#------------------------------------------------------------------------------
#$Date: 2024-11-04 12:17:28 +0100 (Mon 04 de Nov de 2024) $
#$Revision: 295754 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/30/1573013.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_1573013
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            'C48 H38 B2'
_chemical_formula_weight         636.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 92.113(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.8935(12)
_cell_length_b                   7.5081(4)
_cell_length_c                   11.7916(7)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.94
_cell_measurement_theta_min      4.45
_cell_volume                     1760.02(18)
_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 0.997
_diffrn_measured_fraction_theta_max 0.985
_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  0.0398
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27436
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.178
_diffrn_reflns_theta_min         2.222
_diffrn_source                   'I-mu-S microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8784
_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    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0427
_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)+(0.0658P)²+0.6866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3139
_reflns_number_total             3433
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03781b2.cif
_cod_data_source_block           ic22339
_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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1573013
_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   0.928
_shelx_estimated_absorpt_t_max   0.961
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.82662(5) 0.27365(16) 0.33337(9) 0.0190(3) Uani 1 1 d . . . . .
C2 C 0.88018(6) 0.36167(17) 0.38967(10) 0.0229(3) Uani 1 1 d . . . . .
C3 C 0.94300(6) 0.27968(18) 0.39717(10) 0.0268(3) Uani 1 1 d . . . . .
H3 H 0.979100 0.338712 0.436485 0.032 Uiso 1 1 calc R U . . .
C4 C 0.95445(6) 0.11405(18) 0.34882(10) 0.0259(3) Uani 1 1 d . . . . .
C5 C 0.90054(6) 0.02879(17) 0.29357(10) 0.0241(3) Uani 1 1 d . . . . .
H5 H 0.907498 -0.084730 0.260401 0.029 Uiso 1 1 calc R U . . .
C6 C 0.83654(6) 0.10476(16) 0.28531(9) 0.0211(3) Uani 1 1 d . . . . .
C7 C 0.87105(6) 0.54466(18) 0.43963(12) 0.0311(3) Uani 1 1 d . . . . .
H7A H 0.849455 0.622821 0.382571 0.047 Uiso 1 1 calc R U . . .
H7B H 0.915054 0.593692 0.463096 0.047 Uiso 1 1 calc R U . . .
H7C H 0.842726 0.536344 0.505678 0.047 Uiso 1 1 calc R U . . .
C8 C 1.02398(7) 0.0326(2) 0.35462(12) 0.0355(3) Uani 1 1 d . . . . .
H8A H 1.048669 0.069805 0.288226 0.053 Uiso 1 1 calc R U . . .
H8B H 1.020201 -0.097516 0.355487 0.053 Uiso 1 1 calc R U . . .
H8C H 1.048151 0.072751 0.423896 0.053 Uiso 1 1 calc R U . . .
C9 C 0.77908(6) 0.00628(17) 0.22682(11) 0.0271(3) Uani 1 1 d . . . . .
H9A H 0.741167 -0.000112 0.277417 0.041 Uiso 1 1 calc R U . . .
H9B H 0.793605 -0.114497 0.207884 0.041 Uiso 1 1 calc R U . . .
H9C H 0.765114 0.069413 0.157129 0.041 Uiso 1 1 calc R U . . .
C10 C 0.71422(6) 0.34237(16) 0.40711(10) 0.0207(3) Uani 1 1 d . . . . .
H10 H 0.725586 0.271598 0.471793 0.025 Uiso 1 1 calc R U . . .
C11 C 0.75895(5) 0.36149(15) 0.32345(10) 0.0188(3) Uani 1 1 d . . . . .
C12 C 0.74437(5) 0.46976(15) 0.22091(10) 0.0186(3) Uani 1 1 d . . . . .
C13 C 0.79312(6) 0.48232(15) 0.13753(10) 0.0206(3) Uani 1 1 d . . . . .
H13 H 0.834853 0.422358 0.149169 0.025 Uiso 1 1 calc R U . . .
C14 C 0.78172(6) 0.57952(16) 0.03942(10) 0.0228(3) Uani 1 1 d . . . . .
H14 H 0.815344 0.586055 -0.015586 0.027 Uiso 1 1 calc R U . . .
C15 C 0.72076(6) 0.66801(17) 0.02130(10) 0.0251(3) Uani 1 1 d . . . . .
H15 H 0.712591 0.734727 -0.046265 0.030 Uiso 1 1 calc R U . . .
C16 C 0.67207(6) 0.65848(16) 0.10203(10) 0.0240(3) Uani 1 1 d . . . . .
H16 H 0.630715 0.719669 0.088922 0.029 Uiso 1 1 calc R U . . .
C17 C 0.68220(6) 0.56083(15) 0.20273(10) 0.0196(3) Uani 1 1 d . . . . .
C18 C 0.63060(5) 0.54603(15) 0.28914(10) 0.0197(3) Uani 1 1 d . . . . .
