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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/4/02/69/4026933.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_4026933
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         'C69 H54 N6 O6 , C5 H12'
_chemical_formula_sum            'C74 H66 N6 O6'
_chemical_formula_weight         1135.33
_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                   17.9054(8)
_cell_length_b                   17.9054(8)
_cell_length_c                   11.0374(7)
_cell_measurement_reflns_used    5030
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.26
_cell_volume                     3064.5(3)
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15295
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker AXS, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       polyhedral
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.989
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3556
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0881P)²+1.2353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                2697
_reflns_number_total             3556
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202273s_si_005.cif
_cod_data_source_block           gl1759
_cod_database_code               4026933
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
O11 O 0.27665(10) -0.21783(10) 0.79364(16) 0.0497(5) Uani 1 1 d .
O12 O 0.22299(10) -0.12242(10) 1.00366(13) 0.0433(4) Uani 1 1 d .
H12A H 0.2750 -0.0876 0.9877 0.065 Uiso 1 1 calc R
N11 N 0.43449(11) -0.09456(11) 0.81702(16) 0.0390(4) Uani 1 1 d .
H11B H 0.3794 -0.1124 0.8059 0.047 Uiso 1 1 calc R
N12 N 0.35144(11) -0.01079(11) 0.87492(15) 0.0356(4) Uani 1 1 d .
C1 C 0.30314(14) -0.27068(14) 0.7972(2) 0.0389(5) Uani 1 1 d .
C2 C 0.39514(13) -0.24179(13) 0.79964(19) 0.0369(5) Uani 1 1 d .
C11 C 0.45559(14) -0.15546(14) 0.81094(19) 0.0372(5) Uani 1 1 d .
H11A H 0.5149 -0.1391 0.8145 0.045 Uiso 1 1 calc R
C13 C 0.48647(13) -0.00595(13) 0.83845(18) 0.0352(5) Uani 1 1 d .
C14 C 0.57636(14) 0.03866(14) 0.83593(19) 0.0404(5) Uani 1 1 d .
H14A H 0.6067 0.0087 0.8202 0.048 Uiso 1 1 calc R
C15 C 0.62106(15) 0.12639(15) 0.8564(2) 0.0473(6) Uani 1 1 d .
H15A H 0.6823 0.1569 0.8535 0.057 Uiso 1 1 calc R
C16 C 0.57771(16) 0.17049(15) 0.8809(2) 0.0514(6) Uani 1 1 d .
H16A H 0.6093 0.2309 0.8952 0.062 Uiso 1 1 calc R
C17 C 0.48805(15) 0.12671(14) 0.8849(2) 0.0447(6) Uani 1 1 d .
H17A H 0.4583 0.1569 0.9027 0.054 Uiso 1 1 calc R
C18 C 0.44245(13) 0.03883(13) 0.86258(18) 0.0359(5) Uani 1 1 d .
C19 C 0.29979(13) -0.01337(13) 0.79087(18) 0.0325(5) Uani 1 1 d .
C101 C 0.17290(14) -0.12216(14) 0.91257(19) 0.0374(5) Uani 1 1 d .
C102 C 0.20644(13) -0.07012(13) 0.80843(17) 0.0324(5) Uani 1 1 d .
C103 C 0.14847(14) -0.07539(14) 0.71940(19) 0.0379(5) Uani 1 1 d .
H10A H 0.1706 -0.0407 0.6489 0.046 Uiso 1 1 calc R
C104 C 0.06026(14) -0.12894(16) 0.7295(2) 0.0468(6) Uani 1 1 d .
C105 C 0.02976(15) -0.17893(18) 0.8336(2) 0.0579(7) Uani 1 1 d .
H10B H -0.0305 -0.2162 0.8433 0.069 Uiso 1 1 calc R
C106 C 0.08497(15) -0.17562(17) 0.9229(2) 0.0530(7) Uani 1 1 d .
