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_1553226
_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         'C23 H14 Cl2 N2 O'
_chemical_formula_sum            'C23 H14 Cl2 N2 O'
_chemical_formula_weight         405.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2015-03-27 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.585(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9936(3)
_cell_length_b                   20.9137(5)
_cell_length_c                   10.6975(4)
_cell_measurement_reflns_used    7377
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.1290
_cell_measurement_theta_min      5.3150
_cell_volume                     1857.78(12)
_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-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.6525
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1801817000
_diffrn_orient_matrix_UB_12      0.0172607000
_diffrn_orient_matrix_UB_13      0.0509047000
_diffrn_orient_matrix_UB_21      -0.0018264000
_diffrn_orient_matrix_UB_22      -0.0125444000
_diffrn_orient_matrix_UB_23      -0.1425004000
_diffrn_orient_matrix_UB_31      -0.0445519000
_diffrn_orient_matrix_UB_32      0.0704534000
_diffrn_orient_matrix_UB_33      -0.0379287000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16358
_diffrn_reflns_theta_full        70.08
_diffrn_reflns_theta_max         70.08
_diffrn_reflns_theta_min         4.23
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79501
_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_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0434P)^2^+2.0432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                3092
_reflns_number_total             3521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00417a2.cif
_cod_data_source_block           hnu_m405_1
_cod_original_cell_volume        1857.79(10)
_cod_database_code               1553226
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C12(H12), C14(H14), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'