#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:50:30 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179866 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/62/7016228.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_7016228
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         'C25 H42 N4 O Zr'
_chemical_formula_sum            'C25 H42 N4 O Zr'
_chemical_formula_weight         505.85
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c 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            8
_cell_length_a                   16.5820(15)
_cell_length_b                   17.7264(4)
_cell_length_c                   18.8172(15)
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.549
_cell_measurement_theta_min      2.298
_cell_volume                     5531.1(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0669
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            154892
_diffrn_reflns_theta_full        27.73
_diffrn_reflns_theta_max         27.73
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         6474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0303
_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)+(0.0318P)²+2.5423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                4514
_reflns_number_total             6474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10448a.txt
_cod_data_source_block           ls036_0m
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7016228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
C1 C 0.82039(13) 0.21268(13) 0.23624(15) 0.0567(7) Uani 1 1 d . . .
H1A H 0.8542 0.2071 0.1952 0.085 Uiso 1 1 calc R . .
H1B H 0.8161 0.1651 0.2604 0.085 Uiso 1 1 calc R . .
H1C H 0.8435 0.2494 0.2677 0.085 Uiso 1 1 calc R . .
C2 C 0.73614(11) 0.23891(10) 0.21300(10) 0.0321(4) Uani 1 1 d . . .
H2 H 0.7014 0.2418 0.2550 0.038 Uiso 1 1 calc R . .
C3 C 0.70204(11) 0.18029(10) 0.16250(10) 0.0316(4) Uani 1 1 d . . .
H3A H 0.7410 0.1688 0.1256 0.038 Uiso 1 1 calc R . .
H3B H 0.6900 0.1341 0.1881 0.038 Uiso 1 1 calc R . .
C4 C 0.76769(11) 0.37328(11) 0.21977(9) 0.0296(4) Uani 1 1 d . . .
C5 C 0.72185(12) 0.40309(11) 0.27687(10) 0.0354(5) Uani 1 1 d . . .
C6 C 0.75591(15) 0.45917(13) 0.31957(12) 0.0493(6) Uani 1 1 d . . .
H6 H 0.7268 0.4774 0.3581 0.059 Uiso 1 1 calc R . .
C7 C 0.83167(15) 0.48817(13) 0.30596(13) 0.0546(6) Uani 1 1 d . . .
H7 H 0.8534 0.5253 0.3352 0.065 Uiso 1 1 calc R . .
C8 C 0.87475(14) 0.46158(12) 0.24860(13) 0.0493(6) Uani 1 1 d . . .
H8 H 0.9250 0.4823 0.2386 0.059 Uiso 1 1 calc R . .
C9 C 0.84442(12) 0.40388(12) 0.20494(11) 0.0389(5) Uani 1 1 d . . .
C10 C 0.89517(15) 0.37491(16) 0.14404(13) 0.0622(7) Uani 1 1 d . . .
H10A H 0.9142 0.3251 0.1550 0.093 Uiso 1 1 calc R . .
H10B H 0.9403 0.4079 0.1369 0.093 Uiso 1 1 calc R . .
H10C H 0.8631 0.3733 0.1016 0.093 Uiso 1 1 calc R . .
C11 C 0.63657(13) 0.37686(13) 0.29123(12) 0.0475(6) Uani 1 1 d . . .
H11A H 0.6379 0.3312 0.3187 0.071 Uiso 1 1 calc R . .
H11B H 0.6096 0.3676 0.2469 0.071 Uiso 1 1 calc R . .
H11C H 0.6081 0.4151 0.3172 0.071 Uiso 1 1 calc R . .
C12 C 0.56458(11) 0.15875(10) 0.12126(10) 0.0298(4) Uani 1 1 d . . .
C13 C 0.52059(12) 0.13482(11) 0.18093(10) 0.0325(4) Uani 1 1 d . . .
C14 C 0.45645(12) 0.08470(12) 0.16887(12) 0.0412(5) Uani 1 1 d . . .
H14 H 0.4265 0.0672 0.2073 0.049 Uiso 1 1 calc R . .
C15 C 0.43693(13) 0.06091(12) 0.10109(12) 0.0444(5) Uani 1 1 d . . .
H15 H 0.3938 0.0282 0.0942 0.053 Uiso 1 1 calc R . .
C16 C 0.48138(13) 0.08560(11) 0.04370(12) 0.0418(5) Uani 1 1 d . . .
