#------------------------------------------------------------------------------
#$Date: 2020-07-04 05:00:23 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253749 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/83/1558387.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_1558387
loop_
_publ_author_name
'Jena, Satyam'
'Dhanalakshmi, Pandi'
'Bano, Gulista'
'Thilagar, Pakkirisamy'
_publ_section_title
;
 Delayed Fluorescence, Room Temperature Phosphorescence, and
 Mechanofluorochromic Naphthalimides: Differential Imaging of Normoxia and
 Hypoxia Live Cancer Cells.
;
_journal_issue                   26
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              5393
_journal_page_last               5406
_journal_paper_doi               10.1021/acs.jpcb.0c04115
_journal_volume                  124
_journal_year                    2020
_chemical_formula_sum            'C27 H22 N2 O2'
_chemical_formula_weight         406.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                79.620(5)
_cell_angle_beta                 73.190(5)
_cell_angle_gamma                70.550(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8985(7)
_cell_length_b                   11.3746(11)
_cell_length_c                   13.1673(13)
_cell_measurement_reflns_used    3650
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.9
_cell_volume                     1063.19(18)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9085
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.907
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       square
_exptl_crystal_F_000             428
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0864
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2540
_refine_ls_wR_factor_ref         0.2757
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2664
_reflns_number_total             3650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp0c04115_si_001.cif
_cod_data_source_block           Compound4
_cod_depositor_comments
'Adding full bibliography for 1558383--1558387.cif.'
_cod_database_code               1558387
_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, -z'
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
O2 O 1.4308(3) 0.7409(3) 0.33913(19) 0.0928(8) Uani 1 1 d . . . . .
O1 O 1.0942(4) 0.5695(2) 0.21834(17) 0.0836(8) Uani 1 1 d . . . . .
N2 N 1.2666(3) 0.6535(2) 0.27774(17) 0.0582(7) Uani 1 1 d . . . . .
C19 C 0.9661(3) 0.6341(2) 0.39213(19) 0.0428(6) Uani 1 1 d . . . . .
C10 C 0.8639(4) 0.7911(3) 1.0293(2) 0.0632(8) Uani 1 1 d . . . . .
H8 H 0.890936 0.788679 1.093988 0.076 Uiso 1 1 calc R U . . .
C9 C 0.7552(3) 0.8994(3) 0.9878(2) 0.0607(8) Uani 1 1 d . . . . .
H7 H 0.710007 0.970824 1.024143 0.073 Uiso 1 1 calc R U . . .
C8 C 0.7120(3) 0.9036(2) 0.8924(2) 0.0512(7) Uani 1 1 d . . . . .
H6 H 0.639311 0.977677 0.864289 0.061 Uiso 1 1 calc R U . . .
C7 C 0.7775(3) 0.7969(2) 0.83886(18) 0.0429(6) Uani 1 1 d . . . . .
N1 N 0.7282(2) 0.79738(18) 0.74235(16) 0.0447(6) Uani 1 1 d . . . . .
C13 C 0.8700(3) 0.7706(2) 0.64816(19) 0.0415(6) Uani 1 1 d . . . . .
C14 C 1.0328(3) 0.8000(3) 0.6307(2) 0.0583(8) Uani 1 1 d . . . . .
H11 H 1.051935 0.834652 0.683674 0.070 Uiso 1 1 calc R U . . .
C15 C 1.1684(3) 0.7793(3) 0.5360(2) 0.0597(8) Uani 1 1 d . . . . .
H12 H 1.276089 0.800774 0.526682 0.072 Uiso 1 1 calc R U . . .
C16 C 1.1467(3) 0.7276(2) 0.4559(2) 0.0461(6) Uani 1 1 d . . . . .
C17 C 1.2918(3) 0.7101(3) 0.3552(2) 0.0587(8) Uani 1 1 d . . . . .
C25 C 1.4149(5) 0.6361(4) 0.1755(3) 0.0963(13) Uani 1 1 d . . . . .
H16 H 1.490086 0.678086 0.194547 0.116 Uiso 1 1 calc R U . . .
C26 C 1.3717(6) 0.7242(5) 0.0903(3) 0.1222(17) Uani 1 1 d . . . . .
H17 H 1.483374 0.724590 0.036359 0.183 Uiso 1 1 calc R U . . .
H19 H 1.312691 0.805819 0.115299 0.183 Uiso 1 1 calc R U . . .
H18 H 1.289451 0.702308 0.060874 0.183 Uiso 1 1 calc R U . . .
C27 C 1.5478(7) 0.5168(4) 0.1724(4) 0.145(2) Uani 1 1 d . . . . .
