#------------------------------------------------------------------------------
#$Date: 2023-11-06 08:56:42 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287311 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/98/1569878.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_1569878
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_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C26 H22 N2 O2'
_chemical_formula_sum            'C26 H22 N2 O2'
_chemical_formula_weight         394.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 98.725(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.2867(14)
_cell_length_b                   7.6954(9)
_cell_length_c                   11.8213(14)
_cell_measurement_reflns_used    8689
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.11
_cell_measurement_theta_min      3.79
_cell_volume                     1014.9(2)
_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    'SHELXD97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1214
_diffrn_reflns_av_unetI/netI     0.1352
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10978
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.160
_diffrn_reflns_theta_max         68.160
_diffrn_reflns_theta_min         3.783
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1587 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3580
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1934
_refine_ls_R_factor_gt           0.0904
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1196P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2204
_refine_ls_wR_factor_ref         0.2730
_reflns_number_gt                1429
_reflns_number_total             3580
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d3sc03987k2.cif
_cod_data_source_block           NH-919
_cod_depositor_comments
'Adding full bibliography for 1569877--1569882.cif.'
_cod_database_code               1569878
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2887(5) 0.6565(9) -0.2287(4) 0.0945(19) Uani 1 1 d . . .
O3 O 0.0317(5) 0.6650(9) 0.0526(4) 0.0902(18) Uani 1 1 d . . .
N5 N 0.1269(8) 0.4083(14) 0.0854(6) 0.084(3) Uani 1 1 d . . .
N6 N 0.3354(6) 0.3731(11) -0.1775(5) 0.080(2) Uani 1 1 d . . .
C2 C 0.0385(10) 0.5229(14) 0.0985(7) 0.083(3) Uani 1 1 d . . .
C7 C 0.2859(9) 0.5338(15) -0.1617(7) 0.087(3) Uani 1 1 d . . .
C8 C 0.2195(8) 0.5452(13) -0.0647(6) 0.086(3) Uani 1 1 d . . .
H8 H 0.1811 0.6513 -0.0510 0.103 Uiso 1 1 calc R . .
C9 C 0.2114(8) 0.4099(12) 0.0057(6) 0.077(3) Uani 1 1 d . . .
C10 C 0.2822(7) 0.2528(13) 0.0001(6) 0.074(2) Uani 1 1 d . . .
C11 C 0.2933(7) 0.1076(13) 0.0785(6) 0.075(2) Uani 1 1 d . . .
C12 C 0.3546(8) -0.0397(12) 0.0546(6) 0.079(2) Uani 1 1 d . . .
H12 H 0.3593 -0.1351 0.1060 0.094 Uiso 1 1 calc R . .
C13 C 0.4097(7) -0.0525(13) -0.0429(6) 0.078(2) Uani 1 1 d . . .
H13 H 0.4511 -0.1550 -0.0587 0.093 Uiso 1 1 calc R . .
C14 C 0.4021(7) 0.0903(12) -0.1167(7) 0.079(2) Uani 1 1 d . . .
H14 H 0.4424 0.0843 -0.1815 0.095 Uiso 1 1 calc R . .
C15 C 0.3393(7) 0.2391(11) -0.1001(6) 0.071(2) Uani 1 1 d . . .
C16 C 0.3863(8) 0.3516(14) -0.2848(5) 0.091(3) Uani 1 1 d . . .
H16A H 0.3431 0.2591 -0.3309 0.109 Uiso 1 1 calc R . .
H16B H 0.4713 0.3205 -0.2665 0.109 Uiso 1 1 calc R . .
H16C H 0.3783 0.4607 -0.3279 0.109 Uiso 1 1 calc R . .
C17 C 0.2519(8) 0.1151(12) 0.1941(6) 0.077(2) Uani 1 1 d . . .
C18 C 0.1682(9) -0.0029(13) 0.2141(7) 0.087(3) Uani 1 1 d . . .
H18 H 0.1301 -0.0624 0.1481 0.105 Uiso 1 1 calc R . .
C19 C 0.3126(8) 0.2405(11) 0.2779(6) 0.070(2) Uani 1 1 d . . .
C20 C 0.2491(8) 0.3437(13) 0.3479(6) 0.084(3) Uani 1 1 d . . .
H20 H 0.1648 0.3286 0.3423 0.101 Uiso 1 1 calc R . .
C21 C 0.3038(10) 0.4630(13) 0.4224(6) 0.089(3) Uani 1 1 d . . .
H21 H 0.2578 0.5282 0.4685 0.107 Uiso 1 1 calc R . .
C22 C 0.4280(11) 0.4911(13) 0.4322(6) 0.090(3) Uani 1 1 d . . .
H22 H 0.4672 0.5761 0.4829 0.108 Uiso 1 1 calc R . .
C23 C 0.4907(8) 0.3897(13) 0.3650(6) 0.086(3) Uani 1 1 d . . .