H16 H 0.4676 0.0693 -0.0017 0.050 Uiso 1 1 calc R . .
C17 C 0.54678(12) 0.13456(11) 0.05230(11) 0.0351(4) Uani 1 1 d . . .
C18 C 0.59490(16) 0.15986(13) -0.01158(11) 0.0526(6) Uani 1 1 d . . .
H18A H 0.5793 0.2102 -0.0244 0.079 Uiso 1 1 calc R . .
H18B H 0.5847 0.1264 -0.0507 0.079 Uiso 1 1 calc R . .
H18C H 0.6513 0.1590 -0.0002 0.079 Uiso 1 1 calc R . .
C19 C 0.53901(13) 0.16166(12) 0.25533(11) 0.0417(5) Uani 1 1 d . . .
H19A H 0.4979 0.1441 0.2872 0.063 Uiso 1 1 calc R . .
H19B H 0.5405 0.2158 0.2561 0.063 Uiso 1 1 calc R . .
H19C H 0.5904 0.1422 0.2700 0.063 Uiso 1 1 calc R . .
C20 C 0.47561(14) 0.32134(13) 0.12900(13) 0.0521(6) Uani 1 1 d . . .
H20A H 0.4420 0.3632 0.1421 0.078 Uiso 1 1 calc R . .
H20B H 0.5007 0.3009 0.1708 0.078 Uiso 1 1 calc R . .
H20C H 0.4434 0.2831 0.1067 0.078 Uiso 1 1 calc R . .
C21 C 0.49973(19) 0.38779(19) 0.02046(17) 0.0870(10) Uani 1 1 d . . .
H21A H 0.4668 0.3537 -0.0065 0.131 Uiso 1 1 calc R . .
H21B H 0.5407 0.4087 -0.0097 0.131 Uiso 1 1 calc R . .
H21C H 0.4668 0.4277 0.0390 0.131 Uiso 1 1 calc R . .
C22 C 0.79672(16) 0.26358(15) -0.01000(14) 0.0650(8) Uani 1 1 d . . .
H22A H 0.7860 0.2187 -0.0369 0.098 Uiso 1 1 calc R . .
H22B H 0.8147 0.2500 0.0368 0.098 Uiso 1 1 calc R . .
H22C H 0.8378 0.2925 -0.0334 0.098 Uiso 1 1 calc R . .
C23 C 0.6962(2) 0.33115(18) -0.07537(12) 0.0823(10) Uani 1 1 d . . .
H23A H 0.7368 0.3619 -0.0973 0.123 Uiso 1 1 calc R . .
H23B H 0.6470 0.3594 -0.0713 0.123 Uiso 1 1 calc R . .
H23C H 0.6869 0.2871 -0.1039 0.123 Uiso 1 1 calc R . .
C24 C 0.64014(17) 0.50753(13) 0.12687(14) 0.0616(7) Uani 1 1 d . . .
H24A H 0.6730 0.5232 0.1662 0.092 Uiso 1 1 calc R . .
H24B H 0.5923 0.4833 0.1444 0.092 Uiso 1 1 calc R . .
H24C H 0.6254 0.5508 0.0991 0.092 Uiso 1 1 calc R . .
C25 C 0.75187(18) 0.49342(15) 0.04731(15) 0.0723(8) Uani 1 1 d . . .
H25A H 0.7312 0.5354 0.0208 0.108 Uiso 1 1 calc R . .
H25B H 0.7788 0.4592 0.0157 0.108 Uiso 1 1 calc R . .
H25C H 0.7894 0.5113 0.0824 0.108 Uiso 1 1 calc R . .
N1 N 0.73532(9) 0.31322(8) 0.17642(8) 0.0279(3) Uani 1 1 d . . .
N2 N 0.68550(12) 0.45453(10) 0.08247(9) 0.0428(4) Uani 1 1 d . . .
N3 N 0.72329(12) 0.30837(10) -0.00472(9) 0.0457(5) Uani 1 1 d . . .
N4 N 0.53780(11) 0.34697(10) 0.07947(9) 0.0427(4) Uani 1 1 d . . .
O O 0.62837(7) 0.21126(7) 0.13109(6) 0.0285(3) Uani 1 1 d . . .
Zr Zr 0.662899(11) 0.339398(10) 0.086488(9) 0.02950(6) Uani 1 1 d . . .
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
N1 C2 C3 108.26(15) . . ?
