Cu-Catalyzed Cascade Annulation of Alkynols with 2-Azidobenzaldehydes: Access to 6H-Isochromeno[4,3-c]quinoline.
Mao, Xiao-Feng; Zhu, Xiao-Ping; Li, Deng-Yuan; Liu, Pei-Nian; The Journal of organic chemistry 82 (2017) 7032–7039; doi:10.1021/acs.joc.7b00937

data_4032579
_publ_section_title
;
 Cu-Catalyzed Cascade Annulation of Alkynols with 2-Azidobenzaldehydes:
 Access to 6H-Isochromeno[4,3-c]quinoline.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7032
_journal_page_last               7039
_journal_paper_doi               10.1021/acs.joc.7b00937
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C23 H16 Cl N O2'
_chemical_formula_sum            'C23 H16 Cl N O2'
_chemical_formula_weight         373.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                76.716(4)
_cell_angle_beta                 84.104(4)
_cell_angle_gamma                75.228(4)
_cell_formula_units_Z            4
_cell_length_a                   10.119(2)
_cell_length_b                   11.447(2)
_cell_length_c                   16.905(3)
_cell_measurement_reflns_used    5591
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.71
_cell_measurement_theta_min      2.37
_cell_volume                     1840.7(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 0.974
_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  0.0220
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.866
_diffrn_reflns_theta_min         1.882
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0371 before and 0.0312 after correction.
The Ratio of minimum to maximum transmission is 0.9292.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.349
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.029(3)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         11302
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0633
_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^)+(0.1000P)^2^+0.7781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1818
_refine_ls_wR_factor_ref         0.2121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7168
_reflns_number_total             11302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00937_si_002.cif
_cod_data_source_block           mo_dm16421_0m
_cod_depositor_comments          'Adding full bibliography for 4032579.cif.'
_cod_original_cell_volume        1840.8(6)
_cod_database_code               4032579
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-C46
 1.48 with sigma of 0.02
3. Rigid bond restraints
 O4, C43, O4, C46, C42, C43
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
Uanis(C43) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(O4)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C24(H24A,H24B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18),
 C19(H19), C21(H21), C22(H22), C26(H26), C27(H27), C29(H29), C34(H34), C35(H35),
  C36(H36), C37(H37), C41(H41), C42(H42), C44(H44), C45(H45)
5.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              17051
_shelx_hkl_checksum              14642
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'