#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:50:30 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179866 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/62/7016226.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_7016226
loop_
_publ_author_name
'Ayinla, Rashidat O.'
'Schafer, Laurel L.'
_publ_section_title
;
 Intermolecular hydroamination of oxygen-substituted allenes. New
 routes for the synthesis of N,O-chelated zirconium and titanium amido
 complexes.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7769
_journal_page_last               7776
_journal_paper_doi               10.1039/c1dt10448a
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C18 H36 N4 O Zr'
_chemical_formula_sum            'C18 H36 N4 O Zr'
_chemical_formula_weight         415.73
_chemical_name_systematic
;
?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.2760(12)
_cell_length_b                   13.5998(9)
_cell_length_c                   9.8227(5)
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.826
_cell_measurement_theta_min      2.358
_cell_volume                     2307.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            46460
_diffrn_reflns_theta_full        27.74
_diffrn_reflns_theta_max         27.74
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.487
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0270
_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)+(0.0329P)²+1.0458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0712
_reflns_number_gt                2294
_reflns_number_total             2818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10448a.txt
_cod_data_source_block           ls037_pnma
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               7016226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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_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
C1A C 0.8273(2) 0.2203(5) 0.2793(4) 0.068(3) Uani 0.50 1 d P . .
H1A H 0.8226 0.1485 0.2762 0.081 Uiso 0.50 1 calc PR . .
C2A C 0.9010(3) 0.234(3) 0.3338(5) 0.151(8) Uani 0.50 1 d P . .
H2A1 H 0.9124 0.3032 0.3368 0.227 Uiso 0.50 1 calc PR . .
H2A2 H 0.9385 0.2013 0.2778 0.227 Uiso 0.50 1 calc PR . .
H2A3 H 0.9027 0.2075 0.4242 0.227 Uiso 0.50 1 calc PR . .
C3 C 0.75991(18) 0.2500 0.3632(3) 0.0723(11) Uani 1 2 d S . .
H3A H 0.7616 0.2164 0.4503 0.087 Uiso 0.50 1 calc PR . .
H3B H 0.7617 0.3202 0.3801 0.087 Uiso 0.50 1 calc PR . .
C4A C 0.62104(19) 0.2500 0.3725(3) 0.0911(15) Uani 1 2 d S . .
H4A1 H 0.6218 0.2148 0.4572 0.137 Uiso 0.50 1 calc PR . .
H4A2 H 0.5758 0.2317 0.3217 0.137 Uiso 0.50 1 calc PR . .
H4A3 H 0.6200 0.3194 0.3901 0.137 Uiso 0.50 1 calc PR . .
C5 C 0.87478(15) 0.2500 0.0442(3) 0.0461(7) Uani 1 2 d S . .
C6 C 0.90539(13) 0.3388(2) -0.0034(2) 0.0639(7) Uani 1 1 d . . .
C7 C 0.96752(14) 0.3364(3) -0.0968(3) 0.0856(10) Uani 1 1 d . . .
H7 H 0.9883 0.3953 -0.1282 0.103 Uiso 1 1 calc R . .
C8 C 0.9976(2) 0.2500 -0.1417(4) 0.0944(17) Uani 1 2 d S . .
H8 H 1.0386 0.2500 -0.2029 0.113 Uiso 1 2 calc SR . .
C9 C 0.87277(19) 0.4367(2) 0.0413(3) 0.0951(10) Uani 1 1 d . . .
H9A H 0.8175 0.4358 0.0321 0.143 Uiso 1 1 calc R . .
H9B H 0.8939 0.4880 -0.0144 0.143 Uiso 1 1 calc R . .
H9C H 0.8862 0.4483 0.1348 0.143 Uiso 1 1 calc R . .
C10A C 0.7355(2) 0.1634(2) -0.2312(3) 0.0916(10) Uani 1 1 d . . .
H10A H 0.7023 0.1627 -0.3095 0.137 Uiso 1 1 calc R . .