N1 C2 C1 114.11(17) . . ?
C3 C2 C1 108.05(16) . . ?
O C3 C2 107.88(14) . . ?
C9 C4 C5 119.33(17) . . ?
C9 C4 N1 120.44(17) . . ?
C5 C4 N1 120.21(16) . . ?
C6 C5 C4 118.94(19) . . ?
C6 C5 C11 119.59(19) . . ?
C4 C5 C11 121.45(17) . . ?
C7 C6 C5 121.7(2) . . ?
C8 C7 C6 119.3(2) . . ?
C7 C8 C9 121.4(2) . . ?
C8 C9 C4 119.14(19) . . ?
C8 C9 C10 119.43(19) . . ?
C4 C9 C10 121.42(19) . . ?
C17 C12 C13 122.67(17) . . ?
C17 C12 O 118.60(16) . . ?
C13 C12 O 118.71(16) . . ?
C14 C13 C12 117.08(18) . . ?
C14 C13 C19 120.16(18) . . ?
C12 C13 C19 122.75(18) . . ?
C15 C14 C13 121.3(2) . . ?
C16 C15 C14 120.0(2) . . ?
C15 C16 C17 121.4(2) . . ?
C12 C17 C16 117.47(19) . . ?
C12 C17 C18 122.41(18) . . ?
C16 C17 C18 120.12(18) . . ?
C4 N1 C2 112.84(14) . . ?
C4 N1 Zr 119.90(11) . . ?
C2 N1 Zr 124.55(11) . . ?
C25 N2 C24 110.07(19) . . ?
C25 N2 Zr 128.15(16) . . ?
C24 N2 Zr 121.12(15) . . ?
C22 N3 C23 110.2(2) . . ?
C22 N3 Zr 127.46(15) . . ?
C23 N3 Zr 122.31(18) . . ?
C20 N4 C21 109.39(19) . . ?
C20 N4 Zr 129.93(14) . . ?
C21 N4 Zr 120.53(17) . . ?
C12 O C3 115.34(13) . . ?
C12 O Zr 136.49(10) . . ?
C3 O Zr 106.65(10) . . ?
N3 Zr N2 98.29(7) . . ?
N3 Zr N4 116.62(7) . . ?
N2 Zr N4 96.55(7) . . ?
N3 Zr N1 109.26(7) . . ?
N2 Zr N1 98.14(6) . . ?
N4 Zr N1 128.83(6) . . ?
N3 Zr O 98.57(6) . . ?
N2 Zr O 162.00(5) . . ?
N4 Zr O 81.43(5) . . ?
N1 Zr O 70.27(5) . . ?
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
C1 C2 1.536(3) . ?
C2 N1 1.486(2) . ?
C2 C3 1.517(3) . ?
C3 O 1.464(2) . ?
C4 C9 1.411(3) . ?
C4 C5 1.418(3) . ?
C4 N1 1.445(2) . ?
C5 C6 1.397(3) . ?
C5 C11 1.513(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.377(3) . ?
C8 C9 1.405(3) . ?
C9 C10 1.512(3) . ?
C12 C17 1.398(3) . ?
C12 C13 1.405(3) . ?
C12 O 1.421(2) . ?
C13 C14 1.404(3) . ?
C13 C19 1.510(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.379(3) . ?
C16 C17 1.398(3) . ?
C17 C18 1.511(3) . ?
C20 N4 1.462(3) . ?
C21 N4 1.468(3) . ?
C22 N3 1.457(3) . ?
C23 N3 1.460(3) . ?
C24 N2 1.465(3) . ?
C25 N2 1.458(3) . ?
N1 Zr 2.1263(15) . ?
N2 Zr 2.0763(17) . ?
N3 Zr 2.0617(17) . ?
N4 Zr 2.0830(18) . ?
O Zr 2.4882(12) . ?
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
N1 C2 C3 O -46.40(19) . . . . ?
C1 C2 C3 O -170.45(16) . . . . ?
C9 C4 C5 C6 -3.6(3) . . . . ?
N1 C4 C5 C6 177.60(18) . . . . ?
C9 C4 C5 C11 174.84(19) . . . . ?
N1 C4 C5 C11 -3.9(3) . . . . ?
C4 C5 C6 C7 2.4(3) . . . . ?
C11 C5 C6 C7 -176.1(2) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 -2.1(4) . . . . ?
