#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/99/2229968.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229968
loop_
_publ_author_name
'Afrakssou, Zahra'
'Kandri Rodi, Youssef'
'Capet, Frédéric'
'Essassi, El Mokhtar'
'El Ammari, Lahcen'
_publ_section_title
;
 1,3-Dibenzyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione
;
_journal_coeditor_code           DN2679
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1253
_journal_page_last               o1254
_journal_paper_doi               10.1107/S1600536811015078
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C29 H20 N2 O3'
_chemical_formula_moiety         'C29 H20 N2 O3'
_chemical_formula_sum            'C29 H20 N2 O3'
_chemical_formula_weight         444.47
_chemical_name_systematic
;
1,3-Dibenzyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1389(3)
_cell_length_b                   12.8748(4)
_cell_length_c                   21.5528(8)
_cell_measurement_reflns_used    2629
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.46
_cell_volume                     2258.45(14)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36228
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flat
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.177
_refine_ls_extinction_coef       0.0123(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+0.2421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2137
_reflns_number_total             2629
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2679.cif
_cod_data_source_block           I
_cod_database_code               2229968
_cod_database_fobs_code          2229968
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0570(3) 0.41604(19) 0.84012(11) 0.0512(6) Uani d . 1 1 . .
C C2 0.2441(3) 0.53761(17) 0.81399(10) 0.0420(5) Uani d . 1 1 . .
C C3 0.0919(3) 0.58851(17) 0.82177(9) 0.0375(5) Uani d . 1 1 . .
C C4 0.0807(3) 0.69572(17) 0.81222(9) 0.0387(5) Uani d . 1 1 . .
C C5 0.2294(3) 0.74849(19) 0.79858(10) 0.0439(5) Uani d . 1 1 . .
C C6 0.3764(3) 0.6961(2) 0.79119(12) 0.0508(6) Uani d . 1 1 . .
H H6 0.4711 0.7333 0.7818 0.061 Uiso calc R 1 1 . .
C C7 0.3851(3) 0.5888(2) 0.79761(11) 0.0503(6) Uani d . 1 1 . .
H H7 0.4829 0.5532 0.7910 0.060 Uiso calc R 1 1 . .
C C8 -0.0748(3) 0.75336(18) 0.80889(10) 0.0425(5) Uani d . 1 1 . .
C C9 -0.0669(3) 0.86723(18) 0.81962(10) 0.0471(6) Uani d . 1 1 . .
C C10 0.0803(3) 0.92029(19) 0.81274(10) 0.0507(6) Uani d . 1 1 . .
C C11 0.2320(4) 0.8639(2) 0.79481(12) 0.0546(6) Uani d . 1 1 . .
C C12 0.0849(5) 1.0278(2) 0.82132(12) 0.0674(8) Uani d . 1 1 . .
H H12 0.1826 1.0642 0.8158 0.081 Uiso calc R 1 1 . .
C C13 -0.0569(5) 1.0794(2) 0.83799(13) 0.0758(9) Uani d . 1 1 . .
H H13 -0.0538 1.1507 0.8449 0.091 Uiso calc R 1 1 . .
C C14 -0.2029(5) 1.0266(2) 0.84455(13) 0.0730(9) Uani d . 1 1 . .
H H14 -0.2975 1.0624 0.8558 0.088 Uiso calc R 1 1 . .
C C15 -0.2100(4) 0.9207(2) 0.83451(13) 0.0606(7) Uani d . 1 1 . .
H H15 -0.3095 0.8855 0.8377 0.073 Uiso calc R 1 1 . .
C C16 -0.1814(3) 0.5233(2) 0.86850(12) 0.0506(6) Uani d . 1 1 . .
H H16A -0.2310 0.4552 0.8728 0.061 Uiso calc R 1 1 . .
H H16B -0.2530 0.5651 0.8426 0.061 Uiso calc R 1 1 . .
C C17 -0.1677(3) 0.5729(2) 0.93142(12) 0.0590(7) Uani d . 1 1 . .
C C18 -0.0688(5) 0.5290(4) 0.97586(16) 0.1043(13) Uani d . 1 1 . .
H H18 -0.0091 0.4694 0.9667 0.125 Uiso calc R 1 1 . .
C C19 -0.0579(8) 0.5726(6) 1.0333(2) 0.155(2) Uani d . 1 1 . .
H H19 0.0095 0.5425 1.0631 0.186 Uiso calc R 1 1 . .
