Catalyst-free Synthesis of Pyrrolo[1,2-a]quinolines via Dehydration/[3+2] Cycloaddition Directly from 2-Methylquinolines, Aldehydes and Alkynoates.
Wu, Fu-Song; Zhao, Hai-Yuan; Xu, Yan-Li; Hu, Kun; Pan, Ying-Ming; Ma, Xian-Li; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00280

data_4032413
_publ_section_title
;
 Catalyst-free Synthesis of Pyrrolo[1,2-a]quinolines via Dehydration/[3+2]
 Cycloaddition Directly from 2-Methylquinolines, Aldehydes and Alkynoates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00280
_journal_year                    2017
_chemical_formula_moiety         'C26 H22 N2 O4'
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.45
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                106.234(10)
_cell_angle_beta                 109.319(10)
_cell_angle_gamma                104.799(10)
_cell_formula_units_Z            2
_cell_length_a                   8.679(6)
_cell_length_b                   11.875(8)
_cell_length_c                   12.649(8)
_cell_measurement_reflns_used    4107
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.52
_cell_volume                     1090.6(13)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12647
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.905
_diffrn_reflns_theta_max         25.905
_diffrn_reflns_theta_min         1.861
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0815P)^2^+0.1357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3168
_reflns_number_total             4212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00280_si_001.cif
_cod_data_source_block           12211
_cod_database_code               4032413
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.071) H3(0.089) H4(0.097) H5(0.089) H7(0.074) H8(0.061)
 H13A(0.056) H13B(0.056) H15(0.069) H16(0.071) H19(0.067) H20(0.065)
 H22A(0.077) H22B(0.077) H23A(0.127) H23B(0.127) H23C(0.127) H25A(0.081)
 H25B(0.081) H26A(0.129) H26B(0.129) H26C(0.129)
 Fixed X: H2(0.161801) H3(0.152801) H4(0.211101) H5(0.277599) H7(0.3396)
 H8(0.3543) H13A(0.398301) H13B(0.4077) H15(0.0316) H16(-0.2285) H19(-0.0066)
 H20(0.2529) H22A(0.322201) H22B(0.118901) H23A(0.1747) H23B(0.3791)
 H23C(0.268701) H25A(0.1946) H25B(0.193101) H26A(0.4936) H26B(0.4007)
 H26C(0.4971)
 Fixed Y: H2(-0.0325) H3(-0.2148) H4(-0.2151) H5(-0.0322) H7(0.197901)
 H8(0.3797) H13A(0.5591) H13B(0.6021) H15(0.4163) H16(0.4492) H19(0.7736)
 H20(0.739699) H22A(0.5899) H22B(0.5514) H23A(0.733999) H23B(0.7701)
 H23C(0.773399) H25A(-0.024501) H25B(0.097301) H26A(0.0429) H26B(0.0373)
 H26C(0.168201)
 Fixed Z: H2(0.731999) H3(0.5998) H4(0.434099) H5(0.4009) H7(0.463201)
 H8(0.5904) H13A(0.763101) H13B(0.8947) H15(0.6075) H16(0.5434) H19(0.843201)
 H20(0.9038) H22A(1.2032) H22B(1.125701) H23A(1.0901) H23B(1.1554) H23C(1.2316)
 H25A(0.9952) H25B(1.0842) H26A(1.1066) H26B(1.193301) H26C(1.193101)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'