C7 C8 C9 C4 0.8(3) . . . . ?
C7 C8 C9 C10 -178.0(2) . . . . ?
C5 C4 C9 C8 2.1(3) . . . . ?
N1 C4 C9 C8 -179.18(18) . . . . ?
C5 C4 C9 C10 -179.1(2) . . . . ?
N1 C4 C9 C10 -0.3(3) . . . . ?
C17 C12 C13 C14 -0.1(3) . . . . ?
O C12 C13 C14 178.11(16) . . . . ?
C17 C12 C13 C19 -179.17(18) . . . . ?
O C12 C13 C19 -0.9(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C19 C13 C14 C15 178.19(19) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C13 C12 C17 C16 1.1(3) . . . . ?
O C12 C17 C16 -177.12(16) . . . . ?
C13 C12 C17 C18 -179.32(19) . . . . ?
O C12 C17 C18 2.4(3) . . . . ?
C15 C16 C17 C12 -1.2(3) . . . . ?
C15 C16 C17 C18 179.3(2) . . . . ?
C9 C4 N1 C2 106.6(2) . . . . ?
C5 C4 N1 C2 -74.6(2) . . . . ?
C9 C4 N1 Zr -91.19(19) . . . . ?
C5 C4 N1 Zr 87.56(19) . . . . ?
C3 C2 N1 C4 -179.28(15) . . . . ?
C1 C2 N1 C4 -58.9(2) . . . . ?
C3 C2 N1 Zr 19.5(2) . . . . ?
C1 C2 N1 Zr 139.85(15) . . . . ?
C17 C12 O C3 -106.93(19) . . . . ?
C13 C12 O C3 74.8(2) . . . . ?
C17 C12 O Zr 56.7(2) . . . . ?
C13 C12 O Zr -121.61(16) . . . . ?
C2 C3 O C12 -141.81(15) . . . . ?
C2 C3 O Zr 49.87(15) . . . . ?
C22 N3 Zr N2 112.02(19) . . . . ?
C23 N3 Zr N2 -67.0(2) . . . . ?
C22 N3 Zr N4 -146.32(18) . . . . ?
C23 N3 Zr N4 34.6(2) . . . . ?
C22 N3 Zr N1 10.3(2) . . . . ?
C23 N3 Zr N1 -168.71(19) . . . . ?
C22 N3 Zr O -61.65(19) . . . . ?
C23 N3 Zr O 119.30(19) . . . . ?
C25 N2 Zr N3 -24.6(2) . . . . ?
C24 N2 Zr N3 165.63(18) . . . . ?
C25 N2 Zr N4 -142.8(2) . . . . ?
C24 N2 Zr N4 47.43(18) . . . . ?
C25 N2 Zr N1 86.4(2) . . . . ?
C24 N2 Zr N1 -83.41(18) . . . . ?
C25 N2 Zr O 134.8(2) . . . . ?
C24 N2 Zr O -35.0(3) . . . . ?
C20 N4 Zr N3 137.15(18) . . . . ?
C21 N4 Zr N3 -47.8(2) . . . . ?
C20 N4 Zr N2 -120.15(19) . . . . ?
C21 N4 Zr N2 54.9(2) . . . . ?
C20 N4 Zr N1 -14.2(2) . . . . ?
C21 N4 Zr N1 160.85(19) . . . . ?
C20 N4 Zr O 41.81(18) . . . . ?
C21 N4 Zr O -143.2(2) . . . . ?
C4 N1 Zr N3 113.15(13) . . . . ?
C2 N1 Zr N3 -86.87(15) . . . . ?
C4 N1 Zr N2 11.36(14) . . . . ?
C2 N1 Zr N2 171.34(14) . . . . ?
C4 N1 Zr N4 -93.89(14) . . . . ?
C2 N1 Zr N4 66.09(16) . . . . ?
C4 N1 Zr O -154.42(14) . . . . ?
C2 N1 Zr O 5.55(13) . . . . ?
C12 O Zr N3 -87.51(16) . . . . ?
C3 O Zr N3 77.07(11) . . . . ?
C12 O Zr N2 113.1(2) . . . . ?
C3 O Zr N2 -82.3(2) . . . . ?
C12 O Zr N4 28.31(16) . . . . ?
C3 O Zr N4 -167.10(11) . . . . ?
C12 O Zr N1 165.01(16) . . . . ?
C3 O Zr N1 -30.41(10) . . . . ?
