Aniline assisted dimerization of phenylalanines: convenient synthesis of 2-aroyl-3-arylquinoline in an I<sub>2</sub>-DMSO system.
Ma, Jin-Tian; Chen, Ting; Chen, Xiang-Long; Zhou, You; Yu, Zhi-Cheng; Zhuang, Shi-Yi; Wu, Yan-Dong; Xiang, Jia-Chen; Wu, An-Xin; Organic & biomolecular chemistry 21 (2023) 2091–2095; doi:10.1039/d2ob02283d

data_7159151
_publ_section_title
;
 Aniline assisted dimerization of phenylalanines: convenient synthesis of
 2-aroyl-3-arylquinoline in an I<sub>2</sub>-DMSO system.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2091
_journal_page_last               2095
_journal_paper_doi               10.1039/d2ob02283d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C25 H21 N O'
_chemical_formula_sum            'C25 H21 N O'
_chemical_formula_weight         351.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-12-18 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                99.154(3)
_cell_angle_beta                 93.011(3)
_cell_angle_gamma                102.359(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2419(15)
_cell_length_b                   10.5399(19)
_cell_length_c                   11.222(2)
_cell_measurement_reflns_used    5132
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      30.36
_cell_measurement_theta_min      2.48
_cell_volume                     936.3(3)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.992
_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  0.0212
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            9682
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.374
_diffrn_reflns_theta_min         1.846
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0567
_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^)+(0.1190P)^2^+0.0911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4130
_reflns_number_total             5497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02283d2.cif
_cod_data_source_block           mo_210707a_0m
_cod_depositor_comments          'Adding full bibliography for 7159151.cif.'
_cod_database_code               7159151
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.985
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16), C17(H17),
 C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'