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#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/40/7124074.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_7124074
loop_
_publ_author_name
'Morgan, Matthew M.'
'Nazari, Maryam'
'Pickl, Thomas'
'Rautiainen, J. Mikko'
'Tuononen, Heikki M.'
'Piers, Warren E.'
'Welch, Gregory C.'
'Gelfand, Benjamin S.'
_publ_section_title
;
 Boron--nitrogen substituted dihydroindeno[1,2-b]fluorene derivatives as
 acceptors in organic solar cells
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05103A
_journal_year                    2019
_chemical_formula_moiety         'C24 H26 B2 N2 Cl4'
_chemical_formula_sum            'C24 H26 B2 Cl4 N2'
_chemical_formula_weight         505.89
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-28 deposited with the CCDC.    2019-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                92.380(7)
_cell_angle_beta                 94.987(7)
_cell_angle_gamma                108.870(6)
_cell_formula_units_Z            1
_cell_length_a                   5.8598(9)
_cell_length_b                   6.8679(10)
_cell_length_c                   17.032(3)
_cell_measurement_reflns_used    2552
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.45
_cell_volume                     644.38(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'LinXTL v. 5.9.8 (Spasyuk, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.1271
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6197
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.642
_diffrn_reflns_theta_min         3.612
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             262
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     135
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0804
_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)+(0.1123P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1887
_refine_ls_wR_factor_ref         0.2176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1857
_reflns_number_total             2914
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc05103a2.cif
_cod_data_source_block           MM180208_0m
_cod_original_cell_volume        644.37(17)
_cod_database_code               7124074
_shelx_shelxl_version_number     2014/7
_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   0.911
_shelx_estimated_absorpt_t_max   0.954
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
Cl1 Cl 0.66972(17) 0.75642(15) 0.43863(7) 0.0284(3) Uani 1 1 d . U
Cl2 Cl 0.30125(18) 0.93048(14) 0.36123(7) 0.0301(3) Uani 1 1 d . U
N1 N 0.1724(5) 0.6026(4) 0.4562(2) 0.0200(7) Uani 1 1 d . U
C3 C 0.0542(7) 0.3632(6) 0.3478(2) 0.0225(8) Uani 1 1 d . U
C2 C 0.0066(6) 0.4195(5) 0.4251(2) 0.0199(8) Uani 1 1 d . U
C1 C 0.1703(7) 0.6813(6) 0.5270(2) 0.0224(8) Uani 1 1 d . U
H1 H 0.2878 0.8058 0.5458 0.027 Uiso 1 1 calc R U
C4 C 0.2626(7) 0.5097(6) 0.3260(3) 0.0254(9) Uani 1 1 d . U
C7 C 0.0133(8) 0.1635(7) 0.2280(3) 0.0302(10) Uani 1 1 d . U
H7 H -0.0712 0.0479 0.1942 0.036 Uiso 1 1 calc R U
C8 C -0.0739(7) 0.1897(6) 0.2974(3) 0.0267(9) Uani 1 1 d . U
H8 H -0.2155 0.0945 0.3110 0.032 Uiso 1 1 calc R U
C5 C 0.3473(8) 0.4772(7) 0.2563(3) 0.0307(10) Uani 1 1 d . U
H5 H 0.4886 0.5726 0.2426 0.037 Uiso 1 1 calc R U
C6 C 0.2262(8) 0.3035(6) 0.2051(3) 0.0289(9) Uani 1 1 d . U
C9 C 0.3142(9) 0.2619(8) 0.1263(3) 0.0415(12) Uani 1 1 d . U
C10 C 0.5586(10) 0.4199(10) 0.1146(3) 0.0533(15) Uani 1 1 d . U
H10A H 0.5424 0.5543 0.1127 0.080 Uiso 1 1 calc R U
H10B H 0.6112 0.3837 0.0658 0.080 Uiso 1 1 calc R U
H10C H 0.6760 0.4209 0.1577 0.080 Uiso 1 1 calc R U
C11 C 0.3423(11) 0.0475(9) 0.1237(4) 0.0532(14) Uani 1 1 d . U
H11A H 0.4539 0.0410 0.1674 0.080 Uiso 1 1 calc R U
H11B H 0.4031 0.0225 0.0750 0.080 Uiso 1 1 calc R U
H11C H 0.1875 -0.0552 0.1269 0.080 Uiso 1 1 calc R U
B1 B 0.3585(8) 0.6949(6) 0.3919(3) 0.0227(9) Uani 1 1 d . U
C12 C 0.1243(11) 0.2716(11) 0.0589(3) 0.0568(15) Uani 1 1 d . U
H12A H -0.0294 0.1702 0.0648 0.085 Uiso 1 1 calc R U
H12B H 0.1760 0.2441 0.0088 0.085 Uiso 1 1 calc R U
H12C H 0.1083 0.4064 0.0611 0.085 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'
B B 0.0013 0.0007 '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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C2 122.8(3) . .
