#------------------------------------------------------------------------------
#$Date: 2015-06-05 07:37:04 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138235 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/37/4123705.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_4123705
loop_
_publ_author_name
'Ji, Lei'
'Edkins, Robert M.'
'Lorbach, Andreas'
'Krummenacher, Ivo'
'Brückner, Charlotte'
'Eichhorn, Antonius'
'Braunschweig, Holger'
'Engels, Bernd'
'Low, Paul J.'
'Marder, Todd B.'
_publ_section_title
;
 Electron Delocalization in Reduced Forms of 2-(BMes2)pyrene and
 2,7-Bis(BMes2)pyrene.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6750
_journal_page_last               6753
_journal_paper_doi               10.1021/jacs.5b03805
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         '2(C H Cl3), C52 H52 B2'
_chemical_formula_sum            'C54 H54 B2 Cl6'
_chemical_formula_weight         937.29
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                109.364(6)
_cell_angle_beta                 94.604(7)
_cell_angle_gamma                92.908(7)
_cell_formula_units_Z            1
_cell_length_a                   8.3467(19)
_cell_length_b                   10.442(2)
_cell_length_c                   14.843(3)
_cell_measurement_reflns_used    1430
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.75
_cell_measurement_theta_min      2.46
_cell_volume                     1212.4(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0966
_diffrn_reflns_av_unetI/netI     0.1698
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_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            10390
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.758
_diffrn_reflns_theta_min         1.462
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.884
_refine_ls_R_factor_all          0.1537
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0625P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2351
_reflns_number_total             5162
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b03805_si_002.cif
_cod_data_source_block           cmpd_B2
_cod_depositor_comments
'Adding full bibliography for 4123702--4123707.cif.'
_cod_original_cell_volume        1212.4(5)
_cod_database_code               4123705
_shelxl_version_number           2013-4
_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_max   0.986
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C27(H27)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C4(H4), C5(H5), C13(H13), C22(H22), C11(H11), C20(H20)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C25(H25A,H25B,
 H25C), C24(H24A,H24B,H24C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cl2 Cl 0.24404(13) 0.09830(12) 0.16802(10) 0.0511(4) Uani 1 1 d .
Cl1 Cl 0.05197(17) 0.19109(15) 0.03704(10) 0.0651(5) Uani 1 1 d .
Cl3 Cl 0.0315(2) 0.30706(13) 0.23969(12) 0.0865(6) Uani 1 1 d .
C27 C 0.0596(5) 0.1573(4) 0.1458(3) 0.0375(11) Uani 1 1 d .
H27 H -0.0286 0.0862 0.1410 0.045 Uiso 1 1 calc R
C3 C 0.3819(4) 0.6543(3) 0.0438(2) 0.0156(8) Uani 1 1 d .
C2 C 0.2947(4) 0.7150(3) 0.1208(3) 0.0174(8) Uani 1 1 d .
H2 H 0.2408 0.7935 0.1221 0.021 Uiso 1 1 calc R
C7 C 0.3609(4) 0.5459(4) 0.1919(3) 0.0189(8) Uani 1 1 d .
H7 H 0.3566 0.5111 0.2432 0.023 Uiso 1 1 calc R
C6 C 0.4436(4) 0.4780(4) 0.1146(3) 0.0172(8) Uani 1 1 d .
C4 C 0.3994(4) 0.7088(4) -0.0323(3) 0.0182(8) Uani 1 1 d .
H4 H 0.3515 0.7903 -0.0300 0.022 Uiso 1 1 calc R
C1 C 0.2839(4) 0.6636(4) 0.1969(3) 0.0174(8) Uani 1 1 d .
C8 C 0.4562(4) 0.5332(3) 0.0393(2) 0.0157(8) Uani 1 1 d .
C9 C 0.0357(4) 0.8106(3) 0.2629(3) 0.0163(8) Uani 1 1 d .
C23 C 0.1295(4) 0.6739(4) 0.4328(3) 0.0218(9) Uani 1 1 d .
C5 C 0.5174(4) 0.3535(4) 0.1072(3) 0.0199(9) Uani 1 1 d .
H5 H 0.5074 0.3143 0.1560 0.024 Uiso 1 1 calc R
C18 C 0.2403(4) 0.7225(3) 0.3831(3) 0.0195(9) Uani 1 1 d .
C13 C -0.2164(4) 0.8152(4) 0.1715(3) 0.0234(9) Uani 1 1 d .
H13 H -0.2972 0.7694 0.1204 0.028 Uiso 1 1 calc R
C14 C -0.0869(4) 0.7464(3) 0.1886(3) 0.0181(8) Uani 1 1 d .
C19 C 0.4044(4) 0.7502(4) 0.4222(3) 0.0235(9) Uani 1 1 d .
C10 C 0.0199(4) 0.9479(4) 0.3197(3) 0.0188(8) Uani 1 1 d .
C22 C 0.1840(5) 0.6433(4) 0.5137(3) 0.0265(10) Uani 1 1 d .
H22 H 0.1082 0.6074 0.5453 0.032 Uiso 1 1 calc R
C21 C 0.3460(5) 0.6634(4) 0.5499(3) 0.0250(9) Uani 1 1 d .
