#------------------------------------------------------------------------------
#$Date: 2023-11-06 08:56:42 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287311 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/98/1569877.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_1569877
loop_
_publ_author_name
'Hirako, Naohiro'
'Yasui, Takeshi'
'Yamamoto, Yoshihiko'
_publ_section_title
;
 Rh(iii)-catalyzed highly site- and regio-selective alkenyl C-H
 activation/annulation of 4-amino-2-quinolones with alkynes via
 reversible alkyne insertion.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              10971
_journal_page_last               10978
_journal_paper_doi               10.1039/d3sc03987k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C26 H20 N2 O2'
_chemical_formula_sum            'C26 H20 N2 O2'
_chemical_formula_weight         392.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-06-30 deposited with the CCDC.	2023-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.056(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.3174(4)
_cell_length_b                   18.8450(7)
_cell_length_c                   10.3316(4)
_cell_measurement_reflns_used    20842
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      4.39
_cell_volume                     1956.86(14)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22156
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.150
_diffrn_reflns_theta_max         68.150
_diffrn_reflns_theta_min         4.693
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0632P)²+0.5101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                3262
_reflns_number_total             3536
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d3sc03987k2.cif
_cod_data_source_block           NH-502
_cod_depositor_comments
'Adding full bibliography for 1569877--1569882.cif.'
_cod_original_cell_volume        1956.84(14)
_cod_database_code               1569877
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.21773(9) 0.14836(5) 0.29362(10) 0.0396(3) Uani 1 1 d . . .
O2 O 0.63840(9) -0.00548(5) 0.21677(10) 0.0397(3) Uani 1 1 d . . .
N3 N 0.82275(11) 0.05066(6) 0.33936(11) 0.0316(3) Uani 1 1 d . . .
N4 N 1.16710(11) 0.03920(6) 0.19914(11) 0.0334(3) Uani 1 1 d . . .
C5 C 0.84262(13) 0.11590(7) 0.40684(13) 0.0310(3) Uani 1 1 d . . .
C6 C 0.93076(13) 0.03739(7) 0.28333(13) 0.0309(3) Uani 1 1 d . . .
C7 C 1.03682(14) -0.13392(8) 0.06182(14) 0.0389(3) Uani 1 1 d . . .
H7 H 1.0605 -0.1704 0.0081 0.047 Uiso 1 1 calc R . .
C8 C 0.74179(13) 0.14554(7) 0.47324(13) 0.0313(3) Uani 1 1 d . . .
C9 C 0.77941(14) 0.16691(7) 0.60570(14) 0.0358(3) Uani 1 1 d . . .
H9 H 0.8699 0.1636 0.6519 0.043 Uiso 1 1 calc R . .
C10 C 0.96163(13) -0.02376(7) 0.21147(13) 0.0314(3) Uani 1 1 d . . .
C11 C 1.01412(13) 0.21457(7) 0.44473(13) 0.0314(3) Uani 1 1 d . . .
C12 C 0.60842(13) 0.15215(7) 0.40595(14) 0.0329(3) Uani 1 1 d . . .
H12 H 0.5821 0.1391 0.3150 0.039 Uiso 1 1 calc R . .
C13 C 0.93521(14) 0.27495(7) 0.41212(14) 0.0344(3) Uani 1 1 d . . .
H13 H 0.8486 0.2705 0.3566 0.041 Uiso 1 1 calc R . .
C14 C 1.01705(13) 0.09400(7) 0.31563(13) 0.0309(3) Uani 1 1 d . . .
C15 C 0.88539(14) -0.08604(7) 0.18356(14) 0.0368(3) Uani 1 1 d . . .
H15 H 0.8070 -0.0908 0.2166 0.044 Uiso 1 1 calc R . .
C16 C 0.96187(13) 0.14399(7) 0.39340(13) 0.0311(3) Uani 1 1 d . . .
C17 C 1.14035(13) 0.09807(7) 0.27024(13) 0.0323(3) Uani 1 1 d . . .
C18 C 1.10673(15) 0.34850(7) 0.54164(14) 0.0382(3) Uani 1 1 d . . .
H18 H 1.1384 0.3939 0.5743 0.046 Uiso 1 1 calc R . .
