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_1553229
_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_absolute_configuration ad
_chemical_formula_moiety         'C24 H17 Cl N2 O2'
_chemical_formula_sum            'C24 H17 Cl N2 O2'
_chemical_formula_weight         400.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4973)
;
_audit_update_record
;
2015-03-31 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0462(5)
_cell_length_b                   9.2337(6)
_cell_length_c                   26.6656(13)
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.0550
_cell_measurement_theta_min      4.7860
_cell_volume                     1981.2(2)
_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    '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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -16.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 34

  2 omega  -34.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  -60.0000 28

  3 omega  -84.00   -8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -19.0000  120.0000 76

  4 omega   15.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -180.0000 73

  5 omega   40.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 36

  6 omega   85.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -180.0000 92

  7 omega  100.00  175.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 75

  8 omega   71.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 41

  9 omega   39.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 31

 10 omega   39.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 25

 11 omega   48.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 26

 12 omega  -64.00  -30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   63.0000  150.0000 34

 13 omega  -86.00  -46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -60.0000 40

 14 omega    1.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -180.0000 27

 15 omega   52.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066 -111.0000   90.0000 26

 16 omega   41.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -25.0000  -30.0000 26

 17 omega   46.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -37.0000  -90.0000 46

 18 omega   88.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -63.0000  -90.0000 43

 19 omega   45.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -63.0000  -90.0000 26

 20 omega   84.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066 -111.0000   90.0000 28

 21 omega  106.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066   77.0000   90.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1672514000
_diffrn_orient_matrix_UB_12      0.0810321000
_diffrn_orient_matrix_UB_13      0.0003004000
_diffrn_orient_matrix_UB_21      -0.0930237000
_diffrn_orient_matrix_UB_22      0.1459185000
_diffrn_orient_matrix_UB_23      -0.0012062000
_diffrn_orient_matrix_UB_31      -0.0029491000
_diffrn_orient_matrix_UB_32      0.0025786000
_diffrn_orient_matrix_UB_33      0.0577468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7586
_diffrn_reflns_theta_full        72.47
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95199
_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_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.0082(4)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0489P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                3048
_reflns_number_total             3843
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00417a2.cif
_cod_data_source_block           201412274
_cod_original_cell_volume        1981.1(2)
_cod_database_code               1553229
_chemical_oxdiff_formula         C20H20N4O4Cl1
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'