H10C H 0.0621 -0.2108 0.9928 0.064 Uiso 1 1 calc R
C120 C -0.00021(17) -0.1348(2) 0.6303(3) 0.0683(8) Uani 1 1 d .
H12B H 0.0330 -0.0957 0.5642 0.102 Uiso 1 1 calc R
H12C H -0.0410 -0.1184 0.6625 0.102 Uiso 1 1 calc R
H12D H -0.0320 -0.1941 0.5997 0.102 Uiso 1 1 calc R
C191 C 0.33135(13) 0.03690(14) 0.67598(19) 0.0400(5) Uani 1 1 d .
C192 C 0.3561(2) 0.0041(2) 0.5804(2) 0.0691(8) Uani 1 1 d .
H19A H 0.3540 -0.0497 0.5883 0.083 Uiso 1 1 calc R
C193 C 0.3841(3) 0.0504(3) 0.4730(3) 0.0979(13) Uani 1 1 d .
H19B H 0.4017 0.0284 0.4076 0.118 Uiso 1 1 calc R
C194 C 0.3864(2) 0.1278(3) 0.4608(3) 0.0950(13) Uani 1 1 d .
H19C H 0.4046 0.1588 0.3867 0.114 Uiso 1 1 calc R
C195 C 0.3627(2) 0.1598(3) 0.5549(4) 0.0970(13) Uani 1 1 d .
H19D H 0.3646 0.2135 0.5463 0.116 Uiso 1 1 calc R
C196 C 0.33552(19) 0.1152(2) 0.6639(3) 0.0705(9) Uani 1 1 d .
H19E H 0.3199 0.1389 0.7297 0.085 Uiso 1 1 calc R
C1P C 0.6065(7) 0.1705(7) 0.5438(9) 0.161(3) Uiso 0.67 1 d PD
C2P C 0.6272(10) 0.2550(8) 0.5339(12) 0.228(6) Uiso 0.67 1 d PD
C3P C 0.7006(10) 0.2976(11) 0.5994(14) 0.149(6) 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'
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 129.83(18) . .
C11 N11 H11B 115.1 . .
C13 N11 H11B 115.1 . .
C19 N12 C18 121.98(17) . .
O11 C1 C2 120.14(19) . 2_545
O11 C1 C2 121.28(19) . .
C2 C1 C2 118.6(2) 2_545 .
C11 C2 C1 117.69(19) . 3_655
C11 C2 C1 120.86(19) . .
C1 C2 C1 121.4(2) 3_655 .
N11 C11 C2 122.8(2) . .
N11 C11 H11A 118.6 . .
C2 C11 H11A 118.6 . .
C14 C13 N11 124.64(19) . .
C14 C13 C18 119.61(19) . .
N11 C13 C18 115.75(18) . .
C15 C14 C13 119.7(2) . .
C15 C14 H14A 120.1 . .
C13 C14 H14A 120.1 . .
C14 C15 C16 120.7(2) . .
C14 C15 H15A 119.6 . .
C16 C15 H15A 119.6 . .
C15 C16 C17 120.2(2) . .
C15 C16 H16A 119.9 . .
C17 C16 H16A 119.9 . .
C18 C17 C16 119.6(2) . .
C18 C17 H17A 120.2 . .
C16 C17 H17A 120.2 . .
C17 C18 C13 120.18(19) . .
C17 C18 N12 122.3(2) . .
C13 C18 N12 117.24(18) . .
N12 C19 C102 118.35(18) . .
N12 C19 C191 122.62(18) . .
C102 C19 C191 119.01(17) . .
O12 C101 C106 117.81(19) . .
O12 C101 C102 123.05(19) . .
C106 C101 C102 119.14(19) . .
C103 C102 C101 118.14(19) . .
C103 C102 C19 120.19(18) . .
C101 C102 C19 121.65(18) . .
C104 C103 C102 122.8(2) . .
C104 C103 H10A 118.6 . .
C102 C103 H10A 118.6 . .
