#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:20:41 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179105 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/67/4306782.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_4306782
loop_
_publ_author_name
'Thelma Y. Garcia'
'Marilyn M. Olmstead'
'James C. Fettinger'
'Alan L. Balch'
_publ_section_title
;
Cleavage of the Indium(III) Octaethyloxophlorin Dimer, {InIII(OEPO)}2, with
Lewis Bases. Importance of Outer-Sphere Hydrogen Bonding in Adduct
Structures
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11417
_journal_page_last               11422
_journal_paper_doi               10.1021/ic801605b
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C46 H53 In N6 O'
_chemical_formula_sum            'C46 H53 In N6 O'
_chemical_formula_weight         820.76
_chemical_name_common            In(OEPO)(py)2
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.364(2)
_cell_angle_beta                 89.6920(10)
_cell_angle_gamma                65.9460(10)
_cell_formula_units_Z            1
_cell_length_a                   9.8499(7)
_cell_length_b                   10.3078(7)
_cell_length_c                   10.4743(7)
_cell_measurement_reflns_used    2871
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.2
_cell_volume                     955.08(11)
_computing_cell_refinement       'SAINT 7.16 (Bruker, 2005)'
_computing_data_collection       'Apex2 (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART ApexII'
_diffrn_measurement_method       ω
_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  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15315
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0417
_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)+(0.0410P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                4926
_reflns_number_total             5593
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic801605b_si_001_2.cif
_cod_data_source_block           tg06
_cod_database_code               4306782
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
In1 In 0.5000 0.5000 0.5000 0.01360(7) Uani 1 2 d S . .
N1 N 0.3289(2) 0.71117(19) 0.44848(18) 0.0142(4) Uani 1 1 d . . .
N2 N 0.4356(2) 0.44574(19) 0.33062(18) 0.0145(4) Uani 1 1 d . A .
N3 N 0.3325(2) 0.4153(2) 0.61751(18) 0.0162(4) Uani 1 1 d . . .
C1 C 0.3069(2) 0.8233(2) 0.5135(2) 0.0138(4) Uani 1 1 d . C .
C2 C 0.1919(2) 0.9530(2) 0.4418(2) 0.0150(4) Uani 1 1 d . . .
C3 C 0.1466(2) 0.9168(2) 0.3339(2) 0.0144(4) Uani 1 1 d . . .
C4 C 0.2350(2) 0.7655(2) 0.3375(2) 0.0143(4) Uani 1 1 d . A .
C5 C 0.2307(2) 0.6834(2) 0.2412(2) 0.0143(4) Uani 1 1 d . . .
O1A O 0.1357(5) 0.7534(5) 0.1426(4) 0.0140(9) Uiso 0.35 1 d P A 1
H5 H 0.1581 0.7345 0.1685 0.017 Uiso 0.65 1 d P B 2
C6 C 0.3219(2) 0.5343(2) 0.2402(2) 0.0133(4) Uani 1 1 d . A .
C7 C 0.3076(2) 0.4526(2) 0.1461(2) 0.0147(4) Uani 1 1 d . . .
C8 C 0.4147(3) 0.3136(2) 0.1825(2) 0.0156(4) Uani 1 1 d . A .
C9 C 0.4951(2) 0.3100(2) 0.2985(2) 0.0149(4) Uani 1 1 d . . .
C10 C 0.3868(3) 0.8115(2) 0.6297(2) 0.0166(5) Uani 1 1 d . . .
O1B O 0.3431(13) 0.9313(12) 0.6806(11) 0.023(2) Uiso 0.15 1 d P C 2
H10 H 0.3563 0.8992 0.6652 0.028 Uiso 0.85 1 d P D 1
C11 C 0.1409(3) 1.1005(2) 0.4765(2) 0.0189(5) Uani 1 1 d . . .
H11A H 0.1371 1.0922 0.5718 0.023 Uiso 1 1 calc R . .
H11B H 0.0390 1.1617 0.4366 0.023 Uiso 1 1 calc R . .
C12 C 0.2442(3) 1.1727(3) 0.4303(3) 0.0239(5) Uani 1 1 d . . .
H12A H 0.2110 1.2659 0.4591 0.036 Uiso 1 1 calc R . .
