#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/05/4060520.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_4060520
loop_
_publ_author_name
'Liddle, Stephen T.'
'Arnold, Polly L.'
_publ_section_title
;
Synthesis of Heteroleptic Cerium(III) Anionic Amido-Tethered N-Heterocyclic 
Carbene Complexes
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2597
_journal_page_last               2605
_journal_paper_doi               10.1021/om050061b
_journal_volume                  24
_journal_year                    2005
_chemical_formula_moiety         'C18 H31 N3'
_chemical_formula_sum            'C18 H31 N3'
_chemical_formula_weight         289.46
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 110.878(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.040(4)
_cell_length_b                   9.176(2)
_cell_length_c                   15.583(4)
_cell_measurement_reflns_used    4799
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.03
_cell_measurement_theta_min      2.62
_cell_volume                     1875.8(8)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material
'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17775
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.025
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0487P)²+0.4087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                2359
_reflns_number_total             3301
_reflns_threshold_expression     I>2σ(I)
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4060520
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40644(10) -0.19300(15) 0.38506(10) 0.0531(4) Uani 1 1 d . . .
H1N H 0.3748(13) -0.2065(19) 0.3270(13) 0.063(5) Uiso 1 1 d . . .
N2 N 0.20239(8) -0.11646(14) 0.37689(8) 0.0443(3) Uani 1 1 d . . .
N3 N 0.16037(9) 0.10090(14) 0.32391(8) 0.0456(3) Uani 1 1 d . . .
C1 C 0.19170(11) -0.02848(17) 0.30667(10) 0.0459(4) Uani 1 1 d . . .
H1 H 0.2044 -0.0540 0.2526 0.055 Uiso 1 1 calc R . .
C2 C 0.17630(12) -0.0425(2) 0.44103(11) 0.0551(4) Uani 1 1 d . . .
H2 H 0.1768 -0.0794 0.4981 0.066 Uiso 1 1 calc R . .
C3 C 0.14984(12) 0.0922(2) 0.40825(11) 0.0563(4) Uani 1 1 d . . .
H3 H 0.1277 0.1684 0.4380 0.068 Uiso 1 1 calc R . .
C4 C 0.13870(13) 0.22957(17) 0.26047(12) 0.0541(4) Uani 1 1 d . . .
C5 C 0.04156(16) 0.1973(3) 0.18085(16) 0.0956(7) Uani 1 1 d . . .
H5A H 0.0495 0.1063 0.1512 0.143 Uiso 1 1 calc R . .
H5B H 0.0271 0.2772 0.1363 0.143 Uiso 1 1 calc R . .
H5C H -0.0150 0.1874 0.2034 0.143 Uiso 1 1 calc R . .
C6 C 0.1267(2) 0.3630(2) 0.31216(18) 0.1074(9) Uani 1 1 d . . .
H6A H 0.0674 0.3508 0.3307 0.161 Uiso 1 1 calc R . .
H6B H 0.1168 0.4488 0.2725 0.161 Uiso 1 1 calc R . .
H6C H 0.1881 0.3761 0.3669 0.161 Uiso 1 1 calc R . .
C7 C 0.22714(17) 0.2476(2) 0.22804(17) 0.0880(7) Uani 1 1 d . . .
H7A H 0.2898 0.2636 0.2811 0.132 Uiso 1 1 calc R . .
H7B H 0.2147 0.3316 0.1866 0.132 Uiso 1 1 calc R . .
H7C H 0.2343 0.1595 0.1954 0.132 Uiso 1 1 calc R . .
C8 C 0.23928(12) -0.26667(17) 0.38529(11) 0.0517(4) Uani 1 1 d . . .
H8A H 0.2196 -0.3101 0.3232 0.062 Uiso 1 1 calc R . .
H8B H 0.2058 -0.3238 0.4205 0.062 Uiso 1 1 calc R . .
C9 C 0.35332(12) -0.27781(19) 0.43237(12) 0.0583(4) Uani 1 1 d . . .
H9A H 0.3727 -0.2426 0.4964 0.070 Uiso 1 1 calc R . .
H9B H 0.3742 -0.3812 0.4344 0.070 Uiso 1 1 calc R . .
C10 C 0.51580(13) -0.2226(2) 0.40834(13) 0.0647(5) Uani 1 1 d . . .
C11 C 0.55420(16) -0.1096(3) 0.35773(18) 0.0987(8) Uani 1 1 d . . .
