#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:35:05 +0200 (Sat 23 de Aug de 2025) $
#$Revision: 301870 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/02/7240214.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_7240214
loop_
_publ_author_name
'Kulszewicz-Bajer, Irena'
'Zagorska, Malgorzata'
'Banasiewicz, Marzena'
'Guńka, Piotr A'
'Toman, Petr'
'Kozankiewicz, Boleslaw'
'Wiosna-Salyga, Gabriela'
'Pron, Adam'
_publ_section_title
;
 Effect of the substituent position on the electrochemical, optical and
 structural properties of donor-acceptor type acridone derivatives.
;
_journal_issue                   16
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              8522
_journal_page_last               8534
_journal_paper_doi               10.1039/d0cp00521e
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C31 H28 N2 O2'
_chemical_formula_sum            'C31 H28 N2 O2'
_chemical_formula_weight         460.55
_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_date             2019-08-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-28 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.552(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9995(3)
_cell_length_b                   14.2069(6)
_cell_length_c                   21.3942(9)
_cell_measurement_reflns_used    5342
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      28.6640
_cell_measurement_theta_min      3.7940
_cell_volume                     2390.29(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  11.00   1.00  300.00    --  -11.40 -38.00  60.00   55
  2  ω    -24.00  52.00   1.00  300.00    --  -11.40  38.00-180.00   76
  3  ω    -77.00  13.00   1.00  300.00    --  -11.40 -38.00 -30.00   90
  4  ω    -72.00 -43.00   1.00  300.00    --   11.71 179.00 -90.00   29
  5  ω     56.00  81.00   1.00  300.00    --   11.71 179.00  90.00   25
  6  ω     10.00  52.00   1.00  300.00    --   11.71 -99.00 -90.00   42
  7  ω    -40.00  51.00   1.00  300.00    --   11.71 -19.00 -30.00   91
  8  ω    -27.00  -2.00   1.00  300.00    --   11.71  93.00-165.00   25
  9  ω     56.00  81.00   1.00  300.00    --   11.71 179.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0790030000
_diffrn_orient_matrix_UB_12      -0.0105730000
_diffrn_orient_matrix_UB_13      0.0089628000
_diffrn_orient_matrix_UB_21      -0.0167840000
_diffrn_orient_matrix_UB_22      -0.0339658000
_diffrn_orient_matrix_UB_23      -0.0246601000
_diffrn_orient_matrix_UB_31      0.0401142000
_diffrn_orient_matrix_UB_32      -0.0350393000
_diffrn_orient_matrix_UB_33      0.0211841000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25561
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.868
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.757
_exptl_crystal_size_mid          0.506
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0494
_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)+(0.0705P)²+0.4988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3313
_reflns_number_total             4692
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cp00521e2.cif
_cod_data_source_block           ikb_psmart
_cod_depositor_comments
'Adding full bibliography for 7240214--7240216.cif.'
_cod_database_code               7240214
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C31 N2 O2 H28'
_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.
;
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C29(H29A,H29B), C28(H28A,H28B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C4(H4), C12(H12), C15(H15), C24(H24), C18(H18), C9(H9),
 C11(H11), C21(H21), C16(H16), C10(H10), C17(H17), C23(H23), C22(H22)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.853
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
N1 N 0.62315(16) 0.35612(10) 0.55269(6) 0.0387(3) Uani 1 1 d . . . . .
O1 O 0.17495(15) 0.38920(12) 0.61818(7) 0.0681(4) Uani 1 1 d . . . . .
O2 O 1.25832(19) 0.36988(9) 0.85003(7) 0.0717(5) Uani 1 1 d . . . . .
N2 N 0.9398(2) 0.36538(10) 0.76930(8) 0.0584(5) Uani 1 1 d . . . . .
C7 C 0.6259(2) 0.36165(10) 0.61757(8) 0.0368(4) Uani 1 1 d . . . . .
C2 C 0.4732(2) 0.37142(11) 0.64143(8) 0.0388(4) Uani 1 1 d . . . . .
