#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:39:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178575 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/85/4068527.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_4068527
loop_
_publ_author_name
'Shih, Wei-Chih'
'Wang, Chun-Han'
'Chang, Yang-Ting'
'Yap, Glenn P. A.'
'Ong, Tiow-Gan'
_publ_section_title
;
 Synthesis and Structure of an Amino-Linked N-Heterocyclic Carbene and the
 Reactivity of its Aluminum Adduct
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1060
_journal_paper_doi               10.1021/om800917j
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C18 H28 Br N3'
_chemical_formula_weight         366.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.4620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7287(3)
_cell_length_b                   17.7547(5)
_cell_length_c                   12.5192(4)
_cell_measurement_reflns_used    4909
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.56
_cell_volume                     1869.95(10)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15687
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.200
_exptl_absorpt_correction_T_max  0.6407
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0338
_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)+(0.0412P)²+0.5798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                2641
_reflns_number_total             3289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800917j_si_004.cif
_cod_data_source_block           i9131
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4068527
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br Br 0.03262(3) 0.136192(14) 0.23942(2) 0.03726(12) Uani 1 1 d .
N1 N 0.7357(2) 0.10538(11) 0.73125(17) 0.0273(5) Uani 1 1 d .
N2 N 0.7791(2) 0.16154(12) 0.89037(17) 0.0291(5) Uani 1 1 d .
N3 N 0.4756(2) 0.20698(13) 0.91677(18) 0.0323(5) Uani 1 1 d .
H2 H 0.465(3) 0.2508(15) 0.883(2) 0.037(8) Uiso 1 1 d .
C1 C 0.7930(3) 0.07818(13) 0.5543(2) 0.0298(6) Uani 1 1 d .
C2 C 0.7380(3) 0.07344(14) 0.4398(2) 0.0338(6) Uani 1 1 d .
H2A H 0.8105 0.0636 0.3990 0.041 Uiso 1 1 calc R
C3 C 0.5792(3) 0.08284(13) 0.3840(2) 0.0324(6) Uani 1 1 d .
C4 C 0.4715(3) 0.09676(13) 0.4456(2) 0.0308(6) Uani 1 1 d .
H4A H 0.3643 0.1020 0.4091 0.037 Uiso 1 1 calc R
C5 C 0.5196(3) 0.10303(13) 0.5604(2) 0.0283(6) Uani 1 1 d .
C6 C 0.6811(3) 0.09385(13) 0.6123(2) 0.0262(6) Uani 1 1 d .
C7 C 0.9671(3) 0.06975(17) 0.6113(2) 0.0455(8) Uani 1 1 d .
H7A H 1.0013 0.1110 0.6616 0.068 Uiso 1 1 calc R
H7B H 1.0267 0.0697 0.5570 0.068 Uiso 1 1 calc R
H7C H 0.9844 0.0232 0.6518 0.068 Uiso 1 1 calc R
C8 C 0.5248(4) 0.07954(17) 0.2592(2) 0.0470(8) Uani 1 1 d .
H8A H 0.5985 0.1067 0.2287 0.071 Uiso 1 1 calc R
H8B H 0.4213 0.1019 0.2340 0.071 Uiso 1 1 calc R
H8C H 0.5201 0.0280 0.2355 0.071 Uiso 1 1 calc R
C9 C 0.3989(3) 0.11947(15) 0.6244(2) 0.0361(7) Uani 1 1 d .
H9A H 0.4192 0.0878 0.6888 0.054 Uiso 1 1 calc R
H9B H 0.2940 0.1097 0.5782 0.054 Uiso 1 1 calc R
H9C H 0.4071 0.1713 0.6469 0.054 Uiso 1 1 calc R
C10 C 0.7206(3) 0.17015(14) 0.7820(2) 0.0269(6) Uani 1 1 d .
H1 H 0.676(3) 0.2149(13) 0.7477(19) 0.022(6) Uiso 1 1 d .
C11 C 0.8060(3) 0.05311(14) 0.8120(2) 0.0331(6) Uani 1 1 d .
H11A H 0.8304 0.0033 0.8002 0.040 Uiso 1 1 calc R
C12 C 0.8323(3) 0.08825(15) 0.9106(2) 0.0344(6) Uani 1 1 d .
H12A H 0.8779 0.0670 0.9797 0.041 Uiso 1 1 calc R
C13 C 0.7650(3) 0.21761(15) 0.9730(2) 0.0344(6) Uani 1 1 d .
H13A H 0.7608 0.2676 0.9413 0.041 Uiso 1 1 calc R
H13B H 0.8577 0.2150 1.0362 0.041 Uiso 1 1 calc R
C14 C 0.6161(3) 0.20384(16) 1.0112(2) 0.0365(6) Uani 1 1 d .
H14A H 0.6225 0.1548 1.0463 0.044 Uiso 1 1 calc R
H14B H 0.6079 0.2417 1.0653 0.044 Uiso 1 1 calc R
C15 C 0.3225(3) 0.18257(14) 0.9359(2) 0.0333(6) Uani 1 1 d .
