#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/49/1504922.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_1504922
loop_
_publ_author_name
'Finke, Aaron D.'
'Moore, Jeffrey S.'
_publ_contact_author
; 
Scott R. Wilson 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Iterative synthesis of 1,3,5-polyphenylene dendrons via C-H activation.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4851
_journal_page_last               4854
_journal_paper_doi               10.1021/ol8019605
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C20 H33 B O2'
_chemical_formula_sum            'C20 H33 B O2'
_chemical_formula_weight         316.27
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2008-07-09   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0312(12)
_cell_length_b                   16.3017(17)
_cell_length_c                   10.8502(12)
_cell_measurement_reflns_used    3306
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      22.05
_cell_measurement_theta_min      2.91
_cell_volume                     1951.2(4)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2005)'
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  ba94basx
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24256
_diffrn_reflns_theta_full        25.47
_diffrn_reflns_theta_max         25.47
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_correction_T_min  0.9867
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_id                ba94basx
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (0 4 3) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0068(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1867
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0498P)²+0.6675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                1274
_reflns_number_total             1867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8019605_si_002.cif
_cod_data_source_block           ba94basx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 2ac 2n '
_cod_original_sg_symbol_H-M      'P n m a '
_cod_database_code               1504922
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3271(2) 0.2500 0.6455(2) 0.0308(6) Uani 1 2 d S . .
H1A H 0.2514 0.2500 0.6873 0.037 Uiso 1 2 calc SR . .
C2 C 0.37964(14) 0.17467(10) 0.61648(14) 0.0294(4) Uani 1 1 d . A .
C3 C 0.49186(15) 0.17645(10) 0.55700(14) 0.0304(4) Uani 1 1 d . . .
H3A H 0.5301 0.1261 0.5364 0.036 Uiso 1 1 calc R . .
C4 C 0.5496(2) 0.2500 0.5269(2) 0.0286(5) Uani 1 2 d S . .
C7 C 0.31563(16) 0.09323(10) 0.64487(16) 0.0382(5) Uani 1 1 d DU . .
C8 C 0.2047(3) 0.10271(18) 0.7256(3) 0.0572(10) Uani 0.658(3) 1 d PDU A 1
H8A H 0.1452 0.1376 0.6837 0.086 Uiso 0.658(3) 1 calc PR A 1
H8B H 0.2280 0.1280 0.8040 0.086 Uiso 0.658(3) 1 calc PR A 1
H8C H 0.1690 0.0486 0.7412 0.086 Uiso 0.658(3) 1 calc PR A 1
C9 C 0.2753(3) 0.05454(19) 0.5203(3) 0.0608(10) Uani 0.658(3) 1 d PDU A 1
H9A H 0.2159 0.0905 0.4803 0.091 Uiso 0.658(3) 1 calc PR A 1
H9B H 0.2386 0.0008 0.5356 0.091 Uiso 0.658(3) 1 calc PR A 1
H9C H 0.3460 0.0481 0.4665 0.091 Uiso 0.658(3) 1 calc PR A 1
C10 C 0.4021(3) 0.0327(2) 0.7068(4) 0.0623(10) Uani 0.658(3) 1 d PDU A 1
H10A H 0.4267 0.0543 0.7873 0.094 Uiso 0.658(3) 1 calc PR A 1
H10B H 0.4739 0.0251 0.6549 0.094 Uiso 0.658(3) 1 calc PR A 1
H10C H 0.3610 -0.0201 0.7179 0.094 Uiso 0.658(3) 1 calc PR A 1
B1 B 0.6743(3) 0.2466(6) 0.4598(3) 0.0282(7) Uani 0.50 1 d PD . .
O1 O 0.7467(4) 0.1790(4) 0.4495(4) 0.0400(12) Uani 0.50 1 d PD . .
C15 C 0.8625(3) 0.2070(2) 0.3983(4) 0.0364(9) Uani 0.50 1 d PD . .
C16 C 0.8250(3) 0.2856(2) 0.3300(3) 0.0363(9) Uani 0.50 1 d PD . .
O2 O 0.7220(4) 0.3144(4) 0.4037(4) 0.0378(11) Uani 0.50 1 d PD . .
C17 C 0.9122(8) 0.1403(4) 0.3150(8) 0.048(3) Uani 0.50 1 d PD . .
H17A H 0.9988 0.1467 0.2971 0.058 Uiso 0.50 1 d PR . .
H17B H 0.8654 0.1476 0.2391 0.058 Uiso 0.50 1 d PR . .
H17C H 0.8974 0.0853 0.3482 0.058 Uiso 0.50 1 d PR . .
C18 C 0.9451(3) 0.2216(3) 0.5080(4) 0.0638(18) Uani 0.50 1 d PD . .
