#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:10:27 +0300 (Fri, 05 May 2023) $
#$Revision: 283435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159151.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159151
loop_
_publ_author_name
'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'
_publ_section_title
;
 Aniline assisted dimerization of phenylalanines: convenient synthesis of
 2-aroyl-3-arylquinoline in an I₂-DMSO system.
;
_journal_issue                   10
_journal_name_full               'Organic & 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       'φ and ω 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/[σ²(Fo²)+(0.1190P)²+0.0911P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13785(13) 0.08418(12) 0.73539(9) 0.0558(3) Uani 1 1 d . . . . .
N1 N 0.34376(14) 0.27102(10) 0.96925(9) 0.0392(2) Uani 1 1 d . . . . .
C1 C 0.29901(15) 0.14429(12) 0.92234(11) 0.0348(2) Uani 1 1 d . . . . .
C2 C 0.24917(14) 0.04073(11) 0.99070(10) 0.0329(2) Uani 1 1 d . . . . .
C3 C 0.23391(15) 0.08006(12) 1.11146(11) 0.0359(3) Uani 1 1 d . . . . .
H3 H 0.1985 0.0166 1.1591 0.043 Uiso 1 1 calc R . . . .
C4 C 0.27085(15) 0.21440(12) 1.16450(11) 0.0353(2) Uani 1 1 d . . . . .
C5 C 0.25019(17) 0.25937(13) 1.28743(11) 0.0409(3) Uani 1 1 d . . . . .
H5 H 0.2083 0.1984 1.3360 0.049 Uiso 1 1 calc R . . . .
C6 C 0.29072(18) 0.39088(13) 1.33606(12) 0.0439(3) Uani 1 1 d . . . . .
C7 C 0.3574(2) 0.48249(13) 1.26162(13) 0.0485(3) Uani 1 1 d . . . . .
H7 H 0.3882 0.5717 1.2949 0.058 Uiso 1 1 calc R . . . .
C8 C 0.37759(19) 0.44331(13) 1.14247(13) 0.0462(3) Uani 1 1 d . . . . .
H8 H 0.4210 0.5055 1.0955 0.055 Uiso 1 1 calc R . . . .
C9 C 0.33255(16) 0.30824(12) 1.09068(11) 0.0372(3) Uani 1 1 d . . . . .
C10 C 0.2634(2) 0.44021(16) 1.46514(14) 0.0611(4) Uani 1 1 d . . . . .
H10A H 0.1636 0.4733 1.4667 0.092 Uiso 1 1 calc GR . . . .
H10B H 0.3568 0.5097 1.5008 0.092 Uiso 1 1 calc GR . . . .
H10C H 0.2525 0.3692 1.5102 0.092 Uiso 1 1 calc GR . . . .
C11 C 0.27847(16) 0.12137(12) 0.78534(11) 0.0374(3) Uani 1 1 d . . . . .
C12 C 0.42735(15) 0.14966(11) 0.71678(10) 0.0354(2) Uani 1 1 d . . . . .
C13 C 0.58782(16) 0.16833(13) 0.77227(11) 0.0408(3) Uani 1 1 d . . . . .
H13 H 0.6036 0.1711 0.8554 0.049 Uiso 1 1 calc R . . . .
C14 C 0.72427(17) 0.18278(13) 0.70427(13) 0.0444(3) Uani 1 1 d . . . . .
H14 H 0.8305 0.1935 0.7423 0.053 Uiso 1 1 calc R . . . .
C15 C 0.70486(18) 0.18158(13) 0.58023(13) 0.0444(3) Uani 1 1 d . . . . .
C16 C 0.54482(19) 0.16726(14) 0.52632(12) 0.0474(3) Uani 1 1 d . . . . .
H16 H 0.5298 0.1692 0.4440 0.057 Uiso 1 1 calc R . . . .
C17 C 0.40750(18) 0.15025(13) 0.59248(11) 0.0424(3) Uani 1 1 d . . . . .
H17 H 0.3014 0.1391 0.5541 0.051 Uiso 1 1 calc R . . . .
C18 C 0.8534(2) 0.1945(2) 0.50714(17) 0.0654(5) Uani 1 1 d . . . . .
