#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:30:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178902 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/31/4113195.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_4113195
loop_
_publ_author_name
'Matthew D. LoCoco'
'Xingwang Zhang'
'Richard F. Jordan'
_publ_section_title
;
 Chelate-Controlled Synthesis of Racemic ansa-Zirconocenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15231
_journal_page_last               15244
_journal_paper_doi               10.1021/ja046629+
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C22 H32 Cl2 N2 O2 Zr'
_chemical_formula_weight         518.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 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            8
_cell_length_a                   31.469(6)
_cell_length_b                   10.855(2)
_cell_length_c                   14.079(4)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      15.7
_cell_measurement_theta_min      12.6
_cell_volume                     4809.3(19)
_computing_cell_refinement       'CAD-4 Manual (Enraf-Nonius,1977)'
_computing_data_collection       'CAD-4 Manual (Enraf-Nonius,1977)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'SHELXTL v5.0 (Sheldrick, 1995)'
_computing_publication_material  'SHELXTL v5.0 (Sheldrick, 1995)'
_computing_structure_refinement  'SHELXTL v5.0 (Sheldrick, 1995)'
_computing_structure_solution    'SHELXTL v5.0 (Sheldrick, 1995)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       'θ-2θ 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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3219
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.8541
_exptl_absorpt_correction_T_min  0.8322
_exptl_absorpt_correction_type   'psi scans'
_exptl_absorpt_process_details
; 
Blessing,R. H. Acta Cryst. 1995, A51, 33-38 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       prism
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.229
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.065
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_restrained_S_obs      1.073
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0363P)²+1.7550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0597
_refine_ls_wR_factor_ref         0.0580
_reflns_number_gt                1964
_reflns_number_total             2104
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0466292Bsi20040908_121021.cif
_cod_data_source_block           jor98_3
_cod_original_cell_volume        4809(2)
_cod_database_code               4113195
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
Zr1 Zr 0.0000 0.0000 0.44472(3) 0.03572(10) Uani 1 d S
Cl1 Cl 0.05873(2) 0.15000(6) 0.42264(5) 0.0494(2) Uani 1 d .
N1 N -0.03642(7) 0.1101(2) 0.5358(2) 0.0439(6) Uani 1 d .
C1 C -0.05420(9) 0.2296(3) 0.5282(2) 0.0462(7) Uani 1 d .
C2 C -0.09085(12) 0.2636(3) 0.5788(3) 0.0637(9) Uani 1 d .
H2 H -0.10385(0) 0.2068(0) 0.6188(0) 0.076 Uiso 1 calc R
C3 C -0.10765(14) 0.3794(4) 0.5699(3) 0.0799(12) Uani 1 d .
H3 H -0.13233(0) 0.3990(0) 0.6029(0) 0.096 Uiso 1 calc R
C4 C -0.08918(13) 0.4662(4) 0.5141(3) 0.0721(11) Uani 1 d .
H4 H -0.10045(0) 0.5452(0) 0.5105(0) 0.087 Uiso 1 calc R
C5 C -0.05342(11) 0.4351(3) 0.4628(3) 0.0685(10) Uani 1 d .
H5 H -0.04097(0) 0.4927(0) 0.4226(0) 0.082 Uiso 1 calc R
C6 C -0.03599(10) 0.3186(3) 0.4708(3) 0.0559(8) Uani 1 d .
H6 H -0.01148(0) 0.2997(0) 0.4369(0) 0.067 Uiso 1 calc R
C7 C -0.05282(13) 0.0361(4) 0.6146(3) 0.0581(8) Uani 1 d .
H7A H -0.0395(0) -0.0443(0) 0.6164(0) 0.065(11) Uiso 1 d .
H7B H -0.0824(0) 0.0125(0) 0.6062(0) 0.067(11) Uiso 1 d .
H7C H -0.0493(0) 0.0815(0) 0.6744(0) 0.061(10) Uiso 1 d .
O11 O -0.02965(5) 0.0996(2) 0.31801(14) 0.0465(5) Uani 1 d .
C11 C -0.07586(8) 0.1144(3) 0.3016(2) 0.0504(7) Uani 1 d .
H11A H -0.09002(0) 0.1418(0) 0.3590(0) 0.060 Uiso 1 calc R
H11B H -0.08847(0) 0.0372(0) 0.2813(0) 0.060 Uiso 1 calc R
C12 C -0.07933(10) 0.2103(3) 0.2244(3) 0.0578(8) Uani 1 d .
H12A H -0.08074(0) 0.2927(0) 0.2509(0) 0.069 Uiso 1 calc R
H12B H -0.10412(0) 0.1963(0) 0.1849(0) 0.069 Uiso 1 calc R
C13 C -0.03861(11) 0.1913(4) 0.1689(3) 0.0725(10) Uani 1 d .
H13A H -0.04157(0) 0.1238(0) 0.1242(0) 0.087 Uiso 1 calc R
H13B H -0.03098(0) 0.2653(0) 0.1342(0) 0.087 Uiso 1 calc R
C14 C -0.00675(11) 0.1627(4) 0.2410(3) 0.0682(10) Uani 1 d .
