#------------------------------------------------------------------------------
#$Date: 2024-11-04 13:17:28 +0200 (Mon, 04 Nov 2024) $
#$Revision: 295754 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/30/1573011.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_1573011
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            'C44 H30 B2'
_chemical_formula_weight         580.30
_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
_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                92.2249(14)
_cell_angle_beta                 103.0066(13)
_cell_angle_gamma                95.7954(12)
_cell_formula_units_Z            2
_cell_length_a                   9.0920(3)
_cell_length_b                   10.7481(3)
_cell_length_c                   15.4529(5)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.90
_cell_measurement_theta_min      2.94
_cell_volume                     1460.87(8)
_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 0.994
_diffrn_measured_fraction_theta_max 0.986
_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  0.0293
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10470
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.254
_diffrn_reflns_theta_min         2.941
_diffrn_source                   'I-mu-S microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.818166
_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    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0523
_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)+(0.0790P)²+0.4051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4347
_reflns_number_total             5491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03781b2.cif
_cod_data_source_block           ic22399
_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               1573011
_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   0.936
_shelx_estimated_absorpt_t_max   0.989
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 0.70241(18) 0.48371(14) 0.83665(11) 0.0256(4) Uani 1 1 d . . . . .
C2 C 0.58571(19) 0.56099(15) 0.82545(11) 0.0274(4) Uani 1 1 d . . . . .
H2 H 0.524376 0.567672 0.767661 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5581(2) 0.62820(15) 0.89769(11) 0.0297(4) Uani 1 1 d . . . . .
H3 H 0.479213 0.681197 0.888304 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6440(2) 0.61933(15) 0.98353(11) 0.0294(4) Uani 1 1 d . . . . .
C5 C 0.7586(2) 0.54117(16) 0.99470(11) 0.0318(4) Uani 1 1 d . . . . .
H5 H 0.817338 0.532512 1.052871 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7894(2) 0.47513(16) 0.92267(11) 0.0306(4) Uani 1 1 d . . . . .
H6 H 0.870075 0.423907 0.932108 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6136(2) 0.69317(17) 1.06174(12) 0.0373(4) Uani 1 1 d . . . . .
H7A H 0.648038 0.782061 1.059161 0.056 Uiso 1 1 calc R U . . .
H7B H 0.668721 0.662365 1.117333 0.056 Uiso 1 1 calc R U . . .
H7C H 0.504448 0.682942 1.059415 0.056 Uiso 1 1 calc R U . . .
C8 C 0.60670(19) 0.33105(15) 0.70792(11) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.506850 0.336568 0.715788 0.031 Uiso 1 1 calc R U . . .
C9 C 0.72609(19) 0.40650(15) 0.75969(11) 0.0252(4) Uani 1 1 d . . . . .
C10 C 0.87957(18) 0.41420(15) 0.74158(11) 0.0249(4) Uani 1 1 d . . . . .
C11 C 0.98921(19) 0.51428(16) 0.78004(11) 0.0292(4) Uani 1 1 d . . . . .
H11 H 0.964625 0.574447 0.819631 0.035 Uiso 1 1 calc R U . . .
C12 C 1.1320(2) 0.52777(16) 0.76194(11) 0.0311(4) Uani 1 1 d . . . . .
H12 H 1.203521 0.597030 0.788295 0.037 Uiso 1 1 calc R U . . .
C13 C 1.17044(19) 0.43978(16) 0.70512(11) 0.0297(4) Uani 1 1 d . . . . .
H13 H 1.269335 0.447128 0.693823 0.036 Uiso 1 1 calc R U . . .
C14 C 1.06386(19) 0.34137(15) 0.66507(11) 0.0283(4) Uani 1 1 d . . . . .
H14 H 1.090638 0.281943 0.625837 0.034 Uiso 1 1 calc R U . . .
C15 C 0.91738(18) 0.32701(15) 0.68085(11) 0.0243(3) Uani 1 1 d . . . . .
C16 C 0.79908(18) 0.23043(15) 0.63186(11) 0.0242(3) Uani 1 1 d . . . . .
