#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:04:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178547 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/54/4065402.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_4065402
loop_
_publ_author_name
'Ren, Shikuo'
'Xie, Zuowei'
_publ_section_title
;
 Reaction of a Zirconocene--Carboryne Complex with Pyridines: Ligand C--H
 Activation
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5953
_journal_paper_doi               10.1021/om200772q
_journal_volume                  30
_journal_year                    2011
_chemical_formula_sum            'C21 H27 B10 N Zr'
_chemical_formula_weight         492.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 112.161(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.811(3)
_cell_length_b                   10.573(3)
_cell_length_c                   14.089(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1491.5(7)
_computing_cell_refinement       'BRUKER SMART CCD DIFFRACTOMETER'
_computing_data_collection       'BRUKER SMART CCD DIFFRACTOMETER'
_computing_data_reduction        'BRUKER SMART CCD DIFFRACTOMETER'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER SMART CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA SCAN'
_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  0.0678
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8104
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.492310
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;
;
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0516
_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)+(0.0763P)²+0.2043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                2220
_reflns_number_total             2771
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200772q_si_001.cif
_cod_data_source_block           5
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' 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        1491.6(7)
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               4065402
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
Zr1 Zr 1.80474(5) 0.7500 2.61422(4) 0.0322(2) Uani 1 2 d S
N1 N 1.6917(5) 0.7500 2.4483(3) 0.0406(11) Uani 1 2 d S
C1 C 2.0545(6) 0.7500 2.6772(4) 0.0426(13) Uani 1 2 d S
C2 C 2.1642(8) 0.7500 2.8029(6) 0.080(2) Uani 1 2 d S
H2 H 2.1279 0.7500 2.8661 0.096 Uiso 1 2 calc SR
C11 C 1.6394(5) 0.5926(5) 2.6299(4) 0.0606(13) Uani 1 1 d .
H11A H 1.5430 0.6058 2.6086 0.073 Uiso 1 1 calc R
C12 C 1.7348(5) 0.6063(4) 2.7293(4) 0.0579(12) Uani 1 1 d .
H12A H 1.7162 0.6338 2.7890 0.069 Uiso 1 1 calc R
C13 C 1.8574(5) 0.5612(4) 2.7320(3) 0.0511(11) Uani 1 1 d .
H13A H 1.9383 0.5497 2.7936 0.061 Uiso 1 1 calc R
C14 C 1.8359(5) 0.5127(4) 2.6328(3) 0.0551(12) Uani 1 1 d .
H14A H 1.9004 0.4634 2.6145 0.066 Uiso 1 1 calc R
C15 C 1.7044(6) 0.5295(5) 2.5722(4) 0.0671(14) Uani 1 1 d .
H15A H 1.6599 0.4951 2.5030 0.080 Uiso 1 1 calc R
C21 C 1.8146(7) 0.7500 2.4561(5) 0.0479(15) Uani 1 2 d S
C22 C 1.8438(7) 0.7500 2.3673(4) 0.0504(15) Uani 1 2 d S
H22A H 1.9323 0.7500 2.3729 0.060 Uiso 1 2 calc SR
C23 C 1.7460(8) 0.7500 2.2748(5) 0.0610(18) Uani 1 2 d S
H23A H 1.7666 0.7500 2.2164 0.073 Uiso 1 2 calc SR
C24 C 1.6108(8) 0.7500 2.2651(5) 0.0551(17) Uani 1 2 d S
C25 C 1.5027(10) 0.7500 2.1715(6) 0.081(2) Uani 1 2 d S
H25A H 1.5181 0.7500 2.1108 0.097 Uiso 1 2 calc SR
C26 C 1.3777(11) 0.7500 2.1677(7) 0.094(3) Uani 1 2 d S
H26A H 1.3073 0.7500 2.1042 0.113 Uiso 1 2 calc SR
C27 C 1.3493(8) 0.7500 2.2585(7) 0.082(2) Uani 1 2 d S
H27A H 1.2615 0.7500 2.2548 0.098 Uiso 1 2 calc SR
C28 C 1.4549(7) 0.7500 2.3524(5) 0.0603(18) Uani 1 2 d S
H28A H 1.4380 0.7500 2.4124 0.072 Uiso 1 2 calc SR
C29 C 1.5833(6) 0.7500 2.3578(4) 0.0369(12) Uani 1 2 d S
B3 B 2.1535(5) 0.6200(5) 2.7271(4) 0.0544(13) Uani 1 1 d .
