#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:55:30 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284212 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/88/1568879.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_1568879
loop_
_publ_author_name
'Nan, Jiang'
'Huang, Guanjie'
'Liu, Shilei'
'Wang, Jing'
'Ma, Yangmin'
'Luan, Xinjun'
_publ_section_title
;
 In(OTf)₃-catalyzed reorganization/cycloaddition of two imine
 units and subsequent modular assembly of acridinium photocatalysts.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              5160
_journal_page_last               5166
_journal_paper_doi               10.1039/d3sc00163f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C27 H19 N'
_chemical_formula_weight         357.43
_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
;
2022-11-01 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.886(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.744(2)
_cell_length_b                   6.4582(12)
_cell_length_c                   26.975(5)
_cell_measurement_reflns_used    3944
_cell_measurement_temperature    276(2)
_cell_measurement_theta_max      24.70
_cell_measurement_theta_min      3.02
_cell_volume                     1871.5(6)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      276(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_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  0.1562
_diffrn_reflns_av_unetI/netI     0.1556
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_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       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            34270
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.587
_diffrn_reflns_theta_min         2.406
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0084(18)
_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   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.2476
_refine_ls_R_factor_gt           0.1243
_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)+(0.0618P)²+6.1677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2455
_refine_ls_wR_factor_ref         0.2928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2050
_reflns_number_total             4274
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc00163f2.cif
_cod_data_source_block           SUST_3191_0m
_cod_depositor_comments
'Adding full bibliography for 1568879--1568880.cif.'
_cod_original_cell_volume        1871.4(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1568879
_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
C1 C 0.5407(5) 0.6251(9) 0.5811(2) 0.0487(15) Uani 1 1 d . . . . .
H1 H 0.617070 0.662750 0.595156 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4874(7) 0.7484(11) 0.5458(2) 0.069(2) Uani 1 1 d . . . . .
H2 H 0.527684 0.869160 0.536291 0.083 Uiso 1 1 calc R U . . .
C3 C 0.3742(8) 0.6974(15) 0.5237(3) 0.085(3) Uani 1 1 d . . . . .
H3 H 0.339573 0.783081 0.499410 0.101 Uiso 1 1 calc R U . . .
C4 C 0.3143(7) 0.5233(16) 0.5374(3) 0.083(3) Uani 1 1 d . . . . .
H4 H 0.238057 0.489883 0.522647 0.099 Uiso 1 1 calc R U . . .
C5 C 0.3670(6) 0.3905(12) 0.5742(2) 0.0563(18) Uani 1 1 d . . . . .
C6 C 0.4821(5) 0.4410(9) 0.59694(19) 0.0406(14) Uani 1 1 d . . . . .
C7 C 0.3081(6) 0.2050(14) 0.5883(3) 0.075(2) Uani 1 1 d . . . . .
H7 H 0.231506 0.170499 0.574067 0.090 Uiso 1 1 calc R U . . .
C8 C 0.3605(6) 0.0771(11) 0.6219(3) 0.0632(19) Uani 1 1 d . . . . .
H8 H 0.321166 -0.046574 0.629788 0.076 Uiso 1 1 calc R U . . .
C9 C 0.4738(5) 0.1282(8) 0.6452(2) 0.0411(14) Uani 1 1 d . . . . .
C10 C 0.5369(4) 0.3068(8) 0.63330(17) 0.0316(12) Uani 1 1 d . . . . .
C11 C 0.7673(5) 0.3103(8) 0.74250(18) 0.0365(13) Uani 1 1 d . . . . .
C12 C 0.8352(5) 0.4963(9) 0.73840(19) 0.0447(14) Uani 1 1 d . . . . .
H12 H 0.823459 0.579917 0.710653 0.054 Uiso 1 1 calc R U . . .
C13 C 0.9176(5) 0.5548(10) 0.7744(2) 0.0550(16) Uani 1 1 d . . . . .
H13 H 0.960676 0.678844 0.771058 0.066 Uiso 1 1 calc R U . . .
C14 C 0.9390(6) 0.4340(13) 0.8161(2) 0.072(2) Uani 1 1 d . . . . .
H14 H 0.996428 0.475870 0.840235 0.086 Uiso 1 1 calc R U . . .
C15 C 0.8753(6) 0.2537(13) 0.8215(2) 0.068(2) Uani 1 1 d . . . . .
H15 H 0.889639 0.172798 0.849503 0.081 Uiso 1 1 calc R U . . .
C16 C 0.7879(6) 0.1871(10) 0.78535(19) 0.0512(16) Uani 1 1 d . . . . .
C17 C 0.7218(6) 0.0020(10) 0.7912(2) 0.0607(18) Uani 1 1 d . . . . .
H17 H 0.736631 -0.078910 0.819216 0.073 Uiso 1 1 calc R U . . .
C18 C 0.6365(6) -0.0614(10) 0.7569(2) 0.0593(18) Uani 1 1 d . . . . .
H18 H 0.592544 -0.183811 0.761397 0.071 Uiso 1 1 calc R U . . .
C19 C 0.6152(5) 0.0617(8) 0.71392(19) 0.0390(13) Uani 1 1 d . . . . .
C20 C 0.7732(5) 0.1060(9) 0.60021(19) 0.0413(14) Uani 1 1 d . . . . .
H20 H 0.715859 0.005767 0.609406 0.050 Uiso 1 1 calc R U . . .
