#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:00:23 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233203 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/86/4348630.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_4348630
loop_
_publ_author_name
'Yamashita, Ken-Ichi'
'Sakata, Naoya'
'Ogawa, Takuji'
_publ_section_title
;
 Systematic Structural Elucidation for the Protonated Form of Rare Earth
 Bis(porphyrinato) Double-Decker Complexes: Direct Structural Evidence of
 the Location of the Attached Proton.
;
_journal_issue                   17
_journal_name_full               'Inorganic chemistry'
_journal_page_first              8935
_journal_page_last               8942
_journal_paper_doi               10.1021/acs.inorgchem.6b01442
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C90 H59 Cl6 La N8'
_chemical_formula_weight         1604.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_Hall           '-F 2uv 2vw'
_space_group_name_H-M_alt        'F d d d :2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.844(4)
_cell_length_b                   22.269(5)
_cell_length_c                   30.321(6)
_cell_measurement_reflns_used    17725
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      3.02
_cell_volume                     14749(5)
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_collection       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku FR-E+ SuperBright'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            34077
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         3.019
_diffrn_source                   'Rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7469
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             6512
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.669
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4250
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0613
_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)+(0.1005P)²+59.2313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4003
_reflns_number_total             4250
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b01442_si_002.cif
_cod_data_source_block           LaCHCl3
_cod_original_cell_volume        14750(5)
_cod_original_sg_symbol_H-M      'F d d d'
_cod_database_code               4348630
_shelx_shelxl_version_number     2014/7
_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_min   0.784
_shelx_estimated_absorpt_t_max   0.869
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
La1 La 0.6250 0.6250 0.6250 0.03893(17) Uani 1 4 d S T P . .
N1 N 0.53379(14) 0.59805(13) 0.57247(11) 0.0406(7) Uani 1 1 d . . . . .
N2 N 0.59794(13) 0.71382(13) 0.57206(10) 0.0368(6) Uani 1 1 d . . . . .
C1 C 0.51223(16) 0.53932(16) 0.57297(12) 0.0395(7) Uani 1 1 d . . . . .
C2 C 0.44653(18) 0.54101(18) 0.57145(14) 0.0462(9) Uani 1 1 d . . . . .
H2 H 0.4198 0.5074 0.5728 0.055 Uiso 1 1 calc R U . . .
C3 C 0.42945(17) 0.59966(18) 0.56772(14) 0.0467(9) Uani 1 1 d . . . . .
H3 H 0.3887 0.6142 0.5656 0.056 Uiso 1 1 calc R U . . .
C4 C 0.48389(17) 0.63528(16) 0.56750(14) 0.0415(8) Uani 1 1 d . . . . .
C5 C 0.48681(16) 0.69700(16) 0.55972(13) 0.0418(8) Uani 1 1 d . . . . .
C6 C 0.54050(16) 0.73200(15) 0.55895(12) 0.0391(7) Uani 1 1 d . . . . .
C7 C 0.54392(19) 0.79252(17) 0.54214(14) 0.0478(9) Uani 1 1 d . . . . .
H7 H 0.5109 0.8155 0.5307 0.057 Uiso 1 1 calc R U . . .
C8 C 0.60267(19) 0.81041(17) 0.54562(14) 0.0466(8) Uani 1 1 d . . . . .
H8 H 0.6187 0.8484 0.5373 0.056 Uiso 1 1 calc R U . . .
C9 C 0.63672(16) 0.76091(16) 0.56433(12) 0.0372(7) Uani 1 1 d . . . . .
C10 C 0.70058(17) 0.76155(16) 0.56992(12) 0.0393(7) Uani 1 1 d . . . . .
C11 C 0.42898(17) 0.72823(17) 0.54654(15) 0.0464(9) Uani 1 1 d . . . . .
C12 C 0.4020(2) 0.7141(2) 0.50643(18) 0.0625(12) Uani 1 1 d . . . . .
H12 H 0.4196 0.6842 0.4880 0.075 Uiso 1 1 calc R U . . .
C13 C 0.3491(3) 0.7441(3) 0.4933(2) 0.0821(17) Uani 1 1 d . . . . .