H3 H 2.1103 0.5312 2.7414 0.065 Uiso 1 1 calc R
B4 B 2.1260(5) 0.6691(5) 2.6056(4) 0.0457(11) Uani 1 1 d .
H4 H 2.0636 0.6148 2.5378 0.055 Uiso 1 1 calc R
B5 B 2.3106(6) 0.6665(7) 2.8100(5) 0.0716(17) Uani 1 1 d .
H5 H 2.3711 0.6119 2.8782 0.086 Uiso 1 1 calc R
B6 B 2.2853(6) 0.6148(6) 2.6844(5) 0.0611(15) Uani 1 1 d .
H6 H 2.3282 0.5260 2.6699 0.073 Uiso 1 1 calc R
B7 B 2.2702(8) 0.7500 2.6080(6) 0.0524(18) Uani 1 2 d S
H7 H 2.3036 0.7500 2.5434 0.063 Uiso 1 2 calc SR
B8 B 2.3829(8) 0.7500 2.7343(7) 0.062(2) Uani 1 2 d S
H8 H 2.4913 0.7500 2.7530 0.075 Uiso 1 2 calc SR
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'
B B 0.0013 0.0007 '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'
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
N1 Zr1 C21 33.6(2) . .
N1 Zr1 C1 118.10(19) . .
C21 Zr1 C1 84.5(2) . .
N1 Zr1 C11 87.96(16) . .
C21 Zr1 C11 112.61(17) . .
C1 Zr1 C11 132.59(13) . .
N1 Zr1 C11 87.96(16) . 4_575
C21 Zr1 C11 112.61(17) . 4_575
C1 Zr1 C11 132.59(14) . 4_575
C11 Zr1 C11 83.0(2) . 4_575
N1 Zr1 C13 126.79(11) . 4_575
C21 Zr1 C13 124.30(12) . 4_575
C1 Zr1 C13 79.69(13) . 4_575
C11 Zr1 C13 117.30(17) . 4_575
C11 Zr1 C13 53.77(16) 4_575 4_575
N1 Zr1 C13 126.79(12) . .
C21 Zr1 C13 124.30(12) . .
C1 Zr1 C13 79.69(13) . .
C11 Zr1 C13 53.77(16) . .
C11 Zr1 C13 117.30(17) 4_575 .
C13 Zr1 C13 104.8(2) 4_575 .
N1 Zr1 C14 96.26(11) . 4_575
C21 Zr1 C14 92.73(10) . 4_575
C1 Zr1 C14 83.10(11) . 4_575
C11 Zr1 C14 135.95(16) . 4_575
C11 Zr1 C14 53.54(16) 4_575 4_575
C13 Zr1 C14 32.72(14) 4_575 4_575
C13 Zr1 C14 136.80(16) . 4_575
N1 Zr1 C14 96.26(11) . .
C21 Zr1 C14 92.73(10) . .
C1 Zr1 C14 83.10(11) . .
C11 Zr1 C14 53.54(16) . .
C11 Zr1 C14 135.95(17) 4_575 .
C13 Zr1 C14 136.80(16) 4_575 .
C13 Zr1 C14 32.72(14) . .
C14 Zr1 C14 164.6(2) 4_575 .
N1 Zr1 C12 120.06(15) . 4_575
C21 Zr1 C12 139.73(13) . 4_575
C1 Zr1 C12 108.38(16) . 4_575
C11 Zr1 C12 86.96(17) . 4_575
C11 Zr1 C12 32.17(15) 4_575 4_575
C13 Zr1 C12 32.07(15) 4_575 4_575
C13 Zr1 C12 95.82(15) . 4_575
C14 Zr1 C12 53.18(15) 4_575 4_575
C14 Zr1 C12 125.98(15) . 4_575
N1 Zr1 C12 120.06(16) . .
C21 Zr1 C12 139.73(13) . .
C1 Zr1 C12 108.38(16) . .
C11 Zr1 C12 32.17(16) . .
C11 Zr1 C12 86.96(17) 4_575 .
C13 Zr1 C12 95.82(15) 4_575 .
C13 Zr1 C12 32.07(15) . .
C14 Zr1 C12 125.98(15) 4_575 .
