#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/76/1507675.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_1507675
loop_
_publ_author_name
'Yamaguchi, Ryuichi'
'Hiroto, Satoru'
'Shinokubo, Hiroshi'
_publ_section_title
;
 Synthesis of oxygen-substituted hexa-peri-hexabenzocoronenes through
 Ir-catalyzed direct borylation.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2472
_journal_page_last               2475
_journal_paper_doi               10.1021/ol300743f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C71.63 H53.5 Cl1.25 O4.38'
_chemical_formula_weight         1028.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           205
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-P 2ac 2ab 3'
_symmetry_space_group_name_H-M   'P a -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.814(2)
_cell_length_b                   21.814(2)
_cell_length_c                   21.814(2)
_cell_measurement_reflns_used    3040
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.96
_cell_measurement_theta_min      2.28
_cell_volume                     10380.2(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.2054
_diffrn_reflns_av_sigmaI/netI    0.0834
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            57852
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9721
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4316
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3046
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0590
_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)+(0.1121P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1987
_reflns_number_gt                1346
_reflns_number_total             3046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300743f_si_003.cif
_cod_data_source_block           0614ryu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Rhombohedral' changed to
'rhombohedral' 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 

 Adding full bibliography for 1507674--1507676.cif.
;
_cod_original_sg_symbol_H-M      Pa-3
_cod_original_formula_sum        'C71.63 H53.50 Cl1.25 O4.38'
_cod_database_code               1507675
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'z, x, y'
'-z+1/2, -x, y+1/2'
'z+1/2, -x+1/2, -y'
'-z, x+1/2, -y+1/2'
'y, z, x'
'y+1/2, -z+1/2, -x'
'-y, z+1/2, -x+1/2'
'-y+1/2, -z, x+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'-z, -x, -y'
'z-1/2, x, -y-1/2'
'-z-1/2, x-1/2, y'
'z, -x-1/2, y-1/2'
'-y, -z, -x'
'-y-1/2, z-1/2, x'
'y, -z-1/2, x-1/2'
'y-1/2, z, -x-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
O1 O 0.03708(14) 0.45927(14) 0.39043(16) 0.0810(10) Uani 1 1 d . . .
H62 H 0.0040 0.4488 0.3759 0.122 Uiso 1 1 calc R . .
C1 C 0.23511(15) 0.32010(15) 0.30634(15) 0.0394(9) Uani 1 1 d . . .
C5 C 0.23922(16) 0.19644(16) 0.42603(16) 0.0430(9) Uani 1 1 d . . .
C6 C 0.25394(15) 0.26816(16) 0.33945(15) 0.0400(9) Uani 1 1 d . . .
C9 C 0.22051(15) 0.24815(16) 0.39232(15) 0.0420(9) Uani 1 1 d . . .
C10 C 0.18198(16) 0.35415(16) 0.32569(16) 0.0431(9) Uani 1 1 d . . .
C19 C 0.16341(16) 0.40738(16) 0.29415(16) 0.0457(9) Uani 1 1 d . . .
C23 C 0.16687(16) 0.27980(16) 0.41117(15) 0.0437(9) Uani 1 1 d . . .
C24 C 0.14838(16) 0.33486(16) 0.37786(16) 0.0454(9) Uani 1 1 d . . .
C26 C 0.13396(17) 0.25844(17) 0.46086(16) 0.0502(10) Uani 1 1 d . . .
H2 H 0.0985 0.2790 0.4725 0.060 Uiso 1 1 calc R . .
C27 C 0.09932(17) 0.37036(18) 0.39720(18) 0.0544(11) Uani 1 1 d . . .
H3 H 0.0771 0.3583 0.4315 0.065 Uiso 1 1 calc R . .
C31 C 0.11405(18) 0.44068(18) 0.31595(18) 0.0570(11) Uani 1 1 d . . .
H4 H 0.1018 0.4760 0.2955 0.068 Uiso 1 1 calc R . .
C43 C 0.20477(17) 0.17776(17) 0.47642(16) 0.0484(10) Uani 1 1 d . . .
H11 H 0.2178 0.1441 0.4990 0.058 Uiso 1 1 calc R . .
C46 C 0.11566(18) 0.18738(16) 0.54830(16) 0.0455(10) Uani 1 1 d . . .
C50 C 0.08305(18) 0.42245(18) 0.36704(19) 0.0575(11) Uani 1 1 d . . .
C52 C 0.15203(17) 0.20766(17) 0.49372(16) 0.0464(9) Uani 1 1 d . . .
C63 C 0.0462(2) 0.15374(18) 0.65123(18) 0.0575(11) Uani 1 1 d . . .
C70 C 0.13793(19) 0.19714(16) 0.60679(17) 0.0510(10) Uani 1 1 d . . .