C19 C 0.56829(6) 0.61913(17) 0.27567(11) 0.0250(3) Uani 1 1 d . . . . .
H19 H 0.558465 0.686505 0.208909 0.030 Uiso 1 1 calc R U . . .
C20 C 0.51581(6) 0.60025(17) 0.35742(10) 0.0233(3) Uani 1 1 d . . . . .
C21 C 0.45315(6) 0.67572(19) 0.33362(11) 0.0306(3) Uani 1 1 d . . . . .
H21 H 0.445158 0.735376 0.263368 0.037 Uiso 1 1 calc R U . . .
C22 C 0.40140(6) 0.66583(18) 0.41101(11) 0.0281(3) Uani 1 1 d . . . . .
H22 H 0.359398 0.720625 0.392318 0.034 Uiso 1 1 calc R U . . .
C23 C 0.40991(5) 0.57820(16) 0.51408(10) 0.0207(3) Uani 1 1 d . . . . .
C24 C 0.47335(5) 0.49487(15) 0.53853(9) 0.0195(3) Uani 1 1 d . . . . .
B1 B 0.64593(6) 0.43418(18) 0.39733(11) 0.0199(3) 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'
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
C2 C1 C6 120.07(10) . . ?
C2 C1 C11 119.65(10) . . ?
C6 C1 C11 120.28(10) . . ?
C3 C2 C1 119.13(11) . . ?
C3 C2 C7 119.89(11) . . ?
C1 C2 C7 120.97(10) . . ?
C4 C3 C2 121.97(11) . . ?
C3 C4 C5 117.96(11) . . ?
C3 C4 C8 120.45(12) . . ?
C5 C4 C8 121.58(12) . . ?
C4 C5 C6 122.05(11) . . ?
C5 C6 C1 118.81(11) . . ?
C5 C6 C9 120.41(11) . . ?
C1 C6 C9 120.77(10) . . ?
C11 C10 B1 120.17(10) . . ?
C10 C11 C12 122.55(10) . . ?
C10 C11 C1 120.42(10) . . ?
C12 C11 C1 117.03(10) . . ?
C13 C12 C17 118.65(10) . . ?
C13 C12 C11 119.26(10) . . ?
C17 C12 C11 122.09(10) . . ?
C14 C13 C12 121.63(11) . . ?
C13 C14 C15 119.76(11) . . ?
C16 C15 C14 119.81(11) . . ?
C15 C16 C17 121.76(11) . . ?
C16 C17 C12 118.38(10) . . ?
C16 C17 C18 122.76(10) . . ?
C12 C17 C18 118.85(10) . . ?
C19 C18 C17 122.88(11) . . ?
C19 C18 B1 117.78(11) . . ?
C17 C18 B1 119.25(10) . . ?
C18 C19 C20 123.86(11) . . ?
C21 C20 C24 118.91(11) . 3_666 ?
C21 C20 C19 119.17(11) . . ?
C24 C20 C19 121.92(10) 3_666 . ?
C20 C21 C22 121.46(12) . . ?
C23 C22 C21 121.76(11) . . ?
C22 C23 C24 117.58(11) . . ?
C22 C23 B1 123.35(10) . 3_666 ?
C24 C23 B1 119.07(10) . 3_666 ?
C24 C24 C23 121.38(13) 3_666 . ?
C24 C24 C20 118.85(13) 3_666 3_666 ?
C23 C24 C20 119.77(10) . 3_666 ?
C10 B1 C18 117.10(10) . . ?
C10 B1 C23 125.38(11) . 3_666 ?
C18 B1 C23 117.52(10) . 3_666 ?
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 C2 1.4002(16) . ?
C1 C6 1.4058(17) . ?
C1 C11 1.4998(15) . ?
C2 C3 1.3930(16) . ?
C2 C7 1.5085(18) . ?
C3 C4 1.3903(19) . ?
C4 C5 1.3903(18) . ?
C4 C8 1.5115(16) . ?
C5 C6 1.3952(16) . ?
C6 C9 1.5069(16) . ?
C10 C11 1.3601(16) . ?
C10 B1 1.5241(16) . ?
C11 C12 1.4769(16) . ?
C12 C13 1.4093(16) . ?
C12 C17 1.4226(16) . ?
C13 C14 1.3795(17) . ?
C14 C15 1.3923(17) . ?
C15 C16 1.3847(17) . ?
C16 C17 1.4037(17) . ?
C17 C18 1.4768(16) . ?
C18 C19 1.3597(17) . ?
C18 B1 1.5483(18) . ?
C19 C20 1.4538(17) . ?
C20 C21 1.3884(17) . ?
C20 C24 1.4291(17) 3_666 ?
C21 C22 1.4026(17) . ?
C22 C23 1.3869(17) . ?
C23 C24 1.4284(15) . ?
C23 B1 1.5554(17) 3_666 ?
C24 C24 1.424(2) 3_666 ?
