#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/90/4069036.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_4069036
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            'C87 H129 La3 N6 Si3'
_chemical_formula_weight         1759.96
_chemical_name_systematic
; 
 ? 
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            2
_cell_length_a                   18.1572(9)
_cell_length_b                   18.1572(9)
_cell_length_c                   15.8174(16)
_cell_measurement_temperature    163(2)
_cell_volume                     4516.1(6)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            50255
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    1.476
_exptl_absorpt_correction_T_max  0.7183
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedra
_exptl_crystal_F_000             1812
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.261
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0246
_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)+(0.0340P)²+5.5651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                3463
_reflns_number_total             3901
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om8012103_si_001.cif
_cod_data_source_block           em13
_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:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap & geom' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      P6(3)/m
_cod_database_code               4069036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -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
La1 La 0.333964(10) 0.461166(10) 0.7500 0.01758(6) Uani 1 2 d S
Si1 Si -0.01914(6) 0.21082(6) 0.7500 0.0392(3) Uani 1 2 d S
C14 C 0.43769(19) 0.62954(19) 0.7500 0.0280(6) Uani 1.08 2 d SP
N1 N 0.4731(2) 0.7035(2) 0.7500 0.0295(6) Uani 0.93 2 d SP
N2 N 0.17092(18) 0.33409(18) 0.7500 0.0329(6) Uani 1 2 d S
C1 C 0.40326(15) 0.39715(16) 0.62682(15) 0.0291(5) Uani 1 1 d .
C2 C 0.31484(15) 0.35431(15) 0.60948(16) 0.0293(5) Uani 1 1 d .
C3 C 0.29400(15) 0.41497(16) 0.57860(15) 0.0292(5) Uani 1 1 d .
C4 C 0.36977(17) 0.49535(16) 0.57768(16) 0.0308(5) Uani 1 1 d .
C5 C 0.43690(15) 0.48435(16) 0.60784(16) 0.0308(5) Uani 1 1 d .
C6 C 0.4540(2) 0.3540(2) 0.6442(2) 0.0473(7) Uani 1 1 d .
H6A H 0.4710 0.3398 0.5906 0.071 Uiso 1 1 calc R
H6B H 0.4193 0.3018 0.6766 0.071 Uiso 1 1 calc R
H6C H 0.5049 0.3923 0.6768 0.071 Uiso 1 1 calc R
C7 C 0.25668(19) 0.25932(17) 0.6137(2) 0.0440(7) Uani 1 1 d .
H7A H 0.1974 0.2461 0.6116 0.066 Uiso 1 1 calc R
H7B H 0.2667 0.2376 0.6666 0.066 Uiso 1 1 calc R
H7C H 0.2682 0.2325 0.5656 0.066 Uiso 1 1 calc R
C8 C 0.20864(19) 0.3979(2) 0.5474(2) 0.0452(7) Uani 1 1 d .
H8A H 0.1671 0.3373 0.5540 0.068 Uiso 1 1 calc R
H8B H 0.2129 0.4136 0.4876 0.068 Uiso 1 1 calc R
H8C H 0.1903 0.4316 0.5804 0.068 Uiso 1 1 calc R
C9 C 0.3769(2) 0.57648(19) 0.5455(2) 0.0507(8) Uani 1 1 d .
H9A H 0.4349 0.6236 0.5550 0.076 Uiso 1 1 calc R
H9B H 0.3365 0.5877 0.5757 0.076 Uiso 1 1 calc R
H9C H 0.3642 0.5711 0.4849 0.076 Uiso 1 1 calc R
C10 C 0.52973(17) 0.55171(19) 0.6121(2) 0.0445(7) Uani 1 1 d .
H10A H 0.5569 0.5549 0.5576 0.067 Uiso 1 1 calc R
H10B H 0.5578 0.5371 0.6566 0.067 Uiso 1 1 calc R
H10C H 0.5348 0.6069 0.6248 0.067 Uiso 1 1 calc R
C11 C 0.0992(2) 0.2871(2) 0.7500 0.0331(7) Uani 1 2 d S
C12 C -0.0584(2) 0.2338(2) 0.6512(3) 0.0844(16) Uani 1 1 d .
H12A H -0.0504 0.2913 0.6540 0.127 Uiso 1 1 calc R
H12B H -0.1190 0.1924 0.6443 0.127 Uiso 1 1 calc R
H12C H -0.0267 0.2298 0.6030 0.127 Uiso 1 1 calc R
C13 C -0.0319(3) 0.1032(2) 0.7500 0.0436(10) Uani 1 2 d S
H13A H -0.0107 0.0937 0.8035 0.065 Uiso 0.50 1 calc PR
H13B H 0.0004 0.0982 0.7029 0.065 Uiso 0.50 1 calc PR
H13C H -0.0922 0.0607 0.7436 0.065 Uiso 0.50 1 calc PR
C15 C 0.6667 0.3333 0.7500 0.116(3) Uiso 1 6 d SD
C16 C 0.6234(5) 0.3032(8) 0.67430(17) 0.116(3) Uiso 0.33 1 d PD
C17 C 0.5429(4) 0.2318(7) 0.67424(11) 0.116(3) Uiso 0.33 1 d PD
C18 C 0.5033(6) 0.1947(10) 0.7500 0.116(3) Uiso 0.33 2 d SPD
C19 C 0.0876(2) 0.0490(2) 0.4999(3) 0.0516(8) Uani 1 1 d .
