#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/72/7027244.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7027244
loop_
_publ_author_name
'Wang, Zenglin'
'Hu, Ninghai'
'Sakata, Kazunori'
'Hashimoto, Mamoru'
_publ_section_title
;
 Syntheses, characterization and crystal structures of
 5,14-dihydro-6,8,15,17-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecine
 rare earth(III) complexes
;
_journal_issue                   10
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              1695
_journal_paper_doi               10.1039/a900100j
_journal_year                    1999
_chemical_formula_sum            'C44.6 H45.2 Cl1.2 N8 Yb'
_chemical_formula_weight         908.87
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_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                 93.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.143(3)
_cell_length_b                   16.135(3)
_cell_length_c                   16.239(3)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11.0
_cell_measurement_theta_min      5.0
_cell_volume                     4481.1(14)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5034
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_T_max  0.9041
_exptl_absorpt_correction_T_min  0.7925
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1837
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.571
_refine_diff_density_min         -1.061
_refine_diff_density_rms         0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.118
_refine_ls_goodness_of_fit_obs   1.254
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.326
_refine_ls_restrained_S_obs      1.254
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_obs          0.0705
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2379
_refine_ls_wR_factor_obs         0.1856
_reflns_number_observed          2797
_reflns_number_total             4094
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            900100jsup1.cif
_cod_data_source_block           g027
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Psi-scan'
changed to 'psi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1000P)^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^)+(0.1000P)^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        4481.1(15)
_cod_original_sg_symbol_H-M      C2/m
_cod_original_formula_sum        'C44.60 H45.20 Cl1.20 N8 Yb'
_cod_database_code               7027244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
Yb Yb 0.24415(4) 0.0000 0.75578(4) 0.0415(3) Uani 1 d S
N1 N 0.3045(5) 0.0812(6) 0.6471(5) 0.045(2) Uani 1 d .
N2 N 0.3555(5) 0.0823(6) 0.8225(5) 0.053(2) Uani 1 d .
N3 N 0.1461(5) 0.0890(6) 0.6969(5) 0.045(2) Uani 1 d .
N4 N 0.1858(5) 0.0888(6) 0.8541(5) 0.047(2) Uani 1 d .
C1 C 0.1933(7) 0.0410(9) 0.4425(6) 0.072(4) Uani 1 d .
H1 H 0.1685(7) 0.0697(9) 0.3985(6) 0.072 Uiso 1 calc R
C2 C 0.2303(7) 0.0843(9) 0.5081(7) 0.069(4) Uani 1 d .
H2 H 0.2275(7) 0.1418(9) 0.5084(7) 0.069 Uiso 1 calc R
C3 C 0.2713(6) 0.0441(7) 0.5732(6) 0.051(3) Uani 1 d .
C4 C 0.3510(7) 0.1449(8) 0.6471(7) 0.056(3) Uani 1 d .
C5 C 0.3849(8) 0.1811(8) 0.7218(8) 0.071(4) Uani 1 d .
H5 H 0.4010(8) 0.2359(8) 0.7181(8) 0.071 Uiso 1 calc R
C6 C 0.3969(7) 0.1434(7) 0.8009(7) 0.053(3) Uani 1 d .
C7 C 0.3634(6) 0.0454(7) 0.8994(6) 0.050(3) Uani 1 d .
C8 C 0.3639(7) 0.0892(9) 0.9732(7) 0.070(4) Uani 1 d .
H8 H 0.3624(7) 0.1468(9) 0.9732(7) 0.070 Uiso 1 calc R
C9 C 0.3668(8) 0.0446(10) 1.0481(7) 0.081(5) Uani 1 d .
H9 H 0.3687(8) 0.0731(10) 1.0980(7) 0.081 Uiso 1 calc R
C10 C 0.3761(11) 0.1845(10) 0.5700(8) 0.102(6) Uani 1 d .
H10A H 0.4314(14) 0.1946(53) 0.5755(24) 0.102 Uiso 1 calc R
H10B H 0.3489(41) 0.2361(29) 0.5611(31) 0.102 Uiso 1 calc R
H10C H 0.3640(50) 0.1483(27) 0.5239(12) 0.102 Uiso 1 calc R
C11 C 0.4608(9) 0.1797(9) 0.8571(9) 0.083(4) Uani 1 d .
H11A H 0.4401(13) 0.2236(33) 0.8890(35) 0.083 Uiso 1 calc R
H11B H 0.5011(24) 0.2013(45) 0.8248(9) 0.083 Uiso 1 calc R
H11C H 0.4824(31) 0.1374(14) 0.8935(34) 0.083 Uiso 1 calc R
C12 C 0.0592(10) 0.0000 0.6164(10) 0.060(5) Uani 1 d S
H12 H 0.0196(10) 0.0000 0.5742(10) 0.060 Uiso 1 calc SR
C13 C 0.0856(6) 0.0791(8) 0.6446(6) 0.055(3) Uani 1 d .
C14 C 0.1680(7) 0.1664(7) 0.7275(7) 0.052(3) Uani 1 d .
