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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/89/7218990.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_7218990
loop_
_publ_author_name
'Chamas, Zein'
'Marchi, Enrico'
'Presson, Benjamin'
'Aubert, Emmanuel'
'Fort, Yves'
'Ceroni, Paola'
'Mamane, Victor'
_publ_section_title
;
 Synthesis and Solid-state Fluorescence Properties of Pentacyclic
 7-Substituted-indeno[1’,2’:4,5]pyrido[2,1-a]isoindol-5-ones
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA12155D
_journal_year                    2014
_chemical_formula_moiety         'C25 H17 N O2'
_chemical_formula_sum            'C25 H17 N O2'
_chemical_formula_weight         363.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-10-06 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.472(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6552(3)
_cell_length_b                   8.1691(2)
_cell_length_c                   20.6721(6)
_cell_measurement_reflns_used    6072
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      76.1788
_cell_measurement_theta_min      4.2817
_cell_volume                     1742.28(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR_92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      109.95(10)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9695
_diffrn_reflns_theta_full        70.13
_diffrn_reflns_theta_max         70.13
_diffrn_reflns_theta_min         4.29
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.2276
_exptl_crystal_size_mid          0.1760
_exptl_crystal_size_min          0.0948
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0411P)²+0.9513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                3092
_reflns_number_total             3235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra12155d2.cif
_cod_data_source_block           bpxx
_cod_original_cell_volume        1742.28(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7218990
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O14 O 0.19305(8) 0.40206(11) 0.09486(4) 0.0214(2) Uani 1 1 d .
H14 H 0.1262 0.4305 0.0659 0.032 Uiso 1 1 calc R
O22 O 0.07552(8) 0.47120(11) -0.04593(4) 0.0205(2) Uani 1 1 d .
N1 N 0.26491(10) 0.34542(13) -0.05489(5) 0.0192(2) Uani 1 1 d .
C15 C 0.22271(13) 0.31966(15) -0.16876(6) 0.0214(3) Uani 1 1 d .
C3 C 0.43648(13) 0.21427(16) -0.09169(7) 0.0234(3) Uani 1 1 d .
H3 H 0.4692 0.1658 -0.1259 0.028 Uiso 1 1 calc R
C20 C 0.11829(13) 0.40037(15) -0.15329(6) 0.0206(3) Uani 1 1 d .
C21 C 0.14424(12) 0.41416(14) -0.07996(6) 0.0183(3) Uani 1 1 d .
C6 C 0.31152(12) 0.28397(15) 0.01316(6) 0.0184(3) Uani 1 1 d .
C2 C 0.31779(12) 0.28387(15) -0.10636(6) 0.0213(3) Uani 1 1 d .
C23 C 0.24589(11) 0.12019(15) 0.02132(6) 0.0183(3) Uani 1 1 d .
C5 C 0.45806(12) 0.25670(15) 0.02617(6) 0.0202(3) Uani 1 1 d .
C16 C 0.22197(13) 0.29057(16) -0.23533(7) 0.0250(3) Uani 1 1 d .
H16 H 0.2921 0.2359 -0.2468 0.030 Uiso 1 1 calc R
C27 C 0.21091(13) -0.10423(16) 0.09127(7) 0.0232(3) Uani 1 1 d .
H27 H 0.2244 -0.1522 0.1343 0.028 Uiso 1 1 calc R
C12 C 0.42495(13) 0.38404(15) 0.12118(6) 0.0213(3) Uani 1 1 d .
C17 C 0.11588(14) 0.34378(17) -0.28427(7) 0.0277(3) Uani 1 1 d .
H17 H 0.1136 0.3248 -0.3299 0.033 Uiso 1 1 calc R
C24 C 0.17008(12) 0.03728(16) -0.03372(6) 0.0213(3) Uani 1 1 d .
H24 H 0.1547 0.0854 -0.0768 0.026 Uiso 1 1 calc R
C28 C 0.26591(12) 0.04719(16) 0.08416(6) 0.0213(3) Uani 1 1 d .
H28 H 0.3174 0.1012 0.1223 0.026 Uiso 1 1 calc R
C11 C 0.45491(13) 0.43651(17) 0.18715(7) 0.0250(3) Uani 1 1 d .
H11 H 0.3948 0.4997 0.2037 0.030 Uiso 1 1 calc R
C9 C 0.66419(14) 0.30491(19) 0.20401(7) 0.0311(3) Uani 1 1 d .
H9 H 0.7457 0.2780 0.2330 0.037 Uiso 1 1 calc R
C7 C 0.51458(12) 0.29404(16) 0.09644(7) 0.0220(3) Uani 1 1 d .
C8 C 0.63547(13) 0.25450(17) 0.13780(7) 0.0273(3) Uani 1 1 d .
H8 H 0.6969 0.1944 0.1210 0.033 Uiso 1 1 calc R
C4 C 0.51299(13) 0.21447(16) -0.02339(7) 0.0228(3) Uani 1 1 d .
