Copper-Catalyzed C-H Alkylation of 8-Aminoquinolines via 8-Amide Chelation Assistance
Xia, Xiao-Feng; Zhu, Su-Li; Gu, Zhen; Wang, Haijun; RSC Adv.  (2015) –; doi:10.1039/C4RA16896H

data_7219943
_publ_section_title
;
 Copper-Catalyzed C-H Alkylation of 8-Aminoquinolines via 8-Amide
 Chelation Assistance
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA16896H
_journal_year                    2015
_chemical_formula_moiety         'C26 H25 Br N2 O'
_chemical_formula_sum            'C26 H25 Br N2 O'
_chemical_formula_weight         461.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 2/c 1 1'
_symmetry_space_group_name_Hall  '-I 2yc'
_symmetry_space_group_name_H-M   'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-06-28
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2014-10-19 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.234(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.6160(15)
_cell_length_b                   6.6330(2)
_cell_length_c                   20.9653(10)
_cell_measurement_reflns_used    7401
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      70.7170
_cell_measurement_theta_min      4.2290
_cell_volume                     4250.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9389
_diffrn_measured_fraction_theta_max 0.9938
_diffrn_measurement_details
;
  1 omega  -31.00    8.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  120.0000 26

  2 omega  -68.00  -29.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 26

  3 omega  -25.00   20.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 30

  4 omega  -81.00  -48.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 22

  5 omega   17.00   44.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  120.0000 18

  6 omega  -56.00   -9.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  124.0000 -106.0000 31

  7 omega -112.00  -35.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000    0.0000 51

  8 omega  -68.00  -35.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000    0.0000 22

  9 omega  -14.00   77.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  120.0000 61

 10 omega   32.00  126.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -90.0000 63

 11 omega   37.00   61.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000 -150.0000 16

 12 omega   39.00  115.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000    0.0000 51

 13 omega   92.00  116.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  120.0000 16

 14 omega   28.00  112.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   30.0000 56

 15 omega   -8.00   17.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000 -150.0000 17

 16 omega   25.00  128.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000    0.0000 69

 17 omega   12.00   36.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   30.0000 16

 18 omega   37.00   64.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  120.0000 18

 19 omega   40.00   98.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 39

 20 omega  100.00  130.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 20

 21 omega   47.00   90.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   60.0000 29

 22 omega   52.00   91.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -90.0000 26

 23 omega  110.00  147.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000  -90.0000 25

 24 omega   61.00   97.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000  -90.0000 24

 25 omega   39.00   69.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -90.0000 20

 26 omega  150.00  177.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -90.0000 18

 27 omega  100.00  158.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -60.0000 39

 28 omega  152.00  176.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  120.0000 16

 29 omega   90.00  117.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000   60.0000 18

 30 omega   43.00   68.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000   90.0000 17

 31 omega   43.00   88.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   30.0000 30

 32 omega   48.00  115.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -113.0000  -15.6857 45

 33 omega   52.00   79.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000  -60.0000 18

 34 omega  135.00  169.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000 -120.0000 23

 35 omega   63.00  102.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 26

 36 omega   42.00   84.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  150.0000 28

 37 omega   95.00  119.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000  -30.0000 16

 38 omega   46.00   82.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000  -30.0000 24

 39 omega  112.00  145.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   30.0000 22

 40 omega   51.00   90.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000  150.0000 26

 41 omega   64.00   91.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000   30.0000 18

 42 omega   54.00   88.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000 -120.0000 23

 43 omega   42.00   73.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -150.0000 21

 44 omega   97.00  130.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000  150.0000 22

 45 omega   89.00  114.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000   30.0000 17

 46 omega   48.00   99.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 34

 47 omega  108.00  133.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 17

 48 omega   39.00   64.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -120.0000 17

 49 omega   95.00  129.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000   90.0000 23

 50 omega  135.00  177.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000   90.0000 28

 51 omega   98.00  123.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000 -180.0000 17

 52 omega   58.00  112.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 36

 53 omega   40.00   73.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000   60.0000 22

 54 omega   90.00  151.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000   60.0000 41

 55 omega   41.00   66.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   30.0000 17

 56 omega   69.00   94.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000    0.0000 17

 57 omega   41.00   65.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000    0.0000 16

 58 omega  105.00  129.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000  120.0000 16

 59 omega  113.00  173.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  150.0000 40

 60 omega  144.00  177.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000   60.0000 22

 61 omega   43.00   68.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 17

 62 omega   94.00  145.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 34

 63 omega   43.00   67.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -60.0000 16

 64 omega   43.00   68.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -120.0000 17

 65 omega   72.00  129.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000  -30.0000 38

 66 omega   45.00   70.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -180.0000 17

 67 omega  103.00  154.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  150.0000 34

 68 omega   94.00  134.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 27

 69 omega  147.00  174.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000   30.0000 18

 70 omega   88.00  161.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000 -150.0000 49

 71 omega  120.00  145.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000   90.0000 17

 72 omega   60.00   85.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 17

 73 omega   77.00  114.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 25

 74 omega   91.00  124.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 22

 75 omega  106.00  148.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000    0.0000 28

 76 omega   70.00  122.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000  120.0000 35

 77 omega   78.00  102.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -57.0000  -86.2636 16

 78 omega   96.00  120.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -123.0000 -156.7284 16
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0067755500
_diffrn_orient_matrix_UB_12      0.1045584500
_diffrn_orient_matrix_UB_13      0.0643249500
_diffrn_orient_matrix_UB_21      -0.0412190000
_diffrn_orient_matrix_UB_22      -0.1285485000
_diffrn_orient_matrix_UB_23      0.0082116000
_diffrn_orient_matrix_UB_31      0.0282376000
_diffrn_orient_matrix_UB_32      -0.1625591000
_diffrn_orient_matrix_UB_33      0.0348351000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24627
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.076
_diffrn_reflns_theta_min         4.224
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       needle
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0536P)^2^+4.7172P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3541
_reflns_number_total             4034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra16896h2.cif
_cod_data_source_block           xiaxf0628
_cod_database_code               7219943
_reflns_odcompleteness_completeness 93.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,
 H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C6(H6), C7(H7), C22(H22), C23(H23), C25(H25),
  C26(H26)
;
_shelx_res_checksum              46714
_shelxl_version_number           2013-2