H10B H 0.7262 0.1057 -0.1773 0.137 Uiso 1 1 calc R . .
H10C H 0.7886 0.1642 -0.2602 0.137 Uiso 1 1 calc R . .
C11A C 0.5667(2) 0.3935(3) -0.0321(4) 0.1317(17) Uani 1 1 d . . .
H11A H 0.5207 0.4064 0.0196 0.198 Uiso 1 1 calc R . .
H11B H 0.5592 0.3358 -0.0868 0.198 Uiso 1 1 calc R . .
H11C H 0.5776 0.4487 -0.0901 0.198 Uiso 1 1 calc R . .
C12 C 0.6425(2) 0.4655(2) 0.1399(3) 0.1041(11) Uani 1 1 d . . .
H12A H 0.6498 0.5208 0.0805 0.156 Uiso 1 1 calc R . .
H12B H 0.6875 0.4576 0.1963 0.156 Uiso 1 1 calc R . .
H12C H 0.5979 0.4765 0.1963 0.156 Uiso 1 1 calc R . .
N1 N 0.80989(12) 0.2500 0.1357(2) 0.0435(5) Uani 1 2 d S . .
N2 N 0.71974(13) 0.2500 -0.1507(2) 0.0418(5) Uani 1 2 d S . .
N3 N 0.63105(10) 0.37803(13) 0.05983(18) 0.0545(4) Uani 1 1 d . . .
O1A O 0.69038(13) 0.2257(3) 0.2938(2) 0.0504(13) Uani 0.50 1 d P . .
Zr1 Zr 0.695658(13) 0.2500 0.05510(2) 0.03062(9) Uani 1 2 d S . .
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'
Zr Zr -2.9673 0.5597 '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
C2A C1A C3 117.8(7) . . ?
C2A C1A N1 120.6(7) . . ?
C3 C1A N1 107.0(3) . . ?
C2A C1A H1A 102.9 . . ?
C3 C1A H1A 102.9 . . ?
N1 C1A H1A 102.9 . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
O1A C3 C1A 109.5(3) . . ?
O1A C3 H3A 109.8 . . ?
C1A C3 H3A 109.8 . . ?
O1A C3 H3B 109.8 . . ?
C1A C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
O1A C4A H4A1 109.5 . . ?
O1A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
O1A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C6 C5 C6 119.4(3) . 8_565 ?
C6 C5 N1 120.27(14) . . ?
C6 C5 N1 120.27(14) 8_565 . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 C9 121.5(2) . . ?
C7 C6 C9 119.5(3) . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C7 119.8(4) 8_565 . ?
C7 C8 H8 120.1 8_565 . ?
C7 C8 H8 120.1 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10A H10A 109.5 . . ?
N2 C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
N2 C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
N3 C11A H11A 109.5 . . ?
N3 C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N3 C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 N1 C1A 115.6(2) . 8_565 ?
C5 N1 C1A 115.6(2) . . ?
C1A N1 C1A 31.3(5) 8_565 . ?
C5 N1 Zr1 119.39(16) . . ?
C1A N1 Zr1 122.51(19) 8_565 . ?
C1A N1 Zr1 122.51(19) . . ?
C10A N2 C10A 109.3(3) . 8_565 ?
C10A N2 Zr1 125.02(13) . . ?
C10A N2 Zr1 125.02(13) 8_565 . ?
C12 N3 C11A 109.0(2) . . ?
C12 N3 Zr1 129.31(17) . . ?
C11A N3 Zr1 121.53(16) . . ?
C3 O1A C4A 112.7(2) . 8_565 ?
C3 O1A C4A 112.7(2) . . ?
C4A O1A C4A 0.00(15) 8_565 . ?
C3 O1A Zr1 114.20(18) . . ?
C4A O1A Zr1 121.5(2) 8_565 . ?
C4A O1A Zr1 121.5(2) . . ?