H4 H 0.6020 0.1848 -0.0134 0.027 Uiso 1 1 calc R
C26 C 0.13663(12) -0.18546(16) 0.03604(7) 0.0232(3) Uani 1 1 d .
H26 H 0.0996 -0.2890 0.0411 0.028 Uiso 1 1 calc R
C25 C 0.11678(12) -0.11473(16) -0.02632(7) 0.0238(3) Uani 1 1 d .
H25 H 0.0664 -0.1703 -0.0644 0.029 Uiso 1 1 calc R
C18 C 0.01227(14) 0.42445(18) -0.26826(7) 0.0280(3) Uani 1 1 d .
H18 H -0.0589 0.4601 -0.3030 0.034 Uiso 1 1 calc R
C19 C 0.01200(13) 0.45335(16) -0.20194(7) 0.0248(3) Uani 1 1 d .
H19 H -0.0585 0.5074 -0.1905 0.030 Uiso 1 1 calc R
C13 C 0.30184(12) 0.41340(15) 0.06775(6) 0.0197(3) Uani 1 1 d .
H13 H 0.3049 0.5257 0.0489 0.024 Uiso 1 1 calc R
C10 C 0.57429(14) 0.39489(18) 0.22838(7) 0.0300(3) Uani 1 1 d .
H10 H 0.5954 0.4280 0.2739 0.036 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C13 O14 H14 109.5
C21 N1 C2 111.78(10)
C21 N1 C6 124.25(10)
C2 N1 C6 119.95(10)
C16 C15 C20 119.85(12)
C16 C15 C2 132.13(12)
C20 C15 C2 108.02(11)
C2 C3 C4 119.18(12)
C2 C3 H3 120.4
C4 C3 H3 120.4
C19 C20 C15 122.38(12)
C19 C20 C21 129.22(12)
C15 C20 C21 108.40(11)
O22 C21 N1 124.94(11)
O22 C21 C20 129.24(12)
N1 C21 C20 105.81(10)
N1 C6 C5 107.78(10)
N1 C6 C23 110.52(10)
C5 C6 C23 108.99(10)
N1 C6 C13 113.21(10)
C5 C6 C13 102.65(10)
C23 C6 C13 113.20(10)
C3 C2 N1 120.50(12)
C3 C2 C15 133.50(12)
N1 C2 C15 105.97(11)
C24 C23 C28 118.29(11)
C24 C23 C6 121.28(11)
C28 C23 C6 120.37(11)
C4 C5 C7 131.43(12)
C4 C5 C6 121.43(12)
C7 C5 C6 107.05(10)
C17 C16 C15 118.01(12)
C17 C16 H16 121.0
C15 C16 H16 121.0
C26 C27 C28 120.50(12)
C26 C27 H27 119.8
C28 C27 H27 119.8
C11 C12 C7 120.72(12)
C11 C12 C13 127.93(12)
C7 C12 C13 111.35(11)
C16 C17 C18 121.65(12)
C16 C17 H17 119.2
C18 C17 H17 119.2
C25 C24 C23 120.88(12)
C25 C24 H24 119.6
C23 C24 H24 119.6
C27 C28 C23 120.48(12)
C27 C28 H28 119.8
C23 C28 H28 119.8
C10 C11 C12 118.62(13)
C10 C11 H11 120.7
C12 C11 H11 120.7
C8 C9 C10 120.62(13)
C8 C9 H9 119.7
C10 C9 H9 119.7
C8 C7 C12 120.52(12)
C8 C7 C5 130.57(12)
C12 C7 C5 108.91(11)
C9 C8 C7 118.56(13)
C9 C8 H8 120.7
C7 C8 H8 120.7
C5 C4 C3 119.88(12)
C5 C4 H4 120.1
C3 C4 H4 120.1
C25 C26 C27 119.48(12)
C25 C26 H26 120.3
C27 C26 H26 120.3
C26 C25 C24 120.36(12)
C26 C25 H25 119.8
C24 C25 H25 119.8
C19 C18 C17 120.70(13)
C19 C18 H18 119.6
C17 C18 H18 119.6
C20 C19 C18 117.41(12)
C20 C19 H19 121.3
C18 C19 H19 121.3
O14 C13 C12 110.44(10)
O14 C13 C6 116.73(10)
C12 C13 C6 102.61(10)
O14 C13 H13 108.9
C12 C13 H13 108.9
C6 C13 H13 108.9
C11 C10 C9 120.94(13)
C11 C10 H10 119.5
C9 C10 H10 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O14 C13 1.4109(15)
O14 H14 0.8400
O22 C21 1.2272(15)
N1 C21 1.3799(16)
N1 C2 1.4147(16)
N1 C6 1.4589(16)
C15 C16 1.3945(18)
C15 C20 1.3974(18)
C15 C2 1.4570(19)
C3 C2 1.3502(19)
C3 C4 1.4432(19)
C3 H3 0.9500
C20 C19 1.3828(19)
