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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558283.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_1558283
loop_
_publ_author_name
'Yang, Ping'
'Zheng, Chao'
'Nie, Yu-Han'
'You, Shuli'
_publ_section_title
;
 Palladium-Catalyzed Dearomative 1,4-Difunctionalization of Naphthalenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02816A
_journal_year                    2020
_chemical_formula_sum            'C24 H20 N2 O'
_chemical_formula_weight         352.42
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-02-07 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.4690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8388(4)
_cell_length_b                   11.4187(4)
_cell_length_c                   13.7487(4)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.225
_cell_measurement_theta_min      4.812
_cell_volume                     1848.85(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26778
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_min         2.406
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.044(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0415
_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)+(0.0615P)²+0.3226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2927
_reflns_number_total             3596
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02816a2.cif
_cod_data_source_block           mo_d8v191162_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1558283
_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_min   0.985
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.71382(9) 0.65775(10) 0.27933(8) 0.0649(3) Uani 1 1 d . . . . .
N1 N 0.57392(10) 0.67316(11) 0.11224(9) 0.0528(3) Uani 1 1 d . . . . .
N2 N 0.74563(10) 0.57490(11) 0.51831(10) 0.0568(3) Uani 1 1 d . . . . .
C1 C 0.46001(12) 0.63777(12) 0.06015(11) 0.0511(3) Uani 1 1 d . . . . .
C2 C 0.38885(16) 0.65169(14) -0.04520(12) 0.0687(5) Uani 1 1 d . . . . .
H2A H 0.4133 0.6892 -0.0924 0.082 Uiso 1 1 calc R U . . .
C3 C 0.28045(18) 0.60804(17) -0.07783(16) 0.0845(6) Uani 1 1 d . . . . .
H3 H 0.2307 0.6159 -0.1484 0.101 Uiso 1 1 calc R U . . .
C4 C 0.24450(17) 0.55335(19) -0.00853(18) 0.0903(6) Uani 1 1 d . . . . .
H4 H 0.1712 0.5233 -0.0329 0.108 Uiso 1 1 calc R U . . .
C5 C 0.31604(15) 0.54191(16) 0.09830(16) 0.0764(5) Uani 1 1 d . . . . .
H5 H 0.2908 0.5059 0.1456 0.092 Uiso 1 1 calc R U . . .
C6 C 0.42460(12) 0.58499(13) 0.13217(11) 0.0523(4) Uani 1 1 d . . . . .
C7 C 0.51985(11) 0.58650(12) 0.24103(10) 0.0478(3) Uani 1 1 d . . . . .
C8 C 0.61664(12) 0.64253(12) 0.21597(11) 0.0478(3) Uani 1 1 d . . . . .
C9 C 0.64089(16) 0.72902(17) 0.06192(15) 0.0779(5) Uani 1 1 d . . . . .
H9A H 0.7123 0.7536 0.1152 0.117 Uiso 1 1 calc R U . . .
H9B H 0.6007 0.7959 0.0224 0.117 Uiso 1 1 calc R U . . .
H9C H 0.6540 0.6745 0.0148 0.117 Uiso 1 1 calc R U . . .
C10 C 0.55635(13) 0.46636(12) 0.28690(12) 0.0554(4) Uani 1 1 d . . . . .
H10 H 0.5449 0.4037 0.2406 0.066 Uiso 1 1 calc R U . . .
C11 C 0.60381(13) 0.44586(13) 0.38961(11) 0.0549(4) Uani 1 1 d . . . . .
H11 H 0.6244 0.3694 0.4124 0.066 Uiso 1 1 calc R U . . .
C12 C 0.62618(12) 0.53990(12) 0.47162(11) 0.0500(3) Uani 1 1 d . . . . .
H12 H 0.6072 0.5080 0.5287 0.060 Uiso 1 1 calc R U . . .
C13 C 0.55281(12) 0.64678(12) 0.42806(11) 0.0493(3) Uani 1 1 d . . . . .
C14 C 0.53819(15) 0.72564(14) 0.49829(13) 0.0644(4) Uani 1 1 d . . . . .
H14 H 0.5741 0.7119 0.5708 0.077 Uiso 1 1 calc R U . . .
C15 C 0.47170(17) 0.82354(16) 0.46290(15) 0.0777(5) Uani 1 1 d . . . . .
H15 H 0.4629 0.8756 0.5111 0.093 Uiso 1 1 calc R U . . .
