#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/38/7233839.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_7233839
loop_
_publ_author_name
'Andrea Cappelli'
'Francesca Villafiorita-Monteleone'
'Giorgio Grisci'
'Marco Paolino'
'Vincenzo Razzano'
'Giuseppe Fabio'
'Germano Giuliani'
'Alessandro Donati'
'Raniero Mendichi'
'Antonella Caterina Boccia'
'Mariacecilia Pasini'
'Chiara Botta'
_publ_section_title
;
 Highly emissive supramolecular assemblies based on pi-stacked
 polybenzofulvene hosts and a benzothiadiazole guest
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              7897
_journal_page_last               7905
_journal_paper_doi               10.1039/C4TC01200C
_journal_volume                  2
_journal_year                    2014
_chemical_formula_moiety         'C19 H15 Br O4'
_chemical_formula_sum            'C19 H15 Br O4'
_chemical_formula_weight         387.22
_chemical_name_systematic
;
Ethyl 3-(4-bromophenyl)-6-methoxy-1-oxo-1H-indene-
2-carboxylate
;
_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
_cell_angle_alpha                109.556(5)
_cell_angle_beta                 92.680(4)
_cell_angle_gamma                93.696(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8350(4)
_cell_length_b                   8.8813(5)
_cell_length_c                   11.3291(6)
_cell_measurement_reflns_used    2073
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0295
_cell_measurement_theta_min      2.3115
_cell_volume                     833.72(8)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0827
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.1064
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6259
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.093
_diffrn_reflns_theta_min         2.316
_exptl_absorpt_coefficient_mu    2.485
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             392
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.777
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.777
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0382
_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)+(0.0372P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                1769
_reflns_number_total             3767
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000002.cif
_cod_data_source_block           PCOD1000002
_cod_database_code               7233839
_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
C3 C 0.2220(3) -0.3179(3) 0.5264(3) 0.0354(7) Uani 1 1 d . . . . .
C2 C 0.1997(3) -0.4459(3) 0.5662(3) 0.0372(7) Uani 1 1 d . . . . .
C1 C 0.1590(3) -0.3883(3) 0.6995(3) 0.0423(8) Uani 1 1 d . . . . .
O1 O 0.1321(3) -0.4660(2) 0.7673(2) 0.0645(6) Uani 1 1 d . . . . .
C9 C 0.1607(3) -0.2091(3) 0.7353(3) 0.0357(7) Uani 1 1 d . . . . .
C8 C 0.1369(3) -0.0959(3) 0.8472(3) 0.0445(8) Uani 1 1 d . . . . .
H5 H 0.1152 -0.1242 0.9169 0.053 Uiso 1 1 calc R U . . .
C7 C 0.1465(3) 0.0655(3) 0.8533(3) 0.0413(7) Uani 1 1 d . . . . .
C6 C 0.1818(3) 0.1072(3) 0.7509(3) 0.0431(8) Uani 1 1 d . . . . .
H7 H 0.1884 0.2145 0.7570 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2081(3) -0.0108(3) 0.6376(3) 0.0421(8) Uani 1 1 d . . . . .
H8 H 0.2322 0.0169 0.5680 0.051 Uiso 1 1 calc R U . . .
C4 C 0.1972(3) -0.1691(3) 0.6313(3) 0.0349(7) Uani 1 1 d . . . . .
C10 C 0.2063(3) -0.6172(3) 0.4949(3) 0.0430(8) Uani 1 1 d . . . . .
O2 O 0.1809(3) -0.7213(3) 0.5360(2) 0.0870(8) Uani 1 1 d . . . . .
O3 O 0.2388(4) -0.6468(3) 0.3802(3) 0.1102(11) Uani 1 1 d . . . . .
C11 C 0.2627(5) -0.8113(4) 0.3036(4) 0.1085(17) Uani 1 1 d . . . . .
H11A H 0.2640 -0.8780 0.3561 0.130 Uiso 1 1 calc R U . . .
H11B H 0.1793 -0.8538 0.2396 0.130 Uiso 1 1 calc R U . . .
C12 C 0.3969(5) -0.8159(5) 0.2477(6) 0.143(2) Uani 1 1 d . . . . .
H12A H 0.4105 -0.7256 0.2196 0.214 Uiso 1 1 calc R U . . .
H12B H 0.3949 -0.9133 0.1771 0.214 Uiso 1 1 calc R U . . .
