#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:52:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178448 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/69/4026932.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_4026932
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 Cl3 N6 O6'
_chemical_formula_weight         1196.58
_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                   17.9406(6)
_cell_length_b                   17.9406(6)
_cell_length_c                   10.8992(5)
_cell_measurement_reflns_used    6367
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.63
_cell_measurement_theta_min      2.27
_cell_volume                     3038.1(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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16462
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9591
_exptl_absorpt_correction_T_min  0.9094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker AXS, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       polyhedral
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0974P)²+1.8038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1577
_reflns_number_gt                3196
_reflns_number_total             3967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202273s_si_004.cif
_cod_data_source_block           gl1760
_cod_database_code               4026932
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
Cl1 Cl -0.00943(4) 0.12095(4) 0.88289(6) 0.0513(2) Uani 1 1 d .
O11 O 0.27626(10) 0.49463(10) 0.69920(17) 0.0448(4) Uani 1 1 d .
O12 O 0.22351(10) 0.34284(10) 0.49731(13) 0.0378(4) Uani 1 1 d .
H12A H 0.2753 0.3602 0.5142 0.057 Uiso 1 1 calc R
N11 N 0.43389(11) 0.52860(11) 0.67891(16) 0.0350(4) Uani 1 1 d .
H11A H 0.3787 0.4915 0.6882 0.042 Uiso 1 1 calc R
N12 N 0.35093(11) 0.36076(11) 0.62939(16) 0.0322(4) Uani 1 1 d .
C1 C 0.30314(14) 0.57404(13) 0.6963(2) 0.0347(5) Uani 1 1 d .
C2 C 0.39441(13) 0.63645(13) 0.69434(19) 0.0333(5) Uani 1 1 d .
C11 C 0.45481(14) 0.61044(13) 0.68426(19) 0.0341(5) Uani 1 1 d .
H11B H 0.5140 0.6532 0.6810 0.041 Uiso 1 1 calc R
C13 C 0.48575(13) 0.49178(13) 0.66073(19) 0.0320(4) Uani 1 1 d .
C14 C 0.57553(14) 0.53733(15) 0.6622(2) 0.0368(5) Uani 1 1 d .
H14A H 0.6057 0.5978 0.6749 0.044 Uiso 1 1 calc R
C15 C 0.62036(15) 0.49405(16) 0.6451(2) 0.0436(6) Uani 1 1 d .
H15A H 0.6815 0.5251 0.6465 0.052 Uiso 1 1 calc R
C16 C 0.57722(16) 0.40604(17) 0.6261(2) 0.0477(6) Uani 1 1 d .
H16A H 0.6087 0.3769 0.6149 0.057 Uiso 1 1 calc R
C17 C 0.48747(16) 0.36005(16) 0.6234(2) 0.0427(5) Uani 1 1 d .
H17A H 0.4577 0.2997 0.6092 0.051 Uiso 1 1 calc R
C18 C 0.44201(13) 0.40251(13) 0.64143(18) 0.0322(5) Uani 1 1 d .
C19 C 0.29948(13) 0.31127(12) 0.71383(18) 0.0294(4) Uani 1 1 d .
C101 C 0.17318(13) 0.29252(13) 0.58881(18) 0.0325(4) Uani 1 1 d .
C102 C 0.20619(13) 0.27357(12) 0.69481(18) 0.0288(4) Uani 1 1 d .
C103 C 0.14806(13) 0.21991(13) 0.78475(19) 0.0326(5) Uani 1 1 d .
H10A H 0.1690 0.2066 0.8567 0.039 Uiso 1 1 calc R
C104 C 0.06116(14) 0.18656(15) 0.7694(2) 0.0383(5) Uani 1 1 d .
C105 C 0.02885(15) 0.20561(18) 0.6660(2) 0.0487(6) Uani 1 1 d .
H10C H -0.0314 0.1827 0.6567 0.058 Uiso 1 1 calc R
C106 C 0.08491(15) 0.25805(17) 0.5767(2) 0.0471(6) Uani 1 1 d .
H10B H 0.0628 0.2709 0.5056 0.056 Uiso 1 1 calc R
C191 C 0.33072(13) 0.29329(15) 0.8313(2) 0.0373(5) Uani 1 1 d .
C192 C 0.3637(2) 0.3557(2) 0.9221(2) 0.0601(7) Uani 1 1 d .
H19E H 0.3673 0.4098 0.9094 0.072 Uiso 1 1 calc R
C193 C 0.3913(3) 0.3383(3) 1.0323(3) 0.0851(11) Uani 1 1 d .
H19B H 0.4148 0.3812 1.0943 0.102 Uiso 1 1 calc R
C194 C 0.3850(2) 0.2604(3) 1.0519(3) 0.0824(12) Uani 1 1 d .
H19D H 0.4031 0.2488 1.1279 0.099 Uiso 1 1 calc R
C195 C 0.3530(2) 0.1996(2) 0.9636(4) 0.0833(12) Uani 1 1 d .
H19A H 0.3490 0.1454 0.9776 0.100 Uiso 1 1 calc R
C196 C 0.32579(19) 0.21562(18) 0.8521(3) 0.0613(8) Uani 1 1 d .
H19C H 0.3037 0.1726 0.7902 0.074 Uiso 1 1 calc R
C1P C 0.6192(8) 0.4411(8) 0.9649(12) 0.180(4) Uiso 0.67 1 d PD
C2P C 0.6564(8) 0.3890(8) 0.9524(13) 0.191(5) Uiso 0.67 1 d PD
C3P C 0.5774(7) 0.3190(11) 0.9353(16) 0.118(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'
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
C101 O12 H12A 109.5 . .
C11 N11 C13 130.11(18) . .
C11 N11 H11A 114.9 . .