B1 B 0.1854(5) 0.7359(4) 0.2823(3) 0.0189(10) Uani 1 1 d .
C11 C -0.1131(4) 1.0130(4) 0.3004(3) 0.0252(9) Uani 1 1 d .
H11 H -0.1225 1.1045 0.3394 0.030 Uiso 1 1 calc R
C12 C -0.2318(4) 0.9493(4) 0.2267(3) 0.0253(9) Uani 1 1 d .
C26 C -0.0491(4) 0.6504(4) 0.3995(3) 0.0277(10) Uani 1 1 d .
H26A H -0.0897 0.7357 0.3968 0.042 Uiso 1 1 calc GR
H26B H -0.1065 0.6197 0.4447 0.042 Uiso 1 1 calc GR
H26C H -0.0669 0.5808 0.3356 0.042 Uiso 1 1 calc GR
C20 C 0.4513(5) 0.7200(4) 0.5044(3) 0.0291(10) Uani 1 1 d .
H20 H 0.5612 0.7393 0.5302 0.035 Uiso 1 1 calc R
C15 C 0.1455(5) 1.0246(4) 0.4013(3) 0.0287(10) Uani 1 1 d .
H15A H 0.1387 0.9886 0.4541 0.043 Uiso 1 1 calc GR
H15B H 0.1264 1.1215 0.4238 0.043 Uiso 1 1 calc GR
H15C H 0.2530 1.0138 0.3790 0.043 Uiso 1 1 calc GR
C17 C -0.0894(4) 0.5966(4) 0.1279(3) 0.0272(10) Uani 1 1 d .
H17A H -0.0746 0.5886 0.0615 0.041 Uiso 1 1 calc GR
H17B H -0.1932 0.5496 0.1297 0.041 Uiso 1 1 calc GR
H17C H -0.0020 0.5552 0.1536 0.041 Uiso 1 1 calc GR
C25 C 0.4030(5) 0.6231(4) 0.6351(3) 0.0375(11) Uani 1 1 d .
H25A H 0.3230 0.6439 0.6817 0.056 Uiso 1 1 calc GR
H25B H 0.5063 0.6740 0.6653 0.056 Uiso 1 1 calc GR
H25C H 0.4166 0.5253 0.6137 0.056 Uiso 1 1 calc GR
C24 C 0.5293(4) 0.8159(4) 0.3798(3) 0.0325(11) Uani 1 1 d .
H24A H 0.5948 0.7463 0.3421 0.049 Uiso 1 1 calc GR
H24B H 0.5989 0.8843 0.4316 0.049 Uiso 1 1 calc GR
H24C H 0.4754 0.8600 0.3381 0.049 Uiso 1 1 calc GR
C16 C -0.3741(5) 1.0220(4) 0.2065(4) 0.0428(12) Uani 1 1 d .
H16A H -0.3398 1.0878 0.1763 0.064 Uiso 1 1 calc GR
H16B H -0.4178 1.0700 0.2669 0.064 Uiso 1 1 calc GR
H16C H -0.4574 0.9556 0.1633 0.064 Uiso 1 1 calc GR
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'
Cl Cl 0.1484 0.1585 '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
Cl2 C27 Cl1 110.0(2) . .
Cl2 C27 Cl3 110.1(2) . .
Cl3 C27 Cl1 109.3(2) . .
C2 C3 C4 122.6(3) . .
C2 C3 C8 119.1(3) . .
C8 C3 C4 118.3(3) . .
C3 C2 C1 122.0(3) . .
C6 C7 C1 122.5(3) . .
C7 C6 C8 118.9(3) . .
C7 C6 C5 122.7(3) . .
C8 C6 C5 118.4(3) . .
C5 C4 C3 121.4(3) 2_665 .
C2 C1 B1 120.1(3) . .
C7 C1 C2 117.7(3) . .
C7 C1 B1 122.1(3) . .
C3 C8 C6 119.6(3) . .
C3 C8 C8 120.6(4) . 2_665
C8 C8 C6 119.7(4) 2_665 .
C14 C9 C10 117.4(3) . .
C14 C9 B1 121.8(3) . .
C10 C9 B1 120.8(3) . .
C18 C23 C26 121.8(3) . .
C22 C23 C18 119.7(4) . .
C22 C23 C26 118.5(3) . .
C4 C5 C6 121.5(3) 2_665 .
C23 C18 C19 118.4(3) . .
C23 C18 B1 120.5(3) . .
C19 C18 B1 120.9(3) . .
C14 C13 C12 121.8(4) . .
C9 C14 C17 122.0(3) . .
C13 C14 C9 120.9(3) . .
C13 C14 C17 117.0(3) . .
C18 C19 C24 122.4(3) . .
C20 C19 C18 119.1(4) . .
C20 C19 C24 118.4(4) . .
C9 C10 C15 121.0(3) . .
C11 C10 C9 119.8(3) . .
C11 C10 C15 119.2(3) . .
C23 C22 C21 122.3(4) . .