C14 Zr1 C12 53.18(15) . .
C12 Zr1 C12 73.6(2) 4_575 .
N1 Zr1 C15 74.60(13) . .
C21 Zr1 C15 86.86(14) . .
C1 Zr1 C15 112.98(14) . .
C11 Zr1 C15 32.72(17) . .
C11 Zr1 C15 111.86(19) 4_575 .
C13 Zr1 C15 148.17(17) 4_575 .
C13 Zr1 C15 53.00(16) . .
C14 Zr1 C15 163.8(2) 4_575 .
C14 Zr1 C15 31.21(16) . .
C12 Zr1 C15 119.57(18) 4_575 .
C12 Zr1 C15 52.88(16) . .
C21 N1 C29 124.8(5) . .
C21 N1 Zr1 76.6(3) . .
C29 N1 Zr1 158.6(4) . .
B4 C1 B4 59.9(4) 4_575 .
B4 C1 C2 108.5(4) 4_575 .
B4 C1 C2 108.5(4) . .
B4 C1 B3 59.5(3) 4_575 4_575
B4 C1 B3 106.9(4) . 4_575
C2 C1 B3 59.9(3) . 4_575
B4 C1 B3 106.9(4) 4_575 .
B4 C1 B3 59.5(3) . .
C2 C1 B3 59.9(3) . .
B3 C1 B3 106.1(5) 4_575 .
B4 C1 Zr1 117.2(3) 4_575 .
B4 C1 Zr1 117.2(3) . .
C2 C1 Zr1 126.7(4) . .
B3 C1 Zr1 124.4(3) 4_575 .
B3 C1 Zr1 124.4(3) . .
B3 C2 B3 106.4(5) . 4_575
B3 C2 C1 60.1(3) . .
B3 C2 C1 60.1(3) 4_575 .
B3 C2 B5 106.4(5) . 4_575
B3 C2 B5 59.3(3) 4_575 4_575
C1 C2 B5 108.1(5) . 4_575
B3 C2 B5 59.3(3) . .
B3 C2 B5 106.4(5) 4_575 .
C1 C2 B5 108.1(5) . .
B5 C2 B5 59.4(5) 4_575 .
C12 C11 C15 106.5(5) . .
C12 C11 Zr1 74.9(3) . .
C15 C11 Zr1 74.9(3) . .
C13 C12 C11 109.0(4) . .
C13 C12 Zr1 73.3(2) . .
C11 C12 Zr1 73.0(3) . .
C12 C13 C14 107.1(4) . .
C12 C13 Zr1 74.6(3) . .
C14 C13 Zr1 74.1(2) . .
C15 C14 C13 108.3(4) . .
C15 C14 Zr1 74.9(3) . .
C13 C14 Zr1 73.2(3) . .
C14 C15 C11 109.0(4) . .
C14 C15 Zr1 73.9(3) . .
C11 C15 Zr1 72.4(3) . .
N1 C21 C22 119.7(6) . .
N1 C21 Zr1 69.8(3) . .
C22 C21 Zr1 170.4(5) . .
C23 C22 C21 120.6(7) . .
C22 C23 C24 120.3(6) . .
C25 C24 C23 123.9(7) . .
C25 C24 C29 118.1(7) . .
C23 C24 C29 118.0(6) . .
C26 C25 C24 120.9(8) . .
C25 C26 C27 121.6(8) . .
C28 C27 C26 118.6(8) . .
C29 C28 C27 120.7(7) . .
C28 C29 N1 123.3(5) . .
C28 C29 C24 120.1(6) . .
N1 C29 C24 116.6(5) . .
B4 B3 C2 109.0(4) . .
B4 B3 C1 60.0(3) . .
C2 B3 C1 60.0(3) . .
B4 B3 B5 110.3(4) . .
C2 B3 B5 62.2(4) . .
C1 B3 B5 110.5(4) . .
B4 B3 B6 61.2(3) . .
C2 B3 B6 111.5(5) . .
C1 B3 B6 110.3(4) . .
B5 B3 B6 61.3(3) . .
B3 B4 B4 107.7(3) . 4_575
B3 B4 C1 60.5(3) . .
B4 B4 C1 60.05(19) 4_575 .
B3 B4 B6 60.5(3) . .
B4 B4 B6 109.1(3) 4_575 .