C1 N1 B1 128.2(3) . .
C2 N1 B1 109.0(3) . .
C8 C3 C4 120.7(4) . .
C8 C3 C2 128.8(3) . .
C4 C3 C2 110.5(3) . .
N1 C2 C1 116.6(4) . 2_566
N1 C2 C3 111.8(3) . .
C1 C2 C3 131.6(3) 2_566 .
N1 C1 C2 120.6(3) . 2_566
N1 C1 H1 119.7 . .
C2 C1 H1 119.7 2_566 .
C5 C4 C3 119.4(4) . .
C5 C4 B1 131.2(3) . .
C3 C4 B1 109.4(3) . .
C8 C7 C6 122.7(4) . .
C8 C7 H7 118.6 . .
C6 C7 H7 118.6 . .
C7 C8 C3 118.3(4) . .
C7 C8 H8 120.9 . .
C3 C8 H8 120.9 . .
C4 C5 C6 121.3(4) . .
C4 C5 H5 119.4 . .
C6 C5 H5 119.4 . .
C5 C6 C7 117.5(4) . .
C5 C6 C9 122.9(4) . .
C7 C6 C9 119.6(4) . .
C10 C9 C6 112.3(4) . .
C10 C9 C11 108.2(5) . .
C6 C9 C11 109.1(4) . .
C10 C9 C12 108.7(5) . .
C6 C9 C12 108.4(4) . .
C11 C9 C12 110.2(4) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C4 B1 N1 99.0(3) . .
C4 B1 Cl1 117.8(3) . .
N1 B1 Cl1 108.9(3) . .
C4 B1 Cl2 112.9(3) . .
N1 B1 Cl2 106.3(3) . .
Cl1 B1 Cl2 110.6(2) . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 B1 1.832(5) .
Cl2 B1 1.843(5) .
N1 C1 1.304(5) .
N1 C2 1.368(4) .
N1 B1 1.614(5) .
C3 C8 1.395(5) .
C3 C4 1.399(5) .
C3 C2 1.431(6) .
C2 C1 1.397(5) 2_566
C1 C2 1.397(5) 2_566
C1 H1 0.9300 .
C4 C5 1.364(6) .
C4 B1 1.582(6) .
C7 C8 1.355(6) .
C7 C6 1.405(6) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C5 C6 1.394(6) .
C5 H5 0.9300 .
C6 C9 1.527(6) .
C9 C10 1.527(7) .
C9 C11 1.533(8) .
C9 C12 1.548(8) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
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_4
C1 N1 C2 C1 0.5(6) 2_566
B1 N1 C2 C1 -179.6(4) 2_566
C1 N1 C2 C3 -177.6(4) .
B1 N1 C2 C3 2.3(5) .
C8 C3 C2 N1 -179.6(4) .
C4 C3 C2 N1 1.5(5) .
C8 C3 C2 C1 2.5(8) 2_566
C4 C3 C2 C1 -176.3(4) 2_566
C2 N1 C1 C2 -0.6(7) 2_566
B1 N1 C1 C2 179.6(4) 2_566
C8 C3 C4 C5 -3.1(6) .
C2 C3 C4 C5 175.9(4) .
C8 C3 C4 B1 176.4(4) .
C2 C3 C4 B1 -4.7(5) .
C6 C7 C8 C3 -0.1(7) .
C4 C3 C8 C7 2.2(6) .
C2 C3 C8 C7 -176.6(4) .
C3 C4 C5 C6 1.9(7) .
B1 C4 C5 C6 -177.4(4) .
C4 C5 C6 C7 0.1(7) .
C4 C5 C6 C9 179.7(4) .
C8 C7 C6 C5 -1.0(7) .
C8 C7 C6 C9 179.3(4) .
C5 C6 C9 C10 5.3(7) .
C7 C6 C9 C10 -175.1(5) .
C5 C6 C9 C11 125.2(5) .
C7 C6 C9 C11 -55.2(6) .
C5 C6 C9 C12 -114.7(5) .
C7 C6 C9 C12 64.9(6) .
C5 C4 B1 N1 -175.2(4) .
C3 C4 B1 N1 5.4(4) .
C5 C4 B1 Cl1 -58.2(6) .
C3 C4 B1 Cl1 122.5(3) .
C5 C4 B1 Cl2 72.8(5) .
C3 C4 B1 Cl2 -106.6(3) .
C1 N1 B1 C4 175.4(4) .
C2 N1 B1 C4 -4.6(4) .
C1 N1 B1 Cl1 51.8(5) .
C2 N1 B1 Cl1 -128.1(3) .
C1 N1 B1 Cl2 -67.4(5) .
C2 N1 B1 Cl2 112.7(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350936
