#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:41:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179342 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/39/4323905.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_4323905
loop_
_publ_author_name
'Naoto Koike'
'Hidehiro Uekusa'
'Yuji Ohashi'
'Chokto Harnoode'
'Fusao Kitamura'
'Takeo Ohsaka'
'Koichi Tokuda'
_publ_section_title
;
 Relationship between the Skew Angle and Interplanar Distance in Four
 Bis(phthalocyaninato)lanthanide(III) Tetrabutylammonium Salts
 ([NBun4][LnIIIPc2]; Ln = Nd, Gd, Ho, Lu)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5798
_journal_page_last               5804
_journal_paper_doi               10.1021/ic960158d
_journal_volume                  35
_journal_year                    1996
_chemical_formula_sum            'C80 H70 Ho N17 O'
_chemical_formula_weight         1450.46
_chemical_name_systematic
; 
tetrabutylammonium bis(phtahlocyaninato)-holmium(iii) water solvate  
;
_space_group_IT_number           90
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4ab 2ab'
_symmetry_space_group_name_H-M   'P 4 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.096(5)
_cell_length_b                   18.096
_cell_length_c                   11.079(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      25
_cell_volume                     3628(2)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SAPI-91 (Fan Hai-Fu, 1988)'
_diffrn_ambient_temperature      296(2)
_diffrn_measurement_device       'Rigaku AFC-5R diffractmeter'
_diffrn_measurement_method       '2theta-omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2420
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.148
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_type   \y-scan
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       prism
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.480
_refine_diff_density_min         -.535
_refine_diff_density_rms         .150
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.103
_refine_ls_goodness_of_fit_obs   1.194
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.262
_refine_ls_restrained_S_obs      1.189
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_obs          0.0609
_refine_ls_shift/esd_max         -0.171
_refine_ls_shift/esd_mean        0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[s²(Fo²)+( 0.0991P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1969
_refine_ls_wR_factor_obs         0.1474
_reflns_number_observed          1594
_reflns_number_total             2420
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic960158d_3.cif
_cod_data_source_block           hopc2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[s^2^(Fo^2^)+(
0.0991P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=1/[s^2^(Fo^2^)+( 0.0991P)^2^+0.0000P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3628.0(22)
_cod_database_code               4323905
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y+1/2, x+1/2, z'
'y+1/2, -x+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'y, x, -z'
'-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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Ho Ho 0.5000 0.0000 0.09603(5) 0.0543(3) Uani 1 d S .
N1 N 0.3900(4) 0.0007(14) -0.0288(5) 0.067(2) Uani 1 d . .
N2 N 0.3721(11) 0.1347(9) -0.0503(7) 0.076(3) Uani 1 d . .
N3 N 0.4263(12) 0.0801(12) 0.2209(6) 0.073(3) Uani 1 d . .
N4 N 0.3170(8) 0.0204(9) 0.2469(15) 0.074(5) Uani 1 d . .
N5 N 0.5000 0.0000 -0.4022(11) 0.116(7) Uani 1 d SD .
C1 C 0.3459(14) 0.0705(13) -0.0464(22) 0.071(6) Uani 1 d . .
C2 C 0.2722(13) 0.0448(11) -0.0635(20) 0.076(6) Uani 1 d . .
C3 C 0.2076(12) 0.0877(13) -0.0875(34) 0.100(6) Uani 1 d . .
H1 H 0.2102(12) 0.1389(13) -0.0941(34) 0.120 Uiso 1 calc R .
C4 C 0.1425(12) 0.0518(13) -0.1002(32) 0.120(8) Uani 1 d . .
H2 H 0.0982(12) 0.0778(13) -0.1029(32) 0.144 Uiso 1 calc R .
C5 C 0.1433(11) -0.0269(15) -0.1095(30) 0.123(10) Uani 1 d . .
H3 H 0.1004(11) -0.0507(15) -0.1348(30) 0.148 Uiso 1 calc R .
