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_1553227
_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             2015-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_audit_update_record
;
2015-03-27 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                80.819(6)
_cell_angle_beta                 88.955(5)
_cell_angle_gamma                75.537(7)
_cell_formula_units_Z            2
_cell_length_a                   6.3775(5)
_cell_length_b                   12.1686(10)
_cell_length_c                   13.4121(8)
_cell_measurement_reflns_used    2552
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1740
_cell_measurement_theta_min      3.7960
_cell_volume                     994.70(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -69.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 37

  2 omega  -67.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 29

  3 omega  -67.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 31

  4 omega   14.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 27

  5 omega   -9.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 27

  6 omega   24.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000    0.0000 84

  7 omega   33.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  150.0000 93

  8 omega    7.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -180.0000 56

  9 omega  -13.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   30.0000 90

 10 omega    8.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000   30.0000 38

 11 omega   38.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  -60.0000 90

 12 omega  125.00  172.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000    0.0000 47

 13 omega   45.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -30.0000 30

 14 omega   59.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 49

 15 omega   42.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 53

 16 omega   75.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 39

 17 omega   82.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   60.0000 91

 18 omega   89.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 88

 19 omega   77.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 26

 20 omega   65.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 26

 21 omega   44.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 42

 22 omega   39.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 51

 23 omega   45.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 31

 24 omega  101.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -60.0000 74

 25 omega   58.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 49

 26 omega  103.00  172.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   60.0000 69

 27 omega  106.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -30.0000 27

 28 omega   71.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 25

 29 omega  122.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -90.0000 53

 30 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 45

 31 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 45

 32 omega   35.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 90

 33 omega   26.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   60.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0673917000
_diffrn_orient_matrix_UB_12      0.1232802000
_diffrn_orient_matrix_UB_13      0.0245083000
_diffrn_orient_matrix_UB_21      0.2372413000
_diffrn_orient_matrix_UB_22      0.0078279000
_diffrn_orient_matrix_UB_23      -0.0084315000
_diffrn_orient_matrix_UB_31      -0.0379732000
_diffrn_orient_matrix_UB_32      0.0477990000
_diffrn_orient_matrix_UB_33      -0.1134609000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7140
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0577P)^2^+0.1760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                2754
_reflns_number_total             3554
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00417a2.cif
_cod_data_source_block           20150105a
_cod_original_cell_volume        994.69(12)
_cod_database_code               1553227
_chemical_oxdiff_formula         C20H20N4O4Cl2
_reflns_odcompleteness_completeness 100.00
_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), C3(H3), C4(H4), C10(H10), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'