#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:55:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178588 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/99/4069991.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_4069991
loop_
_publ_author_name
'Enk, Barbara'
'Kopacka, Holger'
'Wurst, Klaus'
'Müller, Thomas'
'Bildstein, Benno'
_publ_section_title
;
 An Efficient, Modular Route to New 2-Acyl-6-aminopentafulvenes and
 Planar-Chiral [N,O]-Functionalized Pentamethylruthenocenes
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              5575
_journal_paper_doi               10.1021/om900549c
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C66 H76 Cl6 N2 Ru2 Zr'
_chemical_formula_weight         1403.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.934(2)
_cell_angle_beta                 96.762(2)
_cell_angle_gamma                99.621(2)
_cell_formula_units_Z            1
_cell_length_a                   11.2220(3)
_cell_length_b                   11.2334(3)
_cell_length_c                   12.8321(3)
_cell_measurement_reflns_used    14459
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      1.0
_cell_volume                     1540.83(7)
_computing_data_collection       COLLECT
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega 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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10050
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0217P)²+1.0068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0656
_reflns_number_gt                6086
_reflns_number_total             6659
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900549c_si_001.cif
_cod_data_source_block           23
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4069991
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Ru1 Ru 0.274565(13) 0.623392(13) 0.681563(12) 0.02777(5) Uani 1 1 d .
Zr1 Zr 0.0000 0.0000 0.5000 0.02936(7) Uani 1 2 d S
Cl1 Cl -0.19022(6) -0.05345(6) 0.36627(6) 0.05973(18) Uani 1 1 d .
Cl2 Cl -0.04916(6) 0.20346(5) 0.57640(5) 0.04641(13) Uani 1 1 d .
Cl3 Cl 0.10710(6) 0.09418(5) 0.37193(5) 0.05062(14) Uani 1 1 d .
N1 N 0.23298(14) 0.74249(15) 0.97121(13) 0.0293(3) Uani 1 1 d .
C1 C 0.3608(2) 0.4805(2) 0.5956(2) 0.0472(6) Uani 1 1 d .
C01 C 0.3135(3) 0.3429(3) 0.5692(3) 0.0826(11) Uani 1 1 d .
H01A H 0.3696 0.3010 0.5306 0.124 Uiso 1 1 calc R
H01B H 0.2336 0.3236 0.5246 0.124 Uiso 1 1 calc R
H01C H 0.3067 0.3153 0.6355 0.124 Uiso 1 1 calc R
C2 C 0.3348(2) 0.5645(3) 0.52953(18) 0.0490(6) Uani 1 1 d .
C02 C 0.2547(3) 0.5294(4) 0.4213(2) 0.0840(11) Uani 1 1 d .
H02A H 0.2143 0.5972 0.4116 0.126 Uiso 1 1 calc R
H02B H 0.1935 0.4558 0.4173 0.126 Uiso 1 1 calc R
H02C H 0.3043 0.5125 0.3651 0.126 Uiso 1 1 calc R
C3 C 0.40351(19) 0.6860(2) 0.58241(18) 0.0411(5) Uani 1 1 d .
C03 C 0.4083(3) 0.8014(3) 0.5414(3) 0.0699(9) Uani 1 1 d .
H03A H 0.4111 0.8714 0.6010 0.105 Uiso 1 1 calc R
H03B H 0.3360 0.7925 0.4887 0.105 Uiso 1 1 calc R
H03C H 0.4809 0.8155 0.5079 0.105 Uiso 1 1 calc R
C4 C 0.47339(18) 0.6753(2) 0.67943(17) 0.0353(4) Uani 1 1 d .
C04 C 0.5729(2) 0.7767(2) 0.7490(2) 0.0519(6) Uani 1 1 d .
H04A H 0.5878 0.7611 0.8205 0.078 Uiso 1 1 calc R
H04B H 0.5477 0.8559 0.7541 0.078 Uiso 1 1 calc R
H04C H 0.6472 0.7784 0.7172 0.078 Uiso 1 1 calc R
C5 C 0.44549(19) 0.5490(2) 0.68715(19) 0.0390(5) Uani 1 1 d .
C05 C 0.5044(2) 0.4948(3) 0.7727(2) 0.0560(7) Uani 1 1 d .
H05A H 0.4420 0.4571 0.8087 0.084 Uiso 1 1 calc R
H05B H 0.5621 0.5600 0.8250 0.084 Uiso 1 1 calc R
H05C H 0.5472 0.4322 0.7398 0.084 Uiso 1 1 calc R
C6 C 0.09213(17) 0.54076(19) 0.70565(16) 0.0336(4) Uani 1 1 d .