H20 H 1.492493 0.455460 0.167072 0.218 Uiso 1 1 calc R U . . .
H22 H 1.591082 0.496361 0.236275 0.218 Uiso 1 1 calc R U . . .
H21 H 1.650231 0.517538 0.111665 0.218 Uiso 1 1 calc R U . . .
C23 C 0.8456(3) 0.71086(19) 0.56872(18) 0.0367(6) Uani 1 1 d . . . . .
C24 C 0.9857(3) 0.69177(19) 0.47200(19) 0.0384(6) Uani 1 1 d . . . . .
C20 C 0.8136(4) 0.5947(2) 0.4083(2) 0.0516(7) Uani 1 1 d . . . . .
H13 H 0.800217 0.557408 0.354901 0.062 Uiso 1 1 calc R U . . .
C21 C 0.6777(3) 0.6101(2) 0.5045(2) 0.0501(7) Uani 1 1 d . . . . .
H14 H 0.576181 0.581132 0.515348 0.060 Uiso 1 1 calc R U . . .
C22 C 0.6930(3) 0.6675(2) 0.5827(2) 0.0421(6) Uani 1 1 d . . . . .
H15 H 0.600964 0.677967 0.646054 0.051 Uiso 1 1 calc R U . . .
C18 C 1.1107(4) 0.6162(2) 0.2900(2) 0.0559(7) Uani 1 1 d . . . . .
C1 C 0.5472(3) 0.8758(2) 0.73269(19) 0.0412(6) Uani 1 1 d . . . . .
C6 C 0.3921(3) 0.8537(2) 0.8059(2) 0.0479(6) Uani 1 1 d . . . . .
H5 H 0.405417 0.787706 0.859020 0.057 Uiso 1 1 calc R U . . .
C5 C 0.2167(3) 0.9310(3) 0.7991(2) 0.0573(8) Uani 1 1 d . . . . .
H4 H 0.112463 0.917215 0.848452 0.069 Uiso 1 1 calc R U . . .
C4 C 0.1965(4) 1.0265(3) 0.7208(3) 0.0654(8) Uani 1 1 d . . . . .
H3 H 0.078750 1.077846 0.716592 0.078 Uiso 1 1 calc R U . . .
C3 C 0.3494(4) 1.0472(3) 0.6481(3) 0.0764(9) Uani 1 1 d . . . . .
H2 H 0.335155 1.112277 0.594243 0.092 Uiso 1 1 calc R U . . .
C2 C 0.5255(4) 0.9719(2) 0.6540(2) 0.0615(8) Uani 1 1 d . . . . .
H1 H 0.628876 0.986717 0.604458 0.074 Uiso 1 1 calc R U . . .
C11 C 0.9324(4) 0.6867(3) 0.9749(2) 0.0670(8) Uani 1 1 d . . . . .
H9 H 1.009227 0.613872 1.001886 0.080 Uiso 1 1 calc R U . . .
C12 C 0.8884(4) 0.6884(2) 0.8800(2) 0.0557(7) Uani 1 1 d . . . . .
H10 H 0.933629 0.616538 0.844248 0.067 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
C18 N2 C17 123.2(2) . . ?
C18 N2 C25 119.6(3) . . ?
C17 N2 C25 117.2(3) . . ?
C20 C19 C24 120.0(2) . . ?
C20 C19 C18 120.1(2) . . ?
C24 C19 C18 120.0(2) . . ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H8 120.2 . . ?
C9 C10 H8 120.2 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H7 119.7 . . ?
C8 C9 H7 119.7 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H6 120.2 . . ?
C7 C8 H6 120.2 . . ?
C12 C7 C8 119.6(2) . . ?
C12 C7 N1 119.64(19) . . ?
C8 C7 N1 120.7(2) . . ?
C13 N1 C7 118.92(16) . . ?
C13 N1 C1 118.16(19) . . ?
C7 N1 C1 117.15(17) . . ?
C14 C13 N1 121.6(2) . . ?
C14 C13 C23 119.0(2) . . ?
N1 C13 C23 119.45(19) . . ?
C13 C14 C15 121.6(2) . . ?
C13 C14 H11 119.2 . . ?
C15 C14 H11 119.2 . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H12 119.4 . . ?
C14 C15 H12 119.4 . . ?
C15 C16 C24 119.0(2) . . ?
C15 C16 C17 119.6(2) . . ?
C24 C16 C17 121.4(2) . . ?
O2 C17 N2 119.8(3) . . ?
O2 C17 C16 122.7(3) . . ?