C6 C 0.2053(12) -0.0701(12) -0.0824(33) 0.097(7) Uani 1 d . .
H4 H 0.2030(12) -0.1212(12) -0.0751(33) 0.116 Uiso 1 calc R .
C7 C 0.2693(11) -0.0314(14) -0.0676(19) 0.086(6) Uani 1 d . .
C8 C 0.3470(12) -0.0541(10) -0.0434(18) 0.053(5) Uani 1 d . .
C9 C 0.3524(14) 0.0754(12) 0.2462(17) 0.070(5) Uani 1 d . .
C10 C 0.3271(11) 0.1521(13) 0.2660(14) 0.084(8) Uani 1 d . .
C11 C 0.2546(10) 0.1784(10) 0.2991(15) 0.109(6) Uani 1 d . .
H5 H 0.2145(10) 0.1462(10) 0.3011(15) 0.130 Uiso 1 calc R .
C12 C 0.2463(9) 0.2482(13) 0.3263(17) 0.134(8) Uani 1 d . .
H6 H 0.1991(9) 0.2651(13) 0.3445(17) 0.161 Uiso 1 calc R .
C13 C 0.3030(12) 0.2972(9) 0.3291(17) 0.136(8) Uani 1 d . .
H7 H 0.2941(12) 0.3460(9) 0.3514(17) 0.163 Uiso 1 calc R .
C14 C 0.3756(10) 0.2748(8) 0.2985(14) 0.095(4) Uani 1 d . .
H8 H 0.4147(10) 0.3082(8) 0.2966(14) 0.115 Uiso 1 calc R .
C15 C 0.3858(10) 0.1997(9) 0.2712(12) 0.083(4) Uani 1 d . .
C16 C 0.4506(18) 0.1542(19) 0.2341(24) 0.107(11) Uani 1 d . .
C17 C 0.4305(7) 0.0023(37) -0.3245(14) 0.148(14) Uani 0.50 d PD .
C17' C 0.4324(8) 0.0001(47) -0.4832(15) 0.164(13) Uani 0.50 d PD .
C19 C 0.3061(10) -0.0197(16) -0.4077(36) 0.194 Uiso 0.50 d PD .
C19' C 0.3145(12) 0.0505(15) -0.4098(40) 0.169(20) Uiso 0.50 d PD .
C18 C 0.3705(10) 0.0346(22) -0.4075(29) 0.194 Uiso 0.50 d PD .
C18' C 0.3642(11) -0.0175(21) -0.4056(29) 0.192 Uiso 0.50 d PD .
C20 C 0.2360(9) 0.0244(12) -0.4358(17) 0.159(9) Uani 1 d D .
O1 O 0.0000 0.0000 -0.4403(100) 0.202(43) Uiso 0.25 d SP .
O2 O -0.0175(50) 0.0417(65) -0.4335(108) 0.139(32) Uiso 0.13 d P .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ho Ho -.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
N3 Ho N3 70.7(2) 2_655 3_545 ?
N3 Ho N3 109.9(4) 2_655 . ?
N3 Ho N3 70.7(2) 3_545 . ?
N3 Ho N3 70.7(2) 2_655 4 ?
N3 Ho N3 109.9(4) 3_545 4 ?
N3 Ho N3 70.7(2) . 4 ?
N3 Ho N1 141.8(8) 2_655 . ?
N3 Ho N1 80.6(5) 3_545 . ?
N3 Ho N1 82.5(5) . . ?
N3 Ho N1 145.0(8) 4 . ?
N3 Ho N1 82.5(5) 2_655 2_655 ?
N3 Ho N1 145.0(8) 3_545 2_655 ?
N3 Ho N1 141.8(8) . 2_655 ?
N3 Ho N1 80.6(5) 4 2_655 ?
N1 Ho N1 110.4(3) . 2_655 ?
N3 Ho N1 145.0(8) 2_655 4 ?
N3 Ho N1 141.8(8) 3_545 4 ?
