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#$Date: 2024-08-05 21:07:04 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572008.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_1572008
loop_
_publ_author_name
'Lee, Yunjeong'
'Jhun, Byung Hak'
'Woo, Sihyun'
'Kim, Seoyeon'
'Bae, Jaehan'
'You, Youngmin'
'Cho, Eun Jin'
_publ_section_title
;
 Charge-recombinative triplet sensitization of alkenes for DeMayo-type [2
 + 2] cycloaddition.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              12058
_journal_page_last               12066
_journal_paper_doi               10.1039/d4sc02601b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C27 H17 N O'
_chemical_formula_weight         371.42
_chemical_melting_point          477
_chemical_name_systematic        A
_chemical_properties_physical    Light-sensitive,Photo-sensitive
_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
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2022-12-08 deposited with the CCDC.	2024-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.935(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.908(4)
_cell_length_b                   5.7056(12)
_cell_length_c                   19.221(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1864.8(7)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3484
_diffrn_reflns_av_unetI/netI     0.1215
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27647
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        21.911
_diffrn_reflns_theta_max         21.911
_diffrn_reflns_theta_min         1.260
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.699
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.699
_refine_ls_R_factor_all          0.2695
_refine_ls_R_factor_gt           0.2381
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.5855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2681
_refine_ls_wR_factor_ref         0.2947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1696
_reflns_number_total             2228
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc02601b2.cif
_cod_data_source_block           LYJ1044_0m
_cod_depositor_comments          'Adding full bibliography for 1572008.cif.'
_cod_original_cell_volume        1864.7(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1572008
_shelx_shelxl_version_number     2017/1
_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   0.931
_shelx_estimated_absorpt_t_max   0.984
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 0.5855(3) 0.6357(9) 0.9502(3) 0.0773(16) Uani 1 1 d . . . . .
N1 N 0.5704(3) 0.5941(9) 0.8250(3) 0.0483(15) Uani 1 1 d . . . . .
C1 C 0.3356(5) -0.2981(15) 0.8645(5) 0.075(2) Uani 1 1 d . . . . .
H1 H 0.313605 -0.387651 0.890467 0.090 Uiso 1 1 calc R U . . .
C2 C 0.3214(4) -0.3580(13) 0.7890(5) 0.070(2) Uani 1 1 d . . . . .
H4 H 0.290392 -0.487309 0.764861 0.084 Uiso 1 1 calc R U . . .
C3 C 0.3534(4) -0.2251(12) 0.7509(4) 0.0573(19) Uani 1 1 d . . . . .
H5 H 0.342655 -0.263629 0.700262 0.069 Uiso 1 1 calc R U . . .
C4 C 0.4021(3) -0.0318(11) 0.7860(3) 0.0446(17) Uani 1 1 d . . . . .
C5 C 0.4373(3) 0.1014(11) 0.7471(3) 0.0470(17) Uani 1 1 d . . . . .
H3 H 0.427646 0.063138 0.696639 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4852(3) 0.2848(11) 0.7835(3) 0.0424(16) Uani 1 1 d . . . . .
C7 C 0.5292(3) 0.4503(11) 0.7607(3) 0.0430(16) Uani 1 1 d . . . . .
C8 C 0.5464(3) 0.5190(10) 0.7015(3) 0.0403(16) Uani 1 1 d . . . . .
C9 C 0.5203(3) 0.4136(10) 0.6249(3) 0.0413(16) Uani 1 1 d . . . . .
C10 C 0.4387(3) 0.3228(11) 0.5852(3) 0.0370(16) Uani 1 1 d . . . . .
C11 C 0.4210(4) 0.1128(11) 0.5450(4) 0.0517(17) Uani 1 1 d . . . . .
H15 H 0.461459 0.025961 0.542379 0.062 Uiso 1 1 calc R U . . .
C12 C 0.3455(5) 0.0296(13) 0.5089(4) 0.068(2) Uani 1 1 d . . . . .
H12 H 0.334998 -0.111279 0.481823 0.081 Uiso 1 1 calc R U . . .
C13 C 0.2855(4) 0.1552(15) 0.5128(4) 0.068(2) Uani 1 1 d . . . . .
H2 H 0.234287 0.098364 0.489156 0.081 Uiso 1 1 calc R U . . .
C14 C 0.3809(4) -0.1115(15) 0.9000(4) 0.066(2) Uani 1 1 d . . . . .