H13 H 0.3311 0.7346 0.4656 0.099 Uiso 1 1 calc R U . . .
C14 C 0.3225(2) 0.7866(3) 0.5193(3) 0.0850(19) Uani 1 1 d . . . . .
H14 H 0.2857 0.8057 0.5103 0.102 Uiso 1 1 calc R U . . .
C15 C 0.3493(3) 0.8016(3) 0.5585(2) 0.0799(17) Uani 1 1 d . . . . .
H15 H 0.3313 0.8318 0.5764 0.096 Uiso 1 1 calc R U . . .
C16 C 0.4034(2) 0.7728(2) 0.57269(18) 0.0610(11) Uani 1 1 d . . . . .
H16 H 0.4220 0.7837 0.5998 0.073 Uiso 1 1 calc R U . . .
C17 C 0.73046(17) 0.82222(16) 0.56945(13) 0.0415(8) Uani 1 1 d . . . . .
C18 C 0.77362(18) 0.83890(18) 0.53784(14) 0.0479(9) Uani 1 1 d . . . . .
H18 H 0.7858 0.8109 0.5158 0.057 Uiso 1 1 calc R U . . .
C19 C 0.7986(2) 0.8953(2) 0.53828(18) 0.0595(11) Uani 1 1 d . . . . .
H19 H 0.8278 0.9061 0.5164 0.071 Uiso 1 1 calc R U . . .
C20 C 0.7821(2) 0.9365(2) 0.5700(2) 0.0685(14) Uani 1 1 d . . . . .
H20 H 0.8001 0.9753 0.5703 0.082 Uiso 1 1 calc R U . . .
C21 C 0.7394(3) 0.9208(2) 0.60097(19) 0.0685(13) Uani 1 1 d . . . . .
H21 H 0.7274 0.9492 0.6227 0.082 Uiso 1 1 calc R U . . .
C22 C 0.7138(2) 0.86440(18) 0.60095(16) 0.0537(10) Uani 1 1 d . . . . .
H22 H 0.6843 0.8542 0.6227 0.064 Uiso 1 1 calc R U . . .
Cl1 Cl 0.77247(19) 0.07374(15) 0.65181(15) 0.1839(14) Uani 1 1 d D U . . .
C23 C 0.7232(11) 0.1264(7) 0.6265(7) 0.189(9) Uani 0.5 1 d D U P A -1
Cl2 Cl 0.6942(4) 0.1670(3) 0.6720(3) 0.181(3) Uani 0.5 1 d D U P A -1
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 '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
N2 La1 N2 153.88(13) 11 14
N2 La1 N2 104.26(13) 11 8
N2 La1 N2 81.71(13) 14 8
N2 La1 N2 81.71(13) 11 .
N2 La1 N2 104.26(13) 14 .
N2 La1 N2 153.88(13) 8 .
N2 La1 N1 135.91(9) 11 .
N2 La1 N1 68.00(9) 14 .
N2 La1 N1 91.61(10) 8 .
N2 La1 N1 68.18(9) . .
N2 La1 N1 68.18(9) 11 11
N2 La1 N1 91.61(10) 14 11
N2 La1 N1 68.00(9) 8 11
N2 La1 N1 135.91(9) . 11
N1 La1 N1 153.52(13) . 11
N2 La1 N1 91.61(10) 11 14
N2 La1 N1 68.18(9) 14 14
N2 La1 N1 135.91(9) 8 14
N2 La1 N1 68.00(9) . 14
N1 La1 N1 105.13(14) . 14
N1 La1 N1 81.02(14) 11 14
N2 La1 N1 68.00(9) 11 8
N2 La1 N1 135.91(9) 14 8
N2 La1 N1 68.18(9) 8 8
N2 La1 N1 91.61(10) . 8
N1 La1 N1 81.02(14) . 8
N1 La1 N1 105.13(14) 11 8
N1 La1 N1 153.52(13) 14 8
C4 N1 C1 107.4(3) . .
C4 N1 La1 122.0(2) . .
C1 N1 La1 117.8(2) . .
