#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:30:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178624 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/35/4073557.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_4073557
loop_
_publ_author_name
'Steffen, Andreas'
'Hagemeister, Timo'
'Braun, Thomas'
'Jutzi, Peter'
'Neumann, Beate'
'Stammler, Hans-Georg'
_publ_section_title
;
 Synthesis of 3,3,3-Trifluoropropyl Substituted Cyclopentadienes and Their
 Zirconocene Derivatives:  Catalytic Applications in the
 Polymerization of Ethylene
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              5289
_journal_paper_doi               10.1021/om700457c
_journal_volume                  26
_journal_year                    2007
_chemical_formula_moiety         'C16 H16 Cl2 F6 Zr'
_chemical_formula_sum            'C16 H16 Cl2 F6 Zr'
_chemical_formula_weight         484.41
_chemical_name_systematic        ?
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 114.193(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.5177(14)
_cell_length_b                   6.6645(7)
_cell_length_c                   14.6427(14)
_cell_measurement_reflns_used    128
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.465
_cell_measurement_theta_min      4.156
_cell_volume                     1826.4(3)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'EVALCCD (Duisenberg, 1998, Thesis. Utrecht University'
_computing_molecular_graphics    'SHELXTL-PLUS (1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24163
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  0.8631
_exptl_absorpt_correction_T_min  0.8404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0177
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0203P)²+1.1328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0433
_reflns_number_gt                2480
_reflns_number_total             2662
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om700457c-file009.cif
_cod_data_source_block           compound6
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1826.6(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4073557
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Zr1 Zr 0.5000 0.16113(2) 0.2500 0.01618(4) Uani 1 2 d S
Cl1 Cl 0.558465(14) -0.08817(4) 0.18419(2) 0.02451(6) Uani 1 1 d .
F1 F 0.23931(6) -0.2294(2) -0.22048(7) 0.0753(4) Uani 1 1 d .
F2 F 0.34769(6) -0.33162(14) -0.14343(8) 0.0522(2) Uani 1 1 d .
F3 F 0.27272(6) -0.38472(16) -0.07901(8) 0.0583(3) Uani 1 1 d .
C1 C 0.36872(6) 0.22590(18) 0.14116(8) 0.0247(2) Uani 1 1 d .
H1 H 0.3330 0.1700 0.1591 0.030 Uiso 1 1 calc R
C2 C 0.40284(6) 0.41388(18) 0.17376(9) 0.0300(3) Uani 1 1 d .
H2 H 0.3947 0.5044 0.2181 0.036 Uiso 1 1 calc R
C3 C 0.45136(7) 0.44231(18) 0.12834(9) 0.0312(3) Uani 1 1 d .
H3 H 0.4811 0.5560 0.1364 0.037 Uiso 1 1 calc R
C4 C 0.44767(6) 0.27122(19) 0.06882(8) 0.0268(2) Uani 1 1 d .
H4 H 0.4745 0.2509 0.0300 0.032 Uiso 1 1 calc R
C5 C 0.39690(6) 0.13503(17) 0.07717(8) 0.0222(2) Uani 1 1 d .
C6 C 0.37586(6) -0.06651(18) 0.02623(8) 0.0260(2) Uani 1 1 d .
H6A H 0.3631 -0.1583 0.0695 0.031 Uiso 1 1 calc R
H6B H 0.4171 -0.1251 0.0171 0.031 Uiso 1 1 calc R
C7 C 0.31222(6) -0.0486(2) -0.07613(8) 0.0272(2) Uani 1 1 d .
H7A H 0.2704 0.0046 -0.0666 0.033 Uiso 1 1 calc R
H7B H 0.3242 0.0478 -0.1183 0.033 Uiso 1 1 calc R
C8 C 0.29315(7) -0.2474(2) -0.12895(9) 0.0363(3) 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
Cl1 Zr1 Cl1 95.235(15) 2_655 .
Cl1 Zr1 C3 132.00(3) 2_655 .
Cl1 Zr1 C3 110.09(3) . .
Cl1 Zr1 C3 110.09(3) 2_655 2_655
Cl1 Zr1 C3 132.00(3) . 2_655
C3 Zr1 C3 82.62(6) . 2_655
Cl1 Zr1 C2 135.01(3) 2_655 2_655
Cl1 Zr1 C2 101.67(3) . 2_655
C3 Zr1 C2 79.92(4) . 2_655
C3 Zr1 C2 33.02(4) 2_655 2_655
Cl1 Zr1 C2 101.67(3) 2_655 .
Cl1 Zr1 C2 135.01(3) . .
C3 Zr1 C2 33.02(4) . .
C3 Zr1 C2 79.92(4) 2_655 .
C2 Zr1 C2 95.14(6) 2_655 .
Cl1 Zr1 C4 81.42(3) 2_655 2_655
Cl1 Zr1 C4 122.71(3) . 2_655
C3 Zr1 C4 113.88(4) . 2_655
C3 Zr1 C4 32.79(4) 2_655 2_655
C2 Zr1 C4 54.35(4) 2_655 2_655
C2 Zr1 C4 101.03(4) . 2_655
Cl1 Zr1 C4 122.71(3) 2_655 .
