Cu(I)-Catalyzed Oxygen and Nitrogen Nucleophiles Triggered Regioselective Synthesis of Furo/Pyrrolo-Annulated Quinolines.
Kumar, Ritush; Chandra, Atish; Mir, Bilal Ahmad; Shukla, Gaurav; The Journal of organic chemistry 84 (2019) 10710–10723; doi:10.1021/acs.joc.9b00662

data_4033811
_publ_section_title
;
 Cu(I)-Catalyzed Oxygen and Nitrogen Nucleophiles Triggered Regioselective
 Synthesis of Furo/Pyrrolo-Annulated Quinolines.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10710
_journal_page_last               10723
_journal_paper_doi               10.1021/acs.joc.9b00662
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C20 H18 N O4 P'
_chemical_formula_sum            'C20 H18 N O4 P'
_chemical_formula_weight         367.35
_chemical_name_systematic        DMP
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-02-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.600(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.298(3)
_cell_length_b                   19.536(10)
_cell_length_c                   14.791(8)
_cell_measurement_reflns_used    4919
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      2.08
_cell_volume                     1803.9(16)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9822
_diffrn_measured_fraction_theta_max 0.9822
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1250
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34593
_diffrn_reflns_theta_full        29.1020
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.7501
_exptl_absorpt_correction_T_min  0.5806
_exptl_absorpt_correction_type   cylinder
_exptl_absorpt_process_details   &#x0091;sadabs&#x0092;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3525
_exptl_crystal_description       needle
_exptl_crystal_F_000             768.8050
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.7279
_refine_diff_density_min         -0.6338
_refine_diff_density_rms         0.1315
_refine_ls_d_res_high            0.7307
_refine_ls_d_res_low             9.7679
_refine_ls_goodness_of_fit_ref   1.0989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0989
_refine_ls_R_factor_all          0.1934
_refine_ls_R_factor_gt           0.0794
_refine_ls_shift/su_max          0.1135
_refine_ls_shift/su_mean         0.0029
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2468
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                1924
_reflns_number_total             4755
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b00662_si_004.cif
_cod_data_source_block           RK_DMP
_cod_depositor_comments
;

2020-10-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.13(C20 H18 N O4 P)'
_cod_original_formula_sum        'C2.667 H2.4 N0.133 O0.533 P0.133'
_cod_original_formula_units_Z    30
_cod_original_formula_weight     48.98
_cod_database_code               4033811
_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 Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C15(H15), C17(H17), C18(H18), C19(H19),
 C21(H21), C23(H23), C25(H25)
2.c Idealised Me refined as rotating group:
 C0aa(H0aa,H0ab,H0ac), C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'