N2 Zr1 N3 97.52(6) . 8_565 ?
N2 Zr1 N3 97.52(6) . . ?
N3 Zr1 N3 114.63(11) 8_565 . ?
N2 Zr1 N1 100.24(8) . . ?
N3 Zr1 N1 119.50(5) 8_565 . ?
N3 Zr1 N1 119.50(5) . . ?
N2 Zr1 O1A 167.67(8) . 8_565 ?
N3 Zr1 O1A 94.27(9) 8_565 8_565 ?
N3 Zr1 O1A 80.77(9) . 8_565 ?
N1 Zr1 O1A 70.56(8) . 8_565 ?
N2 Zr1 O1A 167.67(8) . . ?
N3 Zr1 O1A 80.77(9) 8_565 . ?
N3 Zr1 O1A 94.27(9) . . ?
N1 Zr1 O1A 70.56(8) . . ?
O1A Zr1 O1A 16.04(17) 8_565 . ?
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
C1A C2A 1.393(8) . ?
C1A C3 1.483(5) . ?
C1A N1 1.497(4) . ?
C1A H1A 0.9800 . ?
C2A H2A1 0.9600 . ?
C2A H2A2 0.9600 . ?
C2A H2A3 0.9600 . ?
C3 O1A 1.420(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4A O1A 1.463(4) . ?
C4A H4A1 0.9600 . ?
C4A H4A2 0.9600 . ?
C4A H4A3 0.9600 . ?
C5 C6 1.399(3) . ?
C5 C6 1.399(3) 8_565 ?
C5 N1 1.437(3) . ?
C6 C7 1.412(3) . ?
C6 C9 1.511(4) . ?
C7 C8 1.358(4) . ?
C7 H7 0.9300 . ?
C8 C7 1.358(4) 8_565 ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10A N2 1.445(3) . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C11A N3 1.447(3) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12 N3 1.440(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 C1A 1.497(4) 8_565 ?
N1 Zr1 2.127(2) . ?
N2 C10A 1.445(3) 8_565 ?
N2 Zr1 2.064(2) . ?
N3 Zr1 2.0687(17) . ?
O1A C4A 1.463(4) 8_565 ?
O1A Zr1 2.370(2) . ?
Zr1 N3 2.0687(17) 8_565 ?
Zr1 O1A 2.370(2) 8_565 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2A C1A C3 O1A -177.1(17) . . . . ?
N1 C1A C3 O1A 43.2(4) . . . . ?
C6 C5 C6 C7 -1.1(4) 8_565 . . . ?
N1 C5 C6 C7 -177.9(2) . . . . ?
C6 C5 C6 C9 178.05(19) 8_565 . . . ?
N1 C5 C6 C9 1.2(4) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C9 C6 C7 C8 -178.7(3) . . . . ?
C6 C7 C8 C7 0.2(6) . . . 8_565 ?
C6 C5 N1 C1A -74.2(4) . . . 8_565 ?
C6 C5 N1 C1A 109.0(3) 8_565 . . 8_565 ?
C6 C5 N1 C1A -109.0(3) . . . . ?
C6 C5 N1 C1A 74.2(4) 8_565 . . . ?
C6 C5 N1 Zr1 88.4(2) . . . . ?
C6 C5 N1 Zr1 -88.4(2) 8_565 . . . ?
C2A C1A N1 C5 26.9(17) . . . . ?
C3 C1A N1 C5 165.3(2) . . . . ?
C2A C1A N1 C1A -70.8(17) . . . 8_565 ?
C3 C1A N1 C1A 67.6(3) . . . 8_565 ?
C2A C1A N1 Zr1 -171.1(17) . . . . ?
C3 C1A N1 Zr1 -32.7(5) . . . . ?
C1A C3 O1A C4A 178.2(3) . . . 8_565 ?
C1A C3 O1A C4A 178.2(3) . . . . ?