C1 B4 B6 110.0(4) . .
B3 B4 B7 108.0(4) . .
B4 B4 B7 61.1(2) 4_575 .
C1 B4 B7 109.7(4) . .
B6 B4 B7 59.9(3) . .
B3 B5 B5 106.5(3) . 4_575
B3 B5 B6 59.7(3) . .
B5 B5 B6 108.0(3) 4_575 .
B3 B5 B8 106.2(5) . .
B5 B5 B8 60.2(3) 4_575 .
B6 B5 B8 59.4(3) . .
B3 B5 C2 58.5(3) . .
B5 B5 C2 60.3(3) 4_575 .
B6 B5 C2 107.3(4) . .
B8 B5 C2 107.6(4) . .
B3 B6 B4 58.3(3) . .
B3 B6 B8 106.4(5) . .
B4 B6 B8 106.5(4) . .
B3 B6 B7 106.6(4) . .
B4 B6 B7 60.3(3) . .
B8 B6 B7 59.1(4) . .
B3 B6 B5 59.0(3) . .
B4 B6 B5 106.0(4) . .
B8 B6 B5 60.4(4) . .
B7 B6 B5 107.7(4) . .
B8 B7 B6 60.4(3) . 4_575
B8 B7 B6 60.4(3) . .
B6 B7 B6 108.7(6) 4_575 .
B8 B7 B4 107.1(4) . .
B6 B7 B4 106.4(4) 4_575 .
B6 B7 B4 59.8(3) . .
B8 B7 B4 107.1(4) . 4_575
B6 B7 B4 59.8(3) 4_575 4_575
B6 B7 B4 106.4(4) . 4_575
B4 B7 B4 57.9(4) . 4_575
B7 B8 B6 60.5(3) . .
B7 B8 B6 60.5(3) . 4_575
B6 B8 B6 108.8(6) . 4_575
B7 B8 B5 108.5(5) . 4_575
B6 B8 B5 108.1(5) . 4_575
B6 B8 B5 60.1(3) 4_575 4_575
B7 B8 B5 108.5(5) . .
B6 B8 B5 60.1(3) . .
B6 B8 B5 108.1(5) 4_575 .
B5 B8 B5 59.6(5) 4_575 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zr1 N1 2.191(4) .
Zr1 C21 2.271(6) .
Zr1 C1 2.505(6) .
Zr1 C11 2.512(5) .
Zr1 C11 2.512(4) 4_575
Zr1 C13 2.519(4) 4_575
Zr1 C13 2.519(4) .
Zr1 C14 2.531(5) 4_575
Zr1 C14 2.531(5) .
Zr1 C12 2.537(4) 4_575
Zr1 C12 2.537(4) .
Zr1 C15 2.545(5) .
N1 C21 1.292(8) .
N1 C29 1.368(7) .
C1 B4 1.713(7) 4_575
C1 B4 1.713(7) .
C1 C2 1.720(9) .
C1 B3 1.721(6) 4_575
C1 B3 1.721(6) .
C2 B3 1.717(7) .
C2 B3 1.717(7) 4_575
C2 B5 1.782(9) 4_575
C2 B5 1.782(9) .
C11 C12 1.399(7) .
C11 C15 1.425(7) .
C12 C13 1.397(7) .
C13 C14 1.423(6) .
C14 C15 1.366(7) .
C21 C22 1.401(9) .
C22 C23 1.333(9) .
C23 C24 1.416(11) .
C24 C25 1.394(10) .
C24 C29 1.444(8) .
C25 C26 1.333(14) .
C26 C27 1.424(13) .
C27 C28 1.384(10) .
C28 C29 1.361(9) .
B3 B4 1.705(7) .
B3 B5 1.731(9) .
B3 B6 1.744(8) .
B4 B4 1.710(10) 4_575
B4 B6 1.757(8) .
B4 B7 1.767(8) .
B5 B5 1.767(15) 4_575
B5 B6 1.772(9) .
B5 B8 1.777(9) .
B6 B8 1.759(8) .
B6 B7 1.760(7) .
B7 B8 1.736(12) .
B7 B6 1.760(7) 4_575
B7 B4 1.767(8) 4_575
B8 B6 1.759(8) 4_575
B8 B5 1.777(9) 4_575
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 -0.020 0.000 408.3 87.9
