#------------------------------------------------------------------------------
#$Date: 2019-11-24 14:04:18 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238093 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/47/1554742.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_1554742
loop_
_publ_author_name
'Amaya, Toru'
'Katoh, Shun'
'Moriuchi, Toshiyuki'
'Hirao, Toshikazu'
_publ_section_title
;
 Synthesis of a sumanenyl hafnocene complex
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1032
_journal_paper_doi               10.1039/C9QO00140A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C31 H26 Cl2 Hf'
_chemical_formula_sum            'C31 H26 Cl2 Hf'
_chemical_formula_weight         647.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-01-25 deposited with the CCDC.	2019-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.0903(16)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.1722(5)
_cell_length_b                   16.0848(7)
_cell_length_c                   9.1272(6)
_cell_measurement_reflns_used    9342
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.21
_cell_volume                     1195.02(12)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11659
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.457
_diffrn_reflns_theta_min         3.208
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.599
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             636.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.85
_refine_diff_density_min         -1.71
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0087P)²+5.3003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2442
_reflns_number_total             2822
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c9qo00140a2.cif
_cod_data_source_block           131219SuHfCl2CpMe5
_cod_original_cell_volume        1195.02(11)
_cod_database_code               1554742
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
3 -X,-Y,-Z
4 +X,-1/2-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Hf1 Hf 0.70831(4) 0.2500 0.25500(4) 0.01412(11) Uani 1 2 d S T P
Cl1 Cl 0.52378(17) 0.13839(9) 0.17807(16) 0.0233(3) Uani 1 1 d . . .
C1 C 0.9810(7) 0.2052(4) 0.1893(6) 0.0206(12) Uani 1 1 d . . .
C2 C 0.8708(7) 0.1781(3) 0.0720(6) 0.0178(11) Uani 1 1 d . . .
C3 C 0.7970(9) 0.2500 0.0017(8) 0.0143(15) Uani 1 2 d DS T P
C4 C 1.0980(7) 0.1491(5) 0.2817(8) 0.0370(17) Uani 1 1 d . . .
H4A H 1.1620 0.1824 0.3563 0.044 Uiso 1 1 calc R U .
H4B H 1.0351 0.1069 0.3301 0.044 Uiso 1 1 calc R U .
H4C H 1.1725 0.1218 0.2184 0.044 Uiso 1 1 calc R U .
C5 C 0.8456(8) 0.0903(3) 0.0197(7) 0.0275(14) Uani 1 1 d . . .
H5A H 0.7614 0.0891 -0.0637 0.033 Uiso 1 1 calc R U .
H5B H 0.9490 0.0684 -0.0111 0.033 Uiso 1 1 calc R U .
H5C H 0.8099 0.0561 0.0998 0.033 Uiso 1 1 calc R U .
C6 C 0.6760(10) 0.2500 -0.1307(9) 0.0221(18) Uani 1 2 d DS T P
C7 C 0.8607(9) 0.2500 0.4954(9) 0.0189(17) Uani 1 2 d S T P
H7 H 0.9833 0.2500 0.5118 0.023 Uiso 1 2 calc R U P
C8 C 0.7581(7) 0.1770(3) 0.5112(6) 0.0178(11) Uani 1 1 d . . .
C9 C 0.7803(8) 0.0918(4) 0.5590(6) 0.0251(13) Uani 1 1 d . . .
H9 H 0.8819 0.0645 0.5500 0.030 Uiso 1 1 calc R U .
C10 C 0.6526(7) 0.0500(3) 0.6180(6) 0.0223(13) Uani 1 1 d . . .
H10 H 0.6707 -0.0053 0.6521 0.027 Uiso 1 1 calc R U .
C11 C 0.4959(7) 0.0868(3) 0.6293(6) 0.0189(12) Uani 1 1 d . . .
C12 C 0.3608(8) 0.0741(4) 0.7361(7) 0.0266(14) Uani 1 1 d . . .
H12A H 0.2806 0.0313 0.6988 0.032 Uiso 1 1 calc R U .
H12B H 0.4090 0.0578 0.8353 0.032 Uiso 1 1 calc R U .
C13 C 0.2797(7) 0.1609(4) 0.7387(7) 0.0254(13) Uani 1 1 d . . .
C14 C 0.2048(7) 0.2062(4) 0.8436(7) 0.0295(14) Uani 1 1 d . . .