C1A C3 O1A Zr1 -37.8(3) . . . . ?
C10A N2 Zr1 N3 -37.1(2) . . . 8_565 ?
C10A N2 Zr1 N3 153.3(2) 8_565 . . 8_565 ?
C10A N2 Zr1 N3 -153.3(2) . . . . ?
C10A N2 Zr1 N3 37.1(2) 8_565 . . . ?
C10A N2 Zr1 N1 84.8(2) . . . . ?
C10A N2 Zr1 N1 -84.8(2) 8_565 . . . ?
C10A N2 Zr1 O1A 125.5(4) . . . 8_565 ?
C10A N2 Zr1 O1A -44.0(5) 8_565 . . 8_565 ?
C10A N2 Zr1 O1A 44.0(5) . . . . ?
C10A N2 Zr1 O1A -125.5(4) 8_565 . . . ?
C12 N3 Zr1 N2 -123.6(3) . . . . ?
C11A N3 Zr1 N2 51.6(3) . . . . ?
C12 N3 Zr1 N3 134.5(2) . . . 8_565 ?
C11A N3 Zr1 N3 -50.3(3) . . . 8_565 ?
C12 N3 Zr1 N1 -17.3(3) . . . . ?
C11A N3 Zr1 N1 157.9(3) . . . . ?
C12 N3 Zr1 O1A 44.1(3) . . . 8_565 ?
C11A N3 Zr1 O1A -140.7(3) . . . 8_565 ?
C12 N3 Zr1 O1A 52.8(3) . . . . ?
C11A N3 Zr1 O1A -132.0(3) . . . . ?
C5 N1 Zr1 N2 0.0 . . . . ?
C1A N1 Zr1 N2 161.3(3) 8_565 . . . ?
C1A N1 Zr1 N2 -161.3(3) . . . . ?
C5 N1 Zr1 N3 104.77(7) . . . 8_565 ?
C1A N1 Zr1 N3 -93.9(3) 8_565 . . 8_565 ?
C1A N1 Zr1 N3 -56.6(3) . . . 8_565 ?
C5 N1 Zr1 N3 -104.77(7) . . . . ?
C1A N1 Zr1 N3 56.6(3) 8_565 . . . ?
C1A N1 Zr1 N3 93.9(3) . . . . ?
C5 N1 Zr1 O1A -171.49(9) . . . 8_565 ?
C1A N1 Zr1 O1A -10.2(3) 8_565 . . 8_565 ?
C1A N1 Zr1 O1A 27.2(3) . . . 8_565 ?
C5 N1 Zr1 O1A 171.49(9) . . . . ?
C1A N1 Zr1 O1A -27.2(3) 8_565 . . . ?
C1A N1 Zr1 O1A 10.2(3) . . . . ?
C3 O1A Zr1 N2 58.8(5) . . . . ?
C4A O1A Zr1 N2 -160.6(3) 8_565 . . . ?
C4A O1A Zr1 N2 -160.6(3) . . . . ?
C3 O1A Zr1 N3 141.8(2) . . . 8_565 ?
C4A O1A Zr1 N3 -77.7(2) 8_565 . . 8_565 ?
C4A O1A Zr1 N3 -77.7(2) . . . 8_565 ?
C3 O1A Zr1 N3 -103.9(2) . . . . ?
C4A O1A Zr1 N3 36.6(2) 8_565 . . . ?
C4A O1A Zr1 N3 36.6(2) . . . . ?
C3 O1A Zr1 N1 15.87(17) . . . . ?
C4A O1A Zr1 N1 156.4(2) 8_565 . . . ?
C4A O1A Zr1 N1 156.4(2) . . . . ?
C3 O1A Zr1 O1A -71.3(2) . . . 8_565 ?
C4A O1A Zr1 O1A 69.3(2) 8_565 . . 8_565 ?
C4A O1A Zr1 O1A 69.3(2) . . . 8_565 ?
