#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:30:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178902 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/31/4113106.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_4113106
loop_
_publ_author_name
'Matthew D. LoCoco'
'Richard F. Jordan'
_publ_section_title
;
 Enantioselective Synthesis of ansa-Zirconocenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13918
_journal_page_last               13919
_journal_paper_doi               10.1021/ja045245g
_journal_volume                  126
_journal_year                    2004
_chemical_absolute_configuration 'add info here'
_chemical_formula_moiety         'C25 H36 Cl2 N2 O2 Zr'
_chemical_formula_sum            'C25 H36 Cl2 N2 O2 Zr'
_chemical_formula_weight         558.68
_chemical_name_common
'[(2R,4R)-N,N'-Diphenyl-(2,4)-pentanediamine]ZrCl2(THF2)'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   10.3941(19)
_cell_length_b                   12.017(2)
_cell_length_c                   21.372(4)
_cell_measurement_reflns_used    31,995
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      1.19
_cell_volume                     2669.5(8)
_computing_cell_refinement       'SAINT (Bruker AXS)'
_computing_data_collection       'SMART 5.624 (Bruker AXS)'
_computing_data_reduction        'SAINT (Bruker AXS)'
_computing_molecular_graphics    'shelxtl 5.1 (Bruker AXS)'
_computing_publication_material  'shelxtl 5.1 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       '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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31995
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS, SHELXTL (version 5.1) program library 
(G. Sheldrick, Bruker Analytical X-ray Systems, Madison, WI)
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         6525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0298
_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)+(0.0186P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0515
_refine_ls_wR_factor_ref         0.0524
_reflns_number_gt                6107
_reflns_number_total             6525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja045245gsi20040902_010029.cif
_cod_data_source_block           matt13s
_cod_database_code               4113106
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.8143(2) 0.1582(2) 0.16583(9) 0.0206(5) Uani 1 1 d .
C2 C 0.7418(2) 0.0717(2) 0.19169(11) 0.0250(5) Uani 1 1 d .
H2 H 0.6733 0.0883 0.2196 0.030 Uiso 1 1 calc R
C3 C 0.7692(2) -0.0379(2) 0.17686(12) 0.0296(6) Uani 1 1 d .
H3 H 0.7187 -0.0959 0.1944 0.036 Uiso 1 1 calc R
C4 C 0.8686(2) -0.06395(18) 0.13709(11) 0.0288(5) Uani 1 1 d .
H4 H 0.8868 -0.1392 0.1268 0.035 Uiso 1 1 calc R
C5 C 0.9420(2) 0.0217(2) 0.11227(11) 0.0268(6) Uani 1 1 d .
H5 H 1.0115 0.0045 0.0851 0.032 Uiso 1 1 calc R
C6 C 0.9159(2) 0.13116(19) 0.12632(10) 0.0230(5) Uani 1 1 d .
H6 H 0.9675 0.1886 0.1089 0.028 Uiso 1 1 calc R
C7 C 0.8761(3) 0.32350(18) 0.22305(10) 0.0274(5) Uani 1 1 d .
H7 H 0.9646 0.3134 0.2057 0.033 Uiso 1 1 calc R
C8 C 0.8703(3) 0.2684(2) 0.28760(11) 0.0440(7) Uani 1 1 d .
H8A H 0.7833 0.2760 0.3047 0.066 Uiso 1 1 calc R
H8B H 0.9319 0.3047 0.3157 0.066 Uiso 1 1 calc R
H8C H 0.8919 0.1894 0.2837 0.066 Uiso 1 1 calc R
C9 C 0.8497(2) 0.44781(19) 0.22937(10) 0.0269(6) Uani 1 1 d .
H9A H 0.9201 0.4805 0.2546 0.032 Uiso 1 1 calc R
H9B H 0.7694 0.4567 0.2538 0.032 Uiso 1 1 calc R
C10 C 0.8364(2) 0.5170(2) 0.16981(11) 0.0256(6) Uani 1 1 d .
H10 H 0.8351 0.5970 0.1826 0.031 Uiso 1 1 calc R
C11 C 0.9504(2) 0.5013(2) 0.12621(12) 0.0331(7) Uani 1 1 d .