C8 C 0.4730(2) 0.37297(11) 0.50985(8) 0.0385(4) Uani 1 1 d . . . . .
C13 C 0.31964(19) 0.38866(11) 0.53129(8) 0.0403(4) Uani 1 1 d . . . . .
C1 C 0.3106(2) 0.38279(12) 0.59854(9) 0.0442(4) Uani 1 1 d . . . . .
C6 C 0.7802(2) 0.35966(11) 0.66203(8) 0.0425(4) Uani 1 1 d . . . . .
H6 H 0.883015 0.355182 0.647812 0.051 Uiso 1 1 calc R . . . .
C5 C 0.7792(2) 0.36427(12) 0.72589(9) 0.0468(4) Uani 1 1 d . . . . .
C14 C 1.0355(2) 0.28308(12) 0.78141(8) 0.0445(4) Uani 1 1 d . . . . .
C3 C 0.4782(2) 0.37309(12) 0.70720(8) 0.0469(4) Uani 1 1 d . . . . .
H3 H 0.376822 0.377126 0.722507 0.056 Uiso 1 1 calc R . . . .
C25 C 1.0094(2) 0.45112(12) 0.79339(8) 0.0427(4) Uani 1 1 d . . . . .
C19 C 1.1932(2) 0.28663(12) 0.82210(8) 0.0470(4) Uani 1 1 d . . . . .
C4 C 0.6284(3) 0.36892(13) 0.74937(9) 0.0525(5) Uani 1 1 d . . . . .
H4 H 0.629824 0.369184 0.792939 0.063 Uiso 1 1 calc R . . . .
C20 C 1.1673(2) 0.45160(12) 0.83405(8) 0.0473(4) Uani 1 1 d . . . . .
C12 C 0.1729(2) 0.41170(13) 0.48720(10) 0.0529(5) Uani 1 1 d . . . . .
H12 H 0.071790 0.422733 0.501606 0.064 Uiso 1 1 calc R . . . .
C15 C 0.9810(2) 0.19676(13) 0.75569(9) 0.0537(5) Uani 1 1 d . . . . .
H15 H 0.877285 0.192530 0.727870 0.064 Uiso 1 1 calc R . . . .
C24 C 0.9300(2) 0.53715(13) 0.77908(9) 0.0518(5) Uani 1 1 d . . . . .
H24 H 0.826035 0.539312 0.751262 0.062 Uiso 1 1 calc R . . . .
C26 C 0.7767(2) 0.33033(14) 0.52769(9) 0.0505(5) Uani 1 1 d . . . . .
H26A H 0.875810 0.340345 0.560617 0.061 Uiso 1 1 calc R . . . .
H26B H 0.786500 0.371468 0.492364 0.061 Uiso 1 1 calc R . . . .
C18 C 1.2894(3) 0.20738(14) 0.83656(9) 0.0557(5) Uani 1 1 d . . . . .
H18 H 1.394174 0.211331 0.863719 0.067 Uiso 1 1 calc R . . . .
C9 C 0.4705(2) 0.37630(13) 0.44373(9) 0.0513(5) Uani 1 1 d . . . . .
H9 H 0.568949 0.362808 0.428093 0.062 Uiso 1 1 calc R . . . .
C11 C 0.1749(3) 0.41832(14) 0.42367(10) 0.0622(6) Uani 1 1 d . . . . .
H11 H 0.077385 0.435361 0.395141 0.075 Uiso 1 1 calc R . . . .
C21 C 1.2380(3) 0.53346(14) 0.86013(10) 0.0597(5) Uani 1 1 d . . . . .
H21 H 1.342369 0.532030 0.887679 0.072 Uiso 1 1 calc R . . . .
C16 C 1.0778(3) 0.11677(14) 0.77058(11) 0.0614(5) Uani 1 1 d . . . . .
H16 H 1.038428 0.059193 0.753101 0.074 Uiso 1 1 calc R . . . .