N2 C17 C16 117.5(2) . . ?
C26 C25 C27 128.6(4) . . ?
C26 C25 N2 114.6(3) . . ?
C27 C25 N2 114.0(3) . . ?
C26 C25 H16 95.5 . . ?
C27 C25 H16 95.5 . . ?
N2 C25 H16 95.5 . . ?
C25 C26 H17 109.5 . . ?
C25 C26 H19 109.5 . . ?
H17 C26 H19 109.5 . . ?
C25 C26 H18 109.5 . . ?
H17 C26 H18 109.5 . . ?
H19 C26 H18 109.5 . . ?
C25 C27 H20 109.5 . . ?
C25 C27 H22 109.5 . . ?
H20 C27 H22 109.5 . . ?
C25 C27 H21 109.5 . . ?
H20 C27 H21 109.5 . . ?
H22 C27 H21 109.5 . . ?
C22 C23 C24 118.4(2) . . ?
C22 C23 C13 123.3(2) . . ?
C24 C23 C13 118.23(19) . . ?
C19 C24 C16 119.3(2) . . ?
C19 C24 C23 119.8(2) . . ?
C16 C24 C23 120.8(2) . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H13 119.8 . . ?
C21 C20 H13 119.8 . . ?
C22 C21 C20 120.5(2) . . ?
C22 C21 H14 119.8 . . ?
C20 C21 H14 119.8 . . ?
C21 C22 C23 120.8(2) . . ?
C21 C22 H15 119.6 . . ?
C23 C22 H15 119.6 . . ?
O1 C18 N2 120.4(3) . . ?
O1 C18 C19 121.1(3) . . ?
N2 C18 C19 118.5(2) . . ?
C2 C1 C6 119.7(2) . . ?
C2 C1 N1 121.4(2) . . ?
C6 C1 N1 119.0(2) . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 H5 120.3 . . ?
C5 C6 H5 120.3 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H4 119.8 . . ?
C6 C5 H4 119.8 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H3 120.0 . . ?
C3 C4 H3 120.0 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H2 119.7 . . ?
C2 C3 H2 119.7 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H1 120.0 . . ?
C3 C2 H1 120.0 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H9 119.7 . . ?
C12 C11 H9 119.7 . . ?
C7 C12 C11 119.8(2) . . ?
C7 C12 H10 120.1 . . ?
C11 C12 H10 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
O2 C17 1.211(3) . ?
O1 C18 1.219(3) . ?
N2 C18 1.389(4) . ?
N2 C17 1.392(4) . ?
N2 C25 1.501(4) . ?
C19 C20 1.369(4) . ?
C19 C24 1.404(3) . ?
C19 C18 1.487(4) . ?
C10 C11 1.368(4) . ?
C10 C9 1.370(4) . ?
C10 H8 0.9300 . ?
C9 C8 1.383(3) . ?
C9 H7 0.9300 . ?
C8 C7 1.384(3) . ?
C8 H6 0.9300 . ?
C7 C12 1.378(3) . ?
C7 N1 1.431(3) . ?
N1 C13 1.411(3) . ?
N1 C1 1.439(3) . ?
C13 C14 1.381(3) . ?
C13 C23 1.433(3) . ?
C14 C15 1.386(4) . ?
C14 H11 0.9300 . ?
C15 C16 1.373(3) . ?
C15 H12 0.9300 . ?
C16 C24 1.409(3) . ?
C16 C17 1.474(4) . ?
C25 C26 1.403(5) . ?
C25 C27 1.411(5) . ?
C25 H16 0.9800 . ?
C26 H17 0.9600 . ?
C26 H19 0.9600 . ?
C26 H18 0.9600 . ?
C27 H20 0.9600 . ?
C27 H22 0.9600 . ?
C27 H21 0.9600 . ?
C23 C22 1.402(3) . ?
C23 C24 1.421(3) . ?
C20 C21 1.399(4) . ?
C20 H13 0.9300 . ?
C21 C22 1.367(3) . ?
C21 H14 0.9300 . ?
C22 H15 0.9300 . ?
C1 C2 1.366(4) . ?
C1 C6 1.389(3) . ?
C6 C5 1.390(3) . ?
C6 H5 0.9300 . ?
C5 C4 1.358(4) . ?
C5 H4 0.9300 . ?
C4 C3 1.367(5) . ?
C4 H3 0.9300 . ?
C3 C2 1.385(4) . ?
C3 H2 0.9300 . ?
C2 H1 0.9300 . ?
C11 C12 1.386(4) . ?
C11 H9 0.9300 . ?