C15 C 0.1817(9) 0.2392(9) 0.6861(9) 0.078(4) Uani 1 d .
H15 H 0.1703(9) 0.2386(9) 0.6292(9) 0.078 Uiso 1 calc R
C16 C 0.2097(12) 0.3107(10) 0.7184(12) 0.113(7) Uani 1 d .
H16 H 0.2134(12) 0.3582(10) 0.6865(12) 0.113 Uiso 1 calc R
C17 C 0.2334(10) 0.3098(9) 0.8039(13) 0.101(6) Uani 1 d .
H17 H 0.2560(10) 0.3568(9) 0.8286(13) 0.101 Uiso 1 calc R
C18 C 0.2229(9) 0.2392(9) 0.8510(9) 0.080(4) Uani 1 d .
H18 H 0.2382(9) 0.2398(9) 0.9071(9) 0.080 Uiso 1 calc R
C19 C 0.1896(7) 0.1663(7) 0.8152(7) 0.054(3) Uani 1 d .
C20 C 0.1563(6) 0.0789(8) 0.9260(6) 0.050(3) Uani 1 d .
C21 C 0.1496(10) 0.0000 0.9623(9) 0.058(5) Uani 1 d S
H21 H 0.1394(10) 0.0000 1.0178(9) 0.058 Uiso 1 calc SR
C22 C 0.0310(9) 0.1495(9) 0.6115(8) 0.083(5) Uani 1 d .
H22A H -0.0221(10) 0.1300(16) 0.6074(43) 0.083 Uiso 1 calc R
H22B H 0.0455(30) 0.1662(34) 0.5579(22) 0.083 Uiso 1 calc R
H22C H 0.0355(33) 0.1958(19) 0.6485(26) 0.083 Uiso 1 calc R
C23 C 0.1232(9) 0.1500(9) 0.9727(8) 0.077(4) Uani 1 d .
H23A H 0.1636(13) 0.1739(30) 1.0090(34) 0.077 Uiso 1 calc R
H23B H 0.0818(30) 0.1301(12) 1.0044(37) 0.077 Uiso 1 calc R
H23C H 0.1030(40) 0.1913(23) 0.9343(8) 0.077 Uiso 1 calc R
Cl Cl -0.0691(5) -0.0891(4) 0.7968(4) 0.102(2) Uani 0.60 d P
C24 C -0.0120(14) 0.0000 0.8191(15) 0.046(6) Uani 0.60 d SP
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'
Yb Yb -0.3850 5.5486 '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
N3 Yb N3 74.9(5) 6 .
N3 Yb N4 108.2(3) 6 .
N3 Yb N4 65.8(3) . .
N3 Yb N4 65.8(3) 6 6
N3 Yb N4 108.2(3) . 6
N4 Yb N4 72.9(4) . 6
N3 Yb N1 73.2(3) 6 6
N3 Yb N1 110.7(3) . 6
N4 Yb N1 175.2(3) . 6
N4 Yb N1 111.7(3) 6 6
N3 Yb N1 110.7(3) 6 .
N3 Yb N1 73.2(3) . .
N4 Yb N1 111.7(3) . .
N4 Yb N1 175.2(3) 6 .
N1 Yb N1 63.7(4) 6 .
N3 Yb N2 174.5(3) 6 .
N3 Yb N2 110.6(3) . .
N4 Yb N2 74.8(3) . .
N4 Yb N2 111.5(3) 6 .
N1 Yb N2 104.2(3) 6 .
N1 Yb N2 71.7(3) . .
N3 Yb N2 110.6(3) 6 6
N3 Yb N2 174.5(3) . 6
N4 Yb N2 111.5(3) . 6
N4 Yb N2 74.8(3) 6 6
N1 Yb N2 71.7(3) 6 6
N1 Yb N2 104.2(3) . 6
N2 Yb N2 63.9(4) . 6
N3 Yb C14 26.6(3) 6 6
N3 Yb C14 101.0(4) . 6
N4 Yb C14 115.8(3) . 6
N4 Yb C14 51.3(3) 6 6
N1 Yb C14 67.5(3) 6 6
N1 Yb C14 124.1(3) . 6
N2 Yb C14 148.0(3) . 6
N2 Yb C14 84.4(3) 6 6
N3 Yb C14 101.0(4) 6 .
N3 Yb C14 26.6(3) . .
N4 Yb C14 51.3(3) . .
N4 Yb C14 115.8(3) 6 .
N1 Yb C14 124.1(3) 6 .
N1 Yb C14 67.5(3) . .
N2 Yb C14 84.4(3) . .
N2 Yb C14 148.0(3) 6 .
C14 Yb C14 126.5(5) 6 .
N3 Yb C19 50.4(3) 6 6
N3 Yb C19 116.2(3) . 6
N4 Yb C19 99.5(3) . 6
N4 Yb C19 27.1(3) 6 6
N1 Yb C19 84.9(3) 6 6
N1 Yb C19 148.2(3) . 6
N2 Yb C19 125.1(3) . 6
N2 Yb C19 68.6(3) 6 6
C14 Yb C19 27.8(3) 6 6
C14 Yb C19 134.5(3) . 6
N3 Yb C19 116.2(3) 6 .