H11A H 0.9497 0.4254 0.1095 0.050 Uiso 1 1 calc R
H11B H 1.0305 0.5138 0.1494 0.050 Uiso 1 1 calc R
H11C H 0.9447 0.5546 0.0916 0.050 Uiso 1 1 calc R
C12 C 0.6735(2) 0.58629(18) 0.09880(10) 0.0220(5) Uani 1 1 d .
C13 C 0.6305(2) 0.68494(16) 0.12606(10) 0.0251(5) Uani 1 1 d .
H13 H 0.6297 0.6918 0.1703 0.030 Uiso 1 1 calc R
C14 C 0.5890(2) 0.7728(2) 0.08964(12) 0.0305(6) Uani 1 1 d .
H14 H 0.5579 0.8387 0.1090 0.037 Uiso 1 1 calc R
C15 C 0.5928(2) 0.7652(2) 0.02508(12) 0.0324(6) Uani 1 1 d .
H15 H 0.5653 0.8261 0.0001 0.039 Uiso 1 1 calc R
C16 C 0.6365(3) 0.6693(2) -0.00279(11) 0.0341(6) Uani 1 1 d .
H16 H 0.6391 0.6640 -0.0471 0.041 Uiso 1 1 calc R
C17 C 0.6765(2) 0.5806(2) 0.03337(11) 0.0278(6) Uani 1 1 d .
H17 H 0.7065 0.5147 0.0136 0.033 Uiso 1 1 calc R
C18 C 0.4860(2) 0.09921(19) 0.08796(11) 0.0285(6) Uani 1 1 d .
H18A H 0.5702 0.0611 0.0916 0.034 Uiso 1 1 calc R
H18B H 0.4740 0.1237 0.0441 0.034 Uiso 1 1 calc R
C19 C 0.3782(3) 0.02326(19) 0.10799(11) 0.0323(6) Uani 1 1 d .
H19A H 0.4043 -0.0247 0.1434 0.039 Uiso 1 1 calc R
H19B H 0.3483 -0.0240 0.0730 0.039 Uiso 1 1 calc R
C20 C 0.2764(2) 0.1063(2) 0.12740(11) 0.0294(6) Uani 1 1 d .
H20A H 0.2342 0.1404 0.0906 0.035 Uiso 1 1 calc R
H20B H 0.2102 0.0713 0.1543 0.035 Uiso 1 1 calc R
C21 C 0.3539(2) 0.1900(2) 0.16298(11) 0.0306(6) Uani 1 1 d .
H21A H 0.3115 0.2638 0.1622 0.037 Uiso 1 1 calc R
H21B H 0.3647 0.1665 0.2071 0.037 Uiso 1 1 calc R
C22 C 0.3840(2) 0.41161(19) 0.04374(10) 0.0297(6) Uani 1 1 d .
H22A H 0.3583 0.3327 0.0390 0.036 Uiso 1 1 calc R
H22B H 0.4465 0.4303 0.0104 0.036 Uiso 1 1 calc R
C23 C 0.2672(2) 0.4871(2) 0.03984(12) 0.0265(6) Uani 1 1 d .
H23A H 0.1880 0.4474 0.0529 0.032 Uiso 1 1 calc R
H23B H 0.2553 0.5163 -0.0031 0.032 Uiso 1 1 calc R
C24 C 0.3005(2) 0.57972(19) 0.08537(11) 0.0259(6) Uani 1 1 d .
H24A H 0.3590 0.6349 0.0661 0.031 Uiso 1 1 calc R
H24B H 0.2222 0.6181 0.1005 0.031 Uiso 1 1 calc R
C25 C 0.3664(2) 0.51672(17) 0.13756(11) 0.0239(5) Uani 1 1 d .
H25A H 0.4237 0.5665 0.1618 0.029 Uiso 1 1 calc R
H25B H 0.3025 0.4832 0.1663 0.029 Uiso 1 1 calc R
Cl1 Cl 0.67092(5) 0.28417(5) 0.03189(2) 0.02291(13) Uani 1 1 d .
Cl2 Cl 0.51687(5) 0.36494(5) 0.24511(3) 0.02652(14) Uani 1 1 d .
N1 N 0.78301(17) 0.27076(16) 0.17979(8) 0.0203(4) Uani 1 1 d .
N2 N 0.71360(17) 0.49423(14) 0.13628(9) 0.0201(4) Uani 1 1 d .