C12 H10 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
C11 C10 C9 C8 0.9(4) . . . . ?
C10 C9 C8 C7 0.7(4) . . . . ?
C9 C8 C7 C12 -1.4(4) . . . . ?
C9 C8 C7 N1 177.3(2) . . . . ?
C12 C7 N1 C13 -61.4(3) . . . . ?
C8 C7 N1 C13 119.8(2) . . . . ?
C12 C7 N1 C1 145.8(2) . . . . ?
C8 C7 N1 C1 -32.9(3) . . . . ?
C7 N1 C13 C14 -30.4(3) . . . . ?
C1 N1 C13 C14 122.1(3) . . . . ?
C7 N1 C13 C23 149.3(2) . . . . ?
C1 N1 C13 C23 -58.2(3) . . . . ?
N1 C13 C14 C15 -176.8(2) . . . . ?
C23 C13 C14 C15 3.5(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C24 -2.0(4) . . . . ?
C14 C15 C16 C17 178.4(2) . . . . ?
C18 N2 C17 O2 -179.6(3) . . . . ?
C25 N2 C17 O2 -1.4(4) . . . . ?
C18 N2 C17 C16 1.7(4) . . . . ?
C25 N2 C17 C16 179.9(2) . . . . ?
C15 C16 C17 O2 -0.8(4) . . . . ?
C24 C16 C17 O2 179.5(3) . . . . ?
C15 C16 C17 N2 177.8(2) . . . . ?
C24 C16 C17 N2 -1.8(4) . . . . ?
C18 N2 C25 C26 76.8(5) . . . . ?
C17 N2 C25 C26 -101.5(4) . . . . ?
C18 N2 C25 C27 -86.1(5) . . . . ?
C17 N2 C25 C27 95.6(5) . . . . ?
C14 C13 C23 C22 174.3(2) . . . . ?
N1 C13 C23 C22 -5.4(3) . . . . ?
C14 C13 C23 C24 -4.0(3) . . . . ?
N1 C13 C23 C24 176.31(18) . . . . ?
C20 C19 C24 C16 177.7(2) . . . . ?
C18 C19 C24 C16 -2.5(3) . . . . ?
C20 C19 C24 C23 -1.0(3) . . . . ?
C18 C19 C24 C23 178.81(17) . . . . ?
C15 C16 C24 C19 -177.4(2) . . . . ?
C17 C16 C24 C19 2.3(4) . . . . ?
C15 C16 C24 C23 1.3(4) . . . . ?
C17 C16 C24 C23 -179.03(19) . . . . ?
C22 C23 C24 C19 1.9(3) . . . . ?
C13 C23 C24 C19 -179.69(18) . . . . ?
C22 C23 C24 C16 -176.7(2) . . . . ?
C13 C23 C24 C16 1.7(3) . . . . ?
C24 C19 C20 C21 -0.8(3) . . . . ?
C18 C19 C20 C21 179.4(2) . . . . ?
C19 C20 C21 C22 1.6(4) . . . . ?
C20 C21 C22 C23 -0.7(3) . . . . ?
C24 C23 C22 C21 -1.1(3) . . . . ?
C13 C23 C22 C21 -179.4(2) . . . . ?
C17 N2 C18 O1 178.3(2) . . . . ?
C25 N2 C18 O1 0.1(4) . . . . ?
C17 N2 C18 C19 -1.9(4) . . . . ?
C25 N2 C18 C19 179.8(2) . . . . ?
C20 C19 C18 O1 1.9(4) . . . . ?
C24 C19 C18 O1 -177.9(2) . . . . ?
C20 C19 C18 N2 -177.9(2) . . . . ?
C24 C19 C18 N2 2.3(3) . . . . ?
C13 N1 C1 C2 -34.4(3) . . . . ?
C7 N1 C1 C2 118.6(3) . . . . ?
C13 N1 C1 C6 146.3(2) . . . . ?
C7 N1 C1 C6 -60.7(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
N1 C1 C6 C5 178.27(19) . . . . ?
C1 C6 C5 C4 0.8(4) . . . . ?
C6 C5 C4 C3 -0.1(4) . . . . ?
C5 C4 C3 C2 -0.5(5) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
N1 C1 C2 C3 -178.8(2) . . . . ?
C4 C3 C2 C1 0.3(5) . . . . ?
C9 C10 C11 C12 -1.9(5) . . . . ?
C8 C7 C12 C11 0.5(4) . . . . ?
N1 C7 C12 C11 -178.3(2) . . . . ?
C10 C11 C12 C7 1.2(5) . . . . ?