C16 C 0.41821(16) 0.84418(15) 0.35574(15) 0.0752(5) Uani 1 1 d . . . . .
H16 H 0.3731 0.9104 0.3314 0.090 Uiso 1 1 calc R U . . .
C17 C 0.43128(14) 0.76706(14) 0.28451(13) 0.0616(4) Uani 1 1 d . . . . .
H17 H 0.3946 0.7814 0.2122 0.074 Uiso 1 1 calc R U . . .
C18 C 0.49887(11) 0.66782(12) 0.31957(11) 0.0479(3) Uani 1 1 d . . . . .
C19 C 0.82919(12) 0.49995(12) 0.58510(10) 0.0510(3) Uani 1 1 d . . . . .
C20 C 0.94169(13) 0.52055(14) 0.60127(13) 0.0627(4) Uani 1 1 d . . . . .
H20 H 0.9586 0.5802 0.5638 0.075 Uiso 1 1 calc R U . . .
C21 C 1.02838(15) 0.45408(17) 0.67178(15) 0.0790(6) Uani 1 1 d . . . . .
H21 H 1.1030 0.4697 0.6816 0.095 Uiso 1 1 calc R U . . .
C22 C 1.00597(19) 0.36514(19) 0.72771(15) 0.0868(6) Uani 1 1 d . . . . .
H22 H 1.0647 0.3209 0.7759 0.104 Uiso 1 1 calc R U . . .
C23 C 0.89545(19) 0.34276(17) 0.71126(13) 0.0810(6) Uani 1 1 d . . . . .
H23 H 0.8796 0.2820 0.7483 0.097 Uiso 1 1 calc R U . . .
C24 C 0.80669(15) 0.40845(14) 0.64081(12) 0.0636(4) Uani 1 1 d . . . . .
H24 H 0.7323 0.3915 0.6308 0.076 Uiso 1 1 calc R U . . .
H2 H 0.7672(15) 0.6154(17) 0.4731(14) 0.075(5) 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 0.0033 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
C8 N1 C1 111.39(11) . . ?
C8 N1 C9 123.24(13) . . ?
C1 N1 C9 125.27(13) . . ?
C19 N2 C12 121.25(12) . . ?
C19 N2 H2 113.7(11) . . ?
C12 N2 H2 113.2(11) . . ?
C2 C1 C6 122.22(15) . . ?
C2 C1 N1 128.36(14) . . ?
C6 C1 N1 109.41(12) . . ?
C3 C2 C1 117.51(17) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C4 C3 C2 121.22(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.96(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.53(18) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.52(14) . . ?
C5 C6 C7 130.74(14) . . ?
C1 C6 C7 109.74(12) . . ?
C10 C7 C6 113.53(12) . . ?
C10 C7 C18 111.78(11) . . ?
C6 C7 C18 114.00(12) . . ?
C10 C7 C8 108.99(11) . . ?
C6 C7 C8 100.87(11) . . ?
C18 C7 C8 106.76(11) . . ?
O1 C8 N1 125.94(13) . . ?
O1 C8 C7 125.66(12) . . ?
N1 C8 C7 108.40(11) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 123.04(13) . . ?
C11 C10 H10 118.5 . . ?
C7 C10 H10 118.5 . . ?
C10 C11 C12 123.17(13) . . ?
C10 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
N2 C12 C11 112.27(12) . . ?
N2 C12 C13 109.40(11) . . ?
C11 C12 C13 112.19(11) . . ?
N2 C12 H12 107.6 . . ?
C11 C12 H12 107.6 . . ?
C13 C12 H12 107.6 . . ?
C14 C13 C18 119.10(13) . . ?
C14 C13 C12 118.96(13) . . ?
C18 C13 C12 121.94(12) . . ?
C15 C14 C13 121.30(15) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.60(15) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.16(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.70(15) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 119.15(13) . . ?
C17 C18 C7 120.76(12) . . ?
C13 C18 C7 119.99(12) . . ?
C24 C19 C20 117.95(14) . . ?
C24 C19 N2 123.34(14) . . ?
C20 C19 N2 118.63(14) . . ?
C21 C20 C19 121.07(17) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.78(19) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 118.72(17) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C24 121.61(18) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C19 C24 C23 119.85(17) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
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 C8 1.2166(16) . ?
N1 C8 1.3543(17) . ?
N1 C1 1.4073(18) . ?
N1 C9 1.4486(19) . ?
N2 C19 1.3935(18) . ?
