#------------------------------------------------------------------------------
#$Date: 2022-01-06 23:13:27 +0200 (Thu, 06 Jan 2022) $
#$Revision: 271832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/37/7243723.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_7243723
loop_
_publ_author_name
'Liu, Ying-Hsuan'
'Dadvand, Afshin'
'Titi, Hatem M.'
'Hamzehpoor, Ehsan'
'Perepichka, Dmitrii F.'
_publ_section_title
;
 Halogen bonding vs. π-stacking interactions in new
 bis(acenaphthylene)dione semiconductors
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              8255
_journal_page_last               8259
_journal_paper_doi               10.1039/D1CE01047F
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C24 H8 Cl4 O2'
_chemical_formula_weight         470.10
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-06-01 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                88.717(5)
_cell_angle_beta                 89.773(6)
_cell_angle_gamma                78.865(6)
_cell_formula_units_Z            1
_cell_length_a                   3.8349(4)
_cell_length_b                   8.8365(7)
_cell_length_c                   13.2606(9)
_cell_measurement_reflns_used    1613
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.447
_cell_measurement_theta_min      3.334
_cell_volume                     440.79(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12693
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.447
_diffrn_reflns_theta_min         3.334
_exptl_absorpt_coefficient_mu    6.291
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.7536
_exptl_transmission_factor_min   0.4965
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0331
_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)+(0.0692P)²+0.1386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1613
_reflns_number_total             1722
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01047f2.cif
_cod_data_source_block           s1
_cod_depositor_comments
'Adding full bibliography for 7243723--7243725.cif.'
_cod_database_code               7243723
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_min   0.188
_shelx_estimated_absorpt_t_max   0.834
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
C1 C 0.9265(4) 0.48541(17) 0.04576(11) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.7175(4) 0.61071(18) 0.11240(12) 0.0299(4) Uani 1 1 d . . . . .
C3 C 0.6145(4) 0.53376(18) 0.20381(12) 0.0269(3) Uani 1 1 d . . . . .
C4 C 0.7400(4) 0.37472(17) 0.19588(11) 0.0242(3) Uani 1 1 d . . . . .
C5 C 0.9268(4) 0.33870(17) 0.10277(11) 0.0245(3) Uani 1 1 d . . . . .
C6 C 1.0582(5) 0.18421(19) 0.08766(13) 0.0338(4) Uani 1 1 d . . . . .
H6 H 1.180259 0.153148 0.028609 0.041 Uiso 1 1 calc R U . . .
C7 C 1.0079(5) 0.07397(19) 0.16118(14) 0.0352(4) Uani 1 1 d . . . . .
H7 H 1.099430 -0.029354 0.149069 0.042 Uiso 1 1 calc R U . . .
C8 C 0.8308(4) 0.11057(19) 0.24999(12) 0.0307(4) Uani 1 1 d . . . . .
C9 C 0.6846(4) 0.26745(18) 0.27182(11) 0.0265(3) Uani 1 1 d . . . . .
C10 C 0.4907(4) 0.3347(2) 0.35760(12) 0.0297(3) Uani 1 1 d . . . . .
C11 C 0.3709(4) 0.4917(2) 0.36418(12) 0.0332(4) Uani 1 1 d . . . . .
H11 H 0.246851 0.530489 0.421386 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4310(4) 0.5940(2) 0.28713(13) 0.0325(4) Uani 1 1 d . . . . .
H12 H 0.349015 0.699683 0.292269 0.039 Uiso 1 1 calc R U . . .
Cl1 Cl 0.38834(13) 0.22513(5) 0.45934(3) 0.04481(19) Uani 1 1 d . . . . .
Cl2 Cl 0.79668(13) -0.04139(5) 0.33117(4) 0.0496(2) Uani 1 1 d . . . . .
O1 O 0.6396(5) 0.74782(15) 0.09571(11) 0.0568(4) Uani 1 1 d . . . . .
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'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 C5 131.34(18) 2_765 . ?
C1 C1 C2 123.97(17) 2_765 . ?
C5 C1 C2 104.69(12) . . ?
O1 C2 C3 124.12(15) . . ?
O1 C2 C1 128.59(15) . . ?
C3 C2 C1 107.28(13) . . ?
C12 C3 C4 121.29(15) . . ?
C12 C3 C2 130.33(15) . . ?
C4 C3 C2 108.38(13) . . ?
C3 C4 C9 122.63(14) . . ?
C3 C4 C5 111.43(14) . . ?
C9 C4 C5 125.94(14) . . ?
C6 C5 C4 115.70(14) . . ?
C6 C5 C1 136.10(14) . . ?
C4 C5 C1 108.21(13) . . ?
C5 C6 C7 120.11(15) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 123.39(16) . . ?
C8 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
C7 C8 C9 120.36(15) . . ?
C7 C8 Cl2 116.59(13) . . ?
C9 C8 Cl2 123.06(12) . . ?
C4 C9 C8 114.50(14) . . ?
C4 C9 C10 114.46(14) . . ?
C8 C9 C10 131.04(15) . . ?
C11 C10 C9 122.01(15) . . ?
C11 C10 Cl1 115.49(12) . . ?
C9 C10 Cl1 122.50(13) . . ?
C10 C11 C12 121.70(15) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C3 C12 C11 117.90(15) . . ?
C3 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
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
C1 C1 1.376(3) 2_765 ?
C1 C5 1.486(2) . ?
C1 C2 1.531(2) . ?
C2 O1 1.206(2) . ?
C2 C3 1.467(2) . ?
C3 C12 1.369(2) . ?
C3 C4 1.401(2) . ?
C4 C9 1.411(2) . ?
C4 C5 1.436(2) . ?
C5 C6 1.380(2) . ?
C6 C7 1.402(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.427(2) . ?
C8 Cl2 1.7266(17) . ?
C9 C10 1.433(2) . ?
C10 C11 1.379(2) . ?
C10 Cl1 1.7309(17) . ?
C11 C12 1.397(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
