#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/90/4069037.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_4069037
loop_
_publ_author_name
'Evans, William J.'
'Montalvo, Elizabeth'
'Champagne, Timothy M.'
'Ziller, Joseph W.'
'DiPasquale, Antonio G.'
'Rheingold, Arnold L.'
_publ_section_title
;
 Synthetic Diversity in the Formation of Triazoles from Nitriles and Diazo
 Compounds Using Metallocenes of Electropositive Metals
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              2897
_journal_paper_doi               10.1021/om8012103
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C26 H41 La N2 Si'
_chemical_formula_weight         548.61
_chemical_name_common            em3
_chemical_name_systematic
;
 ?
;
_space_group.centring_type       P
_space_group_IT_number           176
_space_group.IT_number           176
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-P 6c'
_symmetry_space_group_name_H-M   'P 63/m'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   19.6995(12)
_cell_length_b                   19.6995(12)
_cell_length_c                   14.4043(18)
_cell_measurement_reflns_used    7034
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.51
_cell_volume                     4841.0(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         0.3
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34518
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  0.8526
_exptl_absorpt_correction_T_min  0.7902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1692
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.989
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0874P)²+0.6869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1395
_reflns_number_gt                3274
_reflns_number_total             4103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om8012103_si_001.cif
_cod_data_source_block           uci25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_sg_symbol_H-M      P6(3)/m
_cod_database_code               4069037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, x, z+1/2'
'y, -x+y, z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, -x, -z-1/2'
'-y, x-y, -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
C1 C 0.4207(2) 0.2160(2) 0.4378(3) 0.0752(10) Uani 1 1 d .
C2 C 0.4720(2) 0.1853(2) 0.4403(3) 0.0713(9) Uani 1 1 d .
C3 C 0.4305(2) 0.1068(2) 0.4069(3) 0.0748(10) Uani 1 1 d .
C4 C 0.3537(2) 0.0898(2) 0.3861(3) 0.0786(11) Uani 1 1 d .
C5 C 0.3467(2) 0.1559(3) 0.4029(3) 0.0789(11) Uani 1 1 d .
C6 C 0.4403(3) 0.2957(3) 0.4722(4) 0.1029(15) Uani 1 1 d .
H6A H 0.3958 0.3032 0.4626 0.154 Uiso 1 1 calc R
H6B H 0.4852 0.3355 0.4383 0.154 Uiso 1 1 calc R
H6C H 0.4527 0.2999 0.5378 0.154 Uiso 1 1 calc R
C7 C 0.5535(2) 0.2269(3) 0.4773(3) 0.0850(12) Uani 1 1 d .
H7A H 0.5701 0.1891 0.4906 0.127 Uiso 1 1 calc R
H7B H 0.5552 0.2544 0.5338 0.127 Uiso 1 1 calc R
H7C H 0.5884 0.2642 0.4316 0.127 Uiso 1 1 calc R
C8 C 0.4626(3) 0.0521(3) 0.4037(4) 0.1002(15) Uani 1 1 d .
H8A H 0.5194 0.0821 0.4065 0.150 Uiso 1 1 calc R
H8B H 0.4465 0.0224 0.3463 0.150 Uiso 1 1 calc R
H8C H 0.4427 0.0165 0.4560 0.150 Uiso 1 1 calc R
C9 C 0.2846(3) 0.0078(3) 0.3661(4) 0.1119(18) Uani 1 1 d .
H9A H 0.2611 -0.0183 0.4242 0.168 Uiso 1 1 calc R
H9B H 0.3031 -0.0225 0.3323 0.168 Uiso 1 1 calc R
H9C H 0.2459 0.0122 0.3290 0.168 Uiso 1 1 calc R
C10 C 0.2722(3) 0.1578(3) 0.3992(4) 0.1115(17) Uani 1 1 d .
H10A H 0.2455 0.1351 0.3411 0.167 Uiso 1 1 calc R
H10B H 0.2836 0.2117 0.4033 0.167 Uiso 1 1 calc R
H10C H 0.2389 0.1280 0.4507 0.167 Uiso 1 1 calc R
C11 C 0.5633(3) 0.3520(3) 0.2500 0.0581(10) Uani 1 2 d S
C12 C 0.3886(4) 0.3013(4) 0.2500 0.100(2) Uani 1 2 d S
C13 C 0.3570(7) 0.4149(7) 0.2500 0.310(14) Uani 1 2 d S
H13A H 0.3813 0.4478 0.1953 0.372 Uiso 0.50 1 calc PR
H13B H 0.3813 0.4478 0.3047 0.372 Uiso 0.50 1 calc PR
C14 C 0.2196(6) 0.3272(5) 0.3553(5) 0.193(4) Uani 1 1 d .