C17 C 0.82866(18) 0.13170(15) 0.58288(11) 0.0249(4) Uani 1 1 d . . . . .
H17 H 0.931509 0.123725 0.582185 0.030 Uiso 1 1 calc R U . . .
C18 C 0.71220(18) 0.03812(15) 0.53178(10) 0.0238(3) Uani 1 1 d . . . . .
C19 C 0.75438(18) -0.05943(15) 0.48410(11) 0.0252(4) Uani 1 1 d . . . . .
H19 H 0.859092 -0.066382 0.488436 0.030 Uiso 1 1 calc R U . . .
C20 C 0.64530(19) -0.14721(15) 0.43002(11) 0.0259(4) Uani 1 1 d . . . . .
H20 H 0.677745 -0.211939 0.397625 0.031 Uiso 1 1 calc R U . . .
C21 C 0.49119(18) -0.14273(14) 0.42220(10) 0.0238(3) Uani 1 1 d . . . . .
C22 C 0.44542(18) -0.04544(14) 0.47288(10) 0.0225(3) Uani 1 1 d . . . . .
B1 B 0.6325(2) 0.23815(17) 0.63766(12) 0.0244(4) Uani 1 1 d . . . . .
C23 C 0.33329(19) 0.00962(15) 0.16564(11) 0.0258(4) Uani 1 1 d . . . . .
C24 C 0.20349(19) -0.06522(15) 0.17424(11) 0.0277(4) Uani 1 1 d . . . . .
H24 H 0.181608 -0.071320 0.231308 0.033 Uiso 1 1 calc R U . . .
C25 C 0.1054(2) -0.13110(15) 0.10098(12) 0.0299(4) Uani 1 1 d . . . . .
H25 H 0.019257 -0.183068 0.109078 0.036 Uiso 1 1 calc R U . . .
C26 C 0.1316(2) -0.12203(15) 0.01574(11) 0.0296(4) Uani 1 1 d . . . . .
C27 C 0.2611(2) -0.04689(16) 0.00709(11) 0.0315(4) Uani 1 1 d . . . . .
H27 H 0.281556 -0.039248 -0.050220 0.038 Uiso 1 1 calc R U . . .
C28 C 0.3610(2) 0.01713(16) 0.08046(11) 0.0300(4) Uani 1 1 d . . . . .
H28 H 0.449113 0.066607 0.072622 0.036 Uiso 1 1 calc R U . . .
C29 C 0.0237(2) -0.19041(17) -0.06415(12) 0.0368(4) Uani 1 1 d . . . . .
H29A H -0.008165 -0.275195 -0.049271 0.055 Uiso 1 1 calc R U . . .
H29B H 0.074700 -0.195400 -0.113516 0.055 Uiso 1 1 calc R U . . .
H29C H -0.065574 -0.145149 -0.081686 0.055 Uiso 1 1 calc R U . . .
C30 C 0.36977(19) 0.16658(15) 0.29141(11) 0.0264(4) Uani 1 1 d . . . . .
H30 H 0.262386 0.163232 0.281131 0.032 Uiso 1 1 calc R U . . .
C31 C 0.43254(19) 0.08703(15) 0.24337(11) 0.0261(4) Uani 1 1 d . . . . .
C32 C 0.59818(19) 0.07765(15) 0.26378(11) 0.0258(4) Uani 1 1 d . . . . .
C33 C 0.6556(2) -0.02121(16) 0.22418(11) 0.0297(4) Uani 1 1 d . . . . .
H33 H 0.586812 -0.082305 0.185185 0.036 Uiso 1 1 calc R U . . .
C34 C 0.8096(2) -0.03170(16) 0.24057(12) 0.0316(4) Uani 1 1 d . . . . .
H34 H 0.845255 -0.099967 0.213610 0.038 Uiso 1 1 calc R U . . .
C35 C 0.9119(2) 0.05758(16) 0.29642(12) 0.0309(4) Uani 1 1 d . . . . .
H35 H 1.018120 0.053121 0.305624 0.037 Uiso 1 1 calc R U . . .
C36 C 0.8578(2) 0.15330(16) 0.33865(11) 0.0290(4) Uani 1 1 d . . . . .