C C20 -0.1443(10) 0.6593(6) 1.0473(2) 0.164(3) Uani d . 1 1 . .
H H20 -0.1352 0.6888 1.0866 0.197 Uiso calc R 1 1 . .
C C21 -0.2439(9) 0.7032(4) 1.0045(3) 0.152(3) Uani d . 1 1 . .
H H21 -0.3042 0.7624 1.0140 0.183 Uiso calc R 1 1 . .
C C22 -0.2544(6) 0.6587(3) 0.94659(17) 0.1007(13) Uani d . 1 1 . .
H H22 -0.3230 0.6886 0.9171 0.121 Uiso calc R 1 1 . .
C C23 0.3437(3) 0.3524(2) 0.82695(13) 0.0583(7) Uani d . 1 1 . .
H H23A 0.4241 0.3652 0.7946 0.070 Uiso calc R 1 1 . .
H H23B 0.2925 0.2859 0.8184 0.070 Uiso calc R 1 1 . .
C C24 0.4309(3) 0.34610(19) 0.88834(12) 0.0522(6) Uani d . 1 1 . .
C C25 0.5405(5) 0.2681(3) 0.8964(2) 0.1062(14) Uani d . 1 1 . .
H H25 0.5582 0.2207 0.8645 0.127 Uiso calc R 1 1 . .
C C26 0.6266(7) 0.2583(5) 0.9517(3) 0.143(2) Uani d . 1 1 . .
H H26 0.7019 0.2045 0.9563 0.172 Uiso calc R 1 1 . .
C C27 0.6028(6) 0.3250(4) 0.9984(2) 0.1106(15) Uani d . 1 1 . .
H H27 0.6577 0.3162 1.0359 0.133 Uiso calc R 1 1 . .
C C28 0.4987(5) 0.4050(3) 0.99050(14) 0.0869(10) Uani d . 1 1 . .
H H28 0.4856 0.4536 1.0221 0.104 Uiso calc R 1 1 . .
C C29 0.4106(4) 0.4159(2) 0.93574(13) 0.0680(8) Uani d . 1 1 . .
H H29 0.3374 0.4709 0.9312 0.082 Uiso calc R 1 1 . .
N N1 -0.0211(2) 0.51260(15) 0.83808(8) 0.0440(5) Uani d . 1 1 . .
N N2 0.2183(2) 0.43334(15) 0.82446(9) 0.0484(5) Uani d . 1 1 . .
O O1 -0.0047(3) 0.33329(14) 0.85284(11) 0.0743(6) Uani d . 1 1 . .
O O2 0.3554(3) 0.91046(17) 0.77953(12) 0.0851(7) Uani d . 1 1 . .
O O3 -0.2048(2) 0.71168(14) 0.79558(9) 0.0562(5) Uani d . 1 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N2 . . 126.5(2) ?
O1 C1 N1 . . 127.0(2) ?
N2 C1 N1 . . 106.4(2) ?
C7 C2 N2 . . 129.7(2) ?
C7 C2 C3 . . 122.8(2) ?
N2 C2 C3 . . 107.4(2) ?
N1 C3 C4 . . 133.6(2) ?
N1 C3 C2 . . 106.54(18) ?
C4 C3 C2 . . 119.8(2) ?
C3 C4 C5 . . 116.6(2) ?
C3 C4 C8 . . 124.2(2) ?
C5 C4 C8 . . 118.87(18) ?
C6 C5 C4 . . 121.9(2) ?
C6 C5 C11 . . 117.9(2) ?
C4 C5 C11 . . 120.1(2) ?
C5 C6 C7 . . 121.2(2) ?
C5 C6 H6 . . 119.4 ?
C7 C6 H6 . . 119.4 ?
C2 C7 C6 . . 117.5(2) ?
C2 C7 H7 . . 121.3 ?
C6 C7 H7 . . 121.3 ?
O3 C8 C4 . . 122.4(2) ?
O3 C8 C9 . . 120.5(2) ?
C4 C8 C9 . . 117.0(2) ?
C10 C9 C15 . . 120.3(2) ?
C10 C9 C8 . . 120.5(2) ?
C15 C9 C8 . . 119.2(2) ?
C9 C10 C12 . . 119.8(3) ?
C9 C10 C11 . . 120.4(2) ?
C12 C10 C11 . . 119.8(3) ?
