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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/61/4506142.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_4506142
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Howard, Judith A. K.'
'Albesa-Jové, David'
'Collings, Jonathan C.'
'Liu, Zhiqiang'
'Mkhalid, Ibraheem A. I.'
'Thibault, Marie-Hélène'
'Marder, Todd B.'
_publ_section_title
;
 Structural Versatility of
 Pyrene-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane) and
 Pyrene-2,7-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane)
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2794
_journal_paper_doi               10.1021/cg201554t
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C28 H32 B2 O4'
_chemical_formula_sum            'C28 H32 B2 O4'
_chemical_formula_weight         454.16
_chemical_name_systematic
; 
 Pyrene-2,7-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane) 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.286(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4525(1)
_cell_length_b                   11.0823(2)
_cell_length_c                   16.9139(3)
_cell_measurement_reflns_used    2968
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      65.19
_cell_measurement_theta_min      4.77
_cell_volume                     1207.50(4)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT V7.60A (Bruker, 2008)'
_computing_molecular_graphics
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker PLATINUM135 CCD area detector'
_diffrn_measurement_method       'w scans'
_diffrn_radiation_monochromator  'cross-coupled G\"obel mirrors'
_diffrn_radiation_source         'Microstar rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6183
_diffrn_reflns_theta_full        65.74
_diffrn_reflns_theta_max         65.74
_diffrn_reflns_theta_min         4.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker), R(int)=0.083 before correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pyramid
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0608P)²+0.2820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                1718
_reflns_number_total             2045
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg201554t_si_002.cif
_cod_data_source_block           \g-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4506142
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.13474(14) 0.81243(9) 0.32852(6) 0.0360(3) Uani 1 1 d .
O2 O 0.11983(14) 0.94769(9) 0.36751(6) 0.0365(3) Uani 1 1 d .
C1 C 0.1216(2) 0.60839(13) 0.40761(8) 0.0329(4) Uani 1 1 d .
H1 H -0.0067 0.5892 0.3828 0.040 Uiso 1 1 d R
C2 C 0.1848(2) 0.72844(14) 0.41016(8) 0.0332(4) Uani 1 1 d .
C3 C 0.3747(2) 0.75660(14) 0.45003(8) 0.0332(3) Uani 1 1 d .
H3 H 0.4192 0.8366 0.4520 0.040 Uiso 1 1 d R
C4 C 0.6970(2) 0.69603(14) 0.52667(8) 0.0348(4) Uani 1 1 d .
H4 H 0.7406 0.7761 0.5303 0.042 Uiso 1 1 d R
C5 C 0.8193(2) 0.60842(14) 0.56031(9) 0.0351(4) Uani 1 1 d .
H5 H 0.9462 0.6291 0.5856 0.042 Uiso 1 1 d R
C6 C 0.5016(2) 0.66815(13) 0.48622(8) 0.0313(3) Uani 1 1 d .
C7 C 0.4361(2) 0.54626(13) 0.48205(8) 0.0298(3) Uani 1 1 d .
C8 C 0.2424(2) 0.51562(14) 0.44246(8) 0.0317(3) Uani 1 1 d .
C9 C -0.1815(2) 0.92395(13) 0.28408(8) 0.0340(4) Uani 1 1 d .
C10 C -0.0511(2) 1.01953(14) 0.33208(8) 0.0353(4) Uani 1 1 d .
C11 C -0.4142(2) 0.94641(15) 0.28118(9) 0.0401(4) Uani 1 1 d .
H11C H -0.4436 1.0250 0.2592 0.047(3) Uiso 1 1 d R
H11B H -0.4632 0.9423 0.3338 0.047(3) Uiso 1 1 d R
H11A H -0.4832 0.8860 0.2485 0.047(3) Uiso 1 1 d R
C12 C -0.1095(2) 0.90372(15) 0.20159(9) 0.0412(4) Uani 1 1 d .
H12B H 0.0377 0.8896 0.2046 0.046(3) Uiso 1 1 d R
H12C H -0.1403 0.9735 0.1691 0.046(3) Uiso 1 1 d R
H12A H -0.1798 0.8345 0.1787 0.046(3) Uiso 1 1 d R
C13 C -0.1639(2) 1.07237(15) 0.40085(9) 0.0427(4) Uani 1 1 d .
H13B H -0.2758 1.1229 0.3805 0.047(3) Uiso 1 1 d R
H13C H -0.0687 1.1197 0.4339 0.047(3) Uiso 1 1 d R
H13A H -0.2186 1.0079 0.4315 0.047(3) Uiso 1 1 d R
C14 C 0.0374(2) 1.11854(15) 0.28262(10) 0.0424(4) Uani 1 1 d .
H14A H 0.1298 1.0830 0.2465 0.047(3) Uiso 1 1 d R
H14C H 0.1127 1.1753 0.3163 0.047(3) Uiso 1 1 d R
H14B H -0.0732 1.1596 0.2531 0.047(3) Uiso 1 1 d R
B B 0.0531(2) 0.83057(16) 0.36850(10) 0.0341(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'
O O 0.0492 0.0322 '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_3
B O1 C9 106.22(11) .
B O2 C10 106.94(11) .
C2 C1 C8 122.30(13) .
C1 C2 C3 118.36(14) .
C1 C2 B 121.94(13) .
C3 C2 B 119.69(14) .
C6 C3 C2 122.01(14) .
C5 C4 C6 121.39(14) .
C4 C5 C8 121.35(13) 3_666
C3 C6 C7 118.82(13) .
C3 C6 C4 122.39(14) .
C7 C6 C4 118.78(13) .
C6 C7 C8 120.14(13) .
C6 C7 C7 119.99(16) 3_666
C8 C7 C7 119.87(17) 3_666
C1 C8 C7 118.37(14) .
C1 C8 C5 123.01(13) 3_666
C7 C8 C5 118.62(13) 3_666
O1 C9 C12 106.40(11) .
O1 C9 C11 109.15(11) .
C12 C9 C11 110.46(12) .
O1 C9 C10 102.55(11) .
C12 C9 C10 113.43(12) .
C11 C9 C10 114.20(12) .
O2 C10 C14 108.81(11) .
O2 C10 C13 106.17(11) .
C14 C10 C13 110.82(13) .
O2 C10 C9 102.50(11) .
C14 C10 C9 114.61(12) .
C13 C10 C9 113.15(12) .
O2 B O1 113.82(13) .
O2 B C2 122.05(14) .
O1 B C2 124.12(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 B 1.369(2) .
O1 C9 1.4689(17) .
O2 B 1.368(2) .
O2 C10 1.4608(17) .
C1 C2 1.391(2) .
C1 C8 1.400(2) .
C2 C3 1.400(2) .
C2 B 1.559(2) .
C3 C6 1.396(2) .
C4 C5 1.355(2) .
C4 C6 1.433(2) .
C5 C8 1.431(2) 3_666
C6 C7 1.416(2) .
C7 C8 1.425(2) .
C7 C7 1.429(3) 3_666
C8 C5 1.431(2) 3_666
C9 C12 1.512(2) .
C9 C11 1.5200(19) .
C9 C10 1.553(2) .
C10 C14 1.511(2) .
C10 C13 1.524(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11419644