N3 Yb C19 50.4(3) . .
N4 Yb C19 27.1(3) . .
N4 Yb C19 99.5(3) 6 .
N1 Yb C19 148.2(3) 6 .
N1 Yb C19 84.9(3) . .
N2 Yb C19 68.6(3) . .
N2 Yb C19 125.1(3) 6 .
C14 Yb C19 134.5(3) 6 .
C14 Yb C19 27.8(3) . .
C19 Yb C19 125.3(4) 6 .
C4 N1 C3 122.8(9) . .
C4 N1 Yb 134.6(7) . .
C3 N1 Yb 102.5(6) . .
C6 N2 C7 124.0(10) . .
C6 N2 Yb 135.3(8) . .
C7 N2 Yb 100.7(7) . .
C13 N3 C14 121.8(10) . .
C13 N3 Yb 134.5(8) . .
C14 N3 Yb 103.6(6) . .
C20 N4 C19 122.7(9) . .
C20 N4 Yb 135.9(8) . .
C19 N4 Yb 101.4(6) . .
C1 C1 C2 120.2(8) 6 .
C1 C2 C3 121.9(14) . .
C2 C3 C3 117.8(8) . 6
C2 C3 N1 126.7(11) . .
C3 C3 N1 114.8(6) 6 .
C2 C3 Yb 136.9(7) . .
C3 C3 Yb 76.8(2) 6 .
N1 C3 Yb 51.0(5) . .
N1 C4 C5 122.3(10) . .
N1 C4 C10 123.3(12) . .
C5 C4 C10 114.3(11) . .
C4 C5 C6 128.0(11) . .
N2 C6 C5 121.9(11) . .
N2 C6 C11 122.1(11) . .
C5 C6 C11 116.0(11) . .
N2 C7 C8 123.7(11) . .
N2 C7 C7 115.5(6) . 6
C8 C7 C7 120.5(8) . 6
N2 C7 Yb 53.1(5) . .
C8 C7 Yb 137.5(8) . .
C7 C7 Yb 76.2(2) 6 .
C7 C8 C9 118.8(13) . .
C9 C9 C8 120.6(8) 6 .
C13 C12 C13 128.0(16) . 6
N3 C13 C12 122.9(12) . .
N3 C13 C22 124.9(13) . .
C12 C13 C22 112.1(12) . .
C15 C14 N3 130.0(11) . .
C15 C14 C19 116.0(12) . .
N3 C14 C19 113.4(9) . .
C15 C14 Yb 138.3(9) . .
N3 C14 Yb 49.8(5) . .
C19 C14 Yb 76.7(6) . .
C16 C15 C14 127.5(15) . .
C15 C16 C17 116.4(15) . .
C18 C17 C16 120.5(15) . .
C17 C18 C19 121.3(15) . .
C18 C19 N4 125.9(12) . .
C18 C19 C14 118.2(11) . .
N4 C19 C14 115.2(10) . .
C18 C19 Yb 138.1(9) . .
N4 C19 Yb 51.5(5) . .
C14 C19 Yb 75.5(6) . .
N4 C20 C21 121.9(11) . .
N4 C20 C23 122.4(11) . .
C21 C20 C23 115.6(10) . .
C20 C21 C20 128.9(13) 6 .
Cl C24 Cl 109.3(14) . 6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Yb N3 2.362(8) 6
Yb N3 2.362(8) .
Yb N4 2.413(8) .
Yb N4 2.413(8) 6
Yb N1 2.481(8) 6
Yb N1 2.481(8) .
Yb N2 2.509(9) .
Yb N2 2.509(9) 6
Yb C14 3.007(11) 6
Yb C14 3.007(11) .
Yb C19 3.022(11) 6
Yb C19 3.022(11) .
N1 C4 1.301(14) .
N1 C3 1.424(13) .
N2 C6 1.278(14) .
N2 C7 1.381(13) .
N3 C13 1.304(14) .
N3 C14 1.386(14) .
N4 C20 1.313(13) .
N4 C19 1.404(14) .
C1 C1 1.32(3) 6
C1 C2 1.39(2) .
C2 C3 1.389(15) .
C3 C3 1.42(2) 6
C4 C5 1.43(2) .
C4 C10 1.49(2) .
C5 C6 1.42(2) .
C6 C11 1.50(2) .
C7 C8 1.391(15) .
C7 C7 1.47(2) 6
C8 C9 1.41(2) .
C9 C9 1.44(3) 6
C12 C13 1.42(2) .
C12 C13 1.42(2) 6
C13 C22 1.55(2) .
C14 C15 1.38(2) .
C14 C19 1.45(2) .
C15 C16 1.34(2) .
C16 C17 1.42(3) .
C17 C18 1.39(2) .
C18 C19 1.41(2) .
C20 C21 1.411(13) .
C20 C23 1.51(2) .
C21 C20 1.411(13) 6
Cl C24 1.76(2) .
C24 Cl 1.76(2) 6