C9 N2 C6 106.8(3) . .
C9 N2 La1 123.0(2) . .
C6 N2 La1 127.3(2) . .
N1 C1 C10 124.4(3) . 14
N1 C1 C2 108.3(3) . .
C10 C1 C2 126.9(3) 14 .
C3 C2 C1 107.5(3) . .
C3 C2 H2 126.2 . .
C1 C2 H2 126.2 . .
C2 C3 C4 107.7(3) . .
C2 C3 H3 126.1 . .
C4 C3 H3 126.1 . .
N1 C4 C5 125.1(3) . .
N1 C4 C3 108.9(3) . .
C5 C4 C3 125.8(3) . .
C4 C5 C6 125.9(3) . .
C4 C5 C11 117.6(3) . .
C6 C5 C11 116.2(3) . .
N2 C6 C5 126.2(3) . .
N2 C6 C7 109.2(3) . .
C5 C6 C7 124.5(3) . .
C8 C7 C6 107.3(3) . .
C8 C7 H7 126.3 . .
C6 C7 H7 126.3 . .
C7 C8 C9 107.2(3) . .
C7 C8 H8 126.4 . .
C9 C8 H8 126.4 . .
N2 C9 C10 127.0(3) . .
N2 C9 C8 109.4(3) . .
C10 C9 C8 123.4(3) . .
C1 C10 C9 125.2(3) 14 .
C1 C10 C17 118.5(3) 14 .
C9 C10 C17 116.1(3) . .
C12 C11 C16 119.5(4) . .
C12 C11 C5 119.1(4) . .
C16 C11 C5 121.3(4) . .
C11 C12 C13 119.6(5) . .
C11 C12 H12 120.2 . .
C13 C12 H12 120.2 . .
C14 C13 C12 121.4(6) . .
C14 C13 H13 119.3 . .
C12 C13 H13 119.3 . .
C13 C14 C15 119.4(5) . .
C13 C14 H14 120.3 . .
C15 C14 H14 120.3 . .
C14 C15 C16 120.9(5) . .
C14 C15 H15 119.5 . .
C16 C15 H15 119.5 . .
C11 C16 C15 119.2(5) . .
C11 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
C22 C17 C18 118.0(4) . .
C22 C17 C10 119.2(3) . .
C18 C17 C10 122.7(4) . .
C19 C18 C17 120.5(4) . .
C19 C18 H18 119.8 . .
C17 C18 H18 119.8 . .
C18 C19 C20 120.8(4) . .
C18 C19 H19 119.6 . .
C20 C19 H19 119.6 . .
C21 C20 C19 119.3(4) . .
C21 C20 H20 120.4 . .
C19 C20 H20 120.4 . .
C20 C21 C22 120.6(5) . .
C20 C21 H21 119.7 . .
C22 C21 H21 119.7 . .
C21 C22 C17 120.8(5) . .
C21 C22 H22 119.6 . .
C17 C22 H22 119.6 . .
Cl1 C23 Cl2 102.7(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
La1 N2 2.615(3) 11
La1 N2 2.615(3) 14
La1 N2 2.615(3) 8
La1 N2 2.615(3) .
La1 N1 2.620(3) .
La1 N1 2.620(3) 11
La1 N1 2.620(3) 14
La1 N1 2.620(3) 8
N1 C4 1.378(5) .
N1 C1 1.390(4) .
N2 C9 1.368(4) .
N2 C6 1.377(5) .
C1 C10 1.397(5) 14
C1 C2 1.436(5) .
C2 C3 1.363(6) .
C2 H2 0.9500 .
C3 C4 1.429(5) .
C3 H3 0.9500 .
C4 C5 1.396(5) .
C5 C6 1.408(5) .
C5 C11 1.496(5) .
C6 C7 1.443(5) .
C7 C8 1.348(6) .
C7 H7 0.9500 .
C8 C9 1.446(5) .
C8 H8 0.9500 .
C9 C10 1.405(5) .
C10 C1 1.397(5) 14
C10 C17 1.501(5) .
C11 C12 1.387(6) .
C11 C16 1.387(6) .
C12 C13 1.394(7) .
