#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:15:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178555 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/63/4066339.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_4066339
loop_
_publ_author_name
'Denomme, Dan R.'
'Dumbris, Seth M.'
'Hyatt, I. F. Dempsey'
'Abboud, Khalil A.'
'Ghiviriga, Ion'
'McElwee-White, Lisa'
_publ_section_title
;
 Synthesis and Electronic Structure of
 Tetrakis(η3-phenylpropargyl)zirconium†
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5252
_journal_paper_doi               10.1021/om100405n
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C36 H28 Zr'
_chemical_formula_weight         551.80
_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                 116.041(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.7551(14)
_cell_length_b                   8.6203(6)
_cell_length_c                   17.4685(11)
_cell_measurement_reflns_used    90
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     2808.1(3)
_computing_cell_refinement
'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)'
_computing_data_collection       'Bruker SMART v5.624 (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL v6.14 (Bruker 2000)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement  'Bruker SHELXTL v6.14'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SMART CCD area detector'
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9334
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9103
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL  v6.12 (Bruker 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0244
_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)+(0.0401P)²+0.3739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                2730
_reflns_number_total             3226
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om100405n_si_002.cif
_cod_data_source_block           sd02
_cod_depositor_comments
;
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_sg_symbol_H-M      C2/c
_cod_database_code               4066339
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
Zr Zr 0.5000 0.24389(2) 0.2500 0.02348(8) Uani 1 2 d S
C1 C 0.44406(9) 0.36880(18) 0.10662(10) 0.0340(3) Uani 1 1 d .
H1A H 0.4752 0.4381 0.0922 0.041 Uiso 1 1 calc R
H1B H 0.4119 0.3031 0.0585 0.041 Uiso 1 1 calc R
C2 C 0.41543(8) 0.43031(17) 0.15762(10) 0.0307(3) Uani 1 1 d .
C3 C 0.40884(8) 0.44295(17) 0.22503(10) 0.0299(3) Uani 1 1 d .
C4 C 0.37474(8) 0.51762(17) 0.27214(9) 0.0283(3) Uani 1 1 d .
C5 C 0.39790(10) 0.66286(19) 0.30975(12) 0.0417(4) Uani 1 1 d .
H5A H 0.4359 0.7144 0.3038 0.050 Uiso 1 1 calc R
C6 C 0.36563(13) 0.73193(19) 0.35555(15) 0.0514(5) Uani 1 1 d .
H6A H 0.3822 0.8300 0.3816 0.062 Uiso 1 1 calc R
C7 C 0.31002(11) 0.6602(2) 0.36375(12) 0.0454(4) Uani 1 1 d .
H7A H 0.2882 0.7083 0.3954 0.054 Uiso 1 1 calc R
C8 C 0.28583(9) 0.5173(2) 0.32575(11) 0.0407(4) Uani 1 1 d .
H8A H 0.2467 0.4683 0.3304 0.049 Uiso 1 1 calc R
C9 C 0.31837(9) 0.44567(18) 0.28102(10) 0.0341(3) Uani 1 1 d .
H9A H 0.3021 0.3466 0.2562 0.041 Uiso 1 1 calc R
C11 C 0.44713(9) 0.11845(19) 0.33765(10) 0.0347(4) Uani 1 1 d .
H11A H 0.4789 0.0484 0.3836 0.042 Uiso 1 1 calc R
H11B H 0.4162 0.1843 0.3541 0.042 Uiso 1 1 calc R
C12 C 0.41624(8) 0.05801(17) 0.25665(10) 0.0317(3) Uani 1 1 d .
C13 C 0.40713(8) 0.04582(17) 0.18143(10) 0.0303(3) Uani 1 1 d .
C14 C 0.36987(8) -0.02439(17) 0.09775(9) 0.0287(3) Uani 1 1 d .
C15 C 0.39045(10) -0.1675(2) 0.07911(11) 0.0445(4) Uani 1 1 d .
H15A H 0.4295 -0.2217 0.1219 0.053 Uiso 1 1 calc R
C16 C 0.35430(13) -0.23177(19) -0.00151(14) 0.0535(6) Uani 1 1 d .