C10 C 0.3247(3) 0.39920(15) 0.40257(10) 0.0605(5) Uani 1 1 d . . . . .
H10 H 0.326259 0.401992 0.359253 0.073 Uiso 1 1 calc R . . . .
C17 C 1.2321(3) 0.12176(15) 0.81114(11) 0.0640(6) Uani 1 1 d . . . . .
H17 H 1.297134 0.067777 0.821311 0.077 Uiso 1 1 calc R . . . .
C23 C 1.0019(3) 0.61942(14) 0.80524(11) 0.0634(6) Uani 1 1 d . . . . .
H23 H 0.945857 0.676311 0.795270 0.076 Uiso 1 1 calc R . . . .
C22 C 1.1557(3) 0.61806(15) 0.84590(11) 0.0683(6) Uani 1 1 d . . . . .
H22 H 1.203962 0.673689 0.863706 0.082 Uiso 1 1 calc R . . . .
C27 C 0.7753(3) 0.22878(16) 0.50544(10) 0.0696(6) Uani 1 1 d . . . . .
H27A H 0.678695 0.220273 0.471201 0.084 Uiso 1 1 calc R . . . .
H27B H 0.877284 0.217883 0.487972 0.084 Uiso 1 1 calc R . . . .
C29 C 0.7708(3) 0.05602(16) 0.53141(11) 0.0711(6) Uani 1 1 d . . . . .
H29A H 0.683538 0.049515 0.493695 0.085 Uiso 1 1 calc R . . . .
H29B H 0.879615 0.045935 0.518575 0.085 Uiso 1 1 calc R . . . .
C28 C 0.7665(3) 0.15580(16) 0.55485(10) 0.0701(6) Uani 1 1 d . . . . .
H28A H 0.662564 0.164913 0.571373 0.084 Uiso 1 1 calc R . . . .
H28B H 0.861224 0.164979 0.589731 0.084 Uiso 1 1 calc R . . . .
C30 C 0.7461(4) -0.01990(19) 0.57643(13) 0.0908(8) Uani 1 1 d . . . . .
H30A H 0.637257 -0.010323 0.589328 0.109 Uiso 1 1 calc R . . . .
H30B H 0.833632 -0.014068 0.614132 0.109 Uiso 1 1 calc R . . . .
C31 C 0.7509(4) -0.11890(19) 0.55106(16) 0.1103(10) Uani 1 1 d . . . . .
H31A H 0.680385 -0.122645 0.509695 0.165 Uiso 1 1 calc GR . . . .
H31B H 0.709755 -0.161999 0.579307 0.165 Uiso 1 1 calc GR . . . .
H31C H 0.865766 -0.134978 0.548054 0.165 Uiso 1 1 calc GR . . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -5 0.1744
-1 5 -3 0.3260
1 -5 1 0.2299
0 4 5 0.2213
0 0 1 0.3530
5 2 -1 0.0535
-5 -2 1 0.0395
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
C7 N1 C8 120.21(14) . . ?
C7 N1 C26 121.08(13) . . ?
C8 N1 C26 118.70(14) . . ?
C20 O2 C19 118.20(14) . . ?
C14 N2 C5 120.30(14) . . ?
C14 N2 C25 119.57(14) . . ?
C25 N2 C5 119.68(14) . . ?
N1 C7 C2 120.69(14) . . ?
N1 C7 C6 121.63(15) . . ?
C6 C7 C2 117.67(15) . . ?
C7 C2 C1 120.95(15) . . ?
C3 C2 C7 119.79(15) . . ?
C3 C2 C1 119.24(16) . . ?
N1 C8 C13 120.83(15) . . ?
N1 C8 C9 121.16(16) . . ?
C13 C8 C9 118.00(15) . . ?
C8 C13 C1 121.23(14) . . ?
C12 C13 C8 119.39(16) . . ?
C12 C13 C1 119.38(16) . . ?
O1 C1 C2 122.14(17) . . ?
O1 C1 C13 122.49(16) . . ?