N3 Ho N1 80.6(5) . 4 ?
N3 Ho N1 82.5(5) 4 4 ?
N1 Ho N1 70.99(14) . 4 ?
N1 Ho N1 70.99(14) 2_655 4 ?
N3 Ho N1 80.6(5) 2_655 3_545 ?
N3 Ho N1 82.5(5) 3_545 3_545 ?
N3 Ho N1 145.0(8) . 3_545 ?
N3 Ho N1 141.8(8) 4 3_545 ?
N1 Ho N1 70.99(14) . 3_545 ?
N1 Ho N1 70.99(14) 2_655 3_545 ?
N1 Ho N1 110.4(3) 4 3_545 ?
C8 N1 C1 108.2(9) . . ?
C8 N1 Ho 124.9(14) . . ?
C1 N1 Ho 120.9(14) . . ?
C1 N2 C8 126.0(12) . 4 ?
C9 N3 C16 110.0(14) . . ?
C9 N3 Ho 128.4(16) . . ?
C16 N3 Ho 117.2(17) . . ?
C9 N4 C16 124.5(18) . 3_545 ?
C17' N5 C17' 69.5(8) 2_655 4 ?
C17' N5 C17' 69.5(8) 2_655 3_545 ?
C17' N5 C17' 107.4(15) 4 3_545 ?
C17' N5 C17' 107.4(15) 2_655 . ?
C17' N5 C17' 69.5(8) 4 . ?
C17' N5 C17' 69.5(8) 3_545 . ?
C17' N5 C17 70.7(11) 2_655 2_655 ?
C17' N5 C17 110.8(34) 4 2_655 ?
C17' N5 C17 108.2(36) 3_545 2_655 ?
C17' N5 C17 177.6(22) . 2_655 ?
C17' N5 C17 108.2(36) 2_655 4 ?
C17' N5 C17 70.7(11) 4 4 ?
C17' N5 C17 177.6(23) 3_545 4 ?
C17' N5 C17 110.8(34) . 4 ?
C17 N5 C17 71.4(7) 2_655 4 ?
C17' N5 C17 110.8(34) 2_655 3_545 ?
C17' N5 C17 177.6(22) 4 3_545 ?
C17' N5 C17 70.7(11) 3_545 3_545 ?
C17' N5 C17 108.2(36) . 3_545 ?
C17 N5 C17 71.4(7) 2_655 3_545 ?
C17 N5 C17 111.3(14) 4 3_545 ?
C17' N5 C17 177.6(24) 2_655 . ?
C17' N5 C17 108.2(36) 4 . ?
C17' N5 C17 110.8(34) 3_545 . ?
C17' N5 C17 70.7(11) . . ?
C17 N5 C17 111.3(14) 2_655 . ?
C17 N5 C17 71.4(7) 4 . ?
C17 N5 C17 71.4(7) 3_545 . ?
N2 C1 C2 130.7(23) . . ?
N2 C1 N1 125.4(21) . . ?
C2 C1 N1 103.8(18) . . ?
C7 C2 C1 111.4(24) . . ?
C7 C2 C3 120.5(27) . . ?
C1 C2 C3 127.8(22) . . ?
C4 C3 C2 118.1(24) . . ?
C3 C4 C5 118.6(25) . . ?
C6 C5 C4 123.3(25) . . ?
C7 C6 C5 114.9(24) . . ?
C6 C7 C2 123.3(27) . . ?
C6 C7 C8 133.0(24) . . ?
C2 C7 C8 103.6(21) . . ?
N1 C8 N2 128.0(19) . 3_545 ?
N1 C8 C7 112.7(17) . . ?
N2 C8 C7 119.0(18) 3_545 . ?
N4 C9 N3 125.7(23) . . ?
N4 C9 C10 128.4(24) . . ?
N3 C9 C10 105.9(18) . . ?
C15 C10 C11 119.1(21) . . ?
C15 C10 C9 111.0(18) . . ?
C11 C10 C9 129.0(22) . . ?