H14A H 0.00646(0) 0.2376(0) 0.2643(0) 0.082 Uiso 1 calc R
H14B H 0.01515(0) 0.1096(0) 0.2150(0) 0.082 Uiso 1 calc R
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'
Cl Cl 0.1484 0.1585 '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 Zr1 N1 104.52(14) . 2 yes
N1 Zr1 O11 166.27(9) . 2 yes
N1 Zr1 O11 89.09(9) 2 2 ?
N1 Zr1 O11 89.09(9) . . yes
N1 Zr1 O11 166.27(9) 2 . ?
O11 Zr1 O11 77.38(11) 2 . yes
N1 Zr1 Cl1 96.30(7) . . yes
N1 Zr1 Cl1 92.50(7) 2 . yes
O11 Zr1 Cl1 84.76(5) 2 . yes
O11 Zr1 Cl1 84.02(5) . . yes
N1 Zr1 Cl1 92.50(7) . 2 ?
N1 Zr1 Cl1 96.30(7) 2 2 ?
O11 Zr1 Cl1 84.02(5) 2 2 ?
O11 Zr1 Cl1 84.76(5) . 2 ?
Cl1 Zr1 Cl1 165.62(4) . 2 yes
C1 N1 C7 114.9(2) . . yes
C1 N1 Zr1 133.8(2) . . yes
C7 N1 Zr1 110.1(2) . . yes
C6 C1 C2 116.9(3) . . yes
C6 C1 N1 121.3(3) . . yes
C2 C1 N1 121.8(3) . . yes
C3 C2 C1 120.8(4) . . yes
C4 C3 C2 121.6(4) . . yes
C3 C4 C5 118.8(3) . . yes
C4 C5 C6 120.3(4) . . yes
C5 C6 C1 121.5(3) . . yes
C14 O11 C11 108.4(2) . . yes
C14 O11 Zr1 126.5(2) . . yes
C11 O11 Zr1 125.0(2) . . yes
O11 C11 C12 104.9(2) . . yes
C11 C12 C13 102.5(3) . . yes
C14 C13 C12 104.5(3) . . yes
C13 C14 O11 106.0(3) . . yes
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
Zr1 N1 2.094(2) . yes
Zr1 N1 2.094(2) 2 ?
Zr1 O11 2.285(2) 2 ?
Zr1 O11 2.285(2) . yes
Zr1 Cl1 2.4827(7) . yes
Zr1 Cl1 2.4827(7) 2 ?
N1 C1 1.416(4) . yes
N1 C7 1.464(4) . yes
C1 C6 1.384(5) . yes
C1 C2 1.405(5) . yes
C2 C3 1.369(5) . yes
C3 C4 1.358(7) . yes
C4 C5 1.379(6) . yes
C5 C6 1.382(4) . yes
O11 C14 1.471(4) . yes
O11 C11 1.481(3) . yes
C11 C12 1.509(5) . yes
C12 C13 1.515(5) . yes
C13 C14 1.460(5) . yes
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
N1 Zr1 N1 C1 151.1(3) 2
O11 Zr1 N1 C1 -36.8(5) 2
O11 Zr1 N1 C1 -27.0(2) .
Cl1 Zr1 N1 C1 56.9(2) .
Cl1 Zr1 N1 C1 -111.7(2) 2
N1 Zr1 N1 C7 -42.5(2) 2
O11 Zr1 N1 C7 129.6(4) 2
O11 Zr1 N1 C7 139.4(2) .
Cl1 Zr1 N1 C7 -136.7(2) .
Cl1 Zr1 N1 C7 54.7(2) 2
C7 N1 C1 C6 166.3(3) .
Zr1 N1 C1 C6 -27.8(4) .
C7 N1 C1 C2 -13.2(4) .
Zr1 N1 C1 C2 152.7(3) .
C6 C1 C2 C3 0.9(5) .
N1 C1 C2 C3 -179.6(3) .
C1 C2 C3 C4 -1.6(7) .
C2 C3 C4 C5 2.2(7) .
C3 C4 C5 C6 -2.2(6) .
C4 C5 C6 C1 1.5(5) .
C2 C1 C6 C5 -0.9(5) .
N1 C1 C6 C5 179.6(3) .
N1 Zr1 O11 C14 125.2(3) .
N1 Zr1 O11 C14 -47.1(5) 2
O11 Zr1 O11 C14 -57.2(3) 2
Cl1 Zr1 O11 C14 28.8(3) .
Cl1 Zr1 O11 C14 -142.2(3) 2
N1 Zr1 O11 C11 -52.9(2) .
N1 Zr1 O11 C11 134.8(3) 2
O11 Zr1 O11 C11 124.8(3) 2
Cl1 Zr1 O11 C11 -149.3(2) .
Cl1 Zr1 O11 C11 39.7(2) 2
C14 O11 C11 C12 -11.6(4) .
Zr1 O11 C11 C12 166.8(2) .
O11 C11 C12 C13 29.6(4) .
C11 C12 C13 C14 -37.3(4) .
C12 C13 C14 O11 30.7(4) .
C11 O11 C14 C13 -12.0(4) .
Zr1 O11 C14 C13 169.7(3) .
