Tandem Synthesis of Pyrrolo[2,3-b]quinolones via Cadogen-Type Reaction.
Lin, Zhichen; Hu, Zhongyan; Zhang, Xin; Dong, Jinhuan; Liu, Jian-Biao; Chen, De-Zhan; Xu, Xianxiu; Organic letters 19 (2017) 5284–5287; doi:10.1021/acs.orglett.7b02558

data_1547197
_publ_section_title
;
 Tandem Synthesis of Pyrrolo[2,3-b]quinolones via Cadogen-Type Reaction.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5284
_journal_page_last               5287
_journal_paper_doi               10.1021/acs.orglett.7b02558
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C20 H16 N2 O4, C2 H6 O2'
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.095(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1050(12)
_cell_length_b                   17.278(3)
_cell_length_c                   9.698(2)
_cell_measurement_reflns_used    967
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.288
_cell_measurement_theta_min      2.421
_cell_volume                     1015.1(3)
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6305
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.793
_diffrn_reflns_theta_min         2.116
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   none
_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    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 787 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.4182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1317
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.815
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                2420
_reflns_number_total             3535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02558_si_002.cif
_cod_data_source_block           11
_cod_depositor_comments          'Adding full bibliography for 1547197.cif.'
_cod_original_cell_volume        1015.1(4)
_cod_database_code               1547197
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), N1(H1A), N2(H2A)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O5(H5), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'