H12B H 0.2420 1.1883 0.3353 0.036 Uiso 1 1 calc R . .
H12C H 0.3460 1.1106 0.4666 0.036 Uiso 1 1 calc R . .
C13 C 0.0263(3) 1.0168(3) 0.2316(2) 0.0201(5) Uani 1 1 d . . .
H13A H -0.0471 1.0952 0.2711 0.024 Uiso 1 1 calc R . .
H13B H -0.0262 0.9624 0.2012 0.024 Uiso 1 1 calc R . .
C14 C 0.0837(3) 1.0832(3) 0.1157(3) 0.0319(6) Uani 1 1 d . . .
H14A H 0.0005 1.1437 0.0516 0.048 Uiso 1 1 calc R . .
H14B H 0.1576 1.0063 0.0766 0.048 Uiso 1 1 calc R . .
H14C H 0.1301 1.1426 0.1439 0.048 Uiso 1 1 calc R . .
C15 C 0.2004(3) 0.5088(3) 0.0279(2) 0.0204(5) Uani 1 1 d . A .
H15A H 0.1045 0.5819 0.0486 0.024 Uiso 1 1 calc R . .
H15B H 0.1814 0.4284 0.0041 0.024 Uiso 1 1 calc R . .
C16 C 0.2589(3) 0.5765(3) -0.0875(2) 0.0271(6) Uani 1 1 d . . .
H16A H 0.1859 0.6109 -0.1623 0.041 Uiso 1 1 calc R A .
H16B H 0.3532 0.5041 -0.1093 0.041 Uiso 1 1 calc R . .
H16C H 0.2753 0.6579 -0.0654 0.041 Uiso 1 1 calc R . .
C17 C 0.4430(3) 0.1872(3) 0.1169(2) 0.0195(5) Uani 1 1 d . . .
H17A H 0.3525 0.2070 0.0624 0.023 Uiso 1 1 calc R A .
H17B H 0.4608 0.1010 0.1841 0.023 Uiso 1 1 calc R . .
C18 C 0.5745(3) 0.1532(3) 0.0325(2) 0.0243(5) Uani 1 1 d . A .
H18A H 0.5839 0.0723 -0.0098 0.036 Uiso 1 1 calc R . .
H18B H 0.6660 0.1270 0.0865 0.036 Uiso 1 1 calc R . .
H18C H 0.5587 0.2382 -0.0337 0.036 Uiso 1 1 calc R . .
C19 C 0.3844(3) 0.2851(3) 0.6948(2) 0.0189(5) Uani 1 1 d . . .
H19 H 0.4888 0.2276 0.7029 0.023 Uiso 1 1 calc R . .
C20 C 0.2928(3) 0.2314(3) 0.7629(2) 0.0232(5) Uani 1 1 d . . .
H20 H 0.3338 0.1392 0.8176 0.028 Uiso 1 1 calc R . .
C21 C 0.1416(3) 0.3128(3) 0.7507(2) 0.0237(5) Uani 1 1 d . . .
H21 H 0.0762 0.2778 0.7963 0.028 Uiso 1 1 calc R . .
C22 C 0.0870(3) 0.4462(3) 0.6708(2) 0.0235(5) Uani 1 1 d . . .
H22 H -0.0171 0.5049 0.6605 0.028 Uiso 1 1 calc R . .
C23 C 0.1854(3) 0.4937(3) 0.6059(2) 0.0197(5) Uani 1 1 d . . .
H23 H 0.1469 0.5857 0.5508 0.024 Uiso 1 1 calc R . .
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'
In In -0.7276 1.3100 '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
_geom_angle_publ_flag
N1 In1 N1 180.0 2_666 . ?
N1 In1 N2 90.67(7) 2_666 . ?
N1 In1 N2 89.33(7) . . ?
N1 In1 N2 89.33(7) 2_666 2_666 ?
N1 In1 N2 90.67(7) . 2_666 ?
N2 In1 N2 180.000(1) . 2_666 ?
N1 In1 N3 91.43(7) 2_666 2_666 ?
N1 In1 N3 88.57(7) . 2_666 ?
N2 In1 N3 91.22(7) . 2_666 ?
N2 In1 N3 88.78(7) 2_666 2_666 ?
N1 In1 N3 88.57(7) 2_666 . ?