H14 H 0.1522 0.1774 0.9173 0.035 Uiso 1 1 calc R U .
C15 C 0.5950(6) 0.2063(3) 0.5035(6) 0.0151(11) Uani 1 1 d . . .
C16 C 0.4671(6) 0.1613(3) 0.5617(6) 0.0160(11) Uani 1 1 d . . .
C17 C 0.3394(7) 0.2074(4) 0.6244(6) 0.0189(12) Uani 1 1 d . . .
H6A H 0.734(5) 0.2500 -0.220(2) 0.08(4) Uiso 1 2 d DS . P
H6B H 0.609(6) 0.198(4) -0.131(4) 0.08(3) Uiso 1 1 d 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Hf Hf -0.5830 6.1852
;
International Tables for Crystallography
(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 Hf1 Cl1 96.37(7) . 4_565
Cl1 Hf1 C7 121.45(9) . .
Cl1 Hf1 C7 121.45(9) 4_565 .
Cl1 Hf1 C1 134.64(13) . 4_565
Cl1 Hf1 C1 105.50(14) 4_565 4_565
C7 Hf1 C1 79.5(2) . 4_565
Cl1 Hf1 C1 105.50(14) . .
Cl1 Hf1 C1 134.64(13) 4_565 .
C7 Hf1 C1 79.5(2) . .
C1 Hf1 C1 34.0(3) 4_565 .
Cl1 Hf1 C3 87.45(12) . .
Cl1 Hf1 C3 87.45(12) 4_565 .
C7 Hf1 C3 132.3(2) . .
C1 Hf1 C3 55.2(2) 4_565 .
C1 Hf1 C3 55.2(2) . .
Cl1 Hf1 C2 79.45(13) . .
Cl1 Hf1 C2 120.30(14) 4_565 .
C7 Hf1 C2 110.1(2) . .
C1 Hf1 C2 55.20(17) 4_565 .
C1 Hf1 C2 32.83(18) . .
C3 Hf1 C2 33.29(16) . .
Cl1 Hf1 C2 120.30(14) . 4_565
Cl1 Hf1 C2 79.45(13) 4_565 4_565
C7 Hf1 C2 110.1(2) . 4_565
C1 Hf1 C2 32.83(18) 4_565 4_565
C1 Hf1 C2 55.20(17) . 4_565
C3 Hf1 C2 33.29(16) . 4_565
C2 Hf1 C2 54.9(2) . 4_565
Cl1 Hf1 C8 129.71(12) . 4_565
Cl1 Hf1 C8 88.26(12) 4_565 4_565
C7 Hf1 C8 33.34(15) . 4_565
C1 Hf1 C8 90.80(17) 4_565 4_565
C1 Hf1 C8 106.03(18) . 4_565
C3 Hf1 C8 142.84(16) . 4_565
C2 Hf1 C8 138.86(18) . 4_565
C2 Hf1 C8 109.81(18) 4_565 4_565
Cl1 Hf1 C8 88.26(12) . .
Cl1 Hf1 C8 129.71(12) 4_565 .
C7 Hf1 C8 33.34(15) . .
C1 Hf1 C8 106.03(18) 4_565 .
C1 Hf1 C8 90.80(17) . .
C3 Hf1 C8 142.84(16) . .
C2 Hf1 C8 109.81(18) . .
C2 Hf1 C8 138.86(18) 4_565 .
C8 Hf1 C8 53.4(2) 4_565 .
Cl1 Hf1 C15 101.07(12) . 4_565
Cl1 Hf1 C15 78.02(12) 4_565 4_565
C7 Hf1 C15 53.8(2) . 4_565
C1 Hf1 C15 121.90(17) 4_565 4_565
C1 Hf1 C15 133.23(18) . 4_565
C3 Hf1 C15 163.83(12) . 4_565
C2 Hf1 C15 161.63(17) . 4_565
C2 Hf1 C15 134.57(17) 4_565 4_565
C8 Hf1 C15 31.24(16) 4_565 4_565
C8 Hf1 C15 52.09(16) . 4_565
Cl1 Hf1 C15 78.02(12) . .
Cl1 Hf1 C15 101.07(12) 4_565 .
C7 Hf1 C15 53.8(2) . .
C1 Hf1 C15 133.23(18) 4_565 .
