#------------------------------------------------------------------------------
#$Date: 2016-03-25 08:17:47 +0100 (vie 25 de mar de 2016) $
#$Revision: 179718 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/20/7002017.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_7002017
loop_
_publ_author_name
'Radloff, Christian'
'Hahn, F. Ekkehardt'
'Pape, Tania'
'Fröhlich, Roland'
_publ_section_title
;
 Supramolecular structures from mono and dimetalated biscarbene ligands
;
_journal_issue                   35
_journal_name_full               'Dalton Transactions'
_journal_page_first              7215
_journal_paper_doi               10.1039/b907896g
_journal_year                    2009
_chemical_formula_sum            'C16 H24 Br2 N4'
_chemical_formula_weight         432.21
_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                 100.602(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.1257(7)
_cell_length_b                   14.067(2)
_cell_length_c                   12.8338(18)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      75
_cell_measurement_theta_min      1
_cell_volume                     909.6(2)
_computing_cell_refinement       'SAINT (Bruker AXS, 2000)'
_computing_data_collection       'SMART (Bruker AXS, 2000)'
_computing_data_reduction        'SAINT,SADABS (Bruker AXS, 2000)'
_computing_molecular_graphics
;
ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 80
_diffrn_measured_fraction_theta_full 0.865
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_monochromator  goebel-mirror
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_av_sigmaI/netI    0.1978
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4364
_diffrn_reflns_theta_full        71.76
_diffrn_reflns_theta_max         71.76
_diffrn_reflns_theta_min         4.71
_exptl_absorpt_coefficient_mu    5.661
_exptl_absorpt_correction_T_max  0.8485
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Corrections were done with the SADABS program, utilizing the none merged
raw data obtained from the integration process. Integration and final cell
refinement were done with SAINT.

SADABS reports Maximum and minimum effective
transmission: 1.000000 0.672886

;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent plates'
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.843
_refine_ls_R_factor_all          0.1505
_refine_ls_R_factor_gt           0.0734
_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)+(0.0554P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1418
_reflns_number_gt                733
_reflns_number_total             1547
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b907896g.txt
_cod_data_source_block           sad2
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7002017
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.0677(2) 0.23230(7) 0.75788(8) 0.0450(4) Uani 1 1 d . . .
C1 C 0.0258(18) 0.6387(7) 0.8849(8) 0.036(3) Uani 1 1 d . . .
H1 H -0.1067 0.6803 0.8488 0.043 Uiso 1 1 calc R . .
C2 C 0.3826(17) 0.5854(7) 0.9954(7) 0.030(2) Uani 1 1 d . . .
C3 C 0.2780(17) 0.5128(7) 0.9260(7) 0.031(2) Uani 1 1 d . . .
C4 C 0.3889(17) 0.4224(7) 0.9275(7) 0.036(3) Uani 1 1 d . . .
H4 H 0.3174 0.3722 0.8815 0.043 Uiso 1 1 calc R . .
C5 C 0.2688(18) 0.7617(8) 1.0112(7) 0.054(3) Uani 1 1 d . . .
H5A H 0.4367 0.7848 0.9925 0.064 Uiso 1 1 calc R . .
H5B H 0.2926 0.7595 1.0895 0.064 Uiso 1 1 calc R . .
C6 C 0.047(2) 0.8311(8) 0.9689(9) 0.064(3) Uani 1 1 d . . .
H6A H 0.0316 0.8371 0.8919 0.096 Uiso 1 1 calc R . .
H6B H 0.0883 0.8934 1.0021 0.096 Uiso 1 1 calc R . .
H6C H -0.1203 0.8077 0.9854 0.096 Uiso 1 1 calc R . .
C7 C -0.1119(18) 0.4990(7) 0.7675(8) 0.051(3) Uani 1 1 d . . .
H7A H -0.2843 0.5321 0.7476 0.061 Uiso 1 1 calc R . .
H7B H -0.1480 0.4330 0.7877 0.061 Uiso 1 1 calc R . .
C8 C 0.025(2) 0.4969(7) 0.6735(8) 0.057(3) Uani 1 1 d . . .
H8A H 0.0641 0.5621 0.6540 0.086 Uiso 1 1 calc R . .
H8B H -0.0902 0.4662 0.6136 0.086 Uiso 1 1 calc R . .
H8C H 0.1915 0.4611 0.6917 0.086 Uiso 1 1 calc R . .
N1 N 0.2137(15) 0.6639(7) 0.9682(6) 0.039(2) Uani 1 1 d . . .
N2 N 0.0506(14) 0.5480(6) 0.8600(6) 0.030(2) Uani 1 1 d . . .
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 0.0364(5) 0.0587(8) 0.0379(6) -0.0115(7) 0.0014(4) -0.0050(6)
C1 0.030(5) 0.046(7) 0.034(7) 0.005(5) 0.010(5) -0.004(5)
C2 0.029(5) 0.043(7) 0.019(6) 0.002(5) 0.005(5) -0.006(5)
C3 0.027(5) 0.043(7) 0.023(6) 0.005(5) 0.006(5) 0.004(5)
C4 0.026(5) 0.048(7) 0.032(7) -0.001(5) 0.002(5) -0.009(5)
C5 0.045(7) 0.080(10) 0.035(6) 0.017(7) 0.007(5) 0.007(7)
C6 0.059(8) 0.052(8) 0.078(10) 0.003(7) 0.003(7) 0.008(7)
C7 0.041(7) 0.062(8) 0.044(9) -0.016(6) -0.008(6) 0.004(6)
C8 0.063(8) 0.060(9) 0.039(8) -0.017(6) -0.013(6) -0.010(6)
N1 0.027(5) 0.048(6) 0.038(6) -0.002(4) -0.002(4) 0.001(4)
N2 0.026(4) 0.034(5) 0.030(5) -0.001(4) 0.001(4) -0.003(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
N2 C1 N1 111.0(9) . . ?
C4 C2 C3 124.8(9) 3_667 . ?
C4 C2 N1 129.6(9) 3_667 . ?
C3 C2 N1 105.6(8) . . ?
C4 C3 C2 123.5(9) . . ?
C4 C3 N2 128.6(9) . . ?
C2 C3 N2 107.9(9) . . ?
C2 C4 C3 111.7(9) 3_667 . ?
N1 C5 C6 112.5(8) . . ?
N2 C7 C8 111.9(8) . . ?
C1 N1 C2 107.9(9) . . ?
C1 N1 C5 126.6(9) . . ?
C2 N1 C5 124.5(8) . . ?
C1 N2 C3 107.5(8) . . ?
C1 N2 C7 125.0(8) . . ?
C3 N2 C7 126.9(8) . . ?
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
C1 N2 1.326(10) . ?
C1 N1 1.348(10) . ?
C2 C4 1.391(11) 3_667 ?
C2 C3 1.396(12) . ?
C2 N1 1.408(11) . ?
C3 C4 1.391(11) . ?
C3 N2 1.400(10) . ?
C4 C2 1.391(11) 3_667 ?
C5 N1 1.490(13) . ?
C5 C6 1.520(12) . ?
C7 N2 1.488(10) . ?
C7 C8 1.504(13) . ?