C13 N11 H11A 114.9 . .
C19 N12 C18 122.29(17) . .
O11 C1 C2 121.43(19) . .
O11 C1 C2 120.13(19) . 3_565
C2 C1 C2 118.44(19) . 3_565
C11 C2 C1 120.93(19) . .
C11 C2 C1 117.47(19) . 2_665
C1 C2 C1 121.52(19) . 2_665
N11 C11 C2 122.91(19) . .
N11 C11 H11B 118.5 . .
C2 C11 H11B 118.5 . .
C14 C13 N11 124.58(19) . .
C14 C13 C18 119.57(19) . .
N11 C13 C18 115.84(18) . .
C15 C14 C13 119.7(2) . .
C15 C14 H14A 120.2 . .
C13 C14 H14A 120.2 . .
C14 C15 C16 120.7(2) . .
C14 C15 H15A 119.6 . .
C16 C15 H15A 119.6 . .
C15 C16 C17 120.0(2) . .
C15 C16 H16A 120.0 . .
C17 C16 H16A 120.0 . .
C18 C17 C16 119.8(2) . .
C18 C17 H17A 120.1 . .
C16 C17 H17A 120.1 . .
C17 C18 C13 120.24(19) . .
C17 C18 N12 122.4(2) . .
C13 C18 N12 117.04(18) . .
N12 C19 C102 118.21(18) . .
N12 C19 C191 122.82(18) . .
C102 C19 C191 118.93(17) . .
O12 C101 C106 117.49(18) . .
O12 C101 C102 123.05(19) . .
C106 C101 C102 119.46(19) . .
C103 C102 C101 118.57(18) . .
C103 C102 C19 120.03(18) . .
C101 C102 C19 121.37(18) . .
C104 C103 C102 120.40(19) . .
C104 C103 H10A 119.8 . .
C102 C103 H10A 119.8 . .
C103 C104 C105 121.0(2) . .
C103 C104 Cl1 119.46(17) . .
C105 C104 Cl1 119.49(17) . .
C106 C105 C104 119.4(2) . .
C106 C105 H10C 120.3 . .
C104 C105 H10C 120.3 . .
C105 C106 C101 121.2(2) . .
C105 C106 H10B 119.4 . .
C101 C106 H10B 119.4 . .
C196 C191 C192 119.2(2) . .
C196 C191 C19 121.4(2) . .
C192 C191 C19 119.5(2) . .
C191 C192 C193 119.4(3) . .
C191 C192 H19E 120.3 . .
C193 C192 H19E 120.3 . .
C194 C193 C192 120.6(3) . .
C194 C193 H19B 119.7 . .
C192 C193 H19B 119.7 . .
C195 C194 C193 120.1(3) . .
C195 C194 H19D 120.0 . .
C193 C194 H19D 120.0 . .
C194 C195 C196 120.5(3) . .
C194 C195 H19A 119.7 . .
C196 C195 H19A 119.7 . .
C191 C196 C195 120.2(3) . .
C191 C196 H19C 119.9 . .
C195 C196 H19C 119.9 . .
C2P C1P C3P 44.0(7) . .
C3P C2P C3P 145.3(16) 3_665 .
C3P C2P C1P 121.9(16) 3_665 .
C3P C2P C1P 90.3(14) . .
C3P C2P C2P 104.6(7) 3_665 2_655
C3P C2P C2P 44.8(7) . 2_655
C1P C2P C2P 133.5(14) . 2_655
C3P C2P C2P 45.3(7) 3_665 3_665
C3P C2P C2P 104.1(7) . 3_665
C1P C2P C2P 165.2(13) . 3_665
C2P C2P C2P 60.000(2) 2_655 3_665
C2P C3P C2P 89.9(13) 2_655 .
C2P C3P C1P 134.0(13) 2_655 .
C2P C3P C1P 45.8(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C104 1.740(2) .
O11 C1 1.255(3) .
O12 C101 1.345(2) .
O12 H12A 0.8400 .
N11 C11 1.323(3) .
N11 C13 1.399(3) .
N11 H11A 0.8800 .
N12 C19 1.292(3) .
N12 C18 1.423(3) .
C1 C2 1.450(3) .
C1 C2 1.464(3) 3_565
C2 C11 1.382(3) .
C2 C1 1.464(3) 2_665
C11 H11B 0.9500 .
C13 C14 1.395(3) .
C13 C18 1.403(3) .
C14 C15 1.382(3) .
C14 H14A 0.9500 .
C15 C16 1.383(4) .
C15 H15A 0.9500 .
C16 C17 1.395(3) .
C16 H16A 0.9500 .
C17 C18 1.380(3) .
C17 H17A 0.9500 .
C19 C102 1.473(3) .
C19 C191 1.496(3) .
C101 C106 1.389(3) .
C101 C102 1.415(3) .
C102 C103 1.404(3) .
C103 C104 1.373(3) .
C103 H10A 0.9500 .
C104 C105 1.386(3) .
C105 C106 1.377(3) .
C105 H10C 0.9500 .
C106 H10B 0.9500 .
C191 C196 1.370(4) .
C191 C192 1.386(4) .
C192 C193 1.392(4) .
C192 H19E 0.9500 .
C193 C194 1.362(6) .
C193 H19B 0.9500 .
C194 C195 1.349(6) .
C194 H19D 0.9500 .
C195 C196 1.392(4) .
C195 H19A 0.9500 .
C196 H19C 0.9500 .
C1P C2P 1.401(9) .
C1P C3P 1.95(2) .
C2P C3P 1.346(9) 3_665
C2P C3P 1.357(9) .
C2P C2P 1.91(2) 2_655
C2P C2P 1.91(2) 3_665
C3P C2P 1.346(9) 2_655