H23 H 0.5752 0.4022 0.3726 0.103 Uiso 1 1 calc R . .
C24 C 0.4341(9) 0.2696(12) 0.2862(6) 0.081(3) Uani 1 1 d . . .
H24 H 0.4795 0.2076 0.2381 0.097 Uiso 1 1 calc R . .
C25 C 0.1271(8) -0.0536(11) 0.3222(6) 0.072(2) Uani 1 1 d . . .
C26 C 0.2005(8) -0.0569(13) 0.4274(7) 0.083(2) Uani 1 1 d . . .
H26 H 0.2796 -0.0117 0.4337 0.100 Uiso 1 1 calc R . .
C27 C 0.1606(8) -0.1255(12) 0.5244(6) 0.080(2) Uani 1 1 d . . .
H27 H 0.2124 -0.1265 0.5957 0.096 Uiso 1 1 calc R . .
C28 C 0.0462(9) -0.1916(13) 0.5167(7) 0.090(3) Uani 1 1 d . . .
H28 H 0.0204 -0.2437 0.5817 0.108 Uiso 1 1 calc R . .
C29 C -0.0310(8) -0.1820(13) 0.4143(7) 0.088(3) Uani 1 1 d . . .
H29 H -0.1116 -0.2202 0.4096 0.106 Uiso 1 1 calc R . .
C30 C 0.0107(8) -0.1157(11) 0.3176(6) 0.074(2) Uani 1 1 d . . .
H30 H -0.0419 -0.1129 0.2467 0.089 Uiso 1 1 calc R . .
C32 C -0.0486(8) 0.4606(12) 0.1751(6) 0.085(3) Uani 1 1 d . . .
H32A H -0.0347 0.3370 0.1921 0.103 Uiso 1 1 calc R . .
H32B H -0.1308 0.4772 0.1362 0.103 Uiso 1 1 calc R . .
H32C H -0.0366 0.5272 0.2465 0.103 Uiso 1 1 calc R . .
H4 H 0.124(8) 0.314(12) 0.108(7) 0.08(4) Uiso 1 1 d . . .
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
C2 N5 C9 129.8(10) . . ?
C2 N5 H4 120(7) . . ?
C9 N5 H4 107(7) . . ?
C15 N6 C7 123.7(7) . . ?
C15 N6 C16 120.6(8) . . ?
C7 N6 C16 115.7(7) . . ?
O3 C2 N5 122.0(10) . . ?
O3 C2 C32 123.3(9) . . ?
N5 C2 C32 114.7(9) . . ?
O1 C7 N6 123.2(8) . . ?
O1 C7 C8 121.5(10) . . ?
N6 C7 C8 115.1(8) . . ?
C9 C8 C7 122.0(9) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 N5 121.8(9) . . ?
C8 C9 C10 121.7(7) . . ?
N5 C9 C10 116.4(8) . . ?
C15 C10 C11 117.8(8) . . ?
C15 C10 C9 114.6(7) . . ?
C11 C10 C9 127.5(7) . . ?
C12 C11 C10 120.1(7) . . ?
C12 C11 C17 116.8(8) . . ?
C10 C11 C17 122.8(8) . . ?
C11 C12 C13 121.9(8) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 117.9(9) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C15 C14 C13 123.3(7) . . ?
C15 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N6 C15 C14 119.6(7) . . ?
N6 C15 C10 121.4(8) . . ?
C14 C15 C10 118.9(8) . . ?
N6 C16 H16A 109.5 . . ?
N6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C19 125.8(7) . . ?
C18 C17 C11 116.8(8) . . ?
C19 C17 C11 117.2(8) . . ?
C17 C18 C25 130.3(8) . . ?
C17 C18 H18 114.9 . . ?
C25 C18 H18 114.9 . . ?
C24 C19 C20 117.0(8) . . ?
C24 C19 C17 120.6(7) . . ?
C20 C19 C17 122.3(8) . . ?
C21 C20 C19 122.6(9) . . ?
C21 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?
C20 C21 C22 120.5(9) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 117.2(8) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C22 C23 C24 122.3(9) . . ?
C22 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C19 C24 C23 120.3(8) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C30 117.5(7) . . ?
C26 C25 C18 123.9(8) . . ?
C30 C25 C18 118.4(7) . . ?
C25 C26 C27 121.3(8) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C28 C27 C26 120.0(8) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 119.8(8) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C30 119.4(8) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C25 C30 C29 121.8(7) . . ?
C25 C30 H30 119.1 . . ?
C29 C30 H30 119.1 . . ?
C2 C32 H32A 109.5 . . ?
C2 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C2 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 C7 1.235(10) . ?
O3 C2 1.218(10) . ?
N5 C2 1.358(11) . ?
N5 C9 1.438(10) . ?
N5 H4 0.77(9) . ?
N6 C15 1.375(10) . ?
N6 C7 1.382(11) . ?