H18A H 0.9517 0.1979 0.5585 0.098 Uiso 1 1 calc GR . . . .
H18B H 0.8666 0.2740 0.4735 0.098 Uiso 1 1 calc GR . . . .
H18C H 0.8367 0.1200 0.4427 0.098 Uiso 1 1 calc GR . . . .
C19 C 0.21898(14) -0.10106(11) 0.93655(10) 0.0330(2) Uani 1 1 d . . . . .
C20 C 0.31383(16) -0.14675(12) 0.84627(12) 0.0406(3) Uani 1 1 d . . . . .
H20 H 0.3954 -0.0867 0.8173 0.049 Uiso 1 1 calc R . . . .
C21 C 0.28836(18) -0.28016(13) 0.79925(12) 0.0444(3) Uani 1 1 d . . . . .
H21 H 0.3526 -0.3077 0.7388 0.053 Uiso 1 1 calc R . . . .
C22 C 0.16881(17) -0.37350(13) 0.84065(12) 0.0419(3) Uani 1 1 d . . . . .
C23 C 0.07596(16) -0.32824(13) 0.93187(12) 0.0412(3) Uani 1 1 d . . . . .
H23 H -0.0042 -0.3886 0.9617 0.049 Uiso 1 1 calc R . . . .
C24 C 0.10071(15) -0.19500(12) 0.97898(11) 0.0367(3) Uani 1 1 d . . . . .
H24 H 0.0372 -0.1678 1.0400 0.044 Uiso 1 1 calc R . . . .
C25 C 0.1403(3) -0.51812(15) 0.78963(16) 0.0630(4) Uani 1 1 d . . . . .
H25A H 0.2103 -0.5305 0.7250 0.095 Uiso 1 1 calc GR . . . .
H25B H 0.0255 -0.5515 0.7591 0.095 Uiso 1 1 calc GR . . . .
H25C H 0.1670 -0.5646 0.8522 0.095 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 118.26(10) . . ?
N1 C1 C2 124.69(11) . . ?
N1 C1 C11 111.93(10) . . ?
C2 C1 C11 122.67(11) . . ?
C1 C2 C19 122.78(10) . . ?
C3 C2 C1 116.05(11) . . ?
C3 C2 C19 121.16(10) . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.31(10) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 123.10(11) . . ?
C3 C4 C9 117.89(11) . . ?
C5 C4 C9 119.01(11) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.22(11) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 118.75(12) . . ?
C5 C6 C10 121.71(12) . . ?
C7 C6 C10 119.53(13) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.82(13) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.87(12) . . ?
C9 C8 H8 120.1 . . ?
N1 C9 C4 121.44(11) . . ?
N1 C9 C8 119.24(11) . . ?
C8 C9 C4 119.28(11) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C1 117.98(11) . . ?
O1 C11 C12 122.25(11) . . ?
C12 C11 C1 119.73(11) . . ?
C13 C12 C11 121.32(10) . . ?
C13 C12 C17 118.67(12) . . ?
C17 C12 C11 119.90(11) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.37(12) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.12(13) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C18 120.58(14) . . ?
C16 C15 C14 118.10(12) . . ?
C16 C15 C18 121.32(14) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.39(12) . . ?
C17 C16 H16 119.3 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.29(13) . . ?
C16 C17 H17 119.9 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C2 121.66(10) . . ?
C24 C19 C2 120.87(10) . . ?
C24 C19 C20 117.38(11) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.15(11) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.34(12) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C23 117.54(12) . . ?
C21 C22 C25 121.52(13) . . ?
C23 C22 C25 120.94(13) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.34(11) . . ?
C24 C23 H23 119.3 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.24(11) . . ?
C23 C24 H24 119.4 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.2159(16) . ?
N1 C1 1.3199(15) . ?
N1 C9 1.3705(16) . ?
C1 C2 1.4339(16) . ?
C1 C11 1.5125(16) . ?
C2 C3 1.3732(16) . ?
C2 C19 1.4834(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.4071(16) . ?
C4 C5 1.4170(16) . ?
C4 C9 1.4187(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.3685(18) . ?
