Expeditious Synthesis of Pyrano[2,3,4-de]quinolines via Rh(III)-Catalyzed Cascade C–H Activation/Annulation/Lactonization of Quinolin-4-ol with Alkynes
Liao, Gang; Song, Hong; Yin, Xue-Song; Shi, Bing-Feng; Chem. Commun.  (2017) –; doi:10.1039/C7CC04113F

data_7120316
_publ_section_title
;
 Expeditious Synthesis of Pyrano[2,3,4-de]quinolines via Rh(III)-Catalyzed
 Cascade C--H Activation/Annulation/Lactonization of Quinolin-4-ol with
 Alkynes
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04113F
_journal_year                    2017
_chemical_formula_moiety         'C15 H11 N O3'
_chemical_formula_sum            'C15 H11 N O3'
_chemical_formula_weight         253.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1md1z1
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-08-26 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.583(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2462(9)
_cell_length_b                   8.2150(10)
_cell_length_c                   20.228(3)
_cell_measurement_reflns_used    1156
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2369
_cell_measurement_theta_min      2.8109
_cell_volume                     1201.8(3)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4684
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0079(18)
_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   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0537P)^2^+0.0969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                1421
_reflns_number_total             2190
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc04113f2.cif
_cod_data_source_block           140328_lg_1_100p
_cod_original_cell_volume        1201.7(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7120316