H18A H 1.0267 0.2353 0.4788 0.077 Uiso 0.50 1 calc PR . .
H18B H 0.9486 0.1718 0.5586 0.077 Uiso 0.50 1 calc PR . .
H18C H 0.9133 0.2670 0.5575 0.077 Uiso 0.50 1 calc PR . .
C19 C 0.7743(4) 0.2668(10) 0.2018(3) 0.073(4) Uani 0.50 1 d PD . .
H19A H 0.8399 0.2476 0.1483 0.088 Uiso 0.50 1 calc PR . .
H19B H 0.7385 0.3167 0.1669 0.088 Uiso 0.50 1 calc PR . .
H19C H 0.7120 0.2242 0.2082 0.088 Uiso 0.50 1 calc PR . .
C20 C 0.9226(9) 0.3524(5) 0.3269(11) 0.077(4) Uani 0.50 1 d PD . .
H20A H 0.9443 0.3678 0.4113 0.093 Uiso 0.50 1 calc PR . .
H20B H 0.8913 0.4006 0.2832 0.093 Uiso 0.50 1 calc PR . .
H20C H 0.9945 0.3316 0.2841 0.093 Uiso 0.50 1 calc PR . .
C11 C 0.3839(6) 0.0189(3) 0.5999(8) 0.069(2) Uani 0.342(3) 1 d PDU A 2
H11A H 0.4642 0.0174 0.6386 0.104 Uiso 0.342(3) 1 calc PR A 2
H11B H 0.3930 0.0219 0.5102 0.104 Uiso 0.342(3) 1 calc PR A 2
H11C H 0.3389 -0.0308 0.6218 0.104 Uiso 0.342(3) 1 calc PR A 2
C12 C 0.3019(7) 0.0872(4) 0.7878(5) 0.0611(17) Uani 0.342(3) 1 d PDU A 2
H12A H 0.2616 0.0356 0.8093 0.092 Uiso 0.342(3) 1 calc PR A 2
H12B H 0.2532 0.1334 0.8177 0.092 Uiso 0.342(3) 1 calc PR A 2
H12C H 0.3822 0.0889 0.8263 0.092 Uiso 0.342(3) 1 calc PR A 2
C13 C 0.1890(5) 0.0951(4) 0.5893(7) 0.0667(19) Uani 0.342(3) 1 d PDU A 2
H13A H 0.1494 0.0420 0.6024 0.100 Uiso 0.342(3) 1 calc PR A 2
H13B H 0.1947 0.1062 0.5007 0.100 Uiso 0.342(3) 1 calc PR A 2
H13C H 0.1413 0.1384 0.6289 0.100 Uiso 0.342(3) 1 calc PR A 2
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 2.00 0.0400
1.00 0.00 -2.00 0.0400
-1.00 2.00 1.00 0.0700
1.00 -2.00 -1.00 0.1100
-1.00 0.00 0.00 0.0700
1.00 0.00 0.00 0.0000
1.00 -2.00 2.00 0.0700
-1.00 -1.00 1.00 0.0800
1.00 1.00 -1.00 0.0700
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
C2 C1 C2 123.5(2) 7_565
C2 C1 H1A 118.2 7_565
C2 C1 H1A 118.2 .
C1 C2 C3 117.05(15) .
C1 C2 C7 121.69(15) .
C3 C2 C7 121.23(14) .
C4 C3 C2 122.01(16) .
C4 C3 H3A 119.0 .
C2 C3 H3A 119.0 .
C3 C4 C3 118.4(2) 7_565
C3 C4 B1 122.8(4) 7_565
C3 C4 B1 118.8(4) .
C11 C7 C8 132.3(3) .
C11 C7 C13 110.3(4) .
C8 C7 C13 59.0(3) .
C11 C7 C10 46.5(3) .
C8 C7 C10 108.4(2) .
C13 C7 C10 139.5(3) .
C11 C7 C2 113.6(3) .
C8 C7 C2 113.57(16) .
C13 C7 C2 109.0(3) .
C10 C7 C2 111.09(18) .
C11 C7 C9 62.4(3) .
C8 C7 C9 108.2(2) .
C13 C7 C9 53.3(3) .
C10 C7 C9 107.4(2) .
C2 C7 C9 107.91(16) .
C11 C7 C12 108.6(4) .
C8 C7 C12 49.7(3) .
C13 C7 C12 107.8(4) .
C10 C7 C12 65.4(3) .
C2 C7 C12 107.3(3) .
C9 C7 C12 144.1(3) .
C7 C8 H8A 109.5 .
C7 C8 H8B 109.5 .
C7 C8 H8C 109.5 .
C7 C9 H9A 109.5 .
