#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/39/4123943.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_4123943
loop_
_publ_author_name
'Cloke, Ryan R.'
'Marangoni, Tomas'
'Nguyen, Giang D.'
'Joshi, Trinity'
'Rizzo, Daniel J.'
'Bronner, Christopher'
'Cao, Ting'
'Louie, Steven G.'
'Crommie, Michael F.'
'Fischer, Felix R.'
_publ_section_title
;
 Site-Specific Substitutional Boron Doping of Semiconducting Armchair
 Graphene Nanoribbons.
;
_journal_issue                   28
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8872
_journal_page_last               8875
_journal_paper_doi               10.1021/jacs.5b02523
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C46 H30 B2 Br2 Cl12'
_chemical_formula_weight         1189.54
_chemical_name_common            TM101
_chemical_name_systematic        fischer02
_space_group.centring_type       P
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                82.148(2)
_cell_angle_beta                 82.067(2)
_cell_angle_gamma                74.011(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6046(3)
_cell_length_b                   9.8632(4)
_cell_length_c                   14.5013(6)
_cell_measurement_reflns_used    9576
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.46
_cell_volume                     1165.48(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42257
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.395
_diffrn_reflns_theta_min         1.425
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    2.462
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_description       plate
_exptl_crystal_F_000             590
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.270
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0246P)²+4.0798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3474
_reflns_number_total             4281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b02523_si_002.cif
_cod_data_source_block           fischer02
_cod_depositor_comments
;Adding full bibliography for 4123943.cif.

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               4123943
#BEGIN Tags that were not found in dictionaries:
_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   0.908
_shelx_estimated_absorpt_t_max   0.952
#END Tags that were not found in dictionaries
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
C1 C 0.1531(4) -0.3136(3) 0.8468(2) 0.0097(7) Uani 1 1 d . .
C2 C 0.0810(4) -0.2647(4) 0.7631(2) 0.0099(7) Uani 1 1 d . .
C3 C -0.0581(4) -0.3063(4) 0.7466(2) 0.0139(8) Uani 1 1 d . .
H3 H -0.1026 -0.3663 0.7935 0.017 Uiso 1 1 calc R U
C4 C -0.1290(5) -0.2624(4) 0.6655(3) 0.0188(8) Uani 1 1 d . .
H4 H -0.2219 -0.2913 0.6563 0.023 Uiso 1 1 calc R U
C5 C -0.0636(5) -0.1734(4) 0.5949(3) 0.0195(8) Uani 1 1 d . .
H5 H -0.1119 -0.1448 0.5379 0.023 Uiso 1 1 calc R U
C6 C 0.0667(5) -0.1282(4) 0.6071(3) 0.0179(8) Uani 1 1 d . .
H6 H 0.1075 -0.0676 0.5589 0.021 Uiso 1 1 calc R U
C7 C 0.1438(4) -0.1709(4) 0.6920(2) 0.0115(7) Uani 1 1 d . .
C8 C 0.2781(4) -0.1280(4) 0.7095(2) 0.0126(7) Uani 1 1 d . .
C9 C 0.3582(4) -0.1782(3) 0.7899(2) 0.0112(7) Uani 1 1 d . .
C10 C 0.4991(4) -0.1409(4) 0.8078(3) 0.0163(8) Uani 1 1 d . .
H10 H 0.5445 -0.0792 0.7627 0.020 Uiso 1 1 calc R U
C11 C 0.5696(4) -0.1919(4) 0.8883(3) 0.0186(8) Uani 1 1 d . .
H11 H 0.6637 -0.1657 0.8985 0.022 Uiso 1 1 calc R U
C12 C 0.5043(5) -0.2835(4) 0.9571(3) 0.0199(9) Uani 1 1 d . .
H12 H 0.5540 -0.3177 1.0133 0.024 Uiso 1 1 calc R U
C13 C 0.3713(4) -0.3225(4) 0.9429(2) 0.0146(8) Uani 1 1 d . .
