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#$Date: 2016-03-21 03:52:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178448 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/69/4026930.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_4026930
loop_
_publ_author_name
'Carl-Georg Freiherr von Richthofen'
'Anja Stammler'
'Hartmut Bögge'
'Thorsten Glaser'
_publ_contact_author_address
;     Fakultät f. Chemie
      Universität Bielefeld
      33501 Bielefeld
      Germany
;
_publ_contact_author_email       thorsten.glaser@uni-bielefeld.de
_publ_contact_author_fax         '49 521 106 6003'
_publ_contact_author_name        'Prof. Dr. Thorsten. Glaser'
_publ_contact_author_phone       '49 521 106 6105'
_publ_section_title
;
 Probing the Radialene-Character in Triplesalophen Ligands by
 Spectroscopic and Structural Analysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1435
_journal_page_last               1448
_journal_paper_doi               10.1021/jo202273s
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C66 H45 N6 O6 Cl3 , C5 H12'
_chemical_formula_sum            'C71 H57 Br3 N6 O6'
_chemical_formula_weight         1329.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           147
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_space_group_name_H-M   'P -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                120.00
_cell_formula_units_Z            2
_cell_length_a                   18.0254(6)
_cell_length_b                   18.0254(6)
_cell_length_c                   11.0413(5)
_cell_measurement_reflns_used    6361
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.26
_cell_volume                     3106.9(2)
_computing_cell_refinement       'SAINT (Bruker AXS, 2001)'
_computing_data_collection       'SMART (Bruker AXS, 2001)'
_computing_data_reduction        'SAINT (Bruker AXS, 2001)'
_computing_molecular_graphics    'DIAMOND 2.1 (Crystal Impact, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker AXS SMART 1K'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18384
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.006
_exptl_absorpt_correction_T_max  0.7948
_exptl_absorpt_correction_T_min  0.5487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker AXS, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       plates
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.108
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0533P)²+1.5644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                3570
_reflns_number_total             4465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202273s_si_002.cif
_cod_data_source_block           gl1809
_cod_database_code               4026930
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br -0.014105(16) 0.861611(19) 0.61527(2) 0.04920(11) Uani 1 1 d .
O11 O 0.27718(11) 0.78150(11) 0.80190(19) 0.0472(4) Uani 1 1 d .
O12 O 0.22689(11) 0.87948(11) 1.00528(14) 0.0402(4) Uani 1 1 d .
H12A H 0.2783 0.9143 0.9882 0.060 Uiso 1 1 calc R
N11 N 0.43408(12) 0.90399(12) 0.82239(18) 0.0349(4) Uani 1 1 d .
H11B H 0.3791 0.8861 0.8138 0.042 Uiso 1 1 calc R
N12 N 0.35245(12) 0.98891(12) 0.87403(17) 0.0322(4) Uani 1 1 d .
C1 C 0.30346(15) 0.72894(14) 0.8052(2) 0.0351(5) Uani 1 1 d .
C2 C 0.39467(14) 0.75753(14) 0.8073(2) 0.0342(5) Uani 1 1 d .
C11 C 0.45514(15) 0.84346(15) 0.8171(2) 0.0347(5) Uani 1 1 d .
H11A H 0.5140 0.8597 0.8201 0.042 Uiso 1 1 calc R
C13 C 0.48648(14) 0.99252(14) 0.8396(2) 0.0314(5) Uani 1 1 d .
C14 C 0.57537(15) 1.03637(15) 0.8357(2) 0.0370(5) Uani 1 1 d .
H14A H 0.6052 1.0061 0.8219 0.044 Uiso 1 1 calc R
C15 C 0.62046(16) 1.12445(16) 0.8520(2) 0.0441(6) Uani 1 1 d .
H15A H 0.6813 1.1545 0.8490 0.053 Uiso 1 1 calc R
C16 C 0.57771(17) 1.16882(16) 0.8726(3) 0.0483(6) Uani 1 1 d .
H16A H 0.6092 1.2292 0.8835 0.058 Uiso 1 1 calc R
C17 C 0.48867(16) 1.12547(15) 0.8774(2) 0.0424(6) Uani 1 1 d .