H12C H 0.4794 -0.8122 0.3070 0.214 Uiso 1 1 calc R U . . .
O4 O 0.1183(2) 0.1711(2) 0.9674(2) 0.0580(6) Uani 1 1 d . . . . .
C13 C 0.1390(4) 0.3404(3) 0.9872(3) 0.0625(10) Uani 1 1 d . . . . .
H13A H 0.2423 0.3684 0.9747 0.094 Uiso 1 1 calc R U . . .
H13B H 0.1167 0.4000 1.0714 0.094 Uiso 1 1 calc R U . . .
H13C H 0.0716 0.3655 0.9288 0.094 Uiso 1 1 calc R U . . .
C1' C 0.2708(3) -0.3105(3) 0.4058(3) 0.0341(7) Uani 1 1 d . . . . .
C2' C 0.4090(3) -0.3607(3) 0.3618(3) 0.0424(8) Uani 1 1 d . . . . .
H2' H 0.4718 -0.4037 0.4083 0.051 Uiso 1 1 calc R U . . .
C3' C 0.4559(3) -0.3488(3) 0.2510(3) 0.0459(8) Uani 1 1 d . . . . .
H3' H 0.5490 -0.3835 0.2230 0.055 Uiso 1 1 calc R U . . .
C4' C 0.3643(3) -0.2854(3) 0.1824(3) 0.0404(7) Uani 1 1 d . . . . .
Br1 Br 0.42635(4) -0.26859(4) 0.02931(3) 0.06780(16) Uani 1 1 d . . . . .
C5' C 0.2265(3) -0.2343(3) 0.2233(3) 0.0445(8) Uani 1 1 d . . . . .
H5' H 0.1645 -0.1919 0.1759 0.053 Uiso 1 1 calc R U . . .
C6' C 0.1801(3) -0.2459(3) 0.3348(3) 0.0441(8) Uani 1 1 d . . . . .
H6' H 0.0872 -0.2101 0.3627 0.053 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C2 C3 C1' 130.2(2) . .
C2 C3 C4 108.8(2) . .
C1' C3 C4 120.9(2) . .
C3 C2 C10 128.6(3) . .
C3 C2 C1 109.2(2) . .
C10 C2 C1 122.1(2) . .
O1 C1 C2 128.6(3) . .
O1 C1 C9 126.2(3) . .
C2 C1 C9 105.2(2) . .
C8 C9 C4 122.1(3) . .
C8 C9 C1 130.1(3) . .
C4 C9 C1 107.7(2) . .
C9 C8 C7 117.5(3) . .
C9 C8 H5 121.2 . .
C7 C8 H5 121.2 . .
O4 C7 C6 124.8(3) . .
O4 C7 C8 114.1(3) . .
C6 C7 C8 121.1(3) . .
C7 C6 C5 120.4(3) . .
C7 C6 H7 119.8 . .
C5 C6 H7 119.8 . .
C4 C5 C6 118.5(3) . .
C4 C5 H8 120.7 . .
C6 C5 H8 120.7 . .
C5 C4 C9 120.3(3) . .
C5 C4 C3 130.6(3) . .
C9 C4 C3 109.1(2) . .
O2 C10 O3 121.5(3) . .
O2 C10 C2 124.2(3) . .
O3 C10 C2 114.2(3) . .
C10 O3 C11 119.1(3) . .
C12 C11 O3 110.6(3) . .
C12 C11 H11A 109.5 . .
O3 C11 H11A 109.5 . .
C12 C11 H11B 109.5 . .
O3 C11 H11B 109.5 . .
H11A C11 H11B 108.1 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C7 O4 C13 118.6(2) . .
O4 C13 H13A 109.5 . .
O4 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
O4 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C2' C1' C6' 117.9(3) . .
C2' C1' C3 122.0(2) . .
C6' C1' C3 120.1(2) . .
C3' C2' C1' 121.7(3) . .
C3' C2' H2' 119.2 . .
C1' C2' H2' 119.2 . .
C4' C3' C2' 119.4(3) . .
C4' C3' H3' 120.3 . .
C2' C3' H3' 120.3 . .
C3' C4' C5' 120.5(3) . .
C3' C4' Br1 120.1(2) . .
C5' C4' Br1 119.4(2) . .
C4' C5' C6' 120.0(3) . .
C4' C5' H5' 120.0 . .
C6' C5' H5' 120.0 . .
