#------------------------------------------------------------------------------
#$Date: 2024-11-04 12:17:28 +0100 (Mon 04 de Nov de 2024) $
#$Revision: 295754 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/30/1573012.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_1573012
loop_
_publ_author_name
'Anitha, Mandala'
'Chin, To-Jen'
'Liu, Guan-Cheng'
'Hsieh, Chi-Tien'
'Wang, Kuan-Hua'
'Li, Shu-Li'
'Cheng, Mu-Jeng'
'Farrell, Jeffrey M.'
_publ_section_title
;
 Metal-free alkyne annulation enabling π-extension of boron-doped
 polycyclic aromatic hydrocarbons.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              16210
_journal_page_last               16215
_journal_paper_doi               10.1039/d4sc03781b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C42 H24 B2 F2'
_chemical_formula_weight         588.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-03-20 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1524(2)
_cell_length_b                   8.4349(2)
_cell_length_c                   40.5242(11)
_cell_measurement_reflns_used    9422
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.02
_cell_measurement_theta_min      2.18
_cell_volume                     2786.63(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            24293
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.118
_diffrn_reflns_theta_min         2.180
_diffrn_source                   'I-mu-S microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0524
_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)+(0.0737P)²+2.8218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1550
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2393
_reflns_number_total             2723
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03781b2.cif
_cod_data_source_block           ic22216
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               1573012
_shelx_shelxl_version_number     2019/3
_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   0.953
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_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'
'-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_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
F1 F 0.38583(17) 0.98984(18) 0.76749(3) 0.0344(4) Uani 1 1 d . . . . .
C1 C 0.3959(3) 0.9469(3) 0.73520(5) 0.0242(5) Uani 1 1 d . . . . .
C2 C 0.5159(3) 1.0152(3) 0.71605(5) 0.0236(5) Uani 1 1 d . . . . .
H2 H 0.587994 1.092541 0.725011 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5291(2) 0.9686(2) 0.68340(5) 0.0210(4) Uani 1 1 d . . . . .
H3 H 0.610319 1.015711 0.669754 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4248(2) 0.8531(2) 0.67015(5) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.3038(3) 0.7882(2) 0.69054(5) 0.0225(5) Uani 1 1 d . . . . .
H5 H 0.230783 0.711070 0.681834 0.027 Uiso 1 1 calc R U . . .
C6 C 0.2886(3) 0.8342(3) 0.72317(5) 0.0241(5) Uani 1 1 d . . . . .
H6 H 0.206412 0.789384 0.736934 0.029 Uiso 1 1 calc R U . . .
C7 C 0.4234(3) 0.9175(2) 0.61101(5) 0.0208(4) Uani 1 1 d . . . . .
H7 H 0.380857 1.018851 0.616649 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4467(2) 0.8069(2) 0.63491(5) 0.0191(4) Uani 1 1 d . . . . .
C9 C 0.5034(2) 0.6433(2) 0.62759(5) 0.0189(4) Uani 1 1 d . . . . .
C10 C 0.5233(3) 0.5341(2) 0.65336(5) 0.0210(4) Uani 1 1 d . . . . .
H10 H 0.499867 0.566093 0.675339 0.025 Uiso 1 1 calc R U . . .
C11 C 0.5765(3) 0.3802(2) 0.64749(5) 0.0232(5) Uani 1 1 d . . . . .
H11 H 0.588557 0.307799 0.665291 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6120(3) 0.3328(2) 0.61551(5) 0.0222(5) Uani 1 1 d . . . . .
H12 H 0.646873 0.227289 0.611275 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5964(3) 0.4394(2) 0.58983(5) 0.0210(4) Uani 1 1 d . . . . .
H13 H 0.623004 0.406030 0.568094 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5423(2) 0.5957(2) 0.59486(5) 0.0184(4) Uani 1 1 d . . . . .
C15 C 0.5302(2) 0.7115(2) 0.56770(5) 0.0180(4) Uani 1 1 d . . . . .
C16 C 0.5796(2) 0.6794(2) 0.53630(5) 0.0203(4) Uani 1 1 d . . . . .