H6 H 0.0645 0.4544 0.6912 0.040 Uiso 1 1 calc .
C7 C 0.08058(18) 0.6190(2) 0.63304(17) 0.0376(5) Uani 1 1 d .
H7 H 0.0414 0.5921 0.5610 0.045 Uiso 1 1 calc .
C8 C 0.13684(18) 0.74445(19) 0.68454(16) 0.0345(4) Uani 1 1 d .
H8 H 0.1417 0.8134 0.6532 0.041 Uiso 1 1 calc .
C9 C 0.18366(16) 0.74471(17) 0.79153(15) 0.0285(4) Uani 1 1 d .
C10 C 0.15498(16) 0.62106(17) 0.80617(15) 0.0270(4) Uani 1 1 d .
C11 C 0.19365(15) 0.62478(17) 0.91695(15) 0.0279(4) Uani 1 1 d .
C12 C 0.18882(17) 0.51490(19) 0.96301(17) 0.0342(4) Uani 1 1 d .
C13 C 0.20105(19) 0.4046(2) 0.8951(2) 0.0418(5) Uani 1 1 d .
H13 H 0.2136 0.4034 0.8238 0.050 Uiso 1 1 calc .
C14 C 0.1947(2) 0.2968(2) 0.9326(3) 0.0546(7) Uani 1 1 d .
H14 H 0.2036 0.2228 0.8870 0.066 Uiso 1 1 calc .
C15 C 0.1753(2) 0.2982(3) 1.0365(3) 0.0592(8) Uani 1 1 d .
H15 H 0.1727 0.2254 1.0621 0.071 Uiso 1 1 calc .
C16 C 0.1596(2) 0.4052(3) 1.1034(2) 0.0589(7) Uani 1 1 d .
H16 H 0.1442 0.4044 1.1737 0.071 Uiso 1 1 calc .
C17 C 0.1665(2) 0.5147(2) 1.06781(19) 0.0463(5) Uani 1 1 d .
H17 H 0.1563 0.5878 1.1138 0.056 Uiso 1 1 calc .
C18 C 0.30062(17) 0.78318(18) 1.08018(16) 0.0326(4) Uani 1 1 d .
C19 C 0.42314(18) 0.77066(19) 1.09622(17) 0.0362(4) Uani 1 1 d .
C20 C 0.4901(2) 0.8200(2) 1.19892(19) 0.0438(5) Uani 1 1 d .
H20 H 0.5732 0.8150 1.2116 0.053 Uiso 1 1 calc .
C21 C 0.4372(2) 0.8758(2) 1.28213(18) 0.0482(6) Uani 1 1 d .
H21 H 0.4847 0.9104 1.3504 0.058 Uiso 1 1 calc .
C22 C 0.3145(2) 0.8814(2) 1.26622(18) 0.0473(5) Uani 1 1 d .
H22 H 0.2786 0.9170 1.3245 0.057 Uiso 1 1 calc .
C23 C 0.2434(2) 0.8349(2) 1.16453(17) 0.0410(5) Uani 1 1 d .
C24 C 0.22705(17) 0.83458(17) 0.89815(16) 0.0313(4) Uani 1 1 d .
C25 C 0.3506(2) 0.9191(2) 0.90814(19) 0.0427(5) Uani 1 1 d .
H25A H 0.3713 0.9736 0.9797 0.064 Uiso 1 1 calc .
H25B H 0.3469 0.9685 0.8546 0.064 Uiso 1 1 calc .
H25C H 0.4127 0.8693 0.8965 0.064 Uiso 1 1 calc .
C26 C 0.1294(2) 0.9119(2) 0.9235(2) 0.0474(5) Uani 1 1 d .
H26A H 0.1570 0.9705 0.9926 0.071 Uiso 1 1 calc .
H26B H 0.0536 0.8575 0.9263 0.071 Uiso 1 1 calc .
H26C H 0.1157 0.9568 0.8676 0.071 Uiso 1 1 calc .
C191 C 0.4809(2) 0.7028(3) 1.0087(2) 0.0519(6) Uani 1 1 d .
H19A H 0.5628 0.7484 1.0105 0.078 Uiso 1 1 calc R
H19B H 0.4321 0.6954 0.9392 0.078 Uiso 1 1 calc R
H19C H 0.4851 0.6207 1.0198 0.078 Uiso 1 1 calc R
C231 C 0.1083(2) 0.8337(3) 1.1522(2) 0.0618(8) Uani 1 1 d .
H23A H 0.0751 0.8049 1.2111 0.093 Uiso 1 1 calc R
H23B H 0.0681 0.7784 1.0841 0.093 Uiso 1 1 calc R
H23C H 0.0945 0.9169 1.1534 0.093 Uiso 1 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'
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'
Ru Ru -1.2594 0.8363 '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
C2 Ru1 C3 38.88(9) . .
