Copper(i) catalyzed C(sp2)–N bond formation: synthesis of pyrrolo[3,2-c]quinolinone derivatives
Zhang, Zhiguo; Qian, Jingjing; Zhang, Guisheng; Ma, Nana; Liu, Qingfeng; Liu, Tongxin; Sun, Kai; Shi, Lei; Organic Chemistry Frontiers 3 (2016) 344–; doi:10.1039/C5QO00417A

data_1553228
_publ_section_title
;
 Copper(i) catalyzed C(sp2)--N bond formation: synthesis of
 pyrrolo[3,2-c]quinolinone derivatives
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              344
_journal_paper_doi               10.1039/C5QO00417A
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C24 H14 Cl2 N2 O2'
_chemical_formula_sum            'C24 H14 Cl2 N2 O2'
_chemical_formula_weight         433.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_audit_update_record
;
2015-03-27 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                73.584(12)
_cell_angle_beta                 85.490(8)
_cell_angle_gamma                87.120(12)
_cell_formula_units_Z            2
_cell_length_a                   5.2005(5)
_cell_length_b                   13.556(3)
_cell_length_c                   15.6215(13)
_cell_measurement_reflns_used    1606
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      63.5940
_cell_measurement_theta_min      3.8330
_cell_volume                     1052.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    '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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega    9.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 27

  2 omega   16.00   59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 43

  3 omega  -61.00   26.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000 -120.0000 87

  4 omega  -46.00    9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  120.0000 55

  5 omega  -47.00  -14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000   90.0000 33

  6 omega  -85.00   27.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   19.0000   30.0000 112

  7 omega -111.00  -86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000 -148.0000  -74.0000 25

  8 omega   35.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000  -60.0000 58

  9 omega   19.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -180.0000 68

 10 omega  105.00  173.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -30.0000 68

 11 omega   83.00  115.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 32

 12 omega   60.00  128.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -120.0000 68

 13 omega   41.00   96.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 55

 14 omega   47.00  100.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 53

 15 omega   40.00   90.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 50

 16 omega   44.00   98.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 54

 17 omega   63.00  101.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 38

 18 omega   42.00   98.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 56

 19 omega   57.00   86.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 29

 20 omega   80.00  108.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 28

 21 omega   41.00   97.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 56

 22 omega   41.00   68.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 27

 23 omega   48.00   90.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 42

 24 omega   58.00  106.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 48

 25 omega   39.00  167.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000  120.0000 128

 26 omega  -26.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  150.0000 98

 27 omega -111.00  -21.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000   30.0000 90

 28 omega -113.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -150.0000 101

 29 omega -113.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  120.0000 101

 30 omega   35.00  125.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0028011000
_diffrn_orient_matrix_UB_12      0.1084442000
_diffrn_orient_matrix_UB_13      -0.0662925000
_diffrn_orient_matrix_UB_21      0.0003896000
_diffrn_orient_matrix_UB_22      0.0476079000
_diffrn_orient_matrix_UB_23      0.0786176000
_diffrn_orient_matrix_UB_31      0.2972171000
_diffrn_orient_matrix_UB_32      -0.0044780000
_diffrn_orient_matrix_UB_33      -0.0064595000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7415
_diffrn_reflns_theta_full        67.12
_diffrn_reflns_theta_max         67.12
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0022(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1001P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2294
_reflns_number_gt                2071
_reflns_number_total             3744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00417a2.cif
_cod_data_source_block           20150125
_cod_original_cell_volume        1052.6(2)
_cod_database_code               1553228
_chemical_oxdiff_formula         C20H20N4O4Cl2
_reflns_odcompleteness_completeness 99.81
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16),
 C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'