#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:14:00 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178554 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/62/4066244.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_4066244
loop_
_publ_author_name
'Casely, Ian J.'
'Suh, YoungSung'
'Ziller, Joseph W.'
'Evans, William J.'
_publ_section_title
;
 Formation of a [ONN(allyl)O]−Anion via NO Insertion and Coupling
 Using Yttrium and Lanthanide Allyl Metallocenes†
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5209
_journal_paper_doi               10.1021/om100364k
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C46 H70 N4 O4 Y2'
_chemical_formula_weight         920.88
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.9110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6995(8)
_cell_length_b                   15.6446(14)
_cell_length_c                   15.0044(13)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.53
_cell_volume                     2200.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25665
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    2.671
_exptl_absorpt_correction_T_max  0.5738
_exptl_absorpt_correction_T_min  0.4132
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0326
_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)+(0.0167P)²+1.7172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0722
_reflns_number_gt                4825
_reflns_number_total             5334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100364k_si_001.cif
_cod_data_source_block           ijc8
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4066244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Y1 Y 0.031448(19) 0.048704(12) 0.824983(13) 0.01464(6) Uani 1 1 d . . .
C1 C -0.1621(2) 0.03994(14) 0.66173(13) 0.0169(4) Uani 1 1 d . B .
C2 C -0.0784(2) 0.11299(14) 0.65607(13) 0.0160(4) Uani 1 1 d . B .
C3 C -0.1027(2) 0.17462(13) 0.71985(14) 0.0163(4) Uani 1 1 d . B .
C4 C -0.2084(2) 0.14088(14) 0.76146(14) 0.0165(4) Uani 1 1 d . B .
C5 C -0.2448(2) 0.05820(13) 0.72509(13) 0.0159(4) Uani 1 1 d . . .
C6 C -0.1748(2) -0.03891(15) 0.60298(15) 0.0238(5) Uani 1 1 d . . .
H6A H -0.2068 -0.0869 0.6346 0.036 Uiso 1 1 calc R B .
H6B H -0.0817 -0.0524 0.5923 0.036 Uiso 1 1 calc R . .
H6C H -0.2442 -0.0288 0.5437 0.036 Uiso 1 1 calc R . .
C7 C -0.0063(2) 0.12709(15) 0.57962(14) 0.0206(4) Uani 1 1 d . . .
H7A H 0.0555 0.0782 0.5764 0.031 Uiso 1 1 calc R B .
H7B H 0.0513 0.1793 0.5919 0.031 Uiso 1 1 calc R . .
H7C H -0.0787 0.1329 0.5208 0.031 Uiso 1 1 calc R . .
C8 C -0.0385(2) 0.26269(14) 0.73662(16) 0.0228(5) Uani 1 1 d . . .
H8A H 0.0591 0.2614 0.7296 0.034 Uiso 1 1 calc R B .
H8B H -0.0370 0.2811 0.7993 0.034 Uiso 1 1 calc R . .
H8C H -0.0959 0.3028 0.6919 0.034 Uiso 1 1 calc R . .
C9 C -0.2755(2) 0.18910(15) 0.82598(15) 0.0225(5) Uani 1 1 d . . .
H9A H -0.3379 0.2338 0.7918 0.034 Uiso 1 1 calc R B .
H9B H -0.2006 0.2153 0.8750 0.034 Uiso 1 1 calc R . .
H9C H -0.3316 0.1497 0.8533 0.034 Uiso 1 1 calc R . .
C10 C -0.3619(2) 0.00105(15) 0.73936(15) 0.0219(5) Uani 1 1 d . B .
H10A H -0.4046 0.0264 0.7857 0.033 Uiso 1 1 calc R . .
H10B H -0.3224 -0.0552 0.7606 0.033 Uiso 1 1 calc R . .
H10C H -0.4352 -0.0053 0.6810 0.033 Uiso 1 1 calc R . .
C11 C 0.2612(2) -0.01050(14) 0.77748(14) 0.0186(4) Uani 1 1 d . B .
C12 C 0.2822(2) 0.07917(14) 0.78342(15) 0.0194(4) Uani 1 1 d . B .
C13 C 0.3022(2) 0.10371(14) 0.87719(15) 0.0189(4) Uani 1 1 d . B .
C14 C 0.2965(2) 0.02861(14) 0.92923(14) 0.0176(4) Uani 1 1 d . B .