H19 H 0.146(2) 0.082(2) 0.497(2) 0.056(10) Uiso 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'
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
Cnt La1 C14 98.7 . .
Cnt La1 N2 94.1 . .
Cnt La1 N1 112.0 . 3_565
Cnt La1 Cnt 135.5 . .
C14 La1 N1 75.00(9) . 3_565
C14 La1 N2 145.51(9) . .
N1 La1 N2 70.52(9) 3_565 .
C14 La1 C4 78.08(5) . 10_557
N1 La1 C4 92.18(5) 3_565 10_557
N2 La1 C4 102.94(6) . 10_557
C14 La1 C4 78.08(5) . .
N1 La1 C4 92.19(5) 3_565 .
N2 La1 C4 102.94(6) . .
C4 La1 C4 153.74(11) 10_557 .
C14 La1 C5 78.09(6) . 10_557
N1 La1 C5 119.57(6) 3_565 10_557
N2 La1 C5 119.39(6) . 10_557
C4 La1 C5 29.14(7) 10_557 10_557
C4 La1 C5 132.91(8) . 10_557
C14 La1 C5 78.09(6) . .
N1 La1 C5 119.57(6) 3_565 .
N2 La1 C5 119.39(6) . .
C4 La1 C5 132.91(8) 10_557 .
C4 La1 C5 29.14(7) . .
C5 La1 C5 105.88(10) 10_557 .
C14 La1 C3 105.63(5) . 10_557
N1 La1 C3 89.94(5) 3_565 10_557
N2 La1 C3 74.72(5) . 10_557
C4 La1 C3 29.24(8) 10_557 10_557
C4 La1 C3 176.11(7) . 10_557
C5 La1 C3 48.00(7) 10_557 10_557
C5 La1 C3 149.70(7) . 10_557
C14 La1 C3 105.63(5) . .
N1 La1 C3 89.94(5) 3_565 .
N2 La1 C3 74.72(5) . .
C4 La1 C3 176.11(7) 10_557 .
C4 La1 C3 29.24(8) . .
C5 La1 C3 149.70(7) 10_557 .
C5 La1 C3 48.00(7) . .
C3 La1 C3 147.57(10) 10_557 .
C14 La1 C2 123.66(6) . .
N1 La1 C2 115.33(6) 3_565 .
N2 La1 C2 73.13(6) . .
C4 La1 C2 147.64(7) 10_557 .
C4 La1 C2 47.81(7) . .
C5 La1 C2 124.68(7) 10_557 .
C5 La1 C2 47.66(7) . .
C3 La1 C2 128.30(7) 10_557 .
C3 La1 C2 28.92(7) . .
C14 La1 C2 123.66(6) . 10_557
N1 La1 C2 115.33(6) 3_565 10_557
N2 La1 C2 73.13(6) . 10_557
C4 La1 C2 47.81(7) 10_557 10_557
C4 La1 C2 147.64(7) . 10_557
C5 La1 C2 47.66(7) 10_557 10_557
C5 La1 C2 124.68(7) . 10_557
C3 La1 C2 28.92(7) 10_557 10_557
C3 La1 C2 128.30(7) . 10_557
C2 La1 C2 102.25(10) . 10_557
C14 La1 C1 105.26(7) . .
N1 La1 C1 136.76(5) 3_565 .
N2 La1 C1 99.80(7) . .
C4 La1 C1 130.73(7) 10_557 .
C4 La1 C1 47.67(7) . .
C5 La1 C1 102.15(7) 10_557 .
C5 La1 C1 28.84(7) . .
C3 La1 C1 129.26(7) 10_557 .
C3 La1 C1 47.59(7) . .
C2 La1 C1 28.71(7) . .
C2 La1 C1 100.53(7) 10_557 .
C14 La1 C1 105.26(7) . 10_557
N1 La1 C1 136.76(5) 3_565 10_557
N2 La1 C1 99.80(7) . 10_557
C4 La1 C1 47.67(7) 10_557 10_557
C4 La1 C1 130.72(7) . 10_557
C5 La1 C1 28.84(7) 10_557 10_557
C5 La1 C1 102.15(7) . 10_557
C3 La1 C1 47.59(7) 10_557 10_557
C3 La1 C1 129.26(7) . 10_557
C2 La1 C1 100.53(7) . 10_557
C2 La1 C1 28.71(7) 10_557 10_557
C1 La1 C1 85.80(10) . 10_557
C13 Si1 C12 112.29(15) . .