C103 C104 C105 117.3(2) . .
C103 C104 C120 121.4(2) . .
C105 C104 C120 121.3(2) . .
C106 C105 C104 121.5(2) . .
C106 C105 H10B 119.3 . .
C104 C105 H10B 119.3 . .
C101 C106 C105 121.1(2) . .
C101 C106 H10C 119.4 . .
C105 C106 H10C 119.4 . .
C104 C120 H12B 109.5 . .
C104 C120 H12C 109.5 . .
H12B C120 H12C 109.5 . .
C104 C120 H12D 109.5 . .
H12B C120 H12D 109.5 . .
H12C C120 H12D 109.5 . .
C196 C191 C192 119.6(2) . .
C196 C191 C19 120.6(2) . .
C192 C191 C19 119.8(2) . .
C191 C192 C193 119.6(3) . .
C191 C192 H19A 120.2 . .
C193 C192 H19A 120.2 . .
C194 C193 C192 120.4(4) . .
C194 C193 H19B 119.8 . .
C192 C193 H19B 119.8 . .
C195 C194 C193 119.7(3) . .
C195 C194 H19C 120.2 . .
C193 C194 H19C 120.2 . .
C194 C195 C196 121.0(4) . .
C194 C195 H19D 119.5 . .
C196 C195 H19D 119.5 . .
C191 C196 C195 119.7(3) . .
C191 C196 H19E 120.2 . .
C195 C196 H19E 120.2 . .
C3P C2P C3P 86.8(18) . 3_665
C3P C2P C1P 103.3(15) . .
C3P C2P C1P 129.2(15) 3_665 .
C2P C3P C2P 101.2(15) . 2_655
C2P C3P C3P 47.0(9) . 3_665
C2P C3P C3P 94.6(9) 2_655 3_665
C2P C3P C3P 95.2(9) . 2_655
C2P C3P C3P 46.2(9) 2_655 2_655
C3P C3P C3P 60.000(3) 3_665 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11 C1 1.253(3) .
O12 C101 1.349(2) .
O12 H12A 0.8400 .
N11 C11 1.322(3) .
N11 C13 1.401(3) .
N11 H11B 0.8800 .
N12 C19 1.294(3) .
N12 C18 1.420(3) .
C1 C2 1.458(3) 2_545
C1 C2 1.459(3) .
C2 C11 1.380(3) .
C2 C1 1.458(3) 3_655
C11 H11A 0.9500 .
C13 C14 1.394(3) .
C13 C18 1.402(3) .
C14 C15 1.379(3) .
C14 H14A 0.9500 .
C15 C16 1.383(4) .
C15 H15A 0.9500 .
C16 C17 1.391(3) .
C16 H16A 0.9500 .
C17 C18 1.385(3) .
C17 H17A 0.9500 .
C19 C102 1.472(3) .
C19 C191 1.493(3) .
C101 C106 1.379(3) .
C101 C102 1.411(3) .
C102 C103 1.398(3) .
C103 C104 1.383(3) .
C103 H10A 0.9500 .
C104 C105 1.389(3) .
C104 C120 1.507(3) .
C105 C106 1.376(3) .
C105 H10B 0.9500 .
C106 H10C 0.9500 .
C120 H12B 0.9800 .
C120 H12C 0.9800 .
C120 H12D 0.9800 .
C191 C196 1.374(4) .
C191 C192 1.383(4) .
C192 C193 1.389(4) .
C192 H19A 0.9500 .
C193 C194 1.372(6) .
C193 H19B 0.9500 .
C194 C195 1.352(6) .
C194 H19C 0.9500 .
C195 C196 1.390(4) .
C195 H19D 0.9500 .
C196 H19E 0.9500 .
C1P C2P 1.370(9) .
C2P C3P 1.353(9) .
C2P C3P 1.370(9) 3_665
C3P C2P 1.370(9) 2_655
C3P C3P 1.87(3) 3_665
C3P C3P 1.87(3) 2_655