C73 C 0.1020(2) 0.17984(17) 0.65701(18) 0.0577(11) Uani 1 1 d . . .
H17 H 0.1172 0.1867 0.6962 0.069 Uiso 1 1 calc R . .
C75 C 0.05870(18) 0.15930(18) 0.54038(18) 0.0540(10) Uani 1 1 d . . .
C82 C 0.19861(18) 0.22865(19) 0.61648(19) 0.0674(12) Uani 1 1 d . . .
H21 H 0.2312 0.2021 0.6033 0.101 Uiso 1 1 calc R . .
H22 H 0.2036 0.2380 0.6592 0.101 Uiso 1 1 calc R . .
H23 H 0.1997 0.2659 0.5931 0.101 Uiso 1 1 calc R . .
C86 C 0.0341(2) 0.1459(2) 0.47742(19) 0.0771(14) Uani 1 1 d . . .
H33 H 0.0024 0.1154 0.4802 0.116 Uiso 1 1 calc R . .
H34 H 0.0666 0.1309 0.4518 0.116 Uiso 1 1 calc R . .
H35 H 0.0175 0.1827 0.4600 0.116 Uiso 1 1 calc R . .
C92 C 0.0064(2) 0.1387(2) 0.7053(2) 0.0884(16) Uani 1 1 d . . .
H42 H 0.0213 0.1600 0.7409 0.133 Uiso 1 1 calc R . .
H43 H 0.0074 0.0953 0.7127 0.133 Uiso 1 1 calc R . .
H44 H -0.0350 0.1512 0.6970 0.133 Uiso 1 1 calc R . .
C93 C 0.0251(2) 0.1438(2) 0.5918(2) 0.0659(12) Uani 1 1 d . . .
H45 H -0.0133 0.1260 0.5865 0.079 Uiso 1 1 calc R . .
C105 C 0.0757(9) 0.0757(9) 0.0757(9) 0.154(6) Uani 0.57(2) 3 d SPDU A 1
H63 H 0.0498 0.0498 0.0498 0.185 Uiso 0.57(2) 3 calc SPR A 1
Cl1 Cl 0.0824(11) 0.0456(8) 0.1475(7) 0.121(7) Uani 0.189(7) 1 d PDU A 1
C110 C 0.1077(7) 0.1077(7) 0.1077(7) 0.146(5) Uani 0.67(2) 3 d SPDU B 2
H64 H 0.1336 0.1336 0.1336 0.175 Uiso 0.67(2) 3 calc SPR B 2
Cl2 Cl 0.0999(5) 0.0545(6) 0.1633(5) 0.077(3) Uani 0.224(7) 1 d PDU B 2
O2 O 0.0393(6) 0.0214(7) 0.1714(8) 0.175(6) Uani 0.467(9) 1 d P C 3
C111 C 0.0884(7) 0.0015(10) 0.2038(7) 0.153(9) Uani 0.467(9) 1 d P C 3
H65 H 0.1252 0.0100 0.1813 0.229 Uiso 0.467(9) 1 calc PR C 3
H66 H 0.0850 -0.0418 0.2105 0.229 Uiso 0.467(9) 1 calc PR C 3
H67 H 0.0898 0.0223 0.2426 0.229 Uiso 0.467(9) 1 calc PR C 3
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'
Cl Cl 0.1484 0.1585 '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_
_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
C50 O1 H62 109.5 . .
C6 C1 C6 120.4(3) . 9
C6 C1 C10 120.0(3) . .
C6 C1 C10 119.5(3) 9 .
C43 C5 C9 119.4(3) . .
C43 C5 C19 121.3(3) . 5
C9 C5 C19 119.3(3) . 5
C1 C6 C1 119.6(3) . 5
C1 C6 C9 120.7(3) . .
C1 C6 C9 119.7(3) 5 .
C5 C9 C23 118.5(3) . .
C5 C9 C6 121.2(3) . .
C23 C9 C6 120.3(3) . .
C19 C10 C24 119.2(3) . .
C19 C10 C1 120.9(3) . .
C24 C10 C1 119.9(3) . .
C31 C19 C10 119.2(3) . .
C31 C19 C5 121.4(3) . 9
C10 C19 C5 119.3(3) . 9
C26 C23 C9 119.5(3) . .
C26 C23 C24 121.6(3) . .
C9 C23 C24 118.9(3) . .
C27 C24 C10 118.5(3) . .
C27 C24 C23 121.4(3) . .
C10 C24 C23 120.1(3) . .
C52 C26 C23 122.1(3) . .
C52 C26 H2 119.0 . .
C23 C26 H2 119.0 . .
C50 C27 C24 121.4(4) . .
C50 C27 H3 119.3 . .
C24 C27 H3 119.3 . .
