PhI(OAc)2 Oxidative C5 Halogenation of Quinolines Using Copper Halides Under Mild Conditions
Liu, Xingxing; Wu, Zhaoyang; Luo, Xinliang; He, Yongqin; zhou, xiaoqiang; Fan, Yuxing; Huang, Guosheng; RSC Adv.  (2016) –; doi:10.1039/C6RA14863H

data_7226018
_publ_section_title
;
 PhI(OAc)2 Oxidative C5 Halogenation of Quinolines Using Copper Halides
 Under Mild Conditions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA14863H
_journal_year                    2016
_chemical_formula_moiety         'C16 H11 Br N2 O'
_chemical_formula_sum            'C16 H11 Br N2 O'
_chemical_formula_weight         327.18
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-12-01 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.876(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   27.1928(12)
_cell_length_b                   8.0801(3)
_cell_length_c                   25.7427(9)
_cell_measurement_reflns_used    1898
_cell_measurement_temperature    291.73(10)
_cell_measurement_theta_max      21.3610
_cell_measurement_theta_min      4.0520
_cell_volume                     5412.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.73(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega   40.00   75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000   60.0000 35

  2 omega    6.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000  -30.0000 65

  3 omega   -5.00   22.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000  -30.0000 27

  4 omega  -48.00   46.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000  -60.0000 94

  5 omega   35.00   60.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000 -180.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0112085000
_diffrn_orient_matrix_UB_12      0.0057819000
_diffrn_orient_matrix_UB_13      0.0284828000
_diffrn_orient_matrix_UB_21      -0.0238128000
_diffrn_orient_matrix_UB_22      0.0275443000
_diffrn_orient_matrix_UB_23      0.0029435000
_diffrn_orient_matrix_UB_31      -0.0071210000
_diffrn_orient_matrix_UB_32      -0.0831536000
_diffrn_orient_matrix_UB_33      0.0029607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11504
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                3098
_reflns_number_total             5289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra14863h2.cif
_cod_data_source_block           wuchay0330
_cod_database_code               7226018
_chemical_oxdiff_formula         'C44 H28 S8'
_reflns_odcompleteness_completeness 99.24
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
  C15(H15), C16(H16), N4(H4), C17(H17), C19(H19), C22(H22), C23(H23), C24(H24),
 C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_olex2_date_sample_data_collection 2015-03-30
_olex2_submission_special_instructions 'No special instructions were received'