N1 In1 N3 91.43(7) . . ?
N2 In1 N3 88.78(7) . . ?
N2 In1 N3 91.22(7) 2_666 . ?
N3 In1 N3 180.00(8) 2_666 . ?
C4 N1 C1 108.20(18) . . ?
C4 N1 In1 126.58(15) . . ?
C1 N1 In1 124.70(15) . . ?
C6 N2 C9 108.20(18) . . ?
C6 N2 In1 126.60(15) . . ?
C9 N2 In1 125.03(15) . . ?
C23 N3 C19 117.7(2) . . ?
C23 N3 In1 121.60(16) . . ?
C19 N3 In1 120.66(15) . . ?
N1 C1 C10 125.1(2) . . ?
N1 C1 C2 108.52(19) . . ?
C10 C1 C2 126.3(2) . . ?
C3 C2 C1 107.24(19) . . ?
C3 C2 C11 127.6(2) . . ?
C1 C2 C11 125.1(2) . . ?
C2 C3 C4 107.31(19) . . ?
C2 C3 C13 126.4(2) . . ?
C4 C3 C13 126.3(2) . . ?
N1 C4 C5 124.8(2) . . ?
N1 C4 C3 108.70(19) . . ?
C5 C4 C3 126.5(2) . . ?
O1A C5 C6 116.6(3) . . ?
O1A C5 C4 115.9(3) . . ?
C6 C5 C4 127.4(2) . . ?
C6 C5 H5 116.3(2) . . ?
C4 C5 H5 116.3(2) . . ?
N2 C6 C5 125.1(2) . . ?
N2 C6 C7 109.04(19) . . ?
C5 C6 C7 125.8(2) . . ?
C8 C7 C6 106.93(19) . . ?
C8 C7 C15 126.3(2) . . ?
C6 C7 C15 126.7(2) . . ?
C7 C8 C9 107.24(19) . . ?
C7 C8 C17 127.3(2) . . ?
C9 C8 C17 125.4(2) . . ?
N2 C9 C10 124.9(2) . 2_666 ?
N2 C9 C8 108.58(19) . . ?
C10 C9 C8 126.5(2) 2_666 . ?
O1B C10 C9 114.9(5) . 2_666 ?
O1B C10 C1 115.7(5) . . ?
C9 C10 C1 129.3(2) 2_666 . ?
C9 C10 H10 115.3(2) 2_666 . ?
C1 C10 H10 115.5(2) . . ?
C2 C11 C12 111.81(19) . . ?
C2 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C2 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 C14 113.7(2) . . ?
C3 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C3 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 C16 112.3(2) . . ?
C7 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C7 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C17 C18 113.9(2) . . ?
C8 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C8 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 122.8(2) . . ?
N3 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C21 C20 C19 119.2(2) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 118.5(2) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C21 C22 C23 119.2(2) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
N3 C23 C22 122.6(2) . . ?
N3 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
In1 N1 2.1203(18) 2_666 ?
In1 N1 2.1203(18) . ?
In1 N2 2.1204(18) . ?
In1 N2 2.1204(18) 2_666 ?
In1 N3 2.4065(19) 2_666 ?
In1 N3 2.4065(19) . ?
N1 C4 1.376(3) . ?
N1 C1 1.380(3) . ?
N2 C6 1.369(3) . ?
N2 C9 1.379(3) . ?
N3 C23 1.335(3) . ?
N3 C19 1.341(3) . ?
C1 C10 1.413(3) . ?
C1 C2 1.439(3) . ?
C2 C3 1.378(3) . ?
C2 C11 1.503(3) . ?
C3 C4 1.438(3) . ?
C3 C13 1.504(3) . ?
C4 C5 1.432(3) . ?
C5 O1A 1.293(5) . ?
C5 C6 1.431(3) . ?
C5 H5 0.967(2) . ?
C6 C7 1.442(3) . ?
C7 C8 1.379(3) . ?
C7 C15 1.503(3) . ?
C8 C9 1.441(3) . ?
C8 C17 1.500(3) . ?
C9 C10 1.412(3) 2_666 ?
C10 O1B 1.334(12) . ?
C10 C9 1.412(3) 2_666 ?
C10 H10 0.967(2) . ?
C11 C12 1.521(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.513(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.522(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.518(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.373(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