C21 C 0.8634(5) 0.0566(11) 0.5663(2) 0.0550(17) Uani 1 1 d . . . . .
H21 H 0.865562 -0.075518 0.552637 0.066 Uiso 1 1 calc R U . . .
C22 C 0.9504(6) 0.2021(13) 0.5526(2) 0.0640(19) Uani 1 1 d . . . . .
H22 H 1.012046 0.168814 0.530107 0.077 Uiso 1 1 calc R U . . .
C23 C 0.9443(6) 0.3962(12) 0.5727(2) 0.068(2) Uani 1 1 d . . . . .
H23 H 1.001642 0.496202 0.563383 0.082 Uiso 1 1 calc R U . . .
C24 C 0.8543(5) 0.4453(10) 0.6064(2) 0.0523(16) Uani 1 1 d . . . . .
H24 H 0.852678 0.577827 0.619899 0.063 Uiso 1 1 calc R U . . .
C25 C 0.7664(4) 0.3024(8) 0.62083(17) 0.0309(12) Uani 1 1 d . . . . .
C26 C 0.6626(4) 0.3565(7) 0.65645(17) 0.0298(11) Uani 1 1 d . . . . .
H26 H 0.666031 0.505535 0.663114 0.036 Uiso 1 1 calc R U . . .
N1 N 0.5240(4) -0.0053(7) 0.68053(17) 0.0515(13) Uani 1 1 d . . . . .
H1A H 0.498270 -0.131256 0.681800 0.062 Uiso 1 1 calc R U . . .
C27 C 0.6804(4) 0.2423(7) 0.70520(17) 0.0307(11) Uani 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'
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 C1 C6 121.2(6) . . ?
C1 C2 C3 121.3(8) . . ?
C4 C3 C2 119.9(7) . . ?
C3 C4 C5 120.5(7) . . ?
C7 C5 C6 118.2(6) . . ?
C7 C5 C4 121.7(7) . . ?
C6 C5 C4 120.1(7) . . ?
C5 C6 C1 117.0(5) . . ?
C5 C6 C10 120.5(6) . . ?
C1 C6 C10 122.4(5) . . ?
C8 C7 C5 121.3(6) . . ?
C7 C8 C9 120.7(7) . . ?
C10 C9 N1 119.5(5) . . ?
C10 C9 C8 121.4(6) . . ?
N1 C9 C8 119.2(6) . . ?
C9 C10 C6 117.9(5) . . ?
C9 C10 C26 121.4(5) . . ?
C6 C10 C26 120.7(4) . . ?
C12 C11 C16 117.9(5) . . ?
C12 C11 C27 122.6(5) . . ?
C16 C11 C27 119.5(5) . . ?
C13 C12 C11 120.9(6) . . ?
C12 C13 C14 121.5(7) . . ?
C15 C14 C13 119.5(6) . . ?
C14 C15 C16 121.2(6) . . ?
C17 C16 C15 121.0(6) . . ?
C17 C16 C11 119.9(6) . . ?
C15 C16 C11 119.1(6) . . ?
C18 C17 C16 121.3(6) . . ?
C17 C18 C19 119.1(6) . . ?
C27 C19 N1 120.4(5) . . ?
C27 C19 C18 122.4(5) . . ?
N1 C19 C18 117.2(5) . . ?
C21 C20 C25 121.3(5) . . ?
C22 C21 C20 120.4(6) . . ?
C23 C22 C21 118.7(6) . . ?
C22 C23 C24 120.8(6) . . ?
C23 C24 C25 121.5(6) . . ?
C24 C25 C20 117.2(5) . . ?
C24 C25 C26 122.3(5) . . ?
C20 C25 C26 120.4(4) . . ?
C10 C26 C27 110.7(4) . . ?
C10 C26 C25 110.4(4) . . ?
C27 C26 C25 110.6(4) . . ?
C9 N1 C19 121.0(4) . . ?
C19 C27 C11 117.8(5) . . ?
C19 C27 C26 120.0(4) . . ?
C11 C27 C26 122.2(4) . . ?
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
C1 C2 1.362(8) . ?
C1 C6 1.415(8) . ?
C2 C3 1.385(10) . ?
C3 C4 1.351(11) . ?
C4 C5 1.423(10) . ?
C5 C7 1.409(10) . ?
C5 C6 1.411(7) . ?
C6 C10 1.429(7) . ?
C7 C8 1.344(9) . ?
C8 C9 1.400(8) . ?
C9 C10 1.378(7) . ?
C9 N1 1.389(7) . ?
C10 C26 1.514(6) . ?
C11 C12 1.411(7) . ?
C11 C16 1.418(7) . ?
C11 C27 1.431(7) . ?
C12 C13 1.359(7) . ?
C13 C14 1.384(9) . ?
C14 C15 1.359(10) . ?
C15 C16 1.410(9) . ?
C16 C17 1.401(9) . ?
C17 C18 1.356(9) . ?
C18 C19 1.421(7) . ?
C19 C27 1.382(7) . ?
C19 N1 1.390(7) . ?
C20 C21 1.380(7) . ?
C20 C25 1.387(7) . ?
C21 C22 1.380(9) . ?
C22 C23 1.367(9) . ?
C23 C24 1.376(8) . ?
C24 C25 1.380(7) . ?
C25 C26 1.524(6) . ?
C26 C27 1.517(6) . ?