H17A H 0.4594 1.1561 0.8924 0.051 Uiso 1 1 calc R
C18 C 0.44304(14) 1.03807(14) 0.8602(2) 0.0322(5) Uani 1 1 d .
C19 C 0.30096(14) 0.98435(13) 0.78948(19) 0.0292(4) Uani 1 1 d .
C101 C 0.17620(15) 0.87761(15) 0.9146(2) 0.0354(5) Uani 1 1 d .
C102 C 0.20838(14) 0.92829(14) 0.80910(19) 0.0296(4) Uani 1 1 d .
C103 C 0.14981(14) 0.92193(14) 0.7200(2) 0.0335(5) Uani 1 1 d .
H10A H 0.1700 0.9553 0.6483 0.040 Uiso 1 1 calc R
C104 C 0.06353(15) 0.86773(16) 0.7360(2) 0.0391(5) Uani 1 1 d .
C105 C 0.03239(17) 0.81764(19) 0.8387(3) 0.0526(7) Uani 1 1 d .
H10B H -0.0274 0.7800 0.8484 0.063 Uiso 1 1 calc R
C106 C 0.08882(17) 0.82275(19) 0.9268(2) 0.0510(7) Uani 1 1 d .
H10C H 0.0675 0.7881 0.9972 0.061 Uiso 1 1 calc R
C191 C 0.33169(14) 1.03095(16) 0.6718(2) 0.0394(5) Uani 1 1 d .
C192 C 0.3598(2) 0.9977(2) 0.5815(3) 0.0675(9) Uani 1 1 d .
H19A H 0.3607 0.9460 0.5943 0.081 Uiso 1 1 calc R
C193 C 0.3869(3) 1.0411(4) 0.4713(3) 0.0980(14) Uani 1 1 d .
H19B H 0.4070 1.0190 0.4092 0.118 Uiso 1 1 calc R
C194 C 0.3850(2) 1.1146(3) 0.4518(4) 0.0938(15) Uani 1 1 d .
H19C H 0.4029 1.1431 0.3760 0.113 Uiso 1 1 calc R
C195 C 0.3576(2) 1.1472(3) 0.5399(4) 0.0911(14) Uani 1 1 d .
H19D H 0.3565 1.1987 0.5259 0.109 Uiso 1 1 calc R
C196 C 0.3308(2) 1.1056(2) 0.6512(3) 0.0626(9) Uani 1 1 d .
H19E H 0.3119 1.1290 0.7130 0.075 Uiso 1 1 calc R
C1P C 0.6152(9) 1.1795(9) 0.5366(13) 0.190(5) Uiso 0.67 1 d PD
C2P C 0.6272(10) 1.2636(9) 0.5422(14) 0.197(5) Uiso 0.67 1 d PD
C3P C 0.7148(12) 1.2944(14) 0.5694(17) 0.120(5) Uiso 0.33 1 d PD
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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 '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
C101 O12 H12A 109.5 . .
C11 N11 C13 129.5(2) . .
C11 N11 H11B 115.2 . .
C13 N11 H11B 115.2 . .
C19 N12 C18 121.80(19) . .
O11 C1 C2 121.3(2) . .
O11 C1 C2 120.2(2) . 2_665
C2 C1 C2 118.6(2) . 2_665
C11 C2 C1 121.1(2) . .
C11 C2 C1 117.5(2) . 3_565
C1 C2 C1 121.4(2) . 3_565
N11 C11 C2 122.5(2) . .
N11 C11 H11A 118.8 . .
C2 C11 H11A 118.8 . .
C14 C13 N11 124.9(2) . .
C14 C13 C18 119.5(2) . .
N11 C13 C18 115.53(19) . .
C15 C14 C13 119.8(2) . .
C15 C14 H14A 120.1 . .
C13 C14 H14A 120.1 . .
C16 C15 C14 120.5(2) . .
C16 C15 H15A 119.7 . .
C14 C15 H15A 119.7 . .
C15 C16 C17 120.2(2) . .
C15 C16 H16A 119.9 . .
C17 C16 H16A 119.9 . .
C18 C17 C16 119.9(2) . .
C18 C17 H17A 120.0 . .
C16 C17 H17A 120.0 . .
C17 C18 C13 120.1(2) . .
C17 C18 N12 122.7(2) . .
C13 C18 N12 116.97(19) . .