C12 C11 C10 118.8(18) . . ?
C11 C12 C13 123.4(18) . . ?
C12 C13 C14 120.6(17) . . ?
C15 C14 C13 116.7(18) . . ?
C10 C15 C14 121.2(19) . . ?
C10 C15 C16 104.5(21) . . ?
C14 C15 C16 134.1(22) . . ?
N4 C16 N3 130.9(23) 4 . ?
N4 C16 C15 119.1(27) 4 . ?
N3 C16 C15 107.8(24) . . ?
N5 C17 C18 104.8(15) . . ?
N5 C17 C18' 107.8(14) . . ?
C18 C17 C18' 36.0(9) . . ?
N5 C17 C17' 54.4(6) . . ?
C18 C17 C17' 55.0(7) . . ?
C18' C17 C17' 55.1(7) . . ?
N5 C17 C17 54.3(3) . 3_545 ?
C18 C17 C17 139.5(30) . 3_545 ?
C18' C17 C17 111.2(37) . 3_545 ?
C17' C17 C17 88.3(24) . 3_545 ?
N5 C17 C17 54.3(3) . 4 ?
C18 C17 C17 104.8(38) . 4 ?
C18' C17 C17 136.7(35) . 4 ?
C17' C17 C17 90.0(25) . 4 ?
C17 C17 C17 90.00(2) 3_545 4 ?
N5 C17' C18 105.5(15) . . ?
N5 C17' C18' 108.4(14) . . ?
C18 C17' C18' 36.0(9) . . ?
N5 C17' C17' 55.2(4) . 4 ?
C18 C17' C17' 103.4(53) . 4 ?
C18' C17' C17' 135.7(47) . 4 ?
N5 C17' C17' 55.2(4) . 3_545 ?
C18 C17' C17' 143.6(39) . 3_545 ?
C18' C17' C17' 114.8(51) . 3_545 ?
C17' C17' C17' 90.00(2) 4 3_545 ?
N5 C17' C17 54.9(6) . . ?
C18 C17' C17 55.2(7) . . ?
C18' C17' C17 55.2(7) . . ?
C17' C17' C17 89.9(27) 4 . ?
C17' C17' C17 91.7(23) 3_545 . ?
C18' C19 C19' 81.0(13) . . ?
C18' C19 C18 38.0(12) . . ?
C19' C19 C18 43.0(6) . . ?
C18' C19 C20 144.3(16) . . ?
C19' C19 C20 65.0(7) . . ?
C18 C19 C20 107.3(9) . . ?
C18 C19' C19 81.0(13) . . ?
C18 C19' C20 144.8(17) . . ?
C19 C19' C20 65.5(7) . . ?
C18 C19' C18' 38.0(12) . . ?
C19 C19' C18' 43.0(6) . . ?
C20 C19' C18' 107.8(9) . . ?
C18' C18 C19' 99.0(14) . . ?
C18' C18 C19 43.1(7) . . ?
C19' C18 C19 56.0(13) . . ?
C18' C18 C17' 72.2(10) . . ?
C19' C18 C17' 143.2(15) . . ?
C19 C18 C17' 107.2(10) . . ?
C18' C18 C17 72.1(9) . . ?
C19' C18 C17 142.9(17) . . ?
C19 C18 C17 107.2(10) . . ?
C17' C18 C17 69.9(12) . . ?
C18 C18' C19 98.9(14) . . ?
C18 C18' C19' 43.0(7) . . ?
C19 C18' C19' 56.0(13) . . ?
C18 C18' C17' 71.8(9) . . ?
C19 C18' C17' 142.9(15) . . ?
C19' C18' C17' 106.8(10) . . ?
C18 C18' C17 71.9(9) . . ?
C19 C18' C17 143.0(17) . . ?
C19' C18' C17 106.8(10) . . ?
C17' C18' C17 69.7(12) . . ?
C19' C20 C19 49.5(9) . . ?