H13 H 0.3293 -0.3844 0.9895 0.017 Uiso 1 1 calc R U
C14 C 0.2921(4) -0.2730(4) 0.8595(2) 0.0111(7) Uani 1 1 d . .
C15 C -0.0368(4) -0.3424(4) 1.0101(2) 0.0098(7) Uani 1 1 d . .
C16 C -0.0722(4) -0.1966(4) 1.0173(2) 0.0136(8) Uani 1 1 d . .
H16 H -0.0208 -0.1393 0.9720 0.016 Uiso 1 1 calc R U
C17 C -0.1805(4) -0.1341(4) 1.0891(3) 0.0169(8) Uani 1 1 d . .
H17 H -0.2034 -0.0348 1.0922 0.020 Uiso 1 1 calc R U
C18 C 0.1119(4) -0.5731(4) 0.9202(2) 0.0100(7) Uani 1 1 d . .
C19 C 0.2195(4) -0.6387(4) 0.8483(2) 0.0146(8) Uani 1 1 d . .
H19 H 0.2695 -0.5826 0.8014 0.018 Uiso 1 1 calc R U
C20 C 0.2551(4) -0.7837(4) 0.8439(3) 0.0162(8) Uani 1 1 d . .
H20 H 0.3304 -0.8263 0.7950 0.019 Uiso 1 1 calc R U
C21 C 0.1486(5) 0.6919(5) 0.2531(3) 0.0360(11) Uani 1 1 d . .
H21 H 0.0706 0.7038 0.2056 0.043 Uiso 1 1 calc R U
C22 C 0.1781(6) 0.8317(5) 0.2582(3) 0.0379(12) Uani 1 1 d . .
H22 H 0.0724 0.8985 0.2790 0.046 Uiso 1 1 calc R U
C23 C 0.5779(4) 0.5164(4) 0.5070(2) 0.0153(8) Uani 1 1 d . .
H23 H 0.6298 0.4492 0.5590 0.018 Uiso 1 1 calc R U
B1 B 0.0772(5) -0.4103(4) 0.9258(3) 0.0100(8) Uani 1 1 d . .
Cl1 Cl 0.05260(13) 0.64160(12) 0.36564(8) 0.0340(3) Uani 1 1 d . .
Cl2 Cl 0.32844(13) 0.56221(11) 0.21938(8) 0.0321(3) Uani 1 1 d . .
Cl3 Cl 0.31858(14) 0.82573(11) 0.33730(8) 0.0315(3) Uani 1 1 d . .
Cl4 Cl 0.24575(15) 0.89603(12) 0.14064(8) 0.0355(3) Uani 1 1 d . .
Cl5 Cl 0.53555(11) 0.69297(10) 0.53617(7) 0.0215(2) Uani 1 1 d . .
Cl6 Cl 0.71335(12) 0.49872(11) 0.40330(7) 0.0293(3) Uani 1 1 d . .
Br1 Br 0.35308(5) 0.00832(4) 0.62023(3) 0.02237(12) 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C14 C1 C2 119.0(3) . .
C14 C1 B1 120.6(3) . .
C2 C1 B1 120.5(3) . .
C1 C2 C3 120.6(3) . .
C1 C2 C7 121.3(3) . .
C3 C2 C7 118.0(3) . .
C4 C3 C2 121.9(3) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C3 C4 C5 119.6(3) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C6 C5 C4 121.2(3) . .
C6 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
C5 C6 C7 120.8(3) . .
C5 C6 H6 119.6 . .
C7 C6 H6 119.6 . .
C8 C7 C6 123.9(3) . .
C8 C7 C2 117.8(3) . .
C6 C7 C2 118.3(3) . .
C9 C8 C7 123.0(3) . .
C9 C8 Br1 118.5(3) . .
C7 C8 Br1 118.4(3) . .
C8 C9 C10 124.3(3) . .
C8 C9 C14 117.6(3) . .
C10 C9 C14 118.2(3) . .
C11 C10 C9 121.2(3) . .
C11 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
C10 C11 C12 120.8(3) . .
C10 C11 H11 119.6 . .