N12 C19 C102 118.03(19) . .
N12 C19 C191 122.7(2) . .
C102 C19 C191 119.21(19) . .
O12 C101 C106 117.5(2) . .
O12 C101 C102 122.9(2) . .
C106 C101 C102 119.6(2) . .
C103 C102 C101 118.4(2) . .
C103 C102 C19 120.06(19) . .
C101 C102 C19 121.53(19) . .
C104 C103 C102 120.4(2) . .
C104 C103 H10A 119.8 . .
C102 C103 H10A 119.8 . .
C103 C104 C105 121.1(2) . .
C103 C104 Br1 119.45(18) . .
C105 C104 Br1 119.48(18) . .
C106 C105 C104 119.4(2) . .
C106 C105 H10B 120.3 . .
C104 C105 H10B 120.3 . .
C105 C106 C101 121.2(2) . .
C105 C106 H10C 119.4 . .
C101 C106 H10C 119.4 . .
C196 C191 C192 119.5(3) . .
C196 C191 C19 120.8(2) . .
C192 C191 C19 119.7(3) . .
C191 C192 C193 119.1(4) . .
C191 C192 H19A 120.5 . .
C193 C192 H19A 120.5 . .
C194 C193 C192 120.8(4) . .
C194 C193 H19B 119.6 . .
C192 C193 H19B 119.6 . .
C195 C194 C193 120.2(3) . .
C195 C194 H19C 119.9 . .
C193 C194 H19C 119.9 . .
C194 C195 C196 120.2(4) . .
C194 C195 H19D 119.9 . .
C196 C195 H19D 119.9 . .
C191 C196 C195 120.2(4) . .
C191 C196 H19E 119.9 . .
C195 C196 H19E 119.9 . .
C3P C2P C3P 133(2) 3_575 .
C3P C2P C1P 129(2) 3_575 .
C3P C2P C1P 88.4(16) . .
C3P C2P C2P 48.5(10) 3_575 3_575
C3P C2P C2P 95.2(10) . 3_575
C1P C2P C2P 175.9(14) . 3_575
C3P C2P C2P 106.0(11) 3_575 2_775
C3P C2P C2P 37.1(10) . 2_775
C1P C2P C2P 123.2(17) . 2_775
C2P C2P C2P 60.000(10) 3_575 2_775
C2P C3P C2P 94.4(18) 2_775 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C104 1.896(2) .
O11 C1 1.254(3) .
O12 C101 1.345(3) .
O12 H12A 0.8400 .
N11 C11 1.324(3) .
N11 C13 1.403(3) .
N11 H11B 0.8800 .
N12 C19 1.290(3) .
N12 C18 1.424(3) .
C1 C2 1.457(3) .
C1 C2 1.459(3) 2_665
C2 C11 1.382(3) .
C2 C1 1.459(3) 3_565
C11 H11A 0.9500 .
C13 C14 1.388(3) .
C13 C18 1.408(3) .
C14 C15 1.387(3) .
C14 H14A 0.9500 .
C15 C16 1.379(4) .
C15 H15A 0.9500 .
C16 C17 1.391(4) .
C16 H16A 0.9500 .
C17 C18 1.378(3) .
C17 H17A 0.9500 .
C19 C102 1.472(3) .
C19 C191 1.495(3) .
C101 C106 1.385(4) .
C101 C102 1.413(3) .
C102 C103 1.405(3) .
C103 C104 1.373(3) .
C103 H10A 0.9500 .
C104 C105 1.382(4) .
C105 C106 1.377(4) .
C105 H10B 0.9500 .
C106 H10C 0.9500 .
C191 C196 1.372(4) .
C191 C192 1.384(4) .
C192 C193 1.396(5) .
C192 H19A 0.9500 .
C193 C194 1.361(6) .
C193 H19B 0.9500 .
C194 C195 1.351(6) .
C194 H19C 0.9500 .
C195 C196 1.395(5) .
C195 H19D 0.9500 .
C196 H19E 0.9500 .
C1P C2P 1.423(9) .
C2P C3P 1.144(19) 3_575
C2P C3P 1.419(9) .
C2P C2P 1.89(2) 3_575
C2P C2P 1.89(2) 2_775
C3P C2P 1.144(19) 2_775