H36 H 0.928389 0.212970 0.377925 0.035 Uiso 1 1 calc R U . . .
C37 C 0.70238(19) 0.16477(15) 0.32521(11) 0.0256(4) Uani 1 1 d . . . . .
C38 C 0.64380(19) 0.26114(15) 0.37450(10) 0.0245(4) Uani 1 1 d . . . . .
C39 C 0.73596(19) 0.35040(15) 0.43235(11) 0.0258(4) Uani 1 1 d . . . . .
H39 H 0.842663 0.350199 0.440496 0.031 Uiso 1 1 calc R U . . .
C40 C 0.68154(18) 0.44565(15) 0.48225(11) 0.0244(3) Uani 1 1 d . . . . .
C41 C 0.78590(19) 0.53285(15) 0.53930(11) 0.0260(4) Uani 1 1 d . . . . .
H41 H 0.891451 0.529352 0.544297 0.031 Uiso 1 1 calc R U . . .
C42 C 0.73846(19) 0.62568(15) 0.58951(11) 0.0257(4) Uani 1 1 d . . . . .
H42 H 0.812831 0.683101 0.628345 0.031 Uiso 1 1 calc R U . . .
C43 C 0.58606(18) 0.63610(15) 0.58411(10) 0.0239(3) Uani 1 1 d . . . . .
C44 C 0.47726(18) 0.54799(14) 0.52555(10) 0.0234(3) Uani 1 1 d . . . . .
B2 B 0.4702(2) 0.26111(17) 0.36165(12) 0.0247(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'
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
C6 C1 C2 118.02(15) . . ?
C6 C1 C9 121.23(15) . . ?
C2 C1 C9 120.63(15) . . ?
C3 C2 C1 120.90(16) . . ?
C2 C3 C4 121.22(16) . . ?
C5 C4 C3 117.80(15) . . ?
C5 C4 C7 121.31(16) . . ?
C3 C4 C7 120.89(16) . . ?
C4 C5 C6 121.58(16) . . ?
C5 C6 C1 120.46(16) . . ?
C9 C8 B1 120.32(15) . . ?
C8 C9 C10 121.67(14) . . ?
C8 C9 C1 119.56(14) . . ?
C10 C9 C1 118.78(14) . . ?
C11 C10 C15 118.13(15) . . ?
C11 C10 C9 120.05(14) . . ?
C15 C10 C9 121.67(14) . . ?
C12 C11 C10 121.88(15) . . ?
C11 C12 C13 119.80(15) . . ?
C14 C13 C12 119.58(16) . . ?
C13 C14 C15 121.72(15) . . ?
C14 C15 C10 118.81(14) . . ?
C14 C15 C16 121.96(14) . . ?
C10 C15 C16 119.08(14) . . ?
C17 C16 C15 123.32(15) . . ?
C17 C16 B1 117.83(14) . . ?
C15 C16 B1 118.82(13) . . ?
C16 C17 C18 123.79(15) . . ?
C19 C18 C22 119.05(14) . 2_656 ?
C19 C18 C17 119.33(14) . . ?
C22 C18 C17 121.60(14) 2_656 . ?
C18 C19 C20 121.07(15) . . ?
C21 C20 C19 121.95(14) . . ?
C20 C21 C22 117.89(14) . . ?
C20 C21 B1 123.17(14) . 2_656 ?
C22 C21 B1 118.93(14) . 2_656 ?
C22 C22 C18 119.14(17) 2_656 2_656 ?
C22 C22 C21 120.86(18) 2_656 . ?
C18 C22 C21 120.00(14) 2_656 . ?
C8 B1 C16 116.74(14) . . ?
C8 B1 C21 125.63(15) . 2_656 ?
C16 B1 C21 117.38(14) . 2_656 ?
C24 C23 C28 117.66(15) . . ?
C24 C23 C31 121.12(15) . . ?
C28 C23 C31 121.04(15) . . ?
C25 C24 C23 121.35(16) . . ?
C24 C25 C26 121.00(16) . . ?
C27 C26 C25 117.63(15) . . ?