N2 C12 1.4628(19) . ?
N2 H2 0.902(19) . ?
C1 C2 1.380(2) . ?
C1 C6 1.382(2) . ?
C2 C3 1.375(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.5093(19) . ?
C7 C10 1.5047(19) . ?
C7 C18 1.5273(19) . ?
C7 C8 1.5534(19) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.317(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.500(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.5120(19) . ?
C12 H12 0.9800 . ?
C13 C14 1.387(2) . ?
C13 C18 1.3926(19) . ?
C14 C15 1.373(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(2) . ?
C17 H17 0.9300 . ?
C19 C24 1.392(2) . ?
C19 C20 1.391(2) . ?
C20 C21 1.377(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.902(19) 2.520(18) 3.2846(17) 142.9(14) .
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
C8 N1 C1 C2 -178.97(14) . . . . ?
C9 N1 C1 C2 -2.4(2) . . . . ?
C8 N1 C1 C6 1.85(16) . . . . ?
C9 N1 C1 C6 178.38(14) . . . . ?
C6 C1 C2 C3 -1.7(2) . . . . ?
N1 C1 C2 C3 179.25(15) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 179.49(17) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
N1 C1 C6 C5 -179.09(14) . . . . ?
C2 C1 C6 C7 -178.07(13) . . . . ?
N1 C1 C6 C7 1.17(16) . . . . ?
C5 C6 C7 C10 60.7(2) . . . . ?
C1 C6 C7 C10 -119.65(13) . . . . ?
C5 C6 C7 C18 -68.9(2) . . . . ?
C1 C6 C7 C18 110.79(13) . . . . ?
C5 C6 C7 C8 177.07(17) . . . . ?
C1 C6 C7 C8 -3.23(15) . . . . ?
C1 N1 C8 O1 177.03(13) . . . . ?
C9 N1 C8 O1 0.4(2) . . . . ?
C1 N1 C8 C7 -3.96(15) . . . . ?
C9 N1 C8 C7 179.42(13) . . . . ?
C10 C7 C8 O1 -56.96(18) . . . . ?
C6 C7 C8 O1 -176.70(14) . . . . ?
C18 C7 C8 O1 63.94(17) . . . . ?
C10 C7 C8 N1 124.03(12) . . . . ?
C6 C7 C8 N1 4.29(14) . . . . ?
C18 C7 C8 N1 -115.08(12) . . . . ?
C6 C7 C10 C11 -153.80(14) . . . . ?
C18 C7 C10 C11 -23.1(2) . . . . ?
C8 C7 C10 C11 94.64(17) . . . . ?
C7 C10 C11 C12 0.2(2) . . . . ?
C19 N2 C12 C11 -69.72(16) . . . . ?
C19 N2 C12 C13 165.05(12) . . . . ?
C10 C11 C12 N2 -102.76(16) . . . . ?
C10 C11 C12 C13 20.9(2) . . . . ?
N2 C12 C13 C14 -73.47(16) . . . . ?
C11 C12 C13 C14 161.25(14) . . . . ?
N2 C12 C13 C18 107.03(14) . . . . ?
C11 C12 C13 C18 -18.25(18) . . . . ?
C18 C13 C14 C15 0.1(2) . . . . ?
C12 C13 C14 C15 -179.45(15) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C13 0.5(2) . . . . ?
C16 C17 C18 C7 -175.89(14) . . . . ?
C14 C13 C18 C17 -0.3(2) . . . . ?
C12 C13 C18 C17 179.17(13) . . . . ?
C14 C13 C18 C7 176.04(13) . . . . ?
C12 C13 C18 C7 -4.46(19) . . . . ?
C10 C7 C18 C17 -159.01(13) . . . . ?
C6 C7 C18 C17 -28.58(18) . . . . ?
C8 C7 C18 C17 81.89(16) . . . . ?
C10 C7 C18 C13 24.67(18) . . . . ?
C6 C7 C18 C13 155.11(12) . . . . ?
C8 C7 C18 C13 -94.42(14) . . . . ?
C12 N2 C19 C24 -22.5(2) . . . . ?
C12 N2 C19 C20 160.69(13) . . . . ?
C24 C19 C20 C21 -1.3(2) . . . . ?
N2 C19 C20 C21 175.67(14) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C20 C19 C24 C23 1.2(2) . . . . ?
N2 C19 C24 C23 -175.59(15) . . . . ?
C22 C23 C24 C19 -0.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306437