H14A H 0.1904 0.2724 0.3375 0.289 Uiso 1 1 calc R
H14B H 0.1848 0.3418 0.3856 0.289 Uiso 1 1 calc R
H14C H 0.2614 0.3354 0.3976 0.289 Uiso 1 1 calc R
C15 C 0.2449(6) 0.4709(6) 0.2500 0.143(4) Uani 1 2 d S
H15A H 0.2878 0.5153 0.2812 0.215 Uiso 0.50 1 calc PR
H15B H 0.1962 0.4562 0.2823 0.215 Uiso 0.50 1 calc PR
H15C H 0.2412 0.4852 0.1865 0.215 Uiso 0.50 1 calc PR
N1 N 0.5846(3) 0.1991(3) 0.2500 0.0731(11) Uani 1 2 d S
N2 N 0.3771(4) 0.3527(4) 0.2500 0.154(3) Uani 1 2 d S
Si1 Si 0.26252(17) 0.38867(17) 0.2500 0.1250(10) Uani 1 2 d S
La1 La 0.450583(14) 0.201159(14) 0.2500 0.05384(14) Uani 1 2 d S
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 '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 C1 C5 107.8(4) . .
C2 C1 C6 125.0(4) . .
C5 C1 C6 127.1(4) . .
C2 C1 La1 75.4(2) . .
C5 C1 La1 75.9(2) . .
C6 C1 La1 117.9(3) . .
C1 C2 C3 108.1(3) . .
C1 C2 C7 125.4(4) . .
C3 C2 C7 126.4(4) . .
C1 C2 La1 75.5(2) . .
C3 C2 La1 75.9(2) . .
C7 C2 La1 117.9(3) . .
C4 C3 C2 107.1(4) . .
C4 C3 C8 127.7(4) . .
C2 C3 C8 124.9(4) . .
C4 C3 La1 76.4(2) . .
C2 C3 La1 74.9(2) . .
C8 C3 La1 118.5(3) . .
C5 C4 C3 109.7(4) . .
C5 C4 C9 124.4(4) . .
C3 C4 C9 124.9(4) . .
C5 C4 La1 75.1(2) . .
C3 C4 La1 74.8(2) . .
C9 C4 La1 125.6(3) . .
C4 C5 C1 107.3(4) . .
C4 C5 C10 125.2(4) . .
C1 C5 C10 126.9(4) . .
C4 C5 La1 76.4(2) . .
C1 C5 La1 74.7(2) . .
C10 C5 La1 122.1(3) . .
C1 C6 H6A 109.5 . .
C1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C3 C8 H8A 109.5 . .
C3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C4 C9 H9A 109.5 . .
C4 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C4 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C5 C10 H10A 109.5 . .
C5 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C5 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N1 C11 La1 176.4(4) 4_665 .
N2 C12 La1 167.7(6) . .
N2 C13 Si1 117.9(9) . .
N2 C13 H13A 107.8 . .
Si1 C13 H13A 107.8 . .
N2 C13 H13B 107.8 . .
Si1 C13 H13B 107.8 . .
H13A C13 H13B 107.2 . .
Si1 C14 H14A 109.5 . .
Si1 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
Si1 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
Si1 C15 H15A 109.5 . .
Si1 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
Si1 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C11 N1 La1 168.8(4) 3_655 .
C12 N2 C13 176.4(9) . .
C13 Si1 C15 113.9(5) . .
C13 Si1 C14 106.0(3) . 8_556
C15 Si1 C14 110.7(3) . 8_556
C13 Si1 C14 106.0(3) . .
C15 Si1 C14 110.7(3) . .
C14 Si1 C14 109.3(6) 8_556 .
N1 La1 C11 74.83(14) . .
N1 La1 C12 143.01(17) . .
C11 La1 C12 68.18(17) . .
N1 La1 C2 78.08(9) . .
C11 La1 C2 92.05(8) . .
C12 La1 C2 102.77(9) . .