C2 Ru1 C7 102.49(8) . .
C3 Ru1 C7 118.73(8) . .
C2 Ru1 C1 38.65(10) . .
C3 Ru1 C1 64.65(9) . .
C7 Ru1 C1 119.49(9) . .
C2 Ru1 C6 119.58(8) . .
C3 Ru1 C6 152.51(8) . .
C7 Ru1 C6 37.84(8) . .
C1 Ru1 C6 110.10(8) . .
C2 Ru1 C10 157.40(8) . .
C3 Ru1 C10 162.31(8) . .
C7 Ru1 C10 62.40(7) . .
C1 Ru1 C10 131.74(8) . .
C6 Ru1 C10 38.20(7) . .
C2 Ru1 C9 152.30(9) . .
C3 Ru1 C9 125.28(8) . .
C7 Ru1 C9 62.37(7) . .
C1 Ru1 C9 168.75(9) . .
C6 Ru1 C9 63.90(7) . .
C10 Ru1 C9 37.72(7) . .
C2 Ru1 C4 63.80(8) . .
C3 Ru1 C4 38.10(8) . .
C7 Ru1 C4 155.77(8) . .
C1 Ru1 C4 63.29(8) . .
C6 Ru1 C4 166.17(8) . .
C10 Ru1 C4 136.25(7) . .
C9 Ru1 C4 120.20(8) . .
C2 Ru1 C5 63.54(9) . .
C3 Ru1 C5 63.76(8) . .
C7 Ru1 C5 155.93(8) . .
C1 Ru1 C5 37.44(9) . .
C6 Ru1 C5 129.81(8) . .
C10 Ru1 C5 123.37(7) . .
C9 Ru1 C5 138.28(8) . .
C4 Ru1 C5 37.60(8) . .
C2 Ru1 C8 116.71(9) . .
C3 Ru1 C8 106.48(8) . .
C7 Ru1 C8 37.84(8) . .
C1 Ru1 C8 150.87(9) . .
C6 Ru1 C8 64.05(8) . .
C10 Ru1 C8 62.74(7) . .
C9 Ru1 C8 37.08(7) . .
C4 Ru1 C8 127.94(8) . .
C5 Ru1 C8 165.20(8) . .
Cl3 Zr1 Cl3 180.000(1) . 2_556
Cl3 Zr1 Cl2 89.06(2) . .
Cl3 Zr1 Cl2 90.94(2) 2_556 .
Cl3 Zr1 Cl2 90.94(2) . 2_556
Cl3 Zr1 Cl2 89.06(2) 2_556 2_556
Cl2 Zr1 Cl2 180.0 . 2_556
Cl3 Zr1 Cl1 88.88(2) . .
Cl3 Zr1 Cl1 91.12(2) 2_556 .
Cl2 Zr1 Cl1 90.46(2) . .
Cl2 Zr1 Cl1 89.54(2) 2_556 .
Cl3 Zr1 Cl1 91.12(2) . 2_556
Cl3 Zr1 Cl1 88.88(2) 2_556 2_556
Cl2 Zr1 Cl1 89.54(2) . 2_556
Cl2 Zr1 Cl1 90.46(2) 2_556 2_556
Cl1 Zr1 Cl1 180.0 . 2_556
C11 N1 C18 125.61(16) . .
C11 N1 C24 112.53(15) . .
C18 N1 C24 120.42(15) . .
C5 C1 C2 107.8(2) . .
C5 C1 C01 125.7(3) . .
C2 C1 C01 126.4(3) . .
C5 C1 Ru1 72.52(12) . .
C2 C1 Ru1 69.44(12) . .
C01 C1 Ru1 126.58(17) . .
C1 C2 C3 108.1(2) . .
C1 C2 C02 125.6(3) . .
C3 C2 C02 126.2(3) . .
C1 C2 Ru1 71.91(13) . .
C3 C2 Ru1 70.94(12) . .
C02 C2 Ru1 125.21(17) . .
C4 C3 C2 107.4(2) . .
C4 C3 C03 125.7(2) . .
C2 C3 C03 126.9(2) . .
C4 C3 Ru1 72.98(11) . .
C2 C3 Ru1 70.18(12) . .
C03 C3 Ru1 125.11(17) . .
C5 C4 C3 108.1(2) . .
C5 C4 C04 127.1(2) . .
C3 C4 C04 124.1(2) . .
C5 C4 Ru1 71.26(11) . .
C3 C4 Ru1 68.92(11) . .