C19 C 1.08237(13) -0.01938(7) 0.16773(13) 0.0321(3) Uani 1 1 d . . .
C20 C 1.18604(14) 0.28878(8) 0.57607(14) 0.0374(3) Uani 1 1 d . . .
H20 H 1.2718 0.2933 0.6332 0.045 Uiso 1 1 calc R . .
C21 C 1.11674(14) -0.07516(7) 0.09183(14) 0.0361(3) Uani 1 1 d . . .
H21 H 1.1965 -0.0722 0.0608 0.043 Uiso 1 1 calc R . .
C22 C 0.55359(15) 0.19785(7) 0.60381(15) 0.0392(3) Uani 1 1 d . . .
H22 H 0.4893 0.2151 0.6489 0.047 Uiso 1 1 calc R . .
C23 C 0.51446(13) 0.17768(7) 0.47142(15) 0.0363(3) Uani 1 1 d . . .
H23 H 0.4238 0.1814 0.4259 0.044 Uiso 1 1 calc R . .
C24 C 1.14067(13) 0.22258(7) 0.52747(14) 0.0349(3) Uani 1 1 d . . .
H24 H 1.1962 0.1822 0.5507 0.042 Uiso 1 1 calc R . .
C25 C 1.29430(14) 0.03939(8) 0.15765(16) 0.0431(4) Uani 1 1 d . . .
H25A H 1.2773 0.0373 0.0605 0.052 Uiso 1 1 calc R . .
H25B H 1.3471 -0.0019 0.1957 0.052 Uiso 1 1 calc R . .
H25C H 1.3433 0.0829 0.1891 0.052 Uiso 1 1 calc R . .
C26 C 0.68520(15) 0.19303(8) 0.67021(15) 0.0399(3) Uani 1 1 d . . .
H26 H 0.7114 0.2076 0.7604 0.048 Uiso 1 1 calc R . .
C27 C 0.70304(13) 0.00825(7) 0.32556(14) 0.0321(3) Uani 1 1 d . . .
C28 C 0.98134(15) 0.34138(7) 0.45951(14) 0.0381(3) Uani 1 1 d . . .
H28 H 0.9267 0.3820 0.4355 0.046 Uiso 1 1 calc R . .
C29 C 0.67424(17) -0.01893(8) 0.45119(16) 0.0464(4) Uani 1 1 d . . .
H29A H 0.6949 0.0179 0.5197 0.056 Uiso 1 1 calc R . .
H29B H 0.7289 -0.0610 0.4805 0.056 Uiso 1 1 calc R . .
H29C H 0.5799 -0.0316 0.4362 0.056 Uiso 1 1 calc R . .
C30 C 0.92145(15) -0.14043(8) 0.10943(15) 0.0404(3) Uani 1 1 d . . .
H30 H 0.8681 -0.1819 0.0911 0.048 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(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
C6 N3 C5 108.85(10) . . ?
C6 N3 C27 127.23(11) . . ?
C5 N3 C27 123.79(10) . . ?
C17 N4 C19 124.25(11) . . ?
C17 N4 C25 116.64(11) . . ?
C19 N4 C25 119.10(11) . . ?
C16 C5 N3 108.68(11) . . ?
C16 C5 C8 129.84(12) . . ?
N3 C5 C8 121.43(11) . . ?
C14 C6 N3 107.11(11) . . ?
C14 C6 C10 122.37(12) . . ?
N3 C6 C10 130.40(12) . . ?
C21 C7 C30 120.58(13) . . ?
C21 C7 H7 119.7 . . ?
C30 C7 H7 119.7 . . ?
C9 C8 C12 119.08(12) . . ?
C9 C8 C5 119.68(12) . . ?
C12 C8 C5 121.24(12) . . ?
C26 C9 C8 120.26(13) . . ?
C26 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C15 C10 C19 118.26(12) . . ?
C15 C10 C6 126.38(12) . . ?
C19 C10 C6 115.35(12) . . ?
C13 C11 C24 118.22(12) . . ?
C13 C11 C16 119.90(12) . . ?
C24 C11 C16 121.87(12) . . ?
C23 C12 C8 120.35(13) . . ?
C23 C12 H12 119.8 . . ?