C7 C9 H9B 109.5 .
C7 C9 H9C 109.5 .
C7 C10 H10A 109.5 .
C7 C10 H10B 109.5 .
C7 C10 H10C 109.5 .
O1 B1 O2 113.1(3) .
O1 B1 C4 125.6(6) .
O2 B1 C4 121.3(6) .
B1 O1 C15 106.8(4) .
O1 C15 C17 108.5(5) .
O1 C15 C18 106.0(3) .
C17 C15 C18 111.2(5) .
O1 C15 C16 102.0(3) .
C17 C15 C16 114.0(4) .
C18 C15 C16 114.2(3) .
O2 C16 C19 106.1(4) .
O2 C16 C20 109.2(5) .
C19 C16 C20 112.2(7) .
O2 C16 C15 102.3(3) .
C19 C16 C15 111.8(6) .
C20 C16 C15 114.5(5) .
B1 O2 C16 106.4(3) .
C15 C17 H17A 113.2 .
C15 C17 H17B 102.9 .
H17A C17 H17B 109.5 .
C15 C17 H17C 112.1 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.4 .
C15 C18 H18A 109.5 .
C15 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C15 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
C16 C19 H19A 109.5 .
C16 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C16 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C16 C20 H20A 109.5 .
C16 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
C16 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
C7 C11 H11A 109.5 .
C7 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C7 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C7 C12 H12A 109.5 .
C7 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C7 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C7 C13 H13A 109.5 .
C7 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C7 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3940(19) 7_565
C1 C2 1.3940(19) .
C1 H1A 0.9500 .
C2 C3 1.396(2) .
C2 C7 1.535(2) .
C3 C4 1.3962(19) .
C3 H3A 0.9500 .
C4 C3 1.3962(19) 7_565
C4 B1 1.558(4) .
C7 C11 1.507(5) .
C7 C8 1.513(3) .
C7 C13 1.522(5) .
C7 C10 1.528(3) .
C7 C9 1.557(3) .
C7 C12 1.562(5) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
B1 O1 1.366(6) .
B1 O2 1.366(6) .
O1 C15 1.466(5) .
C15 C17 1.517(6) .
C15 C18 1.518(5) .
C15 C16 1.537(4) .
C16 O2 1.467(5) .
C16 C19 1.529(5) .
C16 C20 1.532(6) .
C17 H17A 0.9801 .
C17 H17B 0.9798 .
C17 H17C 0.9794 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 C1 C2 C3 1.1(3) 7_565 .
C2 C1 C2 C7 -177.09(14) 7_565 .
C1 C2 C3 C4 -0.3(3) . .
C7 C2 C3 C4 177.91(17) . .
C2 C3 C4 C3 -0.5(3) . 7_565
C2 C3 C4 B1 -179.6(2) . .
C1 C2 C7 C11 176.7(4) . .
C3 C2 C7 C11 -1.4(4) . .
C1 C2 C7 C8 -10.3(3) . .
C3 C2 C7 C8 171.6(2) . .
C1 C2 C7 C13 53.3(4) . .
C3 C2 C7 C13 -124.8(3) . .
C1 C2 C7 C10 -132.9(2) . .
C3 C2 C7 C10 49.0(3) . .
C1 C2 C7 C9 109.7(2) . .
C3 C2 C7 C9 -68.4(2) . .
C1 C2 C7 C12 -63.2(4) . .
C3 C2 C7 C12 118.7(3) . .
C3 C4 B1 O1 166.1(3) 7_565 .
C3 C4 B1 O1 -14.8(5) . .
C3 C4 B1 O2 -14.0(5) 7_565 .
C3 C4 B1 O2 165.1(3) . .
O2 B1 O1 C15 9.5(5) . .
C4 B1 O1 C15 -170.6(3) . .
B1 O1 C15 C17 -145.4(5) . .
B1 O1 C15 C18 95.1(4) . .
B1 O1 C15 C16 -24.7(4) . .
O1 C15 C16 O2 30.2(3) . .
C17 C15 C16 O2 147.0(5) . .
C18 C15 C16 O2 -83.6(4) . .
O1 C15 C16 C19 -82.8(4) . .
C17 C15 C16 C19 33.9(6) . .
C18 C15 C16 C19 163.3(3) . .
O1 C15 C16 C20 148.1(6) . .
C17 C15 C16 C20 -95.1(6) . .
C18 C15 C16 C20 34.3(6) . .
O1 B1 O2 C16 11.2(5) . .
C4 B1 O2 C16 -168.7(3) . .
C19 C16 O2 B1 91.6(7) . .
C20 C16 O2 B1 -147.3(6) . .
C15 C16 O2 B1 -25.7(4) . .