Cl1 Zr1 C4 81.42(3) . .
C3 Zr1 C4 32.79(4) . .
C3 Zr1 C4 113.88(4) 2_655 .
C2 Zr1 C4 101.03(4) 2_655 .
C2 Zr1 C4 54.35(4) . .
C4 Zr1 C4 146.26(6) 2_655 .
Cl1 Zr1 C1 78.42(3) 2_655 .
Cl1 Zr1 C1 115.45(3) . .
C3 Zr1 C1 54.11(4) . .
C3 Zr1 C1 109.33(4) 2_655 .
C2 Zr1 C1 127.76(4) 2_655 .
C2 Zr1 C1 32.70(4) . .
C4 Zr1 C1 119.58(4) 2_655 .
C4 Zr1 C1 53.68(4) . .
Cl1 Zr1 C1 115.45(3) 2_655 2_655
Cl1 Zr1 C1 78.42(3) . 2_655
C3 Zr1 C1 109.33(4) . 2_655
C3 Zr1 C1 54.11(4) 2_655 2_655
C2 Zr1 C1 32.70(4) 2_655 2_655
C2 Zr1 C1 127.76(4) . 2_655
C4 Zr1 C1 53.68(4) 2_655 2_655
C4 Zr1 C1 119.58(4) . 2_655
C1 Zr1 C1 160.45(6) . 2_655
Cl1 Zr1 C5 90.19(3) 2_655 .
Cl1 Zr1 C5 84.54(3) . .
C3 Zr1 C5 54.34(4) . .
C3 Zr1 C5 133.26(4) 2_655 .
C2 Zr1 C5 132.41(4) 2_655 .
C2 Zr1 C5 54.38(4) . .
C4 Zr1 C5 151.95(4) 2_655 .
C4 Zr1 C5 32.54(4) . .
C1 Zr1 C5 32.41(4) . .
C1 Zr1 C5 150.15(4) 2_655 .
Cl1 Zr1 C5 84.54(3) 2_655 2_655
Cl1 Zr1 C5 90.19(3) . 2_655
C3 Zr1 C5 133.26(4) . 2_655
C3 Zr1 C5 54.34(4) 2_655 2_655
C2 Zr1 C5 54.38(4) 2_655 2_655
C2 Zr1 C5 132.41(4) . 2_655
C4 Zr1 C5 32.54(4) 2_655 2_655
C4 Zr1 C5 151.95(4) . 2_655
C1 Zr1 C5 150.15(4) . 2_655
C1 Zr1 C5 32.41(4) 2_655 2_655
C5 Zr1 C5 172.19(5) . 2_655
C2 C1 C5 108.66(11) . .
C2 C1 Zr1 71.89(6) . .
C5 C1 Zr1 74.24(6) . .
C3 C2 C1 107.73(11) . .
C3 C2 Zr1 73.42(6) . .
C1 C2 Zr1 75.41(6) . .
C2 C3 C4 108.04(10) . .
C2 C3 Zr1 73.56(6) . .
C4 C3 Zr1 74.92(6) . .
C3 C4 C5 108.45(11) . .
C3 C4 Zr1 72.29(6) . .
C5 C4 Zr1 74.70(6) . .
C1 C5 C4 107.11(10) . .
C1 C5 C6 126.35(11) . .
C4 C5 C6 126.53(11) . .
C1 C5 Zr1 73.35(6) . .
C4 C5 Zr1 72.76(6) . .
C6 C5 Zr1 120.19(7) . .
C5 C6 C7 111.65(9) . .
C8 C7 C6 111.79(11) . .
F3 C8 F2 105.49(13) . .
F3 C8 F1 106.91(12) . .
F2 C8 F1 106.05(11) . .
F3 C8 C7 113.24(10) . .
F2 C8 C7 113.05(10) . .
F1 C8 C7 111.57(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zr1 Cl1 2.4649(3) 2_655
Zr1 Cl1 2.4650(3) .
Zr1 C3 2.4949(11) .
Zr1 C3 2.4949(11) 2_655
Zr1 C2 2.4968(11) 2_655
Zr1 C2 2.4968(11) .
Zr1 C4 2.5288(11) 2_655
Zr1 C4 2.5288(11) .
Zr1 C1 2.5422(10) .
Zr1 C1 2.5423(10) 2_655
Zr1 C5 2.5538(10) .
Zr1 C5 2.5539(10) 2_655
F1 C8 1.3481(15) .
F2 C8 1.3442(17) .
F3 C8 1.3417(17) .
C1 C2 1.4190(17) .
C1 C5 1.4223(16) .
C2 C3 1.4185(19) .
C3 C4 1.4182(18) .
C4 C5 1.4242(16) .
C5 C6 1.5110(15) .
C6 C7 1.5367(15) .
C7 C8 1.5030(19) .