C8 C12 H12 119.8 . . ?
C28 C13 C11 121.01(13) . . ?
C28 C13 H13 119.5 . . ?
C11 C13 H13 119.5 . . ?
C6 C14 C16 109.05(11) . . ?
C6 C14 C17 121.73(12) . . ?
C16 C14 C17 129.20(12) . . ?
C30 C15 C10 121.69(13) . . ?
C30 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C5 C16 C14 106.31(11) . . ?
C5 C16 C11 124.67(12) . . ?
C14 C16 C11 128.93(12) . . ?
O1 C17 N4 121.43(12) . . ?
O1 C17 C14 123.70(12) . . ?
N4 C17 C14 114.86(11) . . ?
C28 C18 C20 119.55(13) . . ?
C28 C18 H18 120.2 . . ?
C20 C18 H18 120.2 . . ?
N4 C19 C21 119.77(12) . . ?
N4 C19 C10 121.25(12) . . ?
C21 C19 C10 118.99(12) . . ?
C24 C20 C18 120.33(13) . . ?
C24 C20 H20 119.8 . . ?
C18 C20 H20 119.8 . . ?
C7 C21 C19 121.01(13) . . ?
C7 C21 H21 119.5 . . ?
C19 C21 H21 119.5 . . ?
C26 C22 C23 120.43(13) . . ?
C26 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C12 C23 C22 119.69(13) . . ?
C12 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C20 C24 C11 120.74(13) . . ?
C20 C24 H24 119.6 . . ?
C11 C24 H24 119.6 . . ?
N4 C25 H25A 109.5 . . ?
N4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 C9 120.16(14) . . ?
C22 C26 H26 119.9 . . ?
C9 C26 H26 119.9 . . ?
O2 C27 N3 119.47(12) . . ?
O2 C27 C29 124.47(13) . . ?
N3 C27 C29 115.96(12) . . ?
C18 C28 C13 120.13(13) . . ?
C18 C28 H28 119.9 . . ?
C13 C28 H28 119.9 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C15 C30 C7 119.33(13) . . ?
C15 C30 H30 120.3 . . ?
C7 C30 H30 120.3 . . ?
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 C17 1.2275(16) . ?
O2 C27 1.1985(17) . ?
N3 C6 1.3896(16) . ?
N3 C5 1.4055(17) . ?
N3 C27 1.4509(16) . ?
N4 C17 1.3922(17) . ?
N4 C19 1.4000(18) . ?
N4 C25 1.4698(17) . ?
C5 C16 1.3748(18) . ?
C5 C8 1.4790(17) . ?
C6 C14 1.3812(18) . ?
C6 C10 1.4448(18) . ?
C7 C21 1.374(2) . ?
C7 C30 1.392(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(2) . ?
C8 C12 1.4000(19) . ?
C9 C26 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C15 1.4060(19) . ?
C10 C19 1.4202(18) . ?
C11 C13 1.3954(19) . ?
C11 C24 1.3979(19) . ?
C11 C16 1.4872(18) . ?
C12 C23 1.3875(19) . ?
C12 H12 0.9500 . ?
C13 C28 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C16 1.4365(18) . ?
C14 C17 1.4539(18) . ?
C15 C30 1.380(2) . ?
C15 H15 0.9500 . ?
C18 C28 1.384(2) . ?
C18 C20 1.390(2) . ?
C18 H18 0.9500 . ?
C19 C21 1.4040(19) . ?
C20 C24 1.3861(19) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C26 1.379(2) . ?
C22 C23 1.389(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26 0.9500 . ?
C27 C29 1.486(2) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30 0.9500 . ?
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
C6 N3 C5 C16 0.23(14) . . . . ?
C27 N3 C5 C16 -175.99(12) . . . . ?
C6 N3 C5 C8 177.98(12) . . . . ?
C27 N3 C5 C8 1.76(19) . . . . ?
C5 N3 C6 C14 -0.06(14) . . . . ?
C27 N3 C6 C14 176.00(12) . . . . ?
C5 N3 C6 C10 175.93(13) . . . . ?
C27 N3 C6 C10 -8.0(2) . . . . ?
C16 C5 C8 C9 -54.6(2) . . . . ?
N3 C5 C8 C9 128.16(14) . . . . ?