H17 H 0.388806 -0.073116 0.949926 0.080 Uiso 1 1 calc R U . . .
C15 C 0.4166(4) 0.0271(12) 0.8631(4) 0.0500(17) Uani 1 1 d . . . . .
C16 C 0.4665(4) 0.2178(13) 0.8991(3) 0.0559(19) Uani 1 1 d . . . . .
H16 H 0.476219 0.261055 0.949136 0.067 Uiso 1 1 calc R U . . .
C17 C 0.5005(3) 0.3386(12) 0.8607(3) 0.0476(17) Uani 1 1 d . . . . .
C18 C 0.5998(3) 0.7154(11) 0.7309(3) 0.0454(17) Uani 1 1 d . . . . .
C19 C 0.6356(3) 0.8675(12) 0.6987(4) 0.0511(17) Uani 1 1 d . . . . .
H6 H 0.626871 0.849203 0.647532 0.061 Uiso 1 1 calc R U . . .
C20 C 0.6836(4) 1.0435(13) 0.7430(5) 0.065(2) Uani 1 1 d . . . . .
H7 H 0.707325 1.143494 0.721254 0.078 Uiso 1 1 calc R U . . .
C21 C 0.6975(4) 1.0756(13) 0.8191(5) 0.070(2) Uani 1 1 d . . . . .
H9 H 0.730989 1.195159 0.847797 0.084 Uiso 1 1 calc R U . . .
C22 C 0.6629(4) 0.9347(12) 0.8531(4) 0.0596(19) Uani 1 1 d . . . . .
H8 H 0.671476 0.956654 0.904076 0.072 Uiso 1 1 calc R U . . .
C23 C 0.6149(3) 0.7588(12) 0.8079(4) 0.0476(17) Uani 1 1 d . . . . .
C24 C 0.5562(4) 0.5374(13) 0.8885(4) 0.0536(19) Uani 1 1 d . . . . .
C25 C 0.5678(4) 0.4000(11) 0.5904(4) 0.0574(19) Uani 1 1 d . . . . .
H10 H 0.618803 0.458237 0.615097 0.069 Uiso 1 1 calc R U . . .
H11 H 0.549992 0.332226 0.541691 0.069 Uiso 1 1 calc R U . . .
C26 C 0.3012(4) 0.3655(14) 0.5519(4) 0.061(2) Uani 1 1 d . . . . .
H13 H 0.260584 0.451490 0.554441 0.073 Uiso 1 1 calc R U . . .
C27 C 0.3770(3) 0.4477(11) 0.5872(3) 0.0497(17) Uani 1 1 d . . . . .
H27 H 0.387105 0.590669 0.612985 0.060 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
C23 N1 C24 136.8(5) . . ?
C23 N1 C7 110.3(5) . . ?
C24 N1 C7 112.9(5) . . ?
C14 C1 C2 120.6(7) . . ?
C14 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 119.4(7) . . ?
C3 C2 H4 120.3 . . ?
C1 C2 H4 120.3 . . ?
C2 C3 C4 122.0(7) . . ?
C2 C3 H5 119.0 . . ?
C4 C3 H5 119.0 . . ?
C3 C4 C5 121.8(6) . . ?
C3 C4 C15 118.2(6) . . ?
C5 C4 C15 120.0(6) . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H3 120.0 . . ?
C4 C5 H3 120.0 . . ?
C5 C6 C17 119.4(6) . . ?
C5 C6 C7 133.4(5) . . ?
C17 C6 C7 107.2(6) . . ?
C8 C7 N1 108.7(5) . . ?
C8 C7 C6 144.6(6) . . ?
N1 C7 C6 106.6(5) . . ?
C7 C8 C18 106.1(5) . . ?
C7 C8 C9 128.3(6) . . ?
C18 C8 C9 125.6(5) . . ?
C25 C9 C8 121.4(5) . . ?
C25 C9 C10 119.9(5) . . ?
C8 C9 C10 118.7(4) . . ?
C27 C10 C11 117.5(6) . . ?
C27 C10 C9 120.4(6) . . ?
C11 C10 C9 122.1(5) . . ?
C12 C11 C10 121.7(6) . . ?
C12 C11 H15 119.1 . . ?
C10 C11 H15 119.1 . . ?
C11 C12 C13 119.6(7) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C26 120.0(7) . . ?
C12 C13 H2 120.0 . . ?
C26 C13 H2 120.0 . . ?
C1 C14 C15 121.6(7) . . ?