C22 C21 C25 121.2(4) . .
C20 C21 C22 117.3(4) . .
C20 C21 C25 121.6(4) . .
C1 B1 C18 117.1(3) . .
C9 B1 C1 119.0(3) . .
C9 B1 C18 123.8(3) . .
C12 C11 C10 122.2(4) . .
C13 C12 C16 120.8(4) . .
C11 C12 C13 117.8(3) . .
C11 C12 C16 121.4(4) . .
C21 C20 C19 122.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl2 C27 1.734(4) .
Cl1 C27 1.760(4) .
Cl3 C27 1.758(4) .
C3 C2 1.392(5) .
C3 C4 1.436(5) .
C3 C8 1.421(5) .
C2 C1 1.409(5) .
C7 C6 1.390(5) .
C7 C1 1.399(5) .
C6 C8 1.425(5) .
C6 C5 1.441(5) .
C4 C5 1.354(5) 2_665
C1 B1 1.564(5) .
C8 C8 1.425(7) 2_665
C9 C14 1.404(5) .
C9 C10 1.421(5) .
C9 B1 1.563(5) .
C23 C18 1.402(5) .
C23 C22 1.390(5) .
C23 C26 1.514(5) .
C5 C4 1.354(5) 2_665
C18 C19 1.420(5) .
C18 B1 1.583(6) .
C13 C14 1.380(5) .
C13 C12 1.387(5) .
C14 C17 1.522(5) .
C19 C20 1.390(5) .
C19 C24 1.509(5) .
C10 C11 1.389(5) .
C10 C15 1.508(5) .
C22 C21 1.393(5) .
C21 C20 1.374(5) .
C21 C25 1.510(5) .
C11 C12 1.378(5) .
C12 C16 1.504(5) .
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_4
C3 C2 C1 C7 -1.6(5) .
C3 C2 C1 B1 179.6(3) .
C2 C3 C4 C5 -178.9(3) 2_665
C2 C3 C8 C6 -1.6(5) .
C2 C3 C8 C8 178.8(4) 2_665
C2 C1 B1 C9 30.9(5) .
C2 C1 B1 C18 -151.9(3) .
C7 C6 C8 C3 -1.2(5) .
C7 C6 C8 C8 178.4(4) 2_665
C7 C6 C5 C4 -178.3(3) 2_665
C7 C1 B1 C9 -147.8(3) .
C7 C1 B1 C18 29.4(5) .
C6 C7 C1 C2 -1.3(5) .
C6 C7 C1 B1 177.5(3) .
C4 C3 C2 C1 -177.4(3) .
C4 C3 C8 C6 178.9(3) .
C4 C3 C8 C8 -0.8(6) 2_665
C1 C7 C6 C8 2.7(5) .
C1 C7 C6 C5 -177.3(3) .
C8 C3 C2 C1 3.0(5) .
C8 C3 C4 C5 0.7(5) 2_665
C8 C6 C5 C4 1.7(5) 2_665
C9 C10 C11 C12 -0.6(6) .
C23 C18 C19 C20 4.1(5) .
C23 C18 C19 C24 -173.7(4) .
C23 C18 B1 C1 -126.0(4) .
C23 C18 B1 C9 51.1(5) .
C23 C22 C21 C20 2.2(6) .
C23 C22 C21 C25 -177.1(4) .
C5 C6 C8 C3 178.8(3) .
C5 C6 C8 C8 -1.6(6) 2_665
C18 C23 C22 C21 2.2(6) .
C18 C19 C20 C21 0.4(6) .
C14 C9 C10 C11 -0.1(5) .
C14 C9 C10 C15 179.7(3) .
C14 C9 B1 C1 51.2(5) .
C14 C9 B1 C18 -125.8(4) .
C14 C13 C12 C11 -0.2(6) .
C14 C13 C12 C16 -180.0(3) .
C19 C18 B1 C1 49.5(5) .
C19 C18 B1 C9 -133.4(4) .
C10 C9 C14 C13 0.7(5) .
C10 C9 C14 C17 -175.3(3) .
C10 C9 B1 C1 -128.0(4) .
C10 C9 B1 C18 54.9(5) .
C10 C11 C12 C13 0.8(6) .
C10 C11 C12 C16 -179.5(4) .
C22 C23 C18 C19 -5.3(5) .
C22 C23 C18 B1 170.3(3) .
C22 C21 C20 C19 -3.5(6) .
B1 C9 C14 C13 -178.6(3) .
B1 C9 C14 C17 5.4(5) .
B1 C9 C10 C11 179.1(3) .
B1 C9 C10 C15 -1.0(5) .
B1 C18 C19 C20 -171.5(3) .
B1 C18 C19 C24 10.7(5) .
C12 C13 C14 C9 -0.5(6) .
C12 C13 C14 C17 175.7(3) .
C26 C23 C18 C19 176.0(3) .
C26 C23 C18 B1 -8.3(5) .
C26 C23 C22 C21 -179.1(3) .
C15 C10 C11 C12 179.5(3) .
C25 C21 C20 C19 175.8(4) .
C24 C19 C20 C21 178.2(4) .