C1 Hf1 C15 121.90(17) . .
C3 Hf1 C15 163.83(12) . .
C2 Hf1 C15 134.57(17) . .
C2 Hf1 C15 161.63(17) 4_565 .
C8 Hf1 C15 52.09(16) 4_565 .
C8 Hf1 C15 31.24(16) . .
C15 Hf1 C15 31.1(2) 4_565 .
C2 C1 C1 108.1(3) . 4_565
C2 C1 C4 124.7(6) . .
C1 C1 C4 126.6(4) 4_565 .
C2 C1 Hf1 75.1(3) . .
C1 C1 Hf1 73.01(14) 4_565 .
C4 C1 Hf1 125.3(4) . .
C1 C2 C3 107.9(5) . .
C1 C2 C5 126.5(5) . .
C3 C2 C5 125.4(5) . .
C1 C2 Hf1 72.0(3) . .
C3 C2 Hf1 72.5(4) . .
C5 C2 Hf1 125.5(4) . .
C2 C3 C2 108.0(7) . 4_565
C2 C3 C6 125.9(3) . .
C2 C3 C6 125.9(3) 4_565 .
C2 C3 Hf1 74.2(4) . .
C2 C3 Hf1 74.2(4) 4_565 .
C6 C3 Hf1 121.8(5) . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C2 C5 H5A 109.5 . .
C2 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C2 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C3 C6 H6A 110(2) . .
C3 C6 H6B 109(3) . .
H6A C6 H6B 108(3) . .
C8 C7 C8 107.4(6) 4_565 .
C8 C7 Hf1 80.6(4) 4_565 .
C8 C7 Hf1 80.6(4) . .
C8 C7 H7 124.2 4_565 .
C8 C7 H7 124.2 . .
Hf1 C7 H7 124.2 . .
C15 C8 C9 115.2(5) . .
C15 C8 C7 105.9(5) . .
C9 C8 C7 137.4(6) . .
C15 C8 Hf1 74.5(3) . .
C9 C8 Hf1 134.5(4) . .
C7 C8 Hf1 66.1(4) . .
C10 C9 C8 119.8(5) . .
C10 C9 H9 120.1 . .
C8 C9 H9 120.1 . .
C9 C10 C11 122.6(5) . .
C9 C10 H10 118.7 . .
C11 C10 H10 118.7 . .
C16 C11 C10 117.0(5) . .
C16 C11 C12 107.2(5) . .
C10 C11 C12 133.5(5) . .
C13 C12 C11 102.8(4) . .
C13 C12 H12A 111.2 . .
C11 C12 H12A 111.2 . .
C13 C12 H12B 111.2 . .
C11 C12 H12B 111.2 . .
H12A C12 H12B 109.1 . .
C14 C13 C17 115.9(6) . .
C14 C13 C12 134.4(6) . .
C17 C13 C12 106.9(5) . .
C13 C14 C14 121.6(4) . 4_565
C13 C14 H14 119.2 . .
C14 C14 H14 119.2 4_565 .
C15 C15 C8 109.6(3) 4_565 .
C15 C15 C16 120.8(3) 4_565 .
C8 C15 C16 122.5(5) . .
C15 C15 Hf1 74.46(11) 4_565 .
C8 C15 Hf1 74.2(3) . .
C16 C15 Hf1 142.4(4) . .
C11 C16 C15 121.2(5) . .
C11 C16 C17 112.1(5) . .
C15 C16 C17 118.1(5) . .
C17 C17 C13 122.1(3) 4_565 .
C17 C17 C16 121.0(3) 4_565 .
C13 C17 C16 109.5(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Hf1 Cl1 2.4087(13) .
Hf1 Cl1 2.4087(13) 4_565
Hf1 C7 2.425(8) .
Hf1 C1 2.467(5) 4_565
Hf1 C1 2.467(5) .
Hf1 C3 2.484(7) .
Hf1 C2 2.506(5) .
Hf1 C2 2.506(5) 4_565
Hf1 C8 2.616(6) 4_565
Hf1 C8 2.616(6) .
Hf1 C15 2.621(5) 4_565
Hf1 C15 2.621(5) .
C1 C2 1.406(8) .
C1 C1 1.441(11) 4_565
C1 C4 1.515(8) .
C2 C3 1.430(7) .
C2 C5 1.499(8) .
