#------------------------------------------------------------------------------
#$Date: 2021-07-13 00:32:53 +0300 (Tue, 13 Jul 2021) $
#$Revision: 267469 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/88/4518886.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_4518886
loop_
_publ_author_name
'Yang, Jian'
'Zhao, He'
'Tan, Zhenda'
'Cao, Liang'
'Jiang, Huanfeng'
'Ci, Chenggang'
'Dixneuf, Pierre H.'
'Zhang, Min'
_publ_section_title
;
 syn-Selective Construction of Fused Heterocycles by Catalytic Reductive
 Tandem Functionalization of N-Heteroarenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9271
_journal_page_last               9278
_journal_paper_doi               10.1021/acscatal.1c01328
_journal_year                    2021
_chemical_formula_moiety         'C28 H25 N O2'
_chemical_formula_sum            'C28 H25 N O2'
_chemical_formula_weight         407.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.763(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.627(3)
_cell_length_b                   6.7071(12)
_cell_length_c                   17.181(4)
_cell_measurement_reflns_used    4972
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.383
_cell_measurement_theta_min      3.405
_cell_volume                     2135.6(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.1068
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12245
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.383
_diffrn_reflns_theta_min         3.405
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4972
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1850
_refine_ls_R_factor_gt           0.0730
_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)+(0.0745P)²+0.1719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.2036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2172
_reflns_number_total             4972
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c01328_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518886
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N1 N 0.34120(11) 0.7129(3) 0.15506(15) 0.0423(6) Uani 1 1 d . . . . .
O1 O 0.25873(9) 0.8451(2) 0.23417(12) 0.0456(6) Uani 1 1 d . . . . .
O2 O 0.28924(14) 0.2538(3) 0.17946(19) 0.1011(10) Uani 1 1 d . U . . .
H2A H 0.2707 0.1439 0.1834 0.152 Uiso 1 1 calc R U . . .
C1 C 0.28444(13) 0.6598(4) 0.20068(18) 0.0404(7) Uani 1 1 d . . . . .
H1A H 0.3035 0.5711 0.2432 0.049 Uiso 1 1 calc R U . . .
C2 C 0.22224(14) 0.5567(4) 0.15231(19) 0.0456(8) Uani 1 1 d . . . . .
C3 C 0.19371(15) 0.6993(5) 0.08701(19) 0.0565(9) Uani 1 1 d . . . . .
H3A H 0.1653 0.6241 0.0467 0.068 Uiso 1 1 calc R U . . .
H3B H 0.1620 0.7957 0.1081 0.068 Uiso 1 1 calc R U . . .
C4 C 0.25195(16) 0.8088(4) 0.05052(19) 0.0471(8) Uani 1 1 d . . . . .
C5 C 0.2350(2) 0.9114(5) -0.0194(2) 0.0660(10) Uani 1 1 d . . . . .
H5A H 0.1879 0.9072 -0.0433 0.079 Uiso 1 1 calc R U . . .
C6 C 0.2867(2) 1.0199(5) -0.0543(2) 0.0751(11) Uani 1 1 d . . . . .
H6A H 0.2747 1.0866 -0.1013 0.090 Uiso 1 1 calc R U . . .
C7 C 0.3556(2) 1.0268(5) -0.0184(2) 0.0693(10) Uani 1 1 d . . . . .
H7A H 0.3905 1.1003 -0.0407 0.083 Uiso 1 1 calc R U . . .
C8 C 0.37348(17) 0.9267(4) 0.0501(2) 0.0541(9) Uani 1 1 d . . . . .
H8A H 0.4206 0.9326 0.0736 0.065 Uiso 1 1 calc R U . . .
C9 C 0.32259(15) 0.8163(4) 0.08519(18) 0.0414(7) Uani 1 1 d . . . . .
C10 C 0.41215(14) 0.7440(4) 0.19806(19) 0.0505(8) Uani 1 1 d . . . . .
H10A H 0.4105 0.6988 0.2515 0.061 Uiso 1 1 calc R U . . .
