \w     48.00  73.00   1.00    1.00    --    0.00  38.00-180.00   25
 10  \w     24.00  88.00   1.00    1.00    --    0.00  38.00  30.00   64
 11  \w     29.00  78.00   1.00    1.00    --    0.00  82.00  30.00   49
 12  \w     -8.00  18.00   1.00    1.00    --    0.00  57.00-150.00   26
 13  \w    -18.00  14.00   1.00    1.00    --    0.00  38.00 150.00   32
 14  \w    -19.00  15.00   1.00    1.00    --    0.00  38.00 -30.00   34
 15  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 16  \w    100.00 126.00   1.00    1.00    --   95.80 -82.00   0.00   26
 17  \w    115.00 141.00   1.00    1.00    --   95.80  80.00  18.21   26
 18  \w     52.00  96.00   1.00    1.00    --   95.80 -82.00   0.00   44
 19  \w     18.00  44.00   1.00    1.00    --   95.80 -82.00   0.00   26
 20  \w     64.00  90.00   1.00    1.00    --   95.80  80.00  18.21   26
 21  \w     69.00 135.00   1.00    1.00    --   95.80  67.00 -21.15   66
 22  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 23  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 120.00   26
 24  \w    109.00 135.00   1.00    1.00    --   95.80  77.00 120.00   26
 25  \w    129.00 184.00   1.00    1.00    --   95.80  61.00 -90.00   55
 26  \w      7.00  76.00   1.00    1.00    --   95.80 -61.00   0.00   69
 27  \w     63.00  92.00   1.00    1.00    --   95.80  82.00   0.00   29
 28  \w      8.00 127.00   1.00    1.00    --   95.80 -82.00 -60.00  119
 29  \w     71.00 119.00   1.00    1.00    --   95.80  61.00-180.00   48
 30  \w     63.00  95.00   1.00    1.00    --   95.80  82.00 -60.00   32
 31  \w     16.00 128.00   1.00    1.00    --   95.80 -82.00-150.00  112
 32  \w    113.00 139.00   1.00    1.00    --   95.80  77.00 -60.00   26
 33  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 34  \w    147.00 173.00   1.00    1.00    --   95.80  67.00   1.35   26
 35  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 36  \w     74.00 128.00   1.00    1.00    --   95.80  61.00 150.00   54
 37  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 38  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -30.00   26
 39  \w     71.00 123.00   1.00    1.00    --   95.80  61.00-120.00   52
 40  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 41  \w     65.00  92.00   1.00    1.00    --   95.80  82.00-180.00   27
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 43  \w    144.00 170.00   1.00    1.00    --   95.80  82.00  90.00   26
 44  \w    115.00 153.00   1.00    1.00    --   95.80  61.00 -60.00   38
 45  \w     76.00 169.00   1.00    1.00    --   95.80  30.00  60.00   93
 46  \w     75.00 100.00   1.00    1.00    --   95.80  45.00  60.00   25
 47  \w     75.00 135.00   1.00    1.00    --   95.80  45.00  90.00   60
 48  \w    143.00 169.00   1.00    1.00    --   95.80  45.00  90.00   26
 49  \w     75.00 185.00   1.00    1.00    --   95.80  45.00 150.00  110
 50  \w     71.00 108.00   1.00    1.00    --   95.80  61.00 -90.00   37
 51  \w     72.00 109.00   1.00    1.00    --   95.80  61.00 -60.00   37
 52  \w      6.00 113.00   1.00    1.00    --   95.80 -61.00-180.00  107
 53  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 54  \w     88.00 113.00   1.00    1.00    --   95.80 -61.00   0.00   25
 55  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 56  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 57  \w    156.00 185.00   1.00    1.00    --   95.80  82.00 -90.00   29
 58  \w     79.00 183.00   1.00    1.00    --   95.80  45.00-120.00  104
 59  \w    145.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   40
 60  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 61  \w     72.00 112.00   1.00    1.00    --   95.80  67.00   1.35   40
 62  \w     76.00 156.00   1.00    1.00    --   95.80  45.00-150.00   80
 63  \w     92.00 117.00   1.00    1.00    --   95.80  77.00 -92.81   25
 64  \w     74.00 100.00   1.00    1.00    --   95.80  61.00  90.00   26
 65  \w     65.00 120.00   1.00    1.00    --   95.80  77.00  90.00   55
 66  \w      6.00 107.00   1.00    1.00    --   95.80 -82.00  90.00  101
 67  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -92.81   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0988197000
_diffrn_orient_matrix_UB_12      -0.0765143000
_diffrn_orient_matrix_UB_13      -0.0989941000
_diffrn_orient_matrix_UB_21      0.0036302000
_diffrn_orient_matrix_UB_22      0.1424851000
_diffrn_orient_matrix_UB_23      -0.0619820000
_diffrn_orient_matrix_UB_31      0.1610597000
_diffrn_orient_matrix_UB_32      -0.0501808000
_diffrn_orient_matrix_UB_33      -0.0250860000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1818
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19779
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.029
_diffrn_reflns_theta_max         67.029
_diffrn_reflns_theta_min         5.666
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.792
_refine_diff_density_min         -1.425
_refine_diff_density_rms         0.161
_refine_ls_extinction_coef       0.0289(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0909P)^2^+0.2524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1666
_reflns_number_total             1733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07655g2.cif
_cod_data_source_block           exp_459
_cod_database_code               7124372
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.101
_shelx_estimated_absorpt_t_min   0.090
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
;
_shelx_res_checksum              63531
_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 5.354
_oxdiff_exptl_absorpt_empirical_full_min 0.293