#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:55:58 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178730 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/41/4084108.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_4084108
loop_
_publ_author_name
'Schick, Sabrina'
'Pape, Tania'
'Hahn, F. Ekkehardt'
_publ_section_title
;
 Coordination Chemistry of Bidentate Bis(NHC) Ligands with Two Different
 NHC Donors
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              4035
_journal_paper_doi               10.1021/om500554t
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C5 H5 N5'
_chemical_formula_sum            'C5 H5 N5'
_chemical_formula_weight         135.14
_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                 101.318(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.957(2)
_cell_length_b                   7.1259(16)
_cell_length_c                   8.8994(18)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      75
_cell_measurement_theta_min      1
_cell_volume                     619.2(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, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_computing_structure_solution
;
SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 80
_diffrn_measured_fraction_theta_full 0.853
_diffrn_measured_fraction_theta_max 0.853
_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  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2041
_diffrn_reflns_theta_full        64.99
_diffrn_reflns_theta_max         64.99
_diffrn_reflns_theta_min         7.70
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  0.9428
_exptl_absorpt_correction_T_min  0.7380
_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 ratio of Tmin/Tmax = 0.489560
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0572
_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)+(0.0933P)²+0.0906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1682
_reflns_number_gt                752
_reflns_number_total             906
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500554t_si_002.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 4084108--4084112.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4084108
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
N1 N 0.4794(2) -0.2291(3) 0.5935(3) 0.0374(7) Uani 1 1 d .
N2 N 0.3736(3) -0.2850(3) 0.4725(3) 0.0453(7) Uani 1 1 d .
N3 N 0.30742(19) -0.0338(3) 0.5792(2) 0.0273(6) Uani 1 1 d .
N4 N 0.22809(19) 0.1162(3) 0.6092(2) 0.0270(6) Uani 1 1 d .
N5 N 0.0631(2) 0.2710(3) 0.6871(3) 0.0418(7) Uani 1 1 d .
C1 C 0.2728(3) -0.1655(4) 0.4659(3) 0.0401(8) Uani 1 1 d .
H1 H 0.1887 -0.1695 0.3939 0.048 Uiso 1 1 calc R
C2 C 0.4361(2) -0.0791(3) 0.6547(3) 0.0307(7) Uani 1 1 d .
H2 H 0.4868 -0.0117 0.7392 0.037 Uiso 1 1 calc R
C3 C 0.1177(3) 0.1033(4) 0.6793(3) 0.0372(7) Uani 1 1 d .
H3 H 0.0853 -0.0094 0.7167 0.045 Uiso 1 1 calc R
C4 C 0.2437(2) 0.3021(3) 0.5715(3) 0.0314(7) Uani 1 1 d .
H4 H 0.3113 0.3536 0.5216 0.038 Uiso 1 1 calc R
C5 C 0.1425(2) 0.3944(3) 0.6206(3) 0.0319(7) Uani 1 1 d .
H5 H 0.1274 0.5258 0.6112 0.038 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
N1 0.0414(14) 0.0306(14) 0.0449(14) 0.0068(9) 0.0200(11) 0.0106(9)
N2 0.0500(15) 0.0341(14) 0.0580(17) -0.0101(10) 0.0260(13) -0.0003(10)
N3 0.0249(10) 0.0211(12) 0.0382(12) -0.0016(8) 0.0119(8) 0.0003(8)
N4 0.0248(10) 0.0227(12) 0.0359(13) -0.0005(8) 0.0116(9) 0.0033(7)
N5 0.0328(13) 0.0434(15) 0.0530(15) 0.0012(10) 0.0179(11) 0.0113(10)
C1 0.0354(14) 0.0350(16) 0.0497(18) -0.0134(12) 0.0079(12) -0.0010(11)
C2 0.0289(12) 0.0323(15) 0.0317(15) 0.0020(10) 0.0080(10) 0.0040(10)
C3 0.0307(14) 0.0385(16) 0.0469(17) 0.0049(11) 0.0185(12) 0.0031(10)
C4 0.0280(13) 0.0289(15) 0.0371(14) 0.0014(10) 0.0062(10) -0.0003(10)
C5 0.0303(13) 0.0247(14) 0.0414(16) 0.0001(10) 0.0090(11) 0.0070(9)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 N2 106.9(2)
C1 N2 N1 107.6(2)
C2 N3 C1 106.1(2)
C2 N3 N4 127.1(2)
C1 N3 N4 126.8(2)
C3 N4 C4 108.3(2)
C3 N4 N3 125.09(19)
C4 N4 N3 126.62(19)
C3 N5 C5 106.0(2)
N2 C1 N3 109.4(2)
N1 C2 N3 110.0(2)
N5 C3 N4 109.8(2)
C5 C4 N4 105.2(2)
C4 C5 N5 110.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.311(3)
N1 N2 1.408(3)
N2 C1 1.309(3)
N3 C2 1.363(3)
N3 C1 1.371(3)
N3 N4 1.386(3)
N4 C3 1.369(3)
N4 C4 1.383(3)
N5 C3 1.321(3)
N5 C5 1.389(3)
C4 C5 1.346(3)