H10B H 0.4223 0.8858 0.1998 0.061 Uiso 1 1 calc R U . . .
C11 C 0.47368(14) 0.6377(4) 0.16361(18) 0.0437(7) Uani 1 1 d . . . . .
C12 C 0.46344(16) 0.4711(5) 0.1174(2) 0.0610(9) Uani 1 1 d . . . . .
H12A H 0.4170 0.4223 0.1048 0.073 Uiso 1 1 calc R U . . .
C13 C 0.52125(19) 0.3746(5) 0.0893(2) 0.0709(11) Uani 1 1 d . . . . .
H13A H 0.5136 0.2628 0.0576 0.085 Uiso 1 1 calc R U . . .
C14 C 0.59004(18) 0.4452(5) 0.1088(2) 0.0656(10) Uani 1 1 d . . . . .
H14A H 0.6291 0.3819 0.0897 0.079 Uiso 1 1 calc R U . . .
C15 C 0.60094(16) 0.6082(5) 0.1561(2) 0.0636(10) Uani 1 1 d . . . . .
H15A H 0.6476 0.6542 0.1701 0.076 Uiso 1 1 calc R U . . .
C16 C 0.54301(15) 0.7048(4) 0.18323(19) 0.0542(9) Uani 1 1 d . . . . .
H16A H 0.5508 0.8164 0.2151 0.065 Uiso 1 1 calc R U . . .
C17 C 0.19885(14) 0.8275(4) 0.27380(17) 0.0412(7) Uani 1 1 d . . . . .
C18 C 0.18696(16) 0.9862(4) 0.32351(19) 0.0527(8) Uani 1 1 d . . . . .
H18A H 0.2189 1.0932 0.3277 0.063 Uiso 1 1 calc R U . . .
C19 C 0.12956(17) 0.9855(5) 0.3655(2) 0.0615(9) Uani 1 1 d . . . . .
H19A H 0.1215 1.0935 0.3975 0.074 Uiso 1 1 calc R U . . .
C20 C 0.08139(16) 0.8211(5) 0.36127(19) 0.0556(9) Uani 1 1 d . . . . .
C21 C 0.02266(18) 0.8093(6) 0.4077(2) 0.0745(11) Uani 1 1 d . . . . .
H21A H 0.0141 0.9141 0.4409 0.089 Uiso 1 1 calc R U . . .
C22 C -0.02130(19) 0.6466(8) 0.4041(3) 0.0891(14) Uani 1 1 d . . . . .
H22A H -0.0585 0.6391 0.4362 0.107 Uiso 1 1 calc R U . . .
C23 C -0.01093(19) 0.4924(7) 0.3528(3) 0.0893(13) Uani 1 1 d . . . . .
H23A H -0.0422 0.3840 0.3498 0.107 Uiso 1 1 calc R U . . .
C24 C 0.04448(16) 0.4975(5) 0.3068(2) 0.0664(10) Uani 1 1 d . . . . .
H24A H 0.0507 0.3922 0.2729 0.080 Uiso 1 1 calc R U . . .
C25 C 0.09296(14) 0.6617(4) 0.30986(18) 0.0475(8) Uani 1 1 d . . . . .
C26 C 0.15259(14) 0.6681(4) 0.26440(17) 0.0428(7) Uani 1 1 d . . . . .
C27 C 0.16477(15) 0.5050(4) 0.20662(19) 0.0523(9) Uani 1 1 d . . . . .
H27A H 0.1196 0.4777 0.1752 0.063 Uiso 1 1 calc R U . . .
H27B H 0.1791 0.3844 0.2352 0.063 Uiso 1 1 calc R U . . .
C28 C 0.24944(18) 0.3643(5) 0.1173(2) 0.0701(10) Uani 1 1 d . U . . .
H28A H 0.2090 0.2858 0.0942 0.084 Uiso 1 1 calc R U . . .
H28B H 0.2804 0.3955 0.0768 0.084 Uiso 1 1 calc R U . . .
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
C9 N1 C1 117.6(2) . . ?
C9 N1 C10 119.7(2) . . ?
