#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:59:59 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301175 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/05/7160535.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_7160535
loop_
_publ_author_name
'Jin, Cheng-An'
'Liu, Hao'
'Xie, Bo-Wen'
'Liang, Ren-Xiao'
'Jia, Yi-Xia'
_publ_section_title
;
 Visible-light-induced dearomative 1,4-carbamoylpyridinylation of
 nonactivated naphthalenes.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5576
_journal_page_last               5581
_journal_paper_doi               10.1039/d5ob00550g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39
_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-2018/3
_audit_update_record
;
2024-08-11 deposited with the CCDC.	2025-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.914(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.046(4)
_cell_length_b                   6.758(3)
_cell_length_c                   25.803(11)
_cell_measurement_reflns_used    4025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.578
_cell_measurement_theta_min      2.038
_cell_volume                     1742.5(13)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15747
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         2.038
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       rod
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       0.048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1540
_refine_ls_R_factor_gt           0.0775
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1129P)²+0.3180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.2338
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2099
_reflns_number_total             4025
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob00550g2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160535.cif.'
_cod_original_cell_volume        1742.5(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160535
_shelx_shelxl_version_number     2018/3
_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 0.3745(4) 0.7030(6) 0.54370(14) 0.0881(11) Uani 1 1 d . . . . .
C13 C 0.2132(3) 0.1604(4) 0.31274(11) 0.0389(7) Uani 1 1 d . . . . .
C12 C 0.1223(3) 0.1225(4) 0.35578(11) 0.0398(7) Uani 1 1 d . . . . .
C14 C 0.2317(3) 0.3850(4) 0.30631(11) 0.0455(8) Uani 1 1 d . . . . .
H14A H 0.301607 0.408794 0.283764 0.055 Uiso 1 1 calc R U . . .
H14B H 0.149393 0.441982 0.289837 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1258(3) 0.2532(4) 0.39818(11) 0.0456(8) Uani 1 1 d . . . . .
C15 C 0.2679(3) 0.4831(4) 0.35724(11) 0.0480(8) Uani 1 1 d . . . . .
H15 H 0.326440 0.590035 0.358800 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2196(3) 0.4235(4) 0.40087(12) 0.0465(8) Uani 1 1 d . . . . .
C3 C 0.2652(3) 0.5204(4) 0.45095(12) 0.0487(8) Uani 1 1 d . . . . .
C11 C 0.0390(3) -0.0408(5) 0.35383(12) 0.0508(8) Uani 1 1 d . . . . .
H11 H 0.038658 -0.129423 0.326233 0.061 Uiso 1 1 calc R U . . .
C10 C -0.0439(3) -0.0735(5) 0.39254(14) 0.0626(10) Uani 1 1 d . . . . .
H10 H -0.098764 -0.184709 0.391093 0.075 Uiso 1 1 calc R U . . .
C4 C 0.2888(4) 0.7211(5) 0.45427(14) 0.0609(9) Uani 1 1 d . . . . .
H4 H 0.267124 0.801607 0.425415 0.073 Uiso 1 1 calc R U . . .
C9 C -0.0456(4) 0.0572(6) 0.43302(15) 0.0711(11) Uani 1 1 d . . . . .
H9 H -0.103681 0.037135 0.458361 0.085 Uiso 1 1 calc R U . . .
C8 C 0.0384(3) 0.2180(5) 0.43621(13) 0.0616(10) Uani 1 1 d . . . . .
H8 H 0.037403 0.305082 0.464073 0.074 Uiso 1 1 calc R U . . .
C5 C 0.3445(4) 0.8017(6) 0.50030(18) 0.0789(12) Uani 1 1 d . . . . .
H5 H 0.362268 0.936741 0.500751 0.095 Uiso 1 1 calc R U . . .
C2 C 0.2956(4) 0.4167(6) 0.49684(13) 0.0679(10) Uani 1 1 d . . . . .
H2 H 0.279018 0.281476 0.497728 0.082 Uiso 1 1 calc R U . . .
C1 C 0.3503(5) 0.5117(7) 0.54119(15) 0.0862(13) Uani 1 1 d . . . . .
H1 H 0.371227 0.436383 0.571092 0.103 Uiso 1 1 calc R U . . .
C21 C 0.3503(3) -0.0822(4) 0.27954(11) 0.0404(7) Uani 1 1 d . . . . .
C16 C 0.3428(3) 0.0471(4) 0.32074(10) 0.0376(7) Uani 1 1 d . . . . .
C17 C 0.4468(3) 0.0564(4) 0.35945(12) 0.0468(8) Uani 1 1 d . . . . .
H17 H 0.443390 0.142120 0.387465 0.056 Uiso 1 1 calc R U . . .
C22 C 0.1514(3) 0.0778(4) 0.26033(11) 0.0444(7) Uani 1 1 d . . . . .