O2 C11 C10 . . 121.1(2) ?
O2 C11 C5 . . 121.3(3) ?
C10 C11 C5 . . 117.5(2) ?
C13 C12 C10 . . 119.3(3) ?
C13 C12 H12 . . 120.4 ?
C10 C12 H12 . . 120.4 ?
C14 C13 C12 . . 120.8(3) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 120.5(3) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C9 . . 119.3(3) ?
C14 C15 H15 . . 120.4 ?
C9 C15 H15 . . 120.4 ?
N1 C16 C17 . . 112.2(2) ?
N1 C16 H16A . . 109.2 ?
C17 C16 H16A . . 109.2 ?
N1 C16 H16B . . 109.2 ?
C17 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C22 C17 C18 . . 118.3(3) ?
C22 C17 C16 . . 121.8(3) ?
C18 C17 C16 . . 119.9(3) ?
C19 C18 C17 . . 120.2(5) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C20 C19 C18 . . 120.6(5) ?
C20 C19 H19 . . 119.7 ?
C18 C19 H19 . . 119.7 ?
C21 C20 C19 . . 120.2(5) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C20 C21 C22 . . 118.9(6) ?
C20 C21 H21 . . 120.6 ?
C22 C21 H21 . . 120.6 ?
C17 C22 C21 . . 121.8(5) ?
C17 C22 H22 . . 119.1 ?
C21 C22 H22 . . 119.1 ?
N2 C23 C24 . . 113.6(2) ?
N2 C23 H23A . . 108.8 ?
C24 C23 H23A . . 108.8 ?
N2 C23 H23B . . 108.8 ?
C24 C23 H23B . . 108.8 ?
H23A C23 H23B . . 107.7 ?
C25 C24 C29 . . 118.0(3) ?
C25 C24 C23 . . 117.6(3) ?
C29 C24 C23 . . 124.3(2) ?
C24 C25 C26 . . 120.7(4) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
C27 C26 C25 . . 120.9(4) ?
C27 C26 H26 . . 119.5 ?
C25 C26 H26 . . 119.5 ?
C26 C27 C28 . . 119.2(4) ?
C26 C27 H27 . . 120.4 ?
C28 C27 H27 . . 120.4 ?
C27 C28 C29 . . 120.7(4) ?
C27 C28 H28 . . 119.6 ?
C29 C28 H28 . . 119.6 ?
C24 C29 C28 . . 120.3(3) ?
C24 C29 H29 . . 119.8 ?
C28 C29 H29 . . 119.8 ?
C3 N1 C1 . . 109.50(19) ?
C3 N1 C16 . . 129.55(19) ?
C1 N1 C16 . . 118.3(2) ?
C1 N2 C2 . . 110.11(19) ?
C1 N2 C23 . . 122.9(2) ?
C2 N2 C23 . . 126.6(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.209(3) ?
C1 N2 . 1.374(3) ?
C1 N1 . 1.397(3) ?
C2 C7 . 1.370(3) ?
C2 N2 . 1.377(3) ?
C2 C3 . 1.412(3) ?
C3 N1 . 1.387(3) ?
C3 C4 . 1.398(3) ?
C4 C5 . 1.418(3) ?
C4 C8 . 1.469(3) ?
C5 C6 . 1.383(3) ?
C5 C11 . 1.488(4) ?
C6 C7 . 1.390(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 O3 . 1.220(3) ?
C8 C9 . 1.486(3) ?
C9 C10 . 1.387(4) ?
C9 C15 . 1.391(4) ?
C10 C12 . 1.396(4) ?
C10 C11 . 1.483(4) ?
C11 O2 . 1.215(3) ?
C12 C13 . 1.380(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.376(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.382(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 N1 . 1.467(3) ?
C16 C17 . 1.503(4) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C22 . 1.351(5) ?
C17 C18 . 1.373(5) ?
C18 C19 . 1.362(6) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.353(9) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.353(9) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.375(7) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
C23 N2 . 1.460(3) ?
C23 C24 . 1.504(4) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 C25 . 1.354(4) ?
C24 C29 . 1.371(4) ?
C25 C26 . 1.389(6) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.338(6) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.344(5) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.388(4) ?
C28 H28 . 0.9300 ?
C29 H29 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13 O1 1_565 0.93 2.39 3.312(3) 170.5
C23 H23A O2 3_646 0.97 2.47 3.439(4) 173.7
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656631