C1 C14 H17 119.2 . . ?
C15 C14 H17 119.2 . . ?
C16 C15 C14 123.4(6) . . ?
C16 C15 C4 118.4(6) . . ?
C14 C15 C4 118.2(7) . . ?
C17 C16 C15 120.0(6) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C6 122.0(7) . . ?
C16 C17 C24 128.6(6) . . ?
C6 C17 C24 109.3(5) . . ?
C19 C18 C23 116.2(6) . . ?
C19 C18 C8 134.3(6) . . ?
C23 C18 C8 109.5(6) . . ?
C20 C19 C18 119.8(6) . . ?
C20 C19 H6 120.1 . . ?
C18 C19 H6 120.1 . . ?
C19 C20 C21 121.5(7) . . ?
C19 C20 H7 119.3 . . ?
C21 C20 H7 119.3 . . ?
C22 C21 C20 121.2(7) . . ?
C22 C21 H9 119.4 . . ?
C20 C21 H9 119.4 . . ?
C21 C22 C23 116.7(7) . . ?
C21 C22 H8 121.7 . . ?
C23 C22 H8 121.7 . . ?
C22 C23 N1 130.0(6) . . ?
C22 C23 C18 124.6(7) . . ?
N1 C23 C18 105.4(6) . . ?
O1 C24 N1 124.8(7) . . ?
O1 C24 C17 131.3(6) . . ?
N1 C24 C17 104.0(5) . . ?
C9 C25 H10 120.0 . . ?
C9 C25 H11 120.0 . . ?
H10 C25 H11 120.0 . . ?
C27 C26 C13 119.7(6) . . ?
C27 C26 H13 120.1 . . ?
C13 C26 H13 120.1 . . ?
C26 C27 C10 121.5(6) . . ?
C26 C27 H27 119.3 . . ?
C10 C27 H27 119.3 . . ?
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 C24 1.206(7) . ?
N1 C23 1.392(7) . ?
N1 C24 1.397(7) . ?
N1 C7 1.403(7) . ?
C1 C14 1.350(9) . ?
C1 C2 1.398(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(8) . ?
C2 H4 0.9300 . ?
C3 C4 1.406(8) . ?
C3 H5 0.9300 . ?
C4 C5 1.421(7) . ?
C4 C15 1.425(8) . ?
C5 C6 1.361(8) . ?
C5 H3 0.9300 . ?
C6 C17 1.417(8) . ?
C6 C7 1.447(8) . ?
C7 C8 1.370(7) . ?
C8 C18 1.447(8) . ?
C8 C9 1.462(7) . ?
C9 C25 1.331(7) . ?
C9 C10 1.484(7) . ?
C10 C27 1.382(7) . ?
C10 C11 1.385(8) . ?
C11 C12 1.371(8) . ?
C11 H15 0.9300 . ?
C12 C13 1.372(9) . ?
C12 H12 0.9300 . ?
C13 C26 1.378(9) . ?
C13 H2 0.9300 . ?
C14 C15 1.415(8) . ?
C14 H17 0.9300 . ?
C15 C16 1.407(9) . ?
C16 C17 1.359(8) . ?
C16 H16 0.9300 . ?
C17 C24 1.479(9) . ?
C18 C19 1.399(8) . ?
C18 C23 1.402(8) . ?
C19 C20 1.372(8) . ?
C19 H6 0.9300 . ?
C20 C21 1.380(9) . ?
C20 H7 0.9300 . ?
C21 C22 1.369(9) . ?
C21 H9 0.9300 . ?
C22 C23 1.377(8) . ?
C22 H8 0.9300 . ?
C25 H10 0.9300 . ?
C25 H11 0.9300 . ?
C26 C27 1.373(8) . ?
C26 H13 0.9300 . ?
C27 H27 0.9300 . ?
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
C14 C1 C2 C3 -0.4(10) . . . . ?
C1 C2 C3 C4 1.6(10) . . . . ?
C2 C3 C4 C5 177.9(6) . . . . ?
C2 C3 C4 C15 -1.2(9) . . . . ?
C3 C4 C5 C6 -178.9(5) . . . . ?
C15 C4 C5 C6 0.3(8) . . . . ?
C4 C5 C6 C17 1.1(8) . . . . ?
C4 C5 C6 C7 179.7(5) . . . . ?
C23 N1 C7 C8 0.2(6) . . . . ?