H16 H 0.624463 0.577678 0.531887 0.024 Uiso 1 1 calc R U . . .
C17 C 0.5679(2) 0.7911(2) 0.50919(5) 0.0182(4) Uani 1 1 d . . . . .
C18 C 0.5053(2) 0.9487(2) 0.51378(5) 0.0176(4) Uani 1 1 d . . . . .
C19 C 0.6179(2) 0.7454(2) 0.47783(5) 0.0203(4) Uani 1 1 d . . . . .
H19 H 0.659398 0.641351 0.474599 0.024 Uiso 1 1 calc R U . . .
C20 C 0.6086(2) 0.8486(2) 0.45092(5) 0.0199(4) Uani 1 1 d . . . . .
H20 H 0.645412 0.813428 0.429919 0.024 Uiso 1 1 calc R U . . .
C21 C 0.5466(2) 1.0020(2) 0.45414(5) 0.0184(4) Uani 1 1 d . . . . .
B1 B 0.4651(3) 0.8798(3) 0.57510(6) 0.0189(5) 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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
F1 C1 C2 118.3(2) . . ?
F1 C1 C6 119.0(2) . . ?
C2 C1 C6 122.7(2) . . ?
C1 C2 C3 118.4(2) . . ?
C2 C3 C4 121.1(2) . . ?
C5 C4 C3 118.31(19) . . ?
C5 C4 C8 123.26(19) . . ?
C3 C4 C8 118.43(18) . . ?
C6 C5 C4 121.2(2) . . ?
C1 C6 C5 118.3(2) . . ?
C8 C7 B1 120.34(18) . . ?
C7 C8 C9 122.63(18) . . ?
C7 C8 C4 119.14(18) . . ?
C9 C8 C4 118.12(17) . . ?
C10 C9 C14 118.89(18) . . ?
C10 C9 C8 119.84(18) . . ?
C14 C9 C8 121.25(18) . . ?
C11 C10 C9 121.51(19) . . ?
C12 C11 C10 119.62(19) . . ?
C13 C12 C11 119.82(19) . . ?
C12 C13 C14 122.04(19) . . ?
C13 C14 C9 118.09(18) . . ?
C13 C14 C15 122.29(18) . . ?
C9 C14 C15 119.58(17) . . ?
C16 C15 C14 123.08(18) . . ?
C16 C15 B1 117.75(18) . . ?
C14 C15 B1 119.12(17) . . ?
C15 C16 C17 124.02(19) . . ?
C19 C17 C18 118.65(18) . . ?
C19 C17 C16 119.59(18) . . ?
C18 C17 C16 121.76(18) . . ?
C18 C18 C21 121.5(2) 5_676 5_676 ?
C18 C18 C17 119.0(2) 5_676 . ?
C21 C18 C17 119.51(18) 5_676 . ?
C17 C19 C20 121.70(18) . . ?
C21 C20 C19 121.62(18) . . ?
C20 C21 C18 117.53(18) . 5_676 ?
C20 C21 B1 123.15(18) . 5_676 ?
C18 C21 B1 119.32(18) 5_676 5_676 ?
C7 B1 C15 116.92(18) . . ?
C7 B1 C21 125.46(19) . 5_676 ?
C15 B1 C21 117.58(18) . 5_676 ?
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
F1 C1 1.360(2) . ?
C1 C2 1.376(3) . ?
C1 C6 1.381(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.398(3) . ?
C4 C8 1.491(3) . ?
C5 C6 1.383(3) . ?
C7 C8 1.358(3) . ?
C7 B1 1.528(3) . ?
C8 C9 1.485(3) . ?
C9 C10 1.402(3) . ?
C9 C14 1.422(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.404(3) . ?
C14 C15 1.475(3) . ?
C15 C16 1.362(3) . ?
C15 B1 1.545(3) . ?
C16 C17 1.450(3) . ?
C17 C19 1.389(3) . ?
C17 C18 1.436(3) . ?
C18 C18 1.416(4) 5_676 ?
C18 C21 1.429(3) 5_676 ?
C19 C20 1.397(3) . ?
C20 C21 1.395(3) . ?
C21 B1 1.551(3) 5_676 ?