C04 C4 Ru1 132.87(16) . .
C1 C5 C4 108.7(2) . .
C1 C5 C05 125.2(2) . .
C4 C5 C05 125.9(2) . .
C1 C5 Ru1 70.04(12) . .
C4 C5 Ru1 71.15(11) . .
C05 C5 Ru1 128.88(15) . .
C7 C6 C10 105.61(17) . .
C7 C6 Ru1 70.91(11) . .
C10 C6 Ru1 71.66(10) . .
C6 C7 C8 110.53(17) . .
C6 C7 Ru1 71.26(11) . .
C8 C7 Ru1 72.57(11) . .
C9 C8 C7 106.61(17) . .
C9 C8 Ru1 71.14(10) . .
C7 C8 Ru1 69.59(11) . .
C8 C9 C10 108.57(17) . .
C8 C9 C24 139.26(18) . .
C10 C9 C24 110.26(16) . .
C8 C9 Ru1 71.78(11) . .
C10 C9 Ru1 70.90(10) . .
C24 C9 Ru1 133.41(13) . .
C11 C10 C9 107.81(16) . .
C11 C10 C6 143.42(18) . .
C9 C10 C6 108.64(16) . .
C11 C10 Ru1 125.72(12) . .
C9 C10 Ru1 71.38(10) . .
C6 C10 Ru1 70.14(11) . .
N1 C11 C10 109.44(16) . .
N1 C11 C12 125.95(17) . .
C10 C11 C12 124.61(17) . .
C17 C12 C13 119.4(2) . .
C17 C12 C11 123.3(2) . .
C13 C12 C11 117.17(19) . .
C14 C13 C12 120.2(2) . .
C15 C14 C13 119.9(3) . .
C14 C15 C16 120.6(2) . .
C15 C16 C17 120.5(2) . .
C16 C17 C12 119.3(2) . .
C23 C18 C19 122.24(19) . .
C23 C18 N1 119.72(17) . .
C19 C18 N1 118.04(18) . .
C20 C19 C18 117.5(2) . .
C20 C19 C191 120.1(2) . .
C18 C19 C191 122.36(19) . .
C21 C20 C19 121.2(2) . .
C20 C21 C22 120.5(2) . .
C21 C22 C23 120.7(2) . .
C22 C23 C18 117.7(2) . .
C22 C23 C231 119.1(2) . .
C18 C23 C231 123.01(19) . .
C9 C24 C25 115.33(17) . .
C9 C24 C26 109.02(16) . .
C25 C24 C26 110.19(18) . .
C9 C24 N1 99.42(14) . .
C25 C24 N1 111.38(15) . .
C26 C24 N1 111.08(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 C2 2.151(2) .
Ru1 C3 2.161(2) .
Ru1 C7 2.1820(19) .
Ru1 C1 2.184(2) .
Ru1 C6 2.1865(19) .
Ru1 C10 2.2067(18) .
Ru1 C9 2.2131(18) .
Ru1 C4 2.2147(19) .
Ru1 C5 2.2161(19) .
Ru1 C8 2.2213(19) .
Zr1 Cl3 2.4544(6) .
Zr1 Cl3 2.4544(6) 2_556
Zr1 Cl2 2.4721(5) .
Zr1 Cl2 2.4721(5) 2_556
Zr1 Cl1 2.4789(6) .
Zr1 Cl1 2.4789(6) 2_556
N1 C11 1.334(2) .
N1 C18 1.453(2) .
N1 C24 1.537(2) .
C1 C5 1.413(3) .
C1 C2 1.435(4) .
C1 C01 1.500(4) .
C2 C3 1.435(3) .
C2 C02 1.501(4) .
C3 C4 1.429(3) .
C3 C03 1.492(3) .
C4 C5 1.428(3) .
C4 C04 1.503(3) .
C5 C05 1.501(3) .
C6 C7 1.416(3) .
C6 C10 1.438(3) .
C7 C8 1.428(3) .
C8 C9 1.410(3) .
C9 C10 1.429(3) .
C9 C24 1.495(3) .
C10 C11 1.426(3) .
C11 C12 1.471(3) .
C12 C17 1.397(3) .
C12 C13 1.397(3) .
C13 C14 1.387(3) .
C14 C15 1.373(4) .
C15 C16 1.376(4) .
C16 C17 1.391(3) .
C18 C23 1.397(3) .
C18 C19 1.401(3) .
C19 C20 1.391(3) .
C19 C191 1.498(3) .
C20 C21 1.372(4) .
C21 C22 1.382(4) .
C22 C23 1.395(3) .
C23 C231 1.503(3) .
C24 C25 1.520(3) .
C24 C26 1.532(3) .