C50 C31 C19 120.9(4) . .
C50 C31 H4 119.5 . .
C19 C31 H4 119.5 . .
C52 C43 C5 122.0(3) . .
C52 C43 H11 119.0 . .
C5 C43 H11 119.0 . .
C70 C46 C75 119.7(3) . .
C70 C46 C52 120.2(3) . .
C75 C46 C52 120.2(3) . .
C27 C50 C31 120.7(4) . .
C27 C50 O1 119.7(4) . .
C31 C50 O1 119.5(4) . .
C43 C52 C26 118.6(3) . .
C43 C52 C46 121.4(3) . .
C26 C52 C46 120.0(3) . .
C73 C63 C93 116.8(4) . .
C73 C63 C92 122.7(4) . .
C93 C63 C92 120.4(4) . .
C46 C70 C73 119.0(4) . .
C46 C70 C82 120.6(3) . .
C73 C70 C82 120.4(4) . .
C63 C73 C70 123.1(4) . .
C63 C73 H17 118.5 . .
C70 C73 H17 118.5 . .
C93 C75 C46 118.6(4) . .
C93 C75 C86 120.3(4) . .
C46 C75 C86 121.1(3) . .
C70 C82 H21 109.5 . .
C70 C82 H22 109.5 . .
H21 C82 H22 109.5 . .
C70 C82 H23 109.5 . .
H21 C82 H23 109.5 . .
H22 C82 H23 109.5 . .
C75 C86 H33 109.5 . .
C75 C86 H34 109.5 . .
H33 C86 H34 109.5 . .
C75 C86 H35 109.5 . .
H33 C86 H35 109.5 . .
H34 C86 H35 109.5 . .
C63 C92 H42 109.5 . .
C63 C92 H43 109.5 . .
H42 C92 H43 109.5 . .
C63 C92 H44 109.5 . .
H42 C92 H44 109.5 . .
H43 C92 H44 109.5 . .
C75 C93 C63 122.9(4) . .
C75 C93 H45 118.6 . .
C63 C93 H45 118.6 . .
Cl1 C105 Cl1 107.9(12) 9 5
Cl1 C105 Cl1 107.9(12) 9 .
Cl1 C105 Cl1 107.9(12) 5 .
Cl1 C105 H63 111.0 9 .
Cl1 C105 H63 111.0 5 .
Cl1 C105 H63 111.0 . .
Cl2 C110 Cl2 119.84(13) 9 .
Cl2 C110 Cl2 119.84(13) 9 5
Cl2 C110 Cl2 119.84(13) . 5
Cl2 C110 H64 92.3 9 .
Cl2 C110 H64 92.3 . .
Cl2 C110 H64 92.3 5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C50 1.382(4) .
O1 H62 0.8200 .
C1 C6 1.405(4) .
C1 C6 1.416(4) 9
C1 C10 1.440(4) .
C5 C43 1.392(5) .
C5 C9 1.407(5) .
C5 C19 1.456(5) 5
C6 C1 1.416(4) 5
C6 C9 1.433(4) .
C9 C23 1.420(5) .
C10 C19 1.409(5) .
C10 C24 1.417(5) .
C19 C31 1.383(5) .
C19 C5 1.456(5) 9
C23 C26 1.381(5) .
C23 C24 1.461(5) .
C24 C27 1.387(5) .
C26 C52 1.377(5) .
C26 H2 0.9300 .
C27 C50 1.360(5) .
C27 H3 0.9300 .
C31 C50 1.363(5) .
C31 H4 0.9300 .
C43 C52 1.375(5) .
C43 H11 0.9300 .
C46 C70 1.382(5) .
C46 C75 1.396(5) .
C46 C52 1.498(5) .
C63 C73 1.349(5) .
C63 C93 1.392(6) .
C63 C92 1.502(5) .
C70 C73 1.399(5) .
C70 C82 1.506(5) .
C73 H17 0.9300 .
C75 C93 1.382(5) .
C75 C86 1.504(5) .
C82 H21 0.9600 .
C82 H22 0.9600 .
C82 H23 0.9600 .
C86 H33 0.9600 .
C86 H34 0.9600 .
C86 H35 0.9600 .
C92 H42 0.9600 .
C92 H43 0.9600 .
C92 H44 0.9600 .
C93 H45 0.9300 .
C105 Cl1 1.705(8) 9
C105 Cl1 1.706(8) 5
C105 Cl1 1.706(8) .
C105 H63 0.9800 .
C110 Cl2 1.687(10) 9
C110 Cl2 1.687(10) .
C110 Cl2 1.687(10) 5
C110 H64 0.9800 .
O2 C111 1.354(16) .
C111 H65 0.9600 .
C111 H66 0.9600 .
C111 H67 0.9600 .