C15 C 0.2722(2) -0.04158(14) 0.86809(14) 0.0176(4) Uani 1 1 d . B .
C16 C 0.2452(2) -0.06585(15) 0.69318(15) 0.0241(5) Uani 1 1 d . . .
H16A H 0.3371 -0.0925 0.6943 0.036 Uiso 1 1 calc R B .
H16B H 0.2141 -0.0306 0.6376 0.036 Uiso 1 1 calc R . .
H16C H 0.1741 -0.1104 0.6928 0.036 Uiso 1 1 calc R . .
C17 C 0.3138(2) 0.13689(16) 0.71058(16) 0.0272(5) Uani 1 1 d . . .
H17A H 0.2594 0.1901 0.7077 0.041 Uiso 1 1 calc R B .
H17B H 0.2865 0.1081 0.6506 0.041 Uiso 1 1 calc R . .
H17C H 0.4161 0.1500 0.7262 0.041 Uiso 1 1 calc R . .
C18 C 0.3383(2) 0.19270(15) 0.91379(17) 0.0257(5) Uani 1 1 d . . .
H18A H 0.4133 0.2164 0.8881 0.039 Uiso 1 1 calc R B .
H18B H 0.3720 0.1908 0.9812 0.039 Uiso 1 1 calc R . .
H18C H 0.2531 0.2288 0.8959 0.039 Uiso 1 1 calc R . .
C19 C 0.3258(2) 0.02280(15) 1.03248(15) 0.0208(4) Uani 1 1 d . . .
H19A H 0.2540 -0.0139 1.0487 0.031 Uiso 1 1 calc R B .
H19B H 0.3215 0.0801 1.0581 0.031 Uiso 1 1 calc R . .
H19C H 0.4208 -0.0016 1.0579 0.031 Uiso 1 1 calc R . .
C20 C 0.2748(2) -0.13396(14) 0.89544(16) 0.0222(5) Uani 1 1 d . . .
H20A H 0.3690 -0.1582 0.8981 0.033 Uiso 1 1 calc R B .
H20B H 0.2018 -0.1653 0.8499 0.033 Uiso 1 1 calc R . .
H20C H 0.2554 -0.1387 0.9562 0.033 Uiso 1 1 calc R . .
O1 O -0.05034(16) -0.09066(10) 0.82500(10) 0.0226(3) Uani 1 1 d . B .
O2 O -0.01050(16) -0.12886(12) 1.05311(10) 0.0274(4) Uani 1 1 d . . .
C21 C -0.0947(3) -0.22251(15) 0.91900(18) 0.0316(6) Uani 1 1 d . . .
H21A H -0.0909 -0.2215 0.8537 0.038 Uiso 0.50 1 calc PR A 1
H21B H -0.1951 -0.2310 0.9208 0.038 Uiso 0.50 1 calc PR A 1
H21C H -0.1711 -0.2159 0.9480 0.038 Uiso 0.50 1 d PR A 2
H21D H -0.1371 -0.2453 0.8589 0.038 Uiso 0.50 1 d PR A 2
C22 C -0.0039(3) -0.29323(17) 0.9691(2) 0.0350(6) Uani 1 1 d . . .
H22A H 0.0965 -0.2891 0.9787 0.042 Uiso 1 1 calc R . .
C23 C -0.0550(3) -0.35995(18) 1.00027(18) 0.0372(6) Uani 1 1 d . . .
H23A H -0.1551 -0.3657 0.9916 0.045 Uiso 1 1 calc R B .
H23B H 0.0075 -0.4032 1.0318 0.045 Uiso 1 1 calc R . .
N1 N -0.0204(3) -0.0764(2) 0.9172(3) 0.0173(5) Uani 0.73 1 d P B 1
N2 N -0.0393(2) -0.14074(16) 0.96489(18) 0.0150(5) Uani 0.73 1 d P B 1
N3 N -0.0084(7) -0.0782(5) 0.9683(7) 0.0180(15) Uani 0.27 1 d P B 2
N4 N -0.0486(7) -0.1275(6) 0.9003(5) 0.0176(14) Uani 0.27 1 d P B 2
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'
Y Y -2.7962 3.5667 '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
Cnt1 Y1 O1 98.6 . .
Cnt1 Y1 N1 118.4 . .
Cnt1 Y1 O2 101.0 . 3_557
Cnt2 Y1 O1 103.5 . .
Cnt2 Y1 N1 100.3 . .