H11A H 0.5198 -0.1225 0.2914 0.148 Uiso 1 1 calc R . .
H11B H 0.6279 -0.1212 0.3737 0.148 Uiso 1 1 calc R . .
H11C H 0.5398 -0.0119 0.3754 0.148 Uiso 1 1 calc R . .
C12 C 0.53438(19) -0.3751(3) 0.3786(2) 0.1107(9) Uani 1 1 d . . .
H12A H 0.5074 -0.4477 0.4101 0.166 Uiso 1 1 calc R . .
H12B H 0.6078 -0.3906 0.3946 0.166 Uiso 1 1 calc R . .
H12C H 0.4999 -0.3851 0.3121 0.166 Uiso 1 1 calc R . .
C13 C 0.57099(15) -0.2061(3) 0.51122(15) 0.0967(8) Uani 1 1 d . . .
H13A H 0.5566 -0.1096 0.5307 0.145 Uiso 1 1 calc R . .
H13B H 0.6445 -0.2166 0.5258 0.145 Uiso 1 1 calc R . .
H13C H 0.5474 -0.2814 0.5436 0.145 Uiso 1 1 calc R . .
C14 C -0.09899(17) 0.3180(3) 0.42007(13) 0.0769(6) Uani 1 1 d . . .
H14 H -0.0306 0.3494 0.4497 0.092 Uiso 1 1 calc R . .
C15 C -0.1854(2) 0.3930(2) 0.41770(13) 0.0824(6) Uani 1 1 d . . .
H15 H -0.1867 0.4849 0.4453 0.099 Uiso 1 1 calc R . .
C16 C -0.26985(17) 0.3104(3) 0.36786(13) 0.0770(6) Uani 1 1 d . . .
H16 H -0.3391 0.3357 0.3553 0.092 Uiso 1 1 calc R . .
C17 C -0.23499(15) 0.1843(2) 0.33979(12) 0.0681(5) Uani 1 1 d . . .
H17 H -0.2763 0.1077 0.3047 0.082 Uiso 1 1 calc R . .
C18 C -0.12951(15) 0.1893(2) 0.37169(12) 0.0678(5) Uani 1 1 d . . .
H18 H -0.0858 0.1172 0.3621 0.081 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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
C9 N1 C10 117.16(14) . . ?
C1 N2 C2 108.75(13) . . ?
C1 N2 C8 125.51(13) . . ?
C2 N2 C8 125.71(13) . . ?
C1 N3 C3 107.31(13) . . ?
C1 N3 C4 125.11(13) . . ?
C3 N3 C4 127.56(14) . . ?
N2 C1 N3 109.05(13) . . ?
C3 C2 N2 106.91(14) . . ?
C2 C3 N3 107.97(14) . . ?
N3 C4 C7 108.04(14) . . ?
N3 C4 C6 108.80(15) . . ?
C7 C4 C6 110.63(17) . . ?
N3 C4 C5 107.38(14) . . ?
C7 C4 C5 110.89(18) . . ?
C6 C4 C5 110.98(18) . . ?
N2 C8 C9 112.85(13) . . ?
N1 C9 C8 111.47(13) . . ?
N1 C10 C11 106.20(15) . . ?
N1 C10 C13 109.68(16) . . ?
C11 C10 C13 109.81(19) . . ?
N1 C10 C12 111.77(16) . . ?
C11 C10 C12 109.84(19) . . ?
C13 C10 C12 109.50(19) . . ?
C15 C14 C18 108.14(19) . . ?
C14 C15 C16 108.0(2) . . ?
C17 C16 C15 107.74(19) . . ?
C18 C17 C16 108.16(19) . . ?
C14 C18 C17 107.93(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.448(2) . ?
N1 C10 1.472(2) . ?
N2 C1 1.3246(18) . ?
N2 C2 1.362(2) . ?
N2 C8 1.462(2) . ?
N3 C1 1.3264(19) . ?
N3 C3 1.376(2) . ?
N3 C4 1.500(2) . ?
C2 C3 1.338(2) . ?
C4 C7 1.507(3) . ?
C4 C6 1.507(3) . ?
C4 C5 1.510(3) . ?
C8 C9 1.508(2) . ?
C10 C11 1.514(3) . ?
C10 C13 1.519(3) . ?
C10 C12 1.526(3) . ?
C14 C15 1.383(3) . ?
C14 C18 1.384(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.385(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21781733
