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_4037881
_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.
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_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02953
_journal_year                    2020
_chemical_formula_moiety         'C28 H27 Cl N2 O4 S2'
_chemical_formula_sum            'C28 H27 Cl N2 O4 S2'
_chemical_formula_weight         555.08
_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   mixed
_atom_sites_solution_primary     direct
_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                 92.594(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.350(4)
_cell_length_b                   11.844(5)
_cell_length_c                   27.870(13)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.44
_cell_volume                     2753(2)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            35145
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_min         1.463
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_refine_diff_density_max         1.287
_refine_diff_density_min         -1.338
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0667
_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^)+(0.1067P)^2^+2.7820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1944
_refine_ls_wR_factor_ref         0.2095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4907
_reflns_number_total             6303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02953_si_007.cif
_cod_data_source_block           6
_cod_original_cell_volume        2754(2)
_cod_database_code               4037881
_shelx_shelxl_version_number     2014/7
_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 C(H,H,H) groups
2.a Riding coordinates:
 N0AA(H0AA)
2.b Secondary CH2 refined with riding coordinates:
 C4BA(H4BA,H4BB), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C8BA(H8BA), C4AA(H4AA), C5AA(H5AA), C7AA(H7AA), C8AA(H8AA), C9AA(H9AA),
 C1BA(H1BA), C21(H21), C22(H22), C23(H23), C27(H27), C29(H29), C31(H31),
 C33(H33), C34(H34), C37(H37)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              56244
_shelx_hkl_checksum              90048
_olex2_submission_special_instructions 'No special instructions were received'