Cnt2 Y1 O2 104.4 . 3_557
Cnt1 Y1 Cnt2 135.1 . .
O2 Y1 O1 114.69(6) 3_557 .
O2 Y1 N1 85.11(10) 3_557 .
O1 Y1 N1 32.22(10) . .
O2 Y1 C3 86.38(6) 3_557 .
O1 Y1 C3 125.71(6) . .
N1 Y1 C3 140.18(8) . .
O2 Y1 C14 82.24(6) 3_557 .
O1 Y1 C14 99.64(6) . .
N1 Y1 C14 83.37(8) . .
C3 Y1 C14 133.67(6) . .
O2 Y1 C15 110.62(6) 3_557 .
O1 Y1 C15 77.29(6) . .
N1 Y1 C15 74.99(7) . .
C3 Y1 C15 143.67(6) . .
C14 Y1 C15 30.74(6) . .
O2 Y1 C11 131.29(6) 3_557 .
O1 Y1 C11 89.02(6) . .
N1 Y1 C11 100.07(8) . .
C3 Y1 C11 114.50(6) . .
C14 Y1 C11 50.99(6) . .
C15 Y1 C11 30.90(6) . .
O2 Y1 C1 125.32(6) 3_557 .
O1 Y1 C1 78.04(6) . .
N1 Y1 C1 105.68(10) . .
C3 Y1 C1 51.08(6) . .
C14 Y1 C1 151.04(6) . .
C15 Y1 C1 124.02(6) . .
C11 Y1 C1 100.06(6) . .
O2 Y1 C2 117.29(6) 3_557 .
O1 Y1 C2 107.46(6) . .
N1 Y1 C2 136.35(10) . .
C3 Y1 C2 30.92(6) . .
C14 Y1 C2 133.56(6) . .
C15 Y1 C2 122.64(6) . .
C11 Y1 C2 91.94(6) . .
C1 Y1 C2 30.67(6) . .
O2 Y1 C13 82.60(6) 3_557 .
O1 Y1 C13 127.64(6) . .
N1 Y1 C13 114.03(8) . .
C3 Y1 C13 103.28(6) . .
C14 Y1 C13 30.81(6) . .
C15 Y1 C13 50.77(7) . .
C11 Y1 C13 50.83(7) . .
C1 Y1 C13 133.38(6) . .
C2 Y1 C13 106.09(6) . .
O2 Y1 C4 75.00(6) 3_557 .
O1 Y1 C4 103.82(6) . .
N1 Y1 C4 109.50(7) . .
C3 Y1 C4 31.07(6) . .
C14 Y1 C4 152.45(7) . .
C15 Y1 C4 173.40(6) . .
C11 Y1 C4 142.57(6) . .
C1 Y1 C4 50.63(6) . .
C2 Y1 C4 50.76(6) . .
C13 Y1 C4 128.54(7) . .
O2 Y1 C12 111.15(6) 3_557 .
O1 Y1 C12 119.57(6) . .
N1 Y1 C12 125.56(8) . .
C3 Y1 C12 93.72(6) . .
C14 Y1 C12 50.67(6) . .
C15 Y1 C12 50.57(6) . .
C11 Y1 C12 30.55(7) . .
C1 Y1 C12 104.99(6) . .
C2 Y1 C12 83.01(6) . .
C13 Y1 C12 30.63(7) . .
C4 Y1 C12 124.76(6) . .
C2 C1 C5 107.96(18) . .
C2 C1 C6 126.06(18) . .
C5 C1 C6 125.61(19) . .
C2 C1 Y1 74.69(11) . .
C5 C1 Y1 76.20(11) . .
C6 C1 Y1 120.71(14) . .
C1 C2 C3 108.08(17) . .
C1 C2 C7 123.33(18) . .
C3 C2 C7 127.16(19) . .
C1 C2 Y1 74.65(11) . .
C3 C2 Y1 73.27(11) . .
C7 C2 Y1 128.74(13) . .
C2 C3 C4 107.77(18) . .
C2 C3 C8 126.91(19) . .
C4 C3 C8 125.18(19) . .
C2 C3 Y1 75.81(12) . .
C4 C3 Y1 76.29(11) . .
C8 C3 Y1 117.54(13) . .
C5 C4 C3 107.76(18) . .
C5 C4 C9 127.05(19) . .
C3 C4 C9 125.0(2) . .