C16 C5 C8 C12 125.90(15) . . . . ?
N3 C5 C8 C12 -51.33(18) . . . . ?
C12 C8 C9 C26 1.2(2) . . . . ?
C5 C8 C9 C26 -178.27(12) . . . . ?
C14 C6 C10 C15 174.55(13) . . . . ?
N3 C6 C10 C15 -0.9(2) . . . . ?
C14 C6 C10 C19 -4.48(19) . . . . ?
N3 C6 C10 C19 -179.93(12) . . . . ?
C9 C8 C12 C23 -1.85(19) . . . . ?
C5 C8 C12 C23 177.65(12) . . . . ?
C24 C11 C13 C28 0.6(2) . . . . ?
C16 C11 C13 C28 179.56(12) . . . . ?
N3 C6 C14 C16 -0.13(15) . . . . ?
C10 C6 C14 C16 -176.51(12) . . . . ?
N3 C6 C14 C17 -178.77(11) . . . . ?
C10 C6 C14 C17 4.9(2) . . . . ?
C19 C10 C15 C30 -3.5(2) . . . . ?
C6 C10 C15 C30 177.46(13) . . . . ?
N3 C5 C16 C14 -0.30(14) . . . . ?
C8 C5 C16 C14 -177.80(13) . . . . ?
N3 C5 C16 C11 176.43(12) . . . . ?
C8 C5 C16 C11 -1.1(2) . . . . ?
C6 C14 C16 C5 0.27(15) . . . . ?
C17 C14 C16 C5 178.77(13) . . . . ?
C6 C14 C16 C11 -176.27(13) . . . . ?
C17 C14 C16 C11 2.2(2) . . . . ?
C13 C11 C16 C5 -52.72(19) . . . . ?
C24 C11 C16 C5 126.25(15) . . . . ?
C13 C11 C16 C14 123.25(15) . . . . ?
C24 C11 C16 C14 -57.8(2) . . . . ?
C19 N4 C17 O1 -179.15(12) . . . . ?
C25 N4 C17 O1 1.98(19) . . . . ?
C19 N4 C17 C14 2.10(19) . . . . ?
C25 N4 C17 C14 -176.77(12) . . . . ?
C6 C14 C17 O1 177.86(13) . . . . ?
C16 C14 C17 O1 -0.5(2) . . . . ?
C6 C14 C17 N4 -3.42(19) . . . . ?
C16 C14 C17 N4 178.24(13) . . . . ?
C17 N4 C19 C21 178.00(12) . . . . ?
C25 N4 C19 C21 -3.15(19) . . . . ?
C17 N4 C19 C10 -2.1(2) . . . . ?
C25 N4 C19 C10 176.71(12) . . . . ?
C15 C10 C19 N4 -176.05(12) . . . . ?
C6 C10 C19 N4 3.06(18) . . . . ?
C15 C10 C19 C21 3.81(19) . . . . ?
C6 C10 C19 C21 -177.08(12) . . . . ?
C28 C18 C20 C24 0.7(2) . . . . ?
C30 C7 C21 C19 -1.9(2) . . . . ?
N4 C19 C21 C7 178.67(12) . . . . ?
C10 C19 C21 C7 -1.2(2) . . . . ?
C8 C12 C23 C22 1.1(2) . . . . ?
C26 C22 C23 C12 0.4(2) . . . . ?
C18 C20 C24 C11 -0.9(2) . . . . ?
C13 C11 C24 C20 0.2(2) . . . . ?
C16 C11 C24 C20 -178.74(12) . . . . ?
C23 C22 C26 C9 -1.0(2) . . . . ?
C8 C9 C26 C22 0.2(2) . . . . ?
C6 N3 C27 O2 -54.90(18) . . . . ?
C5 N3 C27 O2 120.60(14) . . . . ?
C6 N3 C27 C29 121.52(14) . . . . ?
C5 N3 C27 C29 -62.97(17) . . . . ?
C20 C18 C28 C13 0.1(2) . . . . ?
C11 C13 C28 C18 -0.7(2) . . . . ?
C10 C15 C30 C7 0.5(2) . . . . ?
C21 C7 C30 C15 2.2(2) . . . . ?