C5' C6' C1' 120.6(3) . .
C5' C6' H6' 119.7 . .
C1' C6' H6' 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C3 C2 1.363(3) .
C3 C1' 1.472(4) .
C3 C4 1.488(4) .
C2 C10 1.471(4) .
C2 C1 1.493(4) .
C1 O1 1.213(3) .
C1 C9 1.504(4) .
C9 C8 1.365(4) .
C9 C4 1.385(4) .
C8 C7 1.408(3) .
C8 H5 0.9300 .
C7 O4 1.364(3) .
C7 C6 1.374(4) .
C6 C5 1.399(4) .
C6 H7 0.9300 .
C5 C4 1.381(3) .
C5 H8 0.9300 .
C10 O2 1.180(3) .
C10 O3 1.288(4) .
O3 C11 1.463(4) .
C11 C12 1.367(5) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
O4 C13 1.441(3) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C1' C2' 1.385(4) .
C1' C6' 1.388(4) .
C2' C3' 1.374(4) .
C2' H2' 0.9300 .
C3' C4' 1.367(4) .
C3' H3' 0.9300 .
C4' C5' 1.374(4) .
C4' Br1 1.893(3) .
C5' C6' 1.380(4) .
C5' H5' 0.9300 .
C6' H6' 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
C1' C3 C2 C10 -5.5(5) . . . .
C4 C3 C2 C10 177.8(3) . . . .
C1' C3 C2 C1 176.7(3) . . . .
C4 C3 C2 C1 0.0(3) . . . .
C3 C2 C1 O1 -179.3(3) . . . .
C10 C2 C1 O1 2.7(5) . . . .
C3 C2 C1 C9 -0.4(3) . . . .
C10 C2 C1 C9 -178.4(2) . . . .
O1 C1 C9 C8 1.5(5) . . . .
C2 C1 C9 C8 -177.5(3) . . . .
O1 C1 C9 C4 179.6(3) . . . .
C2 C1 C9 C4 0.6(3) . . . .
C4 C9 C8 C7 1.8(4) . . . .
C1 C9 C8 C7 179.7(3) . . . .
C9 C8 C7 O4 178.7(2) . . . .
C9 C8 C7 C6 -1.4(4) . . . .
O4 C7 C6 C5 -179.7(3) . . . .
C8 C7 C6 C5 0.5(4) . . . .
C7 C6 C5 C4 0.1(4) . . . .
C6 C5 C4 C9 0.2(4) . . . .
C6 C5 C4 C3 -178.4(3) . . . .
C8 C9 C4 C5 -1.2(4) . . . .
C1 C9 C4 C5 -179.5(2) . . . .
C8 C9 C4 C3 177.7(2) . . . .
C1 C9 C4 C3 -0.7(3) . . . .
C2 C3 C4 C5 179.2(3) . . . .
C1' C3 C4 C5 2.1(4) . . . .
C2 C3 C4 C9 0.4(3) . . . .
C1' C3 C4 C9 -176.6(2) . . . .
C3 C2 C10 O2 -177.7(3) . . . .
C1 C2 C10 O2 -0.1(5) . . . .
C3 C2 C10 O3 0.5(5) . . . .
C1 C2 C10 O3 178.1(3) . . . .
O2 C10 O3 C11 -7.5(6) . . . .
C2 C10 O3 C11 174.3(3) . . . .
C10 O3 C11 C12 -128.8(5) . . . .
C6 C7 O4 C13 -5.5(4) . . . .
C8 C7 O4 C13 174.3(2) . . . .
C2 C3 C1' C2' -59.6(4) . . . .
C4 C3 C1' C2' 116.7(3) . . . .
C2 C3 C1' C6' 122.9(3) . . . .
C4 C3 C1' C6' -60.7(4) . . . .
C6' C1' C2' C3' -0.4(4) . . . .
C3 C1' C2' C3' -177.9(3) . . . .
C1' C2' C3' C4' 0.2(4) . . . .
C2' C3' C4' C5' -0.1(4) . . . .
C2' C3' C4' Br1 -179.8(2) . . . .
C3' C4' C5' C6' 0.4(4) . . . .
Br1 C4' C5' C6' -180.0(2) . . . .
C4' C5' C6' C1' -0.7(4) . . . .
C2' C1' C6' C5' 0.7(4) . . . .
C3 C1' C6' C5' 178.2(3) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168338793