C16 C 0.2902(4) 0.21806(16) 1.0389(2) 0.0449(7) Uani 1 1 d .
H16A H 0.3719 0.2033 1.1033 0.067 Uiso 1 1 calc R
H16B H 0.1888 0.2013 1.0461 0.067 Uiso 1 1 calc R
H16C H 0.2894 0.2719 1.0320 0.067 Uiso 1 1 calc R
C17 C 0.1943(3) 0.20848(17) 0.8338(2) 0.0465(8) Uani 1 1 d .
H17A H 0.2131 0.1861 0.7687 0.070 Uiso 1 1 calc R
H17B H 0.1975 0.2623 0.8281 0.070 Uiso 1 1 calc R
H17C H 0.0918 0.1932 0.8406 0.070 Uiso 1 1 calc R
C18 C 0.3221(4) 0.09705(16) 0.9445(3) 0.0484(8) Uani 1 1 d .
H18A H 0.4090 0.0811 1.0050 0.073 Uiso 1 1 calc R
H18B H 0.3334 0.0754 0.8767 0.073 Uiso 1 1 calc R
H18C H 0.2237 0.0806 0.9573 0.073 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'
Br Br -0.2901 2.4595 '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
C10 N1 C11 108.0(2)
C10 N1 C6 124.2(2)
C11 N1 C6 127.8(2)
C10 N2 C12 108.4(2)
C10 N2 C13 124.3(2)
C12 N2 C13 126.7(2)
C14 N3 C15 117.1(2)
C2 C1 C6 116.9(2)
C2 C1 C7 120.8(2)
C6 C1 C7 122.2(2)
C3 C2 C1 122.5(2)
C2 C3 C4 118.4(2)
C2 C3 C8 121.0(2)
C4 C3 C8 120.6(2)
C3 C4 C5 121.7(2)
C4 C5 C6 117.5(2)
C4 C5 C9 120.1(2)
C6 C5 C9 122.4(2)
C1 C6 C5 122.9(2)
C1 C6 N1 118.6(2)
C5 C6 N1 118.4(2)
N2 C10 N1 109.1(2)
C12 C11 N1 106.9(2)
C11 C12 N2 107.5(2)
N2 C13 C14 110.7(2)
N3 C14 C13 110.1(2)
N3 C15 C18 108.8(2)
N3 C15 C16 113.1(2)
C18 C15 C16 110.3(2)
N3 C15 C17 105.5(2)
C18 C15 C17 110.2(2)
C16 C15 C17 108.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C10 1.337(3)
N1 C11 1.389(3)
N1 C6 1.452(3)
N2 C10 1.325(3)
N2 C12 1.382(3)
N2 C13 1.465(3)
N3 C14 1.460(3)
N3 C15 1.484(3)
C1 C2 1.387(4)
C1 C6 1.392(3)
C1 C7 1.504(3)
C2 C3 1.386(4)
C3 C4 1.389(4)
C3 C8 1.508(3)
C4 C5 1.390(3)
C5 C6 1.395(3)
C5 C9 1.512(4)
C11 C12 1.348(4)
C13 C14 1.520(4)
C15 C18 1.522(4)
C15 C16 1.527(4)
C15 C17 1.528(4)
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
C6 C1 C2 C3 -0.7(4)
C7 C1 C2 C3 -178.3(2)
C1 C2 C3 C4 -0.7(4)
C1 C2 C3 C8 178.2(2)
C2 C3 C4 C5 1.4(4)
C8 C3 C4 C5 -177.4(2)
C3 C4 C5 C6 -0.8(3)
C3 C4 C5 C9 179.0(2)
C2 C1 C6 C5 1.4(4)
C7 C1 C6 C5 178.9(2)
C2 C1 C6 N1 -175.0(2)
C7 C1 C6 N1 2.5(3)
C4 C5 C6 C1 -0.7(4)
C9 C5 C6 C1 179.5(2)
C4 C5 C6 N1 175.7(2)
C9 C5 C6 N1 -4.1(3)
C10 N1 C6 C1 116.4(3)
C11 N1 C6 C1 -65.9(3)
C10 N1 C6 C5 -60.2(3)
C11 N1 C6 C5 117.5(3)
C12 N2 C10 N1 -0.7(3)
C13 N2 C10 N1 -172.1(2)
C11 N1 C10 N2 0.6(3)
C6 N1 C10 N2 178.7(2)
C10 N1 C11 C12 -0.2(3)
C6 N1 C11 C12 -178.2(2)
N1 C11 C12 N2 -0.3(3)
C10 N2 C12 C11 0.6(3)
C13 N2 C12 C11 171.7(2)
C10 N2 C13 C14 91.0(3)
C12 N2 C13 C14 -78.8(3)
C15 N3 C14 C13 170.3(2)
N2 C13 C14 N3 -58.7(3)
C14 N3 C15 C18 -74.5(3)
C14 N3 C15 C16 48.5(3)
C14 N3 C15 C17 167.3(2)