O1 O 0.47896(14) 0.19441(12) 0.13102(7) 0.0223(4) Uani 1 1 d .
O2 O 0.44057(14) 0.43059(12) 0.10562(7) 0.0202(4) Uani 1 1 d .
Zr1 Zr 0.62508(2) 0.342322(17) 0.141183(9) 0.01693(5) 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'
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
C6 C1 C2 118.5(2)
C6 C1 N1 121.5(2)
C2 C1 N1 120.0(2)
C3 C2 C1 120.3(2)
C4 C3 C2 120.9(2)
C3 C4 C5 118.7(2)
C6 C5 C4 121.2(2)
C5 C6 C1 120.3(2)
N1 C7 C9 110.9(2)
N1 C7 C8 110.6(2)
C9 C7 C8 109.66(19)
C7 C9 C10 118.42(19)
N2 C10 C11 110.53(19)
N2 C10 C9 112.27(18)
C11 C10 C9 111.9(2)
C13 C12 C17 117.8(2)
C13 C12 N2 121.2(2)
C17 C12 N2 121.0(2)
C14 C13 C12 121.0(2)
C13 C14 C15 120.2(2)
C16 C15 C14 119.8(2)
C15 C16 C17 120.3(2)
C16 C17 C12 120.9(2)
O1 C18 C19 104.85(19)
C18 C19 C20 101.45(19)
C21 C20 C19 101.88(19)
O1 C21 C20 105.34(18)
O2 C22 C23 106.13(17)
C22 C23 C24 102.73(19)
C25 C24 C23 102.05(19)
O2 C25 C24 104.43(18)
C1 N1 C7 112.85(18)
C1 N1 Zr1 120.19(14)
C7 N1 Zr1 126.96(15)
C12 N2 C10 112.19(17)
C12 N2 Zr1 126.06(14)
C10 N2 Zr1 121.63(14)
C21 O1 C18 107.88(16)
C21 O1 Zr1 123.82(12)
C18 O1 Zr1 127.93(13)
C25 O2 C22 108.69(16)
C25 O2 Zr1 127.40(13)
C22 O2 Zr1 123.82(13)
N1 Zr1 N2 92.01(7)
N1 Zr1 O2 174.98(6)
N2 Zr1 O2 86.96(6)
N1 Zr1 O1 103.90(7)
N2 Zr1 O1 163.97(6)
O2 Zr1 O1 77.35(5)
N1 Zr1 Cl1 96.20(5)
N2 Zr1 Cl1 96.69(6)
O2 Zr1 Cl1 88.80(4)
O1 Zr1 Cl1 79.87(4)
N1 Zr1 Cl2 92.79(5)
N2 Zr1 Cl2 98.66(6)
O2 Zr1 Cl2 82.51(4)
O1 Zr1 Cl2 82.74(4)
Cl1 Zr1 Cl2 161.91(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.390(3)
C1 C2 1.397(3)
C1 N1 1.423(3)
C2 C3 1.385(3)
C3 C4 1.374(3)
C4 C5 1.386(3)
C5 C6 1.376(3)
C7 N1 1.480(3)
C7 C9 1.525(3)
C7 C8 1.531(3)
C9 C10 1.527(3)
C10 N2 1.489(3)
C10 C11 1.520(3)
C12 C13 1.395(3)
C12 C17 1.400(3)
C12 N2 1.428(3)
C13 C14 1.381(3)
C14 C15 1.383(3)
C15 C16 1.375(3)
C16 C17 1.381(3)
C18 O1 1.470(3)
C18 C19 1.507(3)
C19 C20 1.513(3)
C20 C21 1.496(3)
C21 O1 1.469(3)
C22 O2 1.465(2)
C22 C23 1.518(3)
C23 C24 1.519(3)
C24 C25 1.512(3)
C25 O2 1.460(2)
Cl1 Zr1 2.4842(7)
Cl2 Zr1 2.5044(7)
N1 Zr1 2.0286(18)
N2 Zr1 2.0469(17)
O1 Zr1 2.3480(14)
O2 Zr1 2.3196(15)