C3 C2 1.430(7) 4_565
C3 C6 1.492(11) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.98(2) .
C6 H6B 1.00(4) .
C7 C8 1.458(7) 4_565
C7 C8 1.458(7) .
C7 H7 1.0000 .
C8 C15 1.410(7) .
C8 C9 1.444(8) .
C9 C10 1.390(9) .
C9 H9 0.9500 .
C10 C11 1.422(8) .
C10 H10 0.9500 .
C11 C16 1.359(7) .
C11 C12 1.550(8) .
C12 C13 1.547(9) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.388(9) .
C13 C17 1.405(8) .
C14 C14 1.409(13) 4_565
C14 H14 0.9500 .
C15 C15 1.405(10) 4_565
C15 C16 1.414(7) .
C16 C17 1.439(8) .
C17 C17 1.371(11) 4_565
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
_geom_torsion_site_symmetry_4
C1 C1 C2 C3 -2.1(5) 4_565 .
C4 C1 C2 C3 -173.1(6) . .
Hf1 C1 C2 C3 64.1(4) . .
C1 C1 C2 C5 172.5(5) 4_565 .
C4 C1 C2 C5 1.6(9) . .
Hf1 C1 C2 C5 -121.3(5) . .
C1 C1 C2 Hf1 -66.15(13) 4_565 .
C4 C1 C2 Hf1 122.9(5) . .
C1 C2 C3 C2 3.4(8) . 4_565
C5 C2 C3 C2 -171.3(4) . 4_565
Hf1 C2 C3 C2 67.2(5) . 4_565
C1 C2 C3 C6 178.1(7) . .
C5 C2 C3 C6 3.4(10) . .
Hf1 C2 C3 C6 -118.1(7) . .
C1 C2 C3 Hf1 -63.8(4) . .
C5 C2 C3 Hf1 121.5(5) . .
C8 C7 C8 C15 12.3(8) 4_565 .
Hf1 C7 C8 C15 -64.6(4) . .
C8 C7 C8 C9 -152.4(5) 4_565 .
Hf1 C7 C8 C9 130.6(7) . .
C8 C7 C8 Hf1 76.9(5) 4_565 .
C15 C8 C9 C10 -11.4(8) . .
C7 C8 C9 C10 152.4(7) . .
Hf1 C8 C9 C10 -104.2(6) . .
C8 C9 C10 C11 2.3(9) . .
C9 C10 C11 C16 8.7(8) . .
C9 C10 C11 C12 -151.6(6) . .
C16 C11 C12 C13 -11.6(6) . .
C10 C11 C12 C13 150.1(6) . .
C11 C12 C13 C14 -148.4(7) . .
C11 C12 C13 C17 11.3(6) . .
C17 C13 C14 C14 -6.6(7) . 4_565
C12 C13 C14 C14 151.7(5) . 4_565
C9 C8 C15 C15 161.0(4) . 4_565
C7 C8 C15 C15 -7.7(5) . 4_565
Hf1 C8 C15 C15 -66.67(14) . 4_565
C9 C8 C15 C16 10.4(8) . .
C7 C8 C15 C16 -158.3(5) . .
Hf1 C8 C15 C16 142.7(5) . .
C9 C8 C15 Hf1 -132.4(5) . .
C7 C8 C15 Hf1 58.9(4) . .
C10 C11 C16 C15 -9.9(8) . .
C12 C11 C16 C15 155.2(5) . .
C10 C11 C16 C17 -157.2(5) . .
C12 C11 C16 C17 7.9(6) . .
C15 C15 C16 C11 -147.1(4) 4_565 .
C8 C15 C16 C11 0.3(8) . .
Hf1 C15 C16 C11 107.7(7) . .
C15 C15 C16 C17 -1.6(6) 4_565 .
C8 C15 C16 C17 145.8(5) . .
Hf1 C15 C16 C17 -106.9(6) . .
C14 C13 C17 C17 6.6(7) . 4_565
C12 C13 C17 C17 -157.4(3) . 4_565
C14 C13 C17 C16 156.7(5) . .
C12 C13 C17 C16 -7.3(6) . .
C11 C16 C17 C17 150.1(3) . 4_565
C15 C16 C17 C17 1.6(6) . 4_565
C11 C16 C17 C13 -0.4(7) . .
C15 C16 C17 C13 -148.8(5) . .