C1 N1 C10 116.2(2) . . ?
C17 O1 C1 115.82(19) . . ?
N1 C1 O1 107.1(2) . . ?
N1 C1 C2 112.3(2) . . ?
O1 C1 C2 109.7(2) . . ?
C27 C2 C1 108.1(3) . . ?
C27 C2 C3 112.1(2) . . ?
C1 C2 C3 107.8(2) . . ?
C27 C2 C28 109.2(2) . . ?
C1 C2 C28 109.5(2) . . ?
C3 C2 C28 110.1(3) . . ?
C4 C3 C2 113.6(2) . . ?
C9 C4 C5 118.4(3) . . ?
C9 C4 C3 122.2(3) . . ?
C5 C4 C3 119.5(3) . . ?
C4 C5 C6 121.6(3) . . ?
C7 C6 C5 118.8(4) . . ?
C8 C7 C6 120.6(3) . . ?
C9 C8 C7 121.2(3) . . ?
C8 C9 C4 119.5(3) . . ?
C8 C9 N1 121.1(3) . . ?
C4 C9 N1 119.5(3) . . ?
N1 C10 C11 114.5(2) . . ?
C16 C11 C12 118.7(3) . . ?
C16 C11 C10 118.5(3) . . ?
C12 C11 C10 122.7(3) . . ?
C11 C12 C13 120.9(3) . . ?
C14 C13 C12 119.5(3) . . ?
C15 C14 C13 120.0(3) . . ?
C14 C15 C16 120.2(3) . . ?
C11 C16 C15 120.7(3) . . ?
C26 C17 O1 122.8(2) . . ?
C26 C17 C18 122.0(3) . . ?
O1 C17 C18 115.2(2) . . ?
C19 C18 C17 120.5(3) . . ?
C18 C19 C20 120.4(3) . . ?
C25 C20 C21 118.8(3) . . ?
C25 C20 C19 118.9(3) . . ?
C21 C20 C19 122.2(3) . . ?
C22 C21 C20 120.9(4) . . ?
C21 C22 C23 120.4(4) . . ?
C24 C23 C22 120.9(4) . . ?
C23 C24 C25 120.9(4) . . ?
C20 C25 C26 119.7(3) . . ?
C20 C25 C24 118.2(3) . . ?
C26 C25 C24 122.1(3) . . ?
C17 C26 C25 118.4(3) . . ?
C17 C26 C27 120.5(3) . . ?
C25 C26 C27 121.1(3) . . ?
C26 C27 C2 113.4(2) . . ?
O2 C28 C2 107.9(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
N1 C9 1.400(4) . ?
N1 C1 1.423(3) . ?
N1 C10 1.463(3) . ?
O1 C17 1.369(3) . ?
O1 C1 1.470(3) . ?
O2 C28 1.443(4) . ?
C1 C2 1.522(4) . ?
C2 C27 1.529(4) . ?
C2 C3 1.528(4) . ?
C2 C28 1.532(4) . ?
C3 C4 1.499(4) . ?
C4 C9 1.390(4) . ?
C4 C5 1.393(4) . ?
C5 C6 1.391(5) . ?
C6 C7 1.368(5) . ?
C7 C8 1.367(5) . ?
C8 C9 1.388(4) . ?
C10 C11 1.519(4) . ?
C11 C16 1.377(4) . ?
C11 C12 1.373(4) . ?
C12 C13 1.384(4) . ?
C13 C14 1.375(4) . ?
C14 C15 1.366(5) . ?
C15 C16 1.379(4) . ?
C17 C26 1.372(4) . ?
C17 C18 1.396(4) . ?
C18 C19 1.349(4) . ?
C19 C20 1.419(4) . ?
C20 C25 1.417(4) . ?
C20 C21 1.419(4) . ?
C21 C22 1.362(5) . ?
C22 C23 1.384(6) . ?
C23 C24 1.363(4) . ?
C24 C25 1.421(4) . ?
C25 C26 1.421(4) . ?
C26 C27 1.509(4) . ?