C27 C26 C29 121.10(16) . . ?
C25 C26 C29 121.27(16) . . ?
C28 C27 C26 121.49(16) . . ?
C27 C28 C23 120.84(16) . . ?
C31 C30 B2 120.60(15) . . ?
C30 C31 C32 121.94(14) . . ?
C30 C31 C23 119.43(15) . . ?
C32 C31 C23 118.59(13) . . ?
C33 C32 C37 118.27(15) . . ?
C33 C32 C31 120.17(15) . . ?
C37 C32 C31 121.53(14) . . ?
C34 C33 C32 121.72(16) . . ?
C33 C34 C35 119.95(15) . . ?
C36 C35 C34 119.38(16) . . ?
C35 C36 C37 122.02(16) . . ?
C36 C37 C32 118.48(14) . . ?
C36 C37 C38 122.19(15) . . ?
C32 C37 C38 119.30(14) . . ?
C39 C38 C37 122.96(15) . . ?
C39 C38 B2 117.89(14) . . ?
C37 C38 B2 119.15(14) . . ?
C38 C39 C40 124.15(15) . . ?
C41 C40 C44 119.10(14) . 2_666 ?
C41 C40 C39 119.38(14) . . ?
C44 C40 C39 121.53(14) 2_666 . ?
C40 C41 C42 121.32(15) . . ?
C43 C42 C41 121.82(15) . . ?
C42 C43 C44 117.70(14) . . ?
C42 C43 B2 123.01(14) . 2_666 ?
C44 C43 B2 119.29(14) . 2_666 ?
C44 C44 C43 121.51(18) 2_666 . ?
C44 C44 C40 118.55(18) 2_666 2_666 ?
C43 C44 C40 119.93(14) . 2_666 ?
C30 B2 C38 116.73(14) . . ?
C30 B2 C43 125.87(15) . 2_666 ?
C38 B2 C43 117.21(14) . 2_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 C6 1.397(2) . ?
C1 C2 1.397(2) . ?
C1 C9 1.491(2) . ?
C2 C3 1.389(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.388(3) . ?
C4 C7 1.512(2) . ?
C5 C6 1.393(2) . ?
C8 C9 1.363(2) . ?
C8 B1 1.519(2) . ?
C9 C10 1.479(2) . ?
C10 C11 1.404(2) . ?
C10 C15 1.421(2) . ?
C11 C12 1.383(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.383(2) . ?
C14 C15 1.402(2) . ?
C15 C16 1.468(2) . ?
C16 C17 1.363(2) . ?
C16 B1 1.547(2) . ?
C17 C18 1.450(2) . ?
C18 C19 1.392(2) . ?
C18 C22 1.429(2) 2_656 ?
C19 C20 1.396(2) . ?
C20 C21 1.385(2) . ?
C21 C22 1.432(2) . ?
C21 B1 1.548(2) 2_656 ?
C22 C22 1.417(3) 2_656 ?
C23 C24 1.394(2) . ?
C23 C28 1.398(2) . ?
C23 C31 1.494(2) . ?
C24 C25 1.391(2) . ?
C25 C26 1.396(2) . ?
C26 C27 1.394(3) . ?
C26 C29 1.505(2) . ?
C27 C28 1.390(2) . ?
C30 C31 1.359(2) . ?
C30 B2 1.525(2) . ?
C31 C32 1.482(2) . ?
C32 C33 1.408(2) . ?
C32 C37 1.422(2) . ?
C33 C34 1.382(2) . ?
C34 C35 1.388(2) . ?
C35 C36 1.386(2) . ?
C36 C37 1.400(2) . ?
C37 C38 1.473(2) . ?
C38 C39 1.362(2) . ?
C38 B2 1.546(2) . ?
C39 C40 1.449(2) . ?
C40 C41 1.391(2) . ?
C40 C44 1.430(2) 2_666 ?
C41 C42 1.400(2) . ?
C42 C43 1.385(2) . ?
C43 C44 1.427(2) . ?
C43 B2 1.555(2) 2_666 ?
C44 C44 1.424(3) 2_666 ?