C12 C11 H11 119.6 . .
C13 C12 C11 120.1(3) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C12 C13 C14 121.8(3) . .
C12 C13 H13 119.1 . .
C14 C13 H13 119.1 . .
C1 C14 C13 120.8(3) . .
C1 C14 C9 121.3(3) . .
C13 C14 C9 117.9(3) . .
C16 C15 C18 118.4(3) . 2_547
C16 C15 B1 121.1(3) . .
C18 C15 B1 120.5(3) 2_547 .
C17 C16 C15 121.5(3) . .
C17 C16 H16 119.3 . .
C15 C16 H16 119.3 . .
C20 C17 C16 120.0(3) 2_547 .
C20 C17 H17 120.0 2_547 .
C16 C17 H17 120.0 . .
C19 C18 C15 118.9(3) . 2_547
C19 C18 B1 120.9(3) . .
C15 C18 B1 120.2(3) 2_547 .
C20 C19 C18 121.6(3) . .
C20 C19 H19 119.2 . .
C18 C19 H19 119.2 . .
C17 C20 C19 119.6(3) 2_547 .
C17 C20 H20 120.2 2_547 .
C19 C20 H20 120.2 . .
C22 C21 Cl2 112.7(3) . .
C22 C21 Cl1 106.8(3) . .
Cl2 C21 Cl1 112.4(3) . .
C22 C21 H21 108.3 . .
Cl2 C21 H21 108.3 . .
Cl1 C21 H21 108.3 . .
C21 C22 Cl3 113.3(3) . .
C21 C22 Cl4 107.1(3) . .
Cl3 C22 Cl4 111.4(3) . .
C21 C22 H22 108.3 . .
Cl3 C22 H22 108.3 . .
Cl4 C22 H22 108.3 . .
C23 C23 Cl6 110.3(3) 2_666 .
C23 C23 Cl5 109.7(3) 2_666 .
Cl6 C23 Cl5 108.8(2) . .
C23 C23 H23 109.3 2_666 .
Cl6 C23 H23 109.3 . .
Cl5 C23 H23 109.3 . .
C15 B1 C18 119.3(3) . .
C15 B1 C1 119.7(3) . .
C18 B1 C1 120.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C14 1.404(5) .
C1 C2 1.404(5) .
C1 B1 1.578(5) .
C2 C3 1.426(5) .
C2 C7 1.440(5) .
C3 C4 1.363(5) .
C3 H3 0.9500 .
C4 C5 1.415(5) .
C4 H4 0.9500 .
C5 C6 1.356(5) .
C5 H5 0.9500 .
C6 C7 1.436(5) .
C6 H6 0.9500 .
C7 C8 1.399(5) .
C8 C9 1.399(5) .
C8 Br1 1.916(3) .
C9 C10 1.425(5) .
C9 C14 1.447(5) .
C10 C11 1.360(5) .
C10 H10 0.9500 .
C11 C12 1.417(5) .
C11 H11 0.9500 .
C12 C13 1.352(5) .
C12 H12 0.9500 .
C13 C14 1.430(5) .
C13 H13 0.9500 .
C15 C16 1.401(5) .
C15 C18 1.421(5) 2_547
C15 B1 1.561(5) .
C16 C17 1.387(5) .
C16 H16 0.9500 .
C17 C20 1.384(5) 2_547
C17 H17 0.9500 .
C18 C19 1.396(5) .
C18 C15 1.421(5) 2_547
C18 B1 1.562(5) .
C19 C20 1.386(5) .
C19 H19 0.9500 .
C20 C17 1.384(5) 2_547
C20 H20 0.9500 .
C21 C22 1.483(6) .
C21 Cl2 1.772(4) .
C21 Cl1 1.795(5) .
C21 H21 1.0000 .
C22 Cl3 1.762(4) .
C22 Cl4 1.812(5) .
C22 H22 1.0000 .
C23 C23 1.509(7) 2_666
C23 Cl6 1.768(4) .
C23 Cl5 1.776(4) .
C23 H23 1.0000 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139124296