C6 C7 1.4177(19) . ?
C6 C10 1.5046(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.3650(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.4107(17) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.4840(17) . ?
C12 C13 1.3925(18) . ?
C12 C17 1.3971(16) . ?
C13 H13 0.9300 . ?
C13 C14 1.3871(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.3905(19) . ?
C15 C16 1.389(2) . ?
C15 C18 1.503(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.3813(19) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.3995(16) . ?
C19 C24 1.3939(16) . ?
C20 H20 0.9300 . ?
C20 C21 1.3876(18) . ?
C21 H21 0.9300 . ?
C21 C22 1.3904(19) . ?
C22 C23 1.3943(18) . ?
C22 C25 1.5037(19) . ?
C23 H23 0.9300 . ?
C23 C24 1.3868(17) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C13 -167.98(13) . . . . ?
O1 C11 C12 C17 8.22(19) . . . . ?
N1 C1 C2 C3 6.03(18) . . . . ?
N1 C1 C2 C19 -172.63(11) . . . . ?
N1 C1 C11 O1 -108.07(14) . . . . ?
N1 C1 C11 C12 69.46(14) . . . . ?
C1 N1 C9 C4 -1.52(19) . . . . ?
C1 N1 C9 C8 -179.16(11) . . . . ?
C1 C2 C3 C4 -2.03(17) . . . . ?
C1 C2 C19 C20 35.25(17) . . . . ?
C1 C2 C19 C24 -148.48(12) . . . . ?
C1 C11 C12 C13 14.60(17) . . . . ?
C1 C11 C12 C17 -169.19(11) . . . . ?
C2 C1 C11 O1 62.66(17) . . . . ?
C2 C1 C11 C12 -119.81(13) . . . . ?
C2 C3 C4 C5 177.30(12) . . . . ?
C2 C3 C4 C9 -3.09(18) . . . . ?
C2 C19 C20 C21 177.73(11) . . . . ?
C2 C19 C24 C23 -177.63(11) . . . . ?
C3 C2 C19 C20 -143.35(12) . . . . ?
C3 C2 C19 C24 32.93(17) . . . . ?
C3 C4 C5 C6 178.71(12) . . . . ?
C3 C4 C9 N1 5.09(19) . . . . ?
C3 C4 C9 C8 -177.27(11) . . . . ?
C4 C5 C6 C7 -1.2(2) . . . . ?
C4 C5 C6 C10 177.71(14) . . . . ?
C5 C4 C9 N1 -175.29(11) . . . . ?
C5 C4 C9 C8 2.35(19) . . . . ?
C5 C6 C7 C8 1.9(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 N1 175.99(14) . . . . ?
C7 C8 C9 C4 -1.7(2) . . . . ?
C9 N1 C1 C2 -4.24(18) . . . . ?
C9 N1 C1 C11 166.27(11) . . . . ?
C9 C4 C5 C6 -0.9(2) . . . . ?
C10 C6 C7 C8 -177.03(15) . . . . ?
C11 C1 C2 C3 -163.50(11) . . . . ?
C11 C1 C2 C19 17.83(17) . . . . ?
C11 C12 C13 C14 174.14(11) . . . . ?
C11 C12 C17 C16 -175.43(12) . . . . ?
C12 C13 C14 C15 1.3(2) . . . . ?
C13 C12 C17 C16 0.88(19) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C13 C14 C15 C18 -178.73(13) . . . . ?
C14 C15 C16 C17 -2.1(2) . . . . ?
C15 C16 C17 C12 1.3(2) . . . . ?
C17 C12 C13 C14 -2.11(19) . . . . ?
C18 C15 C16 C17 177.48(14) . . . . ?
C19 C2 C3 C4 176.65(10) . . . . ?
C19 C20 C21 C22 -0.5(2) . . . . ?
C20 C19 C24 C23 -1.20(18) . . . . ?
C20 C21 C22 C23 -0.4(2) . . . . ?
C20 C21 C22 C25 179.76(14) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
C22 C23 C24 C19 0.28(19) . . . . ?
C24 C19 C20 C21 1.33(19) . . . . ?
C25 C22 C23 C24 -179.63(14) . . . . ?
