Synthesis of Furo[3,2-b]quinolines and Furo[2,3-b:4,5-b']diquinolines through [4+2] Cycloaddition of Aza-o-Quinone Methides and Furans.
Lei, Lu; Yao, Yi-Yun; Jiang, Li-Juan; Lu, Xiuqiang; Liang, Cui; Mo, Dong-Liang; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b02953

data_4037883
_publ_section_title
;
 Synthesis of Furo[3,2-b]quinolines and Furo[2,3-b:4,5-b']diquinolines
 through [4+2] Cycloaddition of Aza-o-Quinone Methides and Furans.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02953
_journal_year                    2020
_chemical_formula_moiety         'C19 H19 N O3 S'
_chemical_formula_sum            'C19 H19 N O3 S'
_chemical_formula_weight         341.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.696(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9899(5)
_cell_length_b                   8.3035(3)
_cell_length_c                   15.1181(6)
_cell_measurement_reflns_used    3343
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5660
_cell_measurement_theta_min      4.0640
_cell_volume                     1698.74(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     43.00  78.00   1.00    4.00    --   18.47-131.00-141.00   35
  2  \w    -87.00 -61.00   1.00    4.00    --  -18.78 178.00-180.00   26
  3  \w    -89.00  10.00   1.00    4.00    --  -18.78 -77.00 -90.00   99
  4  \w    -31.00  -5.00   1.00    4.00    --  -18.78 -57.00  30.00   26
  5  \w    -46.00  45.00   1.00    4.00    --  -18.78  77.00  30.00   91
  6  \w    -91.00  14.00   1.00    4.00    --  -18.78 -19.00  90.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0444337000
_diffrn_orient_matrix_UB_12      0.0115739000
_diffrn_orient_matrix_UB_13      0.0135978000
_diffrn_orient_matrix_UB_21      0.0266746000
_diffrn_orient_matrix_UB_22      -0.0057522000
_diffrn_orient_matrix_UB_23      0.0465336000
_diffrn_orient_matrix_UB_31      0.0078535000
_diffrn_orient_matrix_UB_32      0.0844695000
_diffrn_orient_matrix_UB_33      0.0012801000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.001
_diffrn_reflns_theta_min         3.360
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.8102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2687
_reflns_number_total             4064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02953_si_003.cif
_cod_data_source_block           3oa
_cod_database_code               4037883
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C009(H009), C00B(H00B), C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00M), C00M(H00N), C00N(H00O)
2.c Idealised Me refined as rotating group:
 C00K(H00C,H00K,H00L), C00O(H00P,H00Q,H00R)
;
_shelx_res_checksum              6178
_shelx_hkl_checksum              30405
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.734
_oxdiff_exptl_absorpt_empirical_full_min 0.502