C13 Si1 C12 112.29(15) . 10_557
C12 Si1 C12 115.3(4) . 10_557
C13 Si1 C11 105.72(17) . .
C12 Si1 C11 105.10(14) . .
C12 Si1 C11 105.10(14) 10_557 .
N1 C14 La1 171.0(3) . .
C14 N1 La1 174.0(3) . 2_665
C11 N2 La1 172.3(3) . .
C5 C1 C2 108.0(2) . .
C5 C1 C6 126.0(2) . .
C2 C1 C6 124.8(2) . .
C5 C1 La1 73.83(13) . .
C2 C1 La1 75.36(13) . .
C6 C1 La1 126.54(18) . .
C1 C2 C3 108.0(2) . .
C1 C2 C7 124.9(2) . .
C3 C2 C7 126.7(2) . .
C1 C2 La1 75.93(13) . .
C3 C2 La1 74.30(13) . .
C7 C2 La1 121.38(18) . .
C2 C3 C4 107.7(2) . .
C2 C3 C8 126.9(2) . .
C4 C3 C8 125.3(2) . .
C2 C3 La1 76.78(14) . .
C4 C3 La1 74.42(13) . .
C8 C3 La1 117.47(17) . .
C5 C4 C3 108.2(2) . .
C5 C4 C9 126.5(3) . .
C3 C4 C9 125.2(3) . .
C5 C4 La1 76.17(14) . .
C3 C4 La1 76.34(14) . .
C9 C4 La1 116.36(18) . .
C4 C5 C1 108.0(2) . .
C4 C5 C10 126.4(3) . .
C1 C5 C10 125.4(2) . .
C4 C5 La1 74.68(14) . .
C1 C5 La1 77.33(14) . .
C10 C5 La1 118.29(17) . .
N2 C11 Si1 179.3(3) . .
C16 C15 C16 51.7(3) 11_657 10_557
C16 C15 C16 51.7(3) 11_657 12_667
C16 C15 C16 51.7(3) 10_557 12_667
C16 C15 C16 119.5(4) 11_657 2_655
C16 C15 C16 150.83(19) 10_557 2_655
C16 C15 C16 150.83(18) 12_667 2_655
C16 C15 C16 150.83(18) 11_657 .
C16 C15 C16 119.5(4) 10_557 .
C16 C15 C16 150.83(18) 12_667 .
C16 C15 C16 51.7(3) 2_655 .
C16 C15 C16 150.83(19) 11_657 3_665
C16 C15 C16 150.83(18) 10_557 3_665
C16 C15 C16 119.5(4) 12_667 3_665
C16 C15 C16 51.7(3) 2_655 3_665
C16 C15 C16 51.7(3) . 3_665
C16 C16 C16 60.002(2) 2_655 3_665
C16 C16 C15 64.14(17) 2_655 .
C16 C16 C15 64.14(17) 3_665 .
C16 C16 C17 139(2) 2_655 .
C16 C16 C17 161(2) 3_665 .
C15 C16 C17 119.63(13) . .
C18 C17 C16 120.09(14) . .
C17 C18 C17 119.7(2) 10_557 .
C19 C19 C19 120.000(4) 9_556 8_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
La1 Cnt 2.562 .
La1 C14 2.671(3) .
La1 N1 2.684(3) 3_565
La1 N2 2.694(3) .
La1 C4 2.799(2) 10_557
La1 C4 2.799(2) .
La1 C5 2.818(2) 10_557
La1 C5 2.818(2) .
La1 C3 2.823(2) 10_557
La1 C3 2.823(2) .
La1 C2 2.855(2) .
La1 C2 2.855(2) 10_557
La1 C1 2.862(2) .
La1 C1 2.862(2) 10_557
Si1 C13 1.849(4) .
Si1 C12 1.850(4) .
Si1 C12 1.850(4) 10_557
Si1 C11 1.886(4) .
C14 N1 1.164(4) .
N1 La1 2.684(3) 2_665
N2 C11 1.146(4) .
C1 C5 1.415(4) .
C1 C2 1.417(3) .
C1 C6 1.504(3) .
C2 C3 1.418(3) .
C2 C7 1.508(3) .
C3 C4 1.420(4) .
C3 C8 1.503(3) .
C4 C5 1.413(4) .
C4 C9 1.501(4) .
C5 C10 1.510(3) .
C15 C16 1.3858(10) 11_657
C15 C16 1.3858(10) 10_557
C15 C16 1.3858(10) 12_667
C15 C16 1.3859(10) 2_655
C15 C16 1.3859(10) .
C15 C16 1.3859(10) 3_665
C16 C16 1.209(7) 2_655
C16 C16 1.209(8) 3_665
C16 C17 1.3865(10) .
C17 C18 1.3862(10) .
C18 C17 1.3862(10) 10_557
C19 C19 1.381(3) 9_556
C19 C19 1.381(3) 8_556