C13 C1 C2 115.35(15) . . ?
C5 C6 C7 120.44(17) . . ?
C6 C5 N2 118.45(18) . . ?
C6 C5 C4 121.77(16) . . ?
C4 C5 N2 119.77(17) . . ?
N2 C14 C19 119.19(15) . . ?
C15 C14 N2 123.17(16) . . ?
C15 C14 C19 117.63(16) . . ?
C4 C3 C2 121.51(17) . . ?
C20 C25 N2 119.20(15) . . ?
C24 C25 N2 123.45(16) . . ?
C24 C25 C20 117.35(16) . . ?
O2 C19 C14 121.74(15) . . ?
C18 C19 O2 117.05(16) . . ?
C18 C19 C14 121.21(17) . . ?
C3 C4 C5 118.69(17) . . ?
O2 C20 C25 121.77(15) . . ?
C21 C20 O2 117.04(16) . . ?
C21 C20 C25 121.19(17) . . ?
C11 C12 C13 121.63(19) . . ?
C16 C15 C14 121.09(18) . . ?
C23 C24 C25 121.23(17) . . ?
N1 C26 C27 113.06(16) . . ?
C19 C18 C17 120.37(18) . . ?
C10 C9 C8 120.49(19) . . ?
C12 C11 C10 118.69(17) . . ?
C20 C21 C22 120.46(18) . . ?
C17 C16 C15 120.31(19) . . ?
C9 C10 C11 121.69(19) . . ?
C16 C17 C18 119.39(18) . . ?
C22 C23 C24 120.42(18) . . ?
C23 C22 C21 119.31(18) . . ?
C28 C27 C26 115.90(18) . . ?
C30 C29 C28 117.0(2) . . ?
C27 C28 C29 114.30(19) . . ?
C29 C30 C31 115.4(2) . . ?
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 C7 1.386(2) . ?
N1 C8 1.392(2) . ?
N1 C26 1.473(2) . ?
O1 C1 1.236(2) . ?
O2 C19 1.383(2) . ?
O2 C20 1.380(2) . ?
N2 C5 1.441(2) . ?
N2 C14 1.396(2) . ?
N2 C25 1.398(2) . ?
C7 C2 1.414(2) . ?
C7 C6 1.414(2) . ?
C2 C1 1.457(2) . ?
C2 C3 1.401(2) . ?
C8 C13 1.404(2) . ?
C8 C9 1.412(3) . ?
C13 C1 1.456(3) . ?
C13 C12 1.403(2) . ?
C6 C5 1.369(3) . ?
C5 C4 1.391(3) . ?
C14 C19 1.396(2) . ?
C14 C15 1.382(2) . ?
C3 C4 1.365(3) . ?
C25 C20 1.396(2) . ?
C25 C24 1.386(2) . ?
C19 C18 1.367(2) . ?
C20 C21 1.367(3) . ?
C12 C11 1.366(3) . ?
C15 C16 1.379(3) . ?
C24 C23 1.376(3) . ?
C26 C27 1.519(3) . ?
C18 C17 1.376(3) . ?
C9 C10 1.366(3) . ?
C11 C10 1.383(3) . ?
C21 C22 1.377(3) . ?
C16 C17 1.375(3) . ?
C23 C22 1.371(3) . ?
C27 C28 1.492(3) . ?
C29 C28 1.506(3) . ?
C29 C30 1.483(3) . ?
C30 C31 1.511(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341181
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0005 -0.9992 -4.9952 -0.0342 0.1571 -0.0708
-0.9988 4.9966 -2.9965 -0.0008 -0.0791 -0.2786
0.9990 -4.9966 0.9983 -0.0171 0.1283 0.2363
-0.0007 3.9966 4.9950 0.0026 -0.2589 -0.0343
-0.0001 0.0000 0.9991 0.0090 -0.0246 0.0212
4.9937 1.9941 -1.0049 -0.4246 -0.1268 0.1092
-4.9937 -1.9941 1.0049 0.4246 0.1268 -0.1092