C20 C21 1.4756(17)
C6 C5 1.5330(17)
C6 C23 1.5383(17)
C6 C13 1.5685(17)
C23 C24 1.3951(18)
C23 C28 1.3964(18)
C5 C4 1.3456(18)
C5 C7 1.4590(18)
C16 C17 1.385(2)
C16 H16 0.9500
C27 C26 1.3851(19)
C27 C28 1.3922(18)
C27 H27 0.9500
C12 C11 1.3884(18)
C12 C7 1.3995(18)
C12 C13 1.5080(18)
C17 C18 1.395(2)
C17 H17 0.9500
C24 C25 1.3898(18)
C24 H24 0.9500
C28 H28 0.9500
C11 C10 1.385(2)
C11 H11 0.9500
C9 C8 1.388(2)
C9 C10 1.397(2)
C9 H9 0.9500
C7 C8 1.3943(19)
C8 H8 0.9500
C4 H4 0.9500
C26 C25 1.3799(19)
C26 H26 0.9500
C25 H25 0.9500
C18 C19 1.3919(19)
C18 H18 0.9500
C19 H19 0.9500
C13 H13 1.0000
C10 H10 0.9500
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
C16 C15 C20 C19 0.2(2)
C2 C15 C20 C19 179.10(12)
C16 C15 C20 C21 179.86(11)
C2 C15 C20 C21 -1.23(14)
C2 N1 C21 O22 177.35(12)
C6 N1 C21 O22 20.06(19)
C2 N1 C21 C20 -1.64(13)
C6 N1 C21 C20 -158.94(11)
C19 C20 C21 O22 2.5(2)
C15 C20 C21 O22 -177.17(12)
C19 C20 C21 N1 -178.60(13)
C15 C20 C21 N1 1.77(13)
C21 N1 C6 C5 -166.63(11)
C2 N1 C6 C5 37.82(14)
C21 N1 C6 C23 74.37(14)
C2 N1 C6 C23 -81.19(13)
C21 N1 C6 C13 -53.81(15)
C2 N1 C6 C13 150.63(11)
C4 C3 C2 N1 -4.67(19)
C4 C3 C2 C15 172.68(13)
C21 N1 C2 C3 178.92(12)
C6 N1 C2 C3 -22.69(18)
C21 N1 C2 C15 0.92(14)
C6 N1 C2 C15 159.31(10)
C16 C15 C2 C3 1.4(3)
C20 C15 C2 C3 -177.37(14)
C16 C15 C2 N1 178.98(13)
C20 C15 C2 N1 0.25(14)
N1 C6 C23 C24 9.48(15)
C5 C6 C23 C24 -108.79(13)
C13 C6 C23 C24 137.67(12)
N1 C6 C23 C28 -173.44(11)
C5 C6 C23 C28 68.28(14)
C13 C6 C23 C28 -45.26(15)
N1 C6 C5 C4 -30.90(16)
C23 C6 C5 C4 89.08(14)
C13 C6 C5 C4 -150.65(12)
N1 C6 C5 C7 146.02(10)
C23 C6 C5 C7 -94.00(12)
C13 C6 C5 C7 26.28(12)
C20 C15 C16 C17 -0.01(19)
C2 C15 C16 C17 -178.61(13)
C15 C16 C17 C18 0.1(2)
C28 C23 C24 C25 -0.56(18)
C6 C23 C24 C25 176.58(11)
C26 C27 C28 C23 0.67(19)
C24 C23 C28 C27 -0.21(18)
C6 C23 C28 C27 -177.37(11)
C7 C12 C11 C10 -1.39(19)
C13 C12 C11 C10 179.59(12)
C11 C12 C7 C8 0.41(19)
C13 C12 C7 C8 179.58(12)
C11 C12 C7 C5 -179.60(11)
C13 C12 C7 C5 -0.43(14)
C4 C5 C7 C8 -20.4(2)
C6 C5 C7 C8 163.11(13)
C4 C5 C7 C12 159.62(14)
C6 C5 C7 C12 -16.88(14)
C10 C9 C8 C7 -0.7(2)
C12 C7 C8 C9 0.6(2)
C5 C7 C8 C9 -179.35(13)
C7 C5 C4 C3 -168.20(13)
C6 C5 C4 C3 7.88(19)
C2 C3 C4 C5 11.72(19)
C28 C27 C26 C25 -0.35(19)
C27 C26 C25 C24 -0.42(19)
C23 C24 C25 C26 0.88(19)
C16 C17 C18 C19 -0.4(2)
C15 C20 C19 C18 -0.5(2)
C21 C20 C19 C18 179.96(12)
C17 C18 C19 C20 0.5(2)
C11 C12 C13 O14 -38.99(17)
C7 C12 C13 O14 141.91(11)
C11 C12 C13 C6 -164.10(12)
C7 C12 C13 C6 16.80(13)
N1 C6 C13 O14 97.91(12)
C5 C6 C13 O14 -146.19(10)
C23 C6 C13 O14 -28.87(15)
N1 C6 C13 C12 -141.21(10)
C5 C6 C13 C12 -25.31(12)
C23 C6 C13 C12 92.01(11)
C12 C11 C10 C9 1.3(2)
C8 C9 C10 C11 -0.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199588