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
C6 C1 C2 C3 -1.5(3)
N1 C1 C2 C3 178.1(2)
C1 C2 C3 C4 0.6(4)
C2 C3 C4 C5 0.5(4)
C3 C4 C5 C6 -0.7(4)
C4 C5 C6 C1 -0.2(3)
C2 C1 C6 C5 1.3(3)
N1 C1 C6 C5 -178.3(2)
N1 C7 C9 C10 -51.0(3)
C8 C7 C9 C10 -173.5(2)
C7 C9 C10 N2 72.2(3)
C7 C9 C10 C11 -52.8(3)
C17 C12 C13 C14 1.7(4)
N2 C12 C13 C14 -178.5(2)
C12 C13 C14 C15 -1.7(4)
C13 C14 C15 C16 0.8(4)
C14 C15 C16 C17 0.0(4)
C15 C16 C17 C12 0.0(4)
C13 C12 C17 C16 -0.8(4)
N2 C12 C17 C16 179.3(2)
O1 C18 C19 C20 35.5(2)
C18 C19 C20 C21 -42.8(2)
C19 C20 C21 O1 34.6(2)
O2 C22 C23 C24 25.6(2)
C22 C23 C24 C25 -38.3(2)
C23 C24 C25 O2 37.5(2)
C6 C1 N1 C7 -73.7(2)
C2 C1 N1 C7 106.7(2)
C6 C1 N1 Zr1 106.0(2)
C2 C1 N1 Zr1 -73.5(2)
C9 C7 N1 C1 172.01(19)
C8 C7 N1 C1 -66.1(3)
C9 C7 N1 Zr1 -7.7(3)
C8 C7 N1 Zr1 114.2(2)
C13 C12 N2 C10 -69.5(3)
C17 C12 N2 C10 110.4(2)
C13 C12 N2 Zr1 114.6(2)
C17 C12 N2 Zr1 -65.6(3)
C11 C10 N2 C12 -79.9(2)
C9 C10 N2 C12 154.4(2)
C11 C10 N2 Zr1 96.3(2)
C9 C10 N2 Zr1 -29.4(2)
C20 C21 O1 C18 -12.7(2)
C20 C21 O1 Zr1 160.86(13)
C19 C18 O1 C21 -14.6(2)
C19 C18 O1 Zr1 172.24(14)
C24 C25 O2 C22 -22.2(2)
C24 C25 O2 Zr1 154.42(13)
C23 C22 O2 C25 -2.3(2)
C23 C22 O2 Zr1 -179.04(14)
C1 N1 Zr1 N2 -146.05(16)
C7 N1 Zr1 N2 33.68(18)
C1 N1 Zr1 O1 31.96(16)
C7 N1 Zr1 O1 -148.30(17)
C1 N1 Zr1 Cl1 -49.10(15)
C7 N1 Zr1 Cl1 130.63(17)
C1 N1 Zr1 Cl2 115.18(15)
C7 N1 Zr1 Cl2 -65.09(18)
C12 N2 Zr1 N1 162.84(18)
C10 N2 Zr1 N1 -12.77(17)
C12 N2 Zr1 O2 -22.08(18)
C10 N2 Zr1 O2 162.31(17)
C12 N2 Zr1 O1 -10.2(4)
C10 N2 Zr1 O1 174.22(19)
C12 N2 Zr1 Cl1 66.36(18)
C10 N2 Zr1 Cl1 -109.25(16)
C12 N2 Zr1 Cl2 -104.03(18)
C10 N2 Zr1 Cl2 80.36(16)
C25 O2 Zr1 N2 -64.71(16)
C22 O2 Zr1 N2 111.39(17)
C25 O2 Zr1 O1 118.64(16)
C22 O2 Zr1 O1 -65.27(16)
C25 O2 Zr1 Cl1 -161.47(15)
C22 O2 Zr1 Cl1 14.62(16)
C25 O2 Zr1 Cl2 34.44(15)
C22 O2 Zr1 Cl2 -149.47(16)
C21 O1 Zr1 N1 117.93(16)
C18 O1 Zr1 N1 -69.89(17)
C21 O1 Zr1 N2 -69.3(3)
C18 O1 Zr1 N2 102.9(3)
C21 O1 Zr1 O2 -57.07(15)
C18 O1 Zr1 O2 115.11(17)
C21 O1 Zr1 Cl1 -148.12(16)
C18 O1 Zr1 Cl1 24.06(16)
C21 O1 Zr1 Cl2 26.84(15)
C18 O1 Zr1 Cl2 -160.98(16)