H16A H 0.3690 -0.3291 -0.0138 0.064 Uiso 1 1 calc R
C17 C 0.29707(10) -0.1548(2) -0.06378(11) 0.0451(4) Uani 1 1 d .
H17A H 0.2724 -0.1990 -0.1189 0.054 Uiso 1 1 calc R
C18 C 0.27584(9) -0.01401(19) -0.04575(10) 0.0393(4) Uani 1 1 d .
H18A H 0.2359 0.0383 -0.0883 0.047 Uiso 1 1 calc R
C19 C 0.31229(8) 0.05195(18) 0.03406(10) 0.0343(3) Uani 1 1 d .
H19A H 0.2978 0.1504 0.0454 0.041 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'
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
C12 Zr C12 96.41(8) 2_655 .
C12 Zr C2 138.02(6) 2_655 .
C12 Zr C2 98.49(5) . .
C12 Zr C2 98.49(5) 2_655 2_655
C12 Zr C2 138.01(6) . 2_655
C2 Zr C2 96.11(7) . 2_655
C12 Zr C3 87.54(6) 2_655 2_655
C12 Zr C3 167.81(5) . 2_655
C2 Zr C3 86.01(5) . 2_655
C2 Zr C3 29.81(5) 2_655 2_655
C12 Zr C3 167.81(5) 2_655 .
C12 Zr C3 87.54(6) . .
C2 Zr C3 29.81(5) . .
C2 Zr C3 86.01(5) 2_655 .
C3 Zr C3 90.96(7) 2_655 .
C12 Zr C13 29.70(5) 2_655 2_655
C12 Zr C13 86.70(5) . 2_655
C2 Zr C13 167.66(5) . 2_655
C2 Zr C13 87.24(5) 2_655 2_655
C3 Zr C13 91.19(5) 2_655 2_655
C3 Zr C13 162.49(5) . 2_655
C12 Zr C13 86.71(5) 2_655 .
C12 Zr C13 29.70(5) . .
C2 Zr C13 87.24(5) . .
C2 Zr C13 167.66(5) 2_655 .
C3 Zr C13 162.49(5) 2_655 .
C3 Zr C13 91.18(5) . .
C13 Zr C13 91.97(7) 2_655 .
C12 Zr C11 32.56(5) 2_655 2_655
C12 Zr C11 105.29(6) . 2_655
C2 Zr C11 105.46(5) . 2_655
C2 Zr C11 108.32(5) 2_655 2_655
C3 Zr C11 84.21(5) 2_655 2_655
C3 Zr C11 135.25(5) . 2_655
C13 Zr C11 62.26(5) 2_655 2_655
C13 Zr C11 82.04(6) . 2_655
C12 Zr C11 105.29(6) 2_655 .
C12 Zr C11 32.56(5) . .
C2 Zr C11 108.31(6) . .
C2 Zr C11 105.46(5) 2_655 .
C3 Zr C11 135.25(5) 2_655 .
C3 Zr C11 84.21(5) . .
C13 Zr C11 82.04(6) 2_655 .
C13 Zr C11 62.26(5) . .
C11 Zr C11 128.49(8) 2_655 .
C12 Zr C1 105.47(5) 2_655 .
C12 Zr C1 107.96(5) . .
C2 Zr C1 32.55(5) . .
C2 Zr C1 105.44(5) 2_655 .
C3 Zr C1 81.89(5) 2_655 .
C3 Zr C1 62.35(6) . .
C13 Zr C1 135.14(5) 2_655 .
C13 Zr C1 83.73(5) . .
C11 Zr C1 72.93(5) 2_655 .
C11 Zr C1 131.95(5) . .
C12 Zr C1 107.96(5) 2_655 2_655
C12 Zr C1 105.47(5) . 2_655
C2 Zr C1 105.44(5) . 2_655
C2 Zr C1 32.54(5) 2_655 2_655
C3 Zr C1 62.35(6) 2_655 2_655
C3 Zr C1 81.89(5) . 2_655
C13 Zr C1 83.73(5) 2_655 2_655
C13 Zr C1 135.14(5) . 2_655
C11 Zr C1 131.95(5) 2_655 2_655
C11 Zr C1 72.93(5) . 2_655
C1 Zr C1 128.88(8) . 2_655
C2 C1 Zr 70.08(9) . .