O2 O1 O2 169.4(100) . 2 ?
O2 O1 O1 95.3(100) . 7_554 ?
O2 O1 O1 95.3(100) 2 7_554 ?
O2 O1 O2 116.0(100) . 7_554 ?
O2 O1 O2 73.8(100) 2 7_554 ?
O1 O1 O2 30.3(38) 7_554 7_554 ?
O2 O1 O2 73.8(100) . 8_554 ?
O2 O1 O2 116.0(100) 2 8_554 ?
O1 O1 O2 30.3(38) 7_554 8_554 ?
O2 O1 O2 60.7(77) 7_554 8_554 ?
O1 O2 O2 76.6(100) . 8_554 ?
O1 O2 O1 54.4(100) . 7_554 ?
O2 O2 O1 29.6(37) 8_554 7_554 ?
O1 O2 O2 5.3(100) . 2 ?
O2 O2 O2 81.5(48) 8_554 2 ?
O1 O2 O2 59.7(38) 7_554 2 ?
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
Ho N3 2.407(8) 2_655 ?
Ho N3 2.407(8) 3_545 ?
Ho N3 2.407(8) . ?
Ho N3 2.407(8) 4 ?
Ho N1 2.423(7) . ?
Ho N1 2.423(7) 2_655 ?
Ho N1 2.423(7) 4 ?
Ho N1 2.423(7) 3_545 ?
N1 C8 1.27(3) . ?
N1 C1 1.51(3) . ?
N2 C1 1.25(3) . ?
N2 C8 1.38(3) 4 ?
N3 C9 1.37(3) . ?
N3 C16 1.42(4) . ?
N4 C9 1.18(3) . ?
N4 C16 1.37(4) 3_545 ?
N5 C17' 1.516(9) 2_655 ?
N5 C17' 1.516(9) 4 ?
N5 C17' 1.516(9) 3_545 ?
N5 C17' 1.516(9) . ?
N5 C17 1.525(10) 2_655 ?
N5 C17 1.525(10) 4 ?
N5 C17 1.525(10) 3_545 ?
N5 C17 1.525(10) . ?
C1 C2 1.43(3) . ?
C2 C7 1.38(2) . ?
C2 C3 1.43(2) . ?
C3 C4 1.35(2) . ?
C4 C5 1.43(3) . ?
C5 C6 1.40(2) . ?
C6 C7 1.36(2) . ?
C7 C8 1.49(3) . ?
C8 N2 1.38(3) 3_545 ?
C9 C10 1.48(3) . ?
C10 C15 1.37(3) . ?
C10 C11 1.44(2) . ?
C11 C12 1.31(3) . ?
C12 C13 1.36(3) . ?
C13 C14 1.42(2) . ?
C14 C15 1.40(2) . ?
C15 C16 1.49(3) . ?
C16 N4 1.37(4) 4 ?
C17 C18 1.538(10) . ?
C17 C18' 1.540(10) . ?
C17 C17' 1.76(2) . ?
C17 C17 1.78(2) 3_545 ?
C17 C17 1.78(2) 4 ?
C17' C18 1.534(10) . ?
C17' C18' 1.538(10) . ?
C17' C17' 1.73(2) 4 ?
C17' C17' 1.73(2) 3_545 ?
C19 C18' 1.054(10) . ?
C19 C19' 1.28(2) . ?
C19 C18 1.524(10) . ?
C19 C20 1.530(10) . ?
C19' C18 1.053(10) . ?
C19' C20 1.524(10) . ?
C19' C18' 1.525(10) . ?
C18 C18' 0.95(2) . ?
O1 O2 0.82(12) . ?
O1 O2 0.82(12) 2 ?
O1 O1 1.32(22) 7_554 ?
O1 O2 1.62(9) 7_554 ?
O1 O2 1.62(9) 8_554 ?
O2 O2 1.60(23) 8_554 ?
O2 O1 1.62(9) 7_554 ?
O2 O2 1.64(23) 2 ?