C24 N1 C7 C8 179.8(5) . . . . ?
C23 N1 C7 C6 179.7(4) . . . . ?
C24 N1 C7 C6 -0.6(6) . . . . ?
C5 C6 C7 C8 1.6(12) . . . . ?
C17 C6 C7 C8 -179.6(8) . . . . ?
C5 C6 C7 N1 -177.6(6) . . . . ?
C17 C6 C7 N1 1.1(6) . . . . ?
N1 C7 C8 C18 -0.8(6) . . . . ?
C6 C7 C8 C18 -180.0(7) . . . . ?
N1 C7 C8 C9 176.8(5) . . . . ?
C6 C7 C8 C9 -2.5(12) . . . . ?
C7 C8 C9 C25 -142.4(6) . . . . ?
C18 C8 C9 C25 34.6(8) . . . . ?
C7 C8 C9 C10 38.2(8) . . . . ?
C18 C8 C9 C10 -144.7(5) . . . . ?
C25 C9 C10 C27 -137.7(6) . . . . ?
C8 C9 C10 C27 41.7(7) . . . . ?
C25 C9 C10 C11 42.2(8) . . . . ?
C8 C9 C10 C11 -138.4(5) . . . . ?
C27 C10 C11 C12 -0.5(8) . . . . ?
C9 C10 C11 C12 179.5(5) . . . . ?
C10 C11 C12 C13 -0.5(9) . . . . ?
C11 C12 C13 C26 1.0(10) . . . . ?
C2 C1 C14 C15 -1.1(10) . . . . ?
C1 C14 C15 C16 -177.6(6) . . . . ?
C1 C14 C15 C4 1.5(9) . . . . ?
C3 C4 C15 C16 178.8(5) . . . . ?
C5 C4 C15 C16 -0.3(8) . . . . ?
C3 C4 C15 C14 -0.3(8) . . . . ?
C5 C4 C15 C14 -179.5(5) . . . . ?
C14 C15 C16 C17 178.1(6) . . . . ?
C4 C15 C16 C17 -1.0(8) . . . . ?
C15 C16 C17 C6 2.4(9) . . . . ?
C15 C16 C17 C24 -177.9(5) . . . . ?
C5 C6 C17 C16 -2.5(8) . . . . ?
C7 C6 C17 C16 178.6(5) . . . . ?
C5 C6 C17 C24 177.7(5) . . . . ?
C7 C6 C17 C24 -1.2(6) . . . . ?
C7 C8 C18 C19 -176.6(6) . . . . ?
C9 C8 C18 C19 5.7(10) . . . . ?
C7 C8 C18 C23 1.1(6) . . . . ?
C9 C8 C18 C23 -176.5(5) . . . . ?
C23 C18 C19 C20 1.3(8) . . . . ?
C8 C18 C19 C20 178.9(6) . . . . ?
C18 C19 C20 C21 -0.2(9) . . . . ?
C19 C20 C21 C22 -1.0(10) . . . . ?
C20 C21 C22 C23 0.9(9) . . . . ?
C21 C22 C23 N1 -178.0(6) . . . . ?
C21 C22 C23 C18 0.3(9) . . . . ?
C24 N1 C23 C22 -0.5(10) . . . . ?
C7 N1 C23 C22 179.0(6) . . . . ?
C24 N1 C23 C18 -179.0(6) . . . . ?
C7 N1 C23 C18 0.5(6) . . . . ?
C19 C18 C23 C22 -1.4(8) . . . . ?
C8 C18 C23 C22 -179.6(5) . . . . ?
C19 C18 C23 N1 177.2(5) . . . . ?
C8 C18 C23 N1 -1.0(6) . . . . ?
C23 N1 C24 O1 -1.0(11) . . . . ?
C7 N1 C24 O1 179.5(6) . . . . ?
C23 N1 C24 C17 179.4(6) . . . . ?
C7 N1 C24 C17 -0.1(6) . . . . ?
C16 C17 C24 O1 1.5(11) . . . . ?
C6 C17 C24 O1 -178.7(6) . . . . ?
C16 C17 C24 N1 -178.9(6) . . . . ?
C6 C17 C24 N1 0.8(6) . . . . ?
C12 C13 C26 C27 -0.4(9) . . . . ?
C13 C26 C27 C10 -0.7(9) . . . . ?
C11 C10 C27 C26 1.2(8) . . . . ?
C9 C10 C27 C26 -178.9(5) . . . . ?