C2 C1 H1A 116.6 . .
Zr C1 H1A 116.6 . .
C2 C1 H1B 116.6 . .
Zr C1 H1B 116.6 . .
H1A C1 H1B 113.6 . .
C3 C2 C1 154.38(16) . .
C3 C2 Zr 77.01(10) . .
C1 C2 Zr 77.37(9) . .
C2 C3 C4 148.94(15) . .
C2 C3 Zr 73.19(10) . .
C4 C3 Zr 137.87(11) . .
C9 C4 C5 118.64(15) . .
C9 C4 C3 120.59(14) . .
C5 C4 C3 120.77(15) . .
C6 C5 C4 120.24(17) . .
C6 C5 H5A 119.9 . .
C4 C5 H5A 119.9 . .
C7 C6 C5 120.65(17) . .
C7 C6 H6A 119.7 . .
C5 C6 H6A 119.7 . .
C6 C7 C8 119.72(17) . .
C6 C7 H7A 120.1 . .
C8 C7 H7A 120.1 . .
C9 C8 C7 120.26(17) . .
C9 C8 H8A 119.9 . .
C7 C8 H8A 119.9 . .
C8 C9 C4 120.47(15) . .
C8 C9 H9A 119.8 . .
C4 C9 H9A 119.8 . .
C12 C11 Zr 70.35(9) . .
C12 C11 H11A 116.6 . .
Zr C11 H11A 116.6 . .
C12 C11 H11B 116.6 . .
Zr C11 H11B 116.6 . .
H11A C11 H11B 113.6 . .
C13 C12 C11 154.59(16) . .
C13 C12 Zr 77.50(10) . .
C11 C12 Zr 77.09(9) . .
C12 C13 C14 149.68(16) . .
C12 C13 Zr 72.80(10) . .
C14 C13 Zr 137.51(11) . .
C19 C14 C15 118.51(14) . .
C19 C14 C13 119.95(14) . .
C15 C14 C13 121.54(14) . .
C16 C15 C14 120.47(16) . .
C16 C15 H15A 119.8 . .
C14 C15 H15A 119.8 . .
C17 C16 C15 120.25(16) . .
C17 C16 H16A 119.9 . .
C15 C16 H16A 119.9 . .
C18 C17 C16 119.74(16) . .
C18 C17 H17A 120.1 . .
C16 C17 H17A 120.1 . .
C17 C18 C19 120.37(15) . .
C17 C18 H18A 119.8 . .
C19 C18 H18A 119.8 . .
C18 C19 C14 120.65(14) . .
C18 C19 H19A 119.7 . .
C14 C19 H19A 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zr C12 2.4043(15) 2_655
Zr C12 2.4043(15) .
Zr C2 2.4043(14) .
Zr C2 2.4044(14) 2_655
Zr C3 2.4474(15) 2_655
Zr C3 2.4474(15) .
Zr C13 2.4573(15) 2_655
Zr C13 2.4573(15) .
Zr C11 2.4884(16) 2_655
Zr C11 2.4884(16) .
Zr C1 2.4955(15) .
Zr C1 2.4955(15) 2_655
C1 C2 1.376(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.249(2) .
C3 C4 1.450(2) .
C4 C9 1.392(2) .
C4 C5 1.398(2) .
C5 C6 1.383(3) .
C5 H5A 0.9500 .
C6 C7 1.371(3) .
C6 H6A 0.9500 .
C7 C8 1.385(3) .
C7 H7A 0.9500 .
C8 C9 1.383(2) .
C8 H8A 0.9500 .
C9 H9A 0.9500 .
C11 C12 1.374(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.247(2) .
C13 C14 1.452(2) .
C14 C19 1.390(2) .
C14 C15 1.391(2) .
C15 C16 1.387(3) .
C15 H15A 0.9500 .
C16 C17 1.378(3) .
C16 H16A 0.9500 .
C17 C18 1.374(2) .
C17 H17A 0.9500 .
C18 C19 1.383(2) .
C18 H18A 0.9500 .
C19 H19A 0.9500 .