C5 C4 Y1 75.75(11) . .
C3 C4 Y1 72.64(11) . .
C9 C4 Y1 121.25(13) . .
C4 C5 C1 108.32(18) . .
C4 C5 C10 127.75(19) . .
C1 C5 C10 123.55(19) . .
C4 C5 Y1 73.98(11) . .
C1 C5 Y1 73.26(11) . .
C10 C5 Y1 124.26(13) . .
C12 C11 C15 107.71(19) . .
C12 C11 C16 127.1(2) . .
C15 C11 C16 124.9(2) . .
C12 C11 Y1 75.92(12) . .
C15 C11 Y1 74.11(11) . .
C16 C11 Y1 120.66(13) . .
C11 C12 C13 108.06(19) . .
C11 C12 C17 126.9(2) . .
C13 C12 C17 123.6(2) . .
C11 C12 Y1 73.53(12) . .
C13 C12 Y1 73.79(11) . .
C17 C12 Y1 129.41(14) . .
C14 C13 C12 107.82(19) . .
C14 C13 C18 127.1(2) . .
C12 C13 C18 124.8(2) . .
C14 C13 Y1 73.83(11) . .
C12 C13 Y1 75.58(11) . .
C18 C13 Y1 121.47(14) . .
C15 C14 C13 108.06(18) . .
C15 C14 C19 125.32(19) . .
C13 C14 C19 126.4(2) . .
C15 C14 Y1 74.65(11) . .
C13 C14 Y1 75.36(11) . .
C19 C14 Y1 120.66(13) . .
C14 C15 C11 108.33(19) . .
C14 C15 C20 125.68(19) . .
C11 C15 C20 125.6(2) . .
C14 C15 Y1 74.61(11) . .
C11 C15 Y1 74.98(11) . .
C20 C15 Y1 121.96(13) . .
N4 O1 N1 38.2(4) . .
N4 O1 Y1 120.2(4) . .
N1 O1 Y1 82.11(16) . .
N2 O2 N3 42.0(3) . .
N2 O2 Y1 149.68(16) . 3_557
N3 O2 Y1 114.5(3) . 3_557
N2 C21 C22 108.0(2) . .
N2 C21 N4 36.5(3) . .
C22 C21 N4 128.6(3) . .
C23 C22 C21 123.3(2) . .
N2 N1 O1 114.8(3) . .
N2 N1 Y1 176.9(2) . .
O1 N1 Y1 65.68(14) . .
N1 N2 O2 115.9(3) . .
N1 N2 C21 120.4(3) . .
O2 N2 C21 123.7(2) . .
N4 N3 O2 107.1(7) . .
N3 N4 O1 112.0(9) . .
N3 N4 C21 118.0(7) . .
O1 N4 C21 129.9(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Y1 Cnt1 2.396 .
Y1 Cnt2 2.390 .
Y1 O2 2.2695(15) 3_557
Y1 O1 2.3201(16) .
Y1 N1 2.522(3) .
Y1 C3 2.647(2) .
Y1 C14 2.662(2) .
Y1 C15 2.663(2) .
Y1 C11 2.674(2) .
Y1 C1 2.6791(19) .
Y1 C2 2.680(2) .
Y1 C13 2.682(2) .
Y1 C4 2.694(2) .
Y1 C12 2.705(2) .
C1 C2 1.417(3) .
C1 C5 1.422(3) .
C1 C6 1.503(3) .
C2 C3 1.420(3) .
C2 C7 1.506(3) .
C3 C4 1.431(3) .
C3 C8 1.506(3) .
C4 C5 1.413(3) .
C4 C9 1.501(3) .
C5 C10 1.504(3) .
C11 C12 1.417(3) .
C11 C15 1.422(3) .
C11 C16 1.508(3) .
C12 C13 1.423(3) .
C12 C17 1.509(3) .
C13 C14 1.420(3) .
C13 C18 1.505(3) .
C14 C15 1.411(3) .
C14 C19 1.504(3) .
C15 C20 1.501(3) .
O1 N4 1.264(8) .
O1 N1 1.357(4) .
O2 N2 1.294(3) .
O2 N3 1.503(10) .
O2 Y1 2.2695(15) 3_557
C21 N2 1.486(3) .
C21 C22 1.491(4) .
C21 N4 1.597(9) .
C22 C23 1.293(4) .
N1 N2 1.274(4) .
N3 N4 1.260(11) .