C20 C 0.4581(3) -0.2046(5) 0.27558(13) 0.0519(8) Uani 1 1 d . . . . .
H20 H 0.460885 -0.291385 0.247754 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5575(3) -0.0646(5) 0.35611(13) 0.0564(9) Uani 1 1 d . . . . .
H18 H 0.629038 -0.058843 0.382007 0.068 Uiso 1 1 calc R U . . .
C19 C 0.5625(3) -0.1925(5) 0.31502(14) 0.0568(9) Uani 1 1 d . . . . .
H19 H 0.637288 -0.272605 0.313608 0.068 Uiso 1 1 calc R U . . .
N2 N 0.2353(2) -0.0626(4) 0.24435(9) 0.0455(7) Uani 1 1 d . . . . .
O1 O 0.0474(2) 0.1308(3) 0.23649(9) 0.0586(7) Uani 1 1 d . . . . .
C23 C 0.2096(4) -0.1715(5) 0.19584(13) 0.0638(10) Uani 1 1 d . . . . .
H23A H 0.128334 -0.124349 0.177071 0.096 Uiso 1 1 calc R U . . .
H23B H 0.200934 -0.309799 0.203252 0.096 Uiso 1 1 calc R U . . .
H23C H 0.282656 -0.152246 0.175118 0.096 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
C1 N1 C5 115.6(4) . . ?
C16 C13 C12 112.8(2) . . ?
C16 C13 C22 101.6(2) . . ?
C12 C13 C22 111.2(2) . . ?
C16 C13 C14 113.8(2) . . ?
C12 C13 C14 109.3(2) . . ?
C22 C13 C14 107.8(2) . . ?
C11 C12 C7 119.8(3) . . ?
C11 C12 C13 120.8(3) . . ?
C7 C12 C13 119.4(2) . . ?
C15 C14 C13 111.5(2) . . ?
C12 C7 C8 118.1(3) . . ?
C12 C7 C6 119.3(2) . . ?
C8 C7 C6 122.6(3) . . ?
C6 C15 C14 122.4(3) . . ?
C15 C6 C3 119.8(3) . . ?
C15 C6 C7 118.6(3) . . ?
C3 C6 C7 121.5(3) . . ?
C4 C3 C2 115.1(3) . . ?
C4 C3 C6 121.8(3) . . ?
C2 C3 C6 123.0(3) . . ?
C10 C11 C12 120.6(3) . . ?
C9 C10 C11 120.2(3) . . ?
C5 C4 C3 119.8(4) . . ?
C10 C9 C8 120.0(3) . . ?
C9 C8 C7 121.2(3) . . ?
N1 C5 C4 125.1(4) . . ?
C1 C2 C3 120.7(4) . . ?
N1 C1 C2 123.7(4) . . ?
C20 C21 C16 122.9(3) . . ?
C20 C21 N2 127.7(3) . . ?
C16 C21 N2 109.4(2) . . ?
C17 C16 C21 119.4(3) . . ?
C17 C16 C13 131.3(2) . . ?
C21 C16 C13 109.3(3) . . ?
C16 C17 C18 118.9(3) . . ?
O1 C22 N2 125.6(3) . . ?
O1 C22 C13 126.1(3) . . ?
N2 C22 C13 108.3(3) . . ?
C21 C20 C19 116.9(3) . . ?
C19 C18 C17 120.7(3) . . ?
C18 C19 C20 121.3(3) . . ?
C22 N2 C21 111.4(2) . . ?
C22 N2 C23 123.6(3) . . ?
C21 N2 C23 125.0(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 C1 1.316(6) . ?
N1 C5 1.312(5) . ?
C13 C16 1.507(4) . ?
C13 C12 1.530(4) . ?
C13 C22 1.534(4) . ?
C13 C14 1.540(4) . ?
C12 C11 1.383(4) . ?
C12 C7 1.404(4) . ?
C14 C15 1.483(4) . ?
C7 C8 1.403(4) . ?
C7 C6 1.485(4) . ?
C15 C6 1.333(4) . ?
C6 C3 1.479(4) . ?
C3 C4 1.378(5) . ?
C3 C2 1.383(4) . ?
C11 C10 1.383(4) . ?
C10 C9 1.370(5) . ?
C4 C5 1.372(5) . ?
C9 C8 1.373(5) . ?
C2 C1 1.376(5) . ?
C21 C20 1.375(4) . ?
C21 C16 1.384(4) . ?
C21 N2 1.400(4) . ?
C16 C17 1.370(4) . ?
C17 C18 1.390(4) . ?
C22 O1 1.210(3) . ?
C22 N2 1.361(4) . ?
C20 C19 1.386(5) . ?
C18 C19 1.373(4) . ?
N2 C23 1.452(4) . ?