C12 H12 0.9500 .
C13 C14 1.362(10) .
C13 H13 0.9500 .
C14 C15 1.364(10) .
C14 H14 0.9500 .
C15 C16 1.412(7) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C22 1.388(6) .
C17 C18 1.395(5) .
C18 C19 1.370(6) .
C18 H18 0.9500 .
C19 C20 1.376(8) .
C19 H19 0.9500 .
C20 C21 1.369(8) .
C20 H20 0.9500 .
C21 C22 1.376(6) .
C21 H21 0.9500 .
C22 H22 0.9500 .
Cl1 C23 1.767(15) .
C23 Cl2 1.768(17) .
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_1
_geom_torsion_site_symmetry_4
C4 N1 C1 C10 168.6(4) . 14
La1 N1 C1 C10 -48.9(4) . 14
C4 N1 C1 C2 -4.3(4) . .
La1 N1 C1 C2 138.3(3) . .
N1 C1 C2 C3 3.2(5) . .
C10 C1 C2 C3 -169.5(4) 14 .
C1 C2 C3 C4 -0.8(5) . .
C1 N1 C4 C5 -171.2(4) . .
La1 N1 C4 C5 48.2(5) . .
C1 N1 C4 C3 3.8(4) . .
La1 N1 C4 C3 -136.8(3) . .
C2 C3 C4 N1 -1.8(5) . .
C2 C3 C4 C5 173.1(4) . .
N1 C4 C5 C6 -5.0(7) . .
C3 C4 C5 C6 -179.2(4) . .
N1 C4 C5 C11 168.4(4) . .
C3 C4 C5 C11 -5.7(6) . .
C9 N2 C6 C5 177.9(4) . .
La1 N2 C6 C5 -21.2(5) . .
C9 N2 C6 C7 0.4(4) . .
La1 N2 C6 C7 161.4(3) . .
C4 C5 C6 N2 -10.4(7) . .
C11 C5 C6 N2 176.1(4) . .
C4 C5 C6 C7 166.7(4) . .
C11 C5 C6 C7 -6.8(6) . .
N2 C6 C7 C8 -0.6(5) . .
C5 C6 C7 C8 -178.1(4) . .
C6 C7 C8 C9 0.5(5) . .
C6 N2 C9 C10 -175.5(4) . .
La1 N2 C9 C10 22.5(5) . .
C6 N2 C9 C8 -0.1(4) . .
La1 N2 C9 C8 -162.1(2) . .
C7 C8 C9 N2 -0.2(5) . .
C7 C8 C9 C10 175.3(4) . .
N2 C9 C10 C1 18.2(6) . 14
C8 C9 C10 C1 -156.6(4) . 14
N2 C9 C10 C17 -166.1(3) . .
C8 C9 C10 C17 19.1(5) . .
C4 C5 C11 C12 -65.5(6) . .
C6 C5 C11 C12 108.5(5) . .
C4 C5 C11 C16 117.3(5) . .
C6 C5 C11 C16 -68.6(5) . .
C16 C11 C12 C13 -1.1(8) . .
C5 C11 C12 C13 -178.3(5) . .
C11 C12 C13 C14 -0.9(9) . .
C12 C13 C14 C15 2.0(10) . .
C13 C14 C15 C16 -1.3(9) . .
C12 C11 C16 C15 1.9(7) . .
C5 C11 C16 C15 179.0(4) . .
C14 C15 C16 C11 -0.7(8) . .
C1 C10 C17 C22 -123.4(4) 14 .
C9 C10 C17 C22 60.5(5) . .
C1 C10 C17 C18 58.2(5) 14 .
C9 C10 C17 C18 -117.9(4) . .
C22 C17 C18 C19 0.2(6) . .
C10 C17 C18 C19 178.6(4) . .
C17 C18 C19 C20 0.4(7) . .
C18 C19 C20 C21 -1.0(8) . .
C19 C20 C21 C22 0.9(8) . .
C20 C21 C22 C17 -0.2(8) . .
C18 C17 C22 C21 -0.3(7) . .
C10 C17 C22 C21 -178.8(4) . .
