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_4032414
_publ_section_title
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 Catalyst-free Synthesis of Pyrrolo[1,2-a]quinolines via Dehydration/[3+2]
 Cycloaddition Directly from 2-Methylquinolines, Aldehydes and Alkynoates.
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_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00280
_journal_year                    2017
_chemical_formula_moiety         'C23 H17 F4 N O2'
_chemical_formula_sum            'C23 H17 F4 N O2'
_chemical_formula_weight         415.38
_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
_atom_sites_solution_secondary   difmap
_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                99.384(3)
_cell_angle_beta                 91.951(3)
_cell_angle_gamma                93.602(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2176(16)
_cell_length_b                   9.2644(18)
_cell_length_c                   13.110(3)
_cell_measurement_reflns_used    5918
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      2.23
_cell_volume                     981.8(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0258
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10764
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         1.58
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0817P)^2^+0.2600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                2877
_reflns_number_total             3590
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00280_si_002.cif
_cod_data_source_block           aaaaa
_cod_database_code               4032414
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C22(H22a,H22b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c)
;
_olex2_submission_special_instructions 'No special instructions were received'