#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:19:26 +0100 (lun 21 de mar de 2016) $
#$Revision: 178602 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/13/4071382.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_4071382
loop_
_publ_author_name
'Normand, Adrien T.'
'Yen, Swee Kuan'
'Huynh, Han Vinh'
'Hor, T. S. Andy'
'Cavell, Kingsley J.'
_publ_section_title
;
 Catalytic Annulation of Heterocycles via a Novel Redox Process Involving
 the Imidazolium Salt N-Heterocyclic Carbene Couple
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              3153
_journal_paper_doi               10.1021/om800140n
_journal_volume                  27
_journal_year                    2008
_chemical_formula_sum            'C8 H13 Br N2'
_chemical_formula_weight         217.11
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.54(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7845(14)
_cell_length_b                   10.725(2)
_cell_length_c                   13.111(3)
_cell_measurement_temperature    150(2)
_cell_volume                     934.7(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2718
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    4.339
_exptl_absorpt_correction_T_max  0.660
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         3.818
_refine_diff_density_min         -1.127
_refine_diff_density_rms         0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.334
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.334
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.1339
_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)+(0.0945P)²+48.2155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3685
_refine_ls_wR_factor_ref         0.3727
_reflns_number_gt                1560
_reflns_number_total             1828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800140n-file002.cif
_cod_data_source_block           asKJC36
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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        934.7(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4071382
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
Br1 Br 0.7395(3) 0.15531(16) 0.80057(14) 0.0309(6) Uani 1 1 d .
N1 N 0.754(2) -0.4681(13) 0.8831(11) 0.024(3) Uani 1 1 d .
C1 C 0.738(2) -0.3590(15) 0.9278(13) 0.025(3) Uani 1 1 d .
N2 N 0.729(2) -0.3764(14) 1.0255(11) 0.027(3) Uani 1 1 d .
C2 C 0.761(2) -0.5604(17) 0.9582(13) 0.027(4) Uani 1 1 d .
H2 H 0.7731 -0.6476 0.9483 0.033 Uiso 1 1 calc R
C3 C 0.746(2) -0.5013(18) 1.0492(14) 0.030(4) Uani 1 1 d .
H3 H 0.7469 -0.5389 1.1149 0.036 Uiso 1 1 calc R
C4 C 0.770(3) -0.4922(18) 0.7722(14) 0.034(4) Uani 1 1 d .
H4A H 0.6480 -0.4620 0.7255 0.052 Uiso 1 1 calc R
H4B H 0.7845 -0.5820 0.7618 0.052 Uiso 1 1 calc R
H4C H 0.8874 -0.4484 0.7569 0.052 Uiso 1 1 calc R
C5 C 0.716(3) -0.2595(19) 1.0842(16) 0.037(4) Uani 1 1 d .
H5A H 0.8468 -0.2368 1.1284 0.044 Uiso 1 1 calc R
H5B H 0.6125 -0.2654 1.1278 0.044 Uiso 1 1 calc R
C6 C 0.653(4) -0.166(2) 0.9925(19) 0.050(6) Uani 1 1 d .
H6A H 0.7143 -0.0831 1.0111 0.060 Uiso 1 1 calc R
H6B H 0.5045 -0.1559 0.9757 0.060 Uiso 1 1 calc R
C7 C 0.730(3) -0.2222(18) 0.8970(16) 0.035(4) Uani 1 1 d .
H7 H 0.6319 -0.2075 0.8303 0.042 Uiso 1 1 calc R
C8 C 0.940(3) -0.1758(17) 0.8911(16) 0.035(4) Uani 1 1 d .
H8A H 1.0307 -0.1887 0.9584 0.053 Uiso 1 1 calc R
H8B H 0.9340 -0.0868 0.8739 0.053 Uiso 1 1 calc R
H8C H 0.9900 -0.2222 0.8371 0.053 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0294(10) 0.0246(9) 0.0402(11) -0.0082(8) 0.0108(7) -0.0004(8)
N1 0.024(7) 0.021(7) 0.026(7) 0.000(6) 0.005(6) -0.004(6)
C1 0.015(7) 0.021(8) 0.037(9) -0.002(7) 0.001(6) 0.001(6)
N2 0.023(7) 0.026(7) 0.033(8) -0.005(6) 0.008(6) -0.004(6)
C2 0.021(8) 0.027(9) 0.034(9) 0.006(7) 0.005(7) 0.003(7)
C3 0.017(8) 0.038(10) 0.030(9) 0.004(8) -0.003(7) -0.009(7)
C4 0.048(11) 0.028(9) 0.033(9) -0.002(8) 0.022(8) 0.005(8)
C5 0.030(9) 0.041(11) 0.042(11) -0.018(9) 0.011(8) -0.005(8)
C6 0.057(14) 0.032(11) 0.067(15) -0.003(10) 0.024(12) 0.013(10)
C7 0.029(10) 0.033(10) 0.043(11) 0.003(8) 0.007(8) -0.001(8)
C8 0.034(10) 0.025(9) 0.049(11) 0.004(8) 0.012(9) -0.010(8)
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
C1 N1 C2 108.0(14)
C1 N1 C4 127.6(15)
C2 N1 C4 124.3(14)
N2 C1 N1 109.4(15)
N2 C1 C7 113.1(15)
N1 C1 C7 137.5(16)
C1 N2 C3 110.1(15)
C1 N2 C5 114.0(15)
C3 N2 C5 135.8(16)
C3 C2 N1 106.8(15)
C2 C3 N2 105.7(15)
N2 C5 C6 100.4(15)
C5 C6 C7 106.4(16)
C1 C7 C8 110.1(15)
C1 C7 C6 99.2(15)
C8 C7 C6 112.3(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.32(2)
N1 C2 1.39(2)
N1 C4 1.50(2)
C1 N2 1.31(2)
C1 C7 1.52(2)
N2 C3 1.37(2)
N2 C5 1.48(2)
C2 C3 1.37(3)
C5 C6 1.56(3)
C6 C7 1.57(3)
C7 C8 1.53(2)