N1 La1 C2 78.08(9) . 8_556
C11 La1 C2 92.05(8) . 8_556
C12 La1 C2 102.77(9) . 8_556
C2 La1 C2 153.80(18) . 8_556
N1 La1 C1 105.19(9) . 8_556
C11 La1 C1 89.15(8) . 8_556
C12 La1 C1 74.85(9) . 8_556
C2 La1 C1 176.71(11) . 8_556
C2 La1 C1 29.08(14) 8_556 8_556
N1 La1 C1 105.19(9) . .
C11 La1 C1 89.15(8) . .
C12 La1 C1 74.85(9) . .
C2 La1 C1 29.08(14) . .
C2 La1 C1 176.71(11) 8_556 .
C1 La1 C1 147.96(18) 8_556 .
N1 La1 C3 78.67(10) . 8_556
C11 La1 C3 119.73(9) . 8_556
C12 La1 C3 119.88(11) . 8_556
C2 La1 C3 133.28(13) . 8_556
C2 La1 C3 29.25(12) 8_556 8_556
C1 La1 C3 48.07(13) 8_556 8_556
C1 La1 C3 150.38(12) . 8_556
N1 La1 C3 78.67(10) . .
C11 La1 C3 119.73(9) . .
C12 La1 C3 119.88(11) . .
C2 La1 C3 29.25(12) . .
C2 La1 C3 133.28(13) 8_556 .
C1 La1 C3 150.38(12) 8_556 .
C1 La1 C3 48.07(13) . .
C3 La1 C3 106.23(18) 8_556 .
N1 La1 C5 124.18(9) . 8_556
C11 La1 C5 114.69(11) . 8_556
C12 La1 C5 73.74(12) . 8_556
C2 La1 C5 148.00(12) . 8_556
C2 La1 C5 48.08(11) 8_556 8_556
C1 La1 C5 29.41(11) 8_556 8_556
C1 La1 C5 128.69(12) . 8_556
C3 La1 C5 47.84(13) 8_556 8_556
C3 La1 C5 125.02(13) . 8_556
N1 La1 C5 124.18(9) . .
C11 La1 C5 114.69(11) . .
C12 La1 C5 73.74(12) . .
C2 La1 C5 48.08(11) . .
C2 La1 C5 148.00(12) 8_556 .
C1 La1 C5 128.69(12) 8_556 .
C1 La1 C5 29.41(11) . .
C3 La1 C5 125.02(13) 8_556 .
C3 La1 C5 47.84(13) . .
C5 La1 C5 102.22(17) 8_556 .
N1 La1 C4 106.03(11) . 8_556
C11 La1 C4 136.03(9) . 8_556
C12 La1 C4 100.55(14) . 8_556
C2 La1 C4 131.68(12) . 8_556
C2 La1 C4 47.48(11) 8_556 8_556
C1 La1 C4 47.47(12) 8_556 8_556
C1 La1 C4 130.33(12) . 8_556
C3 La1 C4 28.75(11) 8_556 8_556
C3 La1 C4 102.97(13) . 8_556
C5 La1 C4 28.48(12) 8_556 8_556
C5 La1 C4 101.10(12) . 8_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.413(7) .
C1 C5 1.433(6) .
C1 C6 1.501(6) .
C1 La1 2.815(4) .
C2 C3 1.424(6) .
C2 C7 1.489(5) .
C2 La1 2.814(4) .
C3 C4 1.409(6) .
C3 C8 1.497(6) .
C3 La1 2.827(4) .
C4 C5 1.397(6) .
C4 C9 1.533(6) .
C4 La1 2.847(4) .
C5 C10 1.489(6) .
C5 La1 2.830(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C6 H6C 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 H7C 0.9700 .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 H8C 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 H9C 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 H10C 0.9700 .
C11 N1 1.147(6) 4_665
C11 La1 2.677(4) .
C12 N2 1.141(8) .
C12 La1 2.792(6) .
C13 N2 1.466(12) .
C13 Si1 1.664(12) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C14 Si1 1.859(8) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 H14C 0.9700 .
C15 Si1 1.819(8) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 H15C 0.9700 .
N1 C11 1.147(6) 3_655
N1 La1 2.661(5) .
Si1 C14 1.859(8) 8_556
La1 C2 2.814(4) 8_556
La1 C1 2.815(4) 8_556
La1 C3 2.827(4) 8_556
La1 C5 2.830(4) 8_556
La1 C4 2.847(4) 8_556