N6 C16 1.478(8) . ?
C2 C32 1.512(11) . ?
C7 C8 1.465(11) . ?
C8 C9 1.345(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.456(11) . ?
C10 C15 1.436(9) . ?
C10 C11 1.445(11) . ?
C11 C12 1.379(12) . ?
C11 C17 1.511(9) . ?
C12 C13 1.394(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(11) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.357(11) . ?
C17 C19 1.475(11) . ?
C18 C25 1.476(10) . ?
C18 H18 0.9500 . ?
C19 C24 1.378(10) . ?
C19 C20 1.417(10) . ?
C20 C21 1.355(12) . ?
C20 H20 0.9500 . ?
C21 C22 1.406(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(10) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.387(10) . ?
C25 C30 1.391(10) . ?
C26 C27 1.398(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(11) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(10) . ?
C28 H28 0.9500 . ?
C29 C30 1.397(9) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
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
C9 N5 C2 O3 -12.5(15) . . . . ?
C9 N5 C2 C32 168.2(8) . . . . ?
C15 N6 C7 O1 175.9(8) . . . . ?
C16 N6 C7 O1 -3.8(13) . . . . ?
C15 N6 C7 C8 -9.4(12) . . . . ?
C16 N6 C7 C8 170.9(7) . . . . ?
O1 C7 C8 C9 176.9(9) . . . . ?
N6 C7 C8 C9 2.2(13) . . . . ?
C7 C8 C9 N5 -166.8(8) . . . . ?
C7 C8 C9 C10 9.2(13) . . . . ?
C2 N5 C9 C8 6.3(13) . . . . ?
C2 N5 C9 C10 -169.8(9) . . . . ?
C8 C9 C10 C15 -13.0(11) . . . . ?
N5 C9 C10 C15 163.2(7) . . . . ?
C8 C9 C10 C11 171.9(8) . . . . ?
N5 C9 C10 C11 -11.9(12) . . . . ?
C15 C10 C11 C12 -1.6(11) . . . . ?
C9 C10 C11 C12 173.4(8) . . . . ?
C15 C10 C11 C17 171.6(7) . . . . ?
C9 C10 C11 C17 -13.4(12) . . . . ?
C10 C11 C12 C13 1.6(13) . . . . ?
C17 C11 C12 C13 -172.0(7) . . . . ?
C11 C12 C13 C14 0.5(13) . . . . ?
C12 C13 C14 C15 -2.7(13) . . . . ?
C7 N6 C15 C14 -172.7(8) . . . . ?
C16 N6 C15 C14 6.9(11) . . . . ?
C7 N6 C15 C10 5.3(12) . . . . ?
C16 N6 C15 C10 -175.1(7) . . . . ?
C13 C14 C15 N6 -179.4(7) . . . . ?
C13 C14 C15 C10 2.6(13) . . . . ?
C11 C10 C15 N6 -178.4(7) . . . . ?
C9 C10 C15 N6 6.0(11) . . . . ?
C11 C10 C15 C14 -0.4(11) . . . . ?
C9 C10 C15 C14 -176.0(8) . . . . ?
C12 C11 C17 C18 -65.3(10) . . . . ?
C10 C11 C17 C18 121.3(9) . . . . ?
C12 C11 C17 C19 110.1(10) . . . . ?
C10 C11 C17 C19 -63.2(10) . . . . ?
C19 C17 C18 C25 -8.5(16) . . . . ?
C11 C17 C18 C25 166.4(8) . . . . ?
C18 C17 C19 C24 136.9(9) . . . . ?
C11 C17 C19 C24 -38.0(11) . . . . ?
C18 C17 C19 C20 -47.1(13) . . . . ?
C11 C17 C19 C20 138.0(8) . . . . ?
C24 C19 C20 C21 -1.7(11) . . . . ?
C17 C19 C20 C21 -177.9(8) . . . . ?
C19 C20 C21 C22 0.9(13) . . . . ?
C20 C21 C22 C23 -1.4(13) . . . . ?
C21 C22 C23 C24 3.0(12) . . . . ?
C20 C19 C24 C23 3.2(11) . . . . ?
C17 C19 C24 C23 179.4(7) . . . . ?
C22 C23 C24 C19 -4.0(12) . . . . ?
C17 C18 C25 C26 -33.4(15) . . . . ?
C17 C18 C25 C30 152.2(9) . . . . ?
C30 C25 C26 C27 2.1(14) . . . . ?
C18 C25 C26 C27 -172.3(8) . . . . ?
C25 C26 C27 C28 0.0(14) . . . . ?
C26 C27 C28 C29 -3.3(14) . . . . ?
C27 C28 C29 C30 4.3(14) . . . . ?
C26 C25 C30 C29 -1.1(13) . . . . ?
C18 C25 C30 C29 173.6(8) . . . . ?
C28 C29 C30 C25 -2.1(14) . . . . ?
