#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:04:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178547 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/54/4065489.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_4065489
loop_
_publ_author_name
'Guisado-Barrios, Gregorio'
'Bouffard, Jean'
'Donnadieu, Bruno'
'Bertrand, Guy'
_publ_section_title
;
 Bis(1,2,3-triazol-5-ylidenes) (i-bitz) as Stable 1,4-Bidentate Ligands
 Based on Mesoionic Carbenes (MICs).
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              6017
_journal_page_last               6021
_journal_paper_doi               10.1021/om200844b
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C18 H16 N6'
_chemical_formula_sum            'C18 H16 N6'
_chemical_formula_weight         316.37
_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                 106.320(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.708(3)
_cell_length_b                   10.536(3)
_cell_length_c                   14.436(4)
_cell_measurement_reflns_used    1952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      2.43
_cell_volume                     1563.0(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10078
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0031(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0486
_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)+(0.0540P)²+0.1346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                2419
_reflns_number_total             3612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200844b_si_002.cif
_cod_data_source_block           7a
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4065489
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
N1 N 0.63044(12) 0.15945(13) 0.48964(9) 0.0182(3) Uani 1 1 d
N2 N 0.55194(13) 0.20261(14) 0.54078(9) 0.0201(3) Uani 1 1 d
N3 N 0.43520(12) 0.17404(13) 0.48480(9) 0.0192(3) Uani 1 1 d
N4 N 0.13272(12) 0.03911(13) 0.23827(9) 0.0184(3) Uani 1 1 d
N5 N 0.20916(13) -0.03015(14) 0.19779(9) 0.0205(3) Uani 1 1 d
N6 N 0.32680(12) -0.00694(13) 0.25497(9) 0.0192(3) Uani 1 1 d
C1 C 0.57160(15) 0.10451(16) 0.40146(11) 0.0203(4) Uani 1 1 d
C2 C 0.44159(15) 0.11517(15) 0.40105(11) 0.0181(4) Uani 1 1 d
C3 C 0.32246(15) 0.07481(15) 0.32853(10) 0.0178(4) Uani 1 1 d
C4 C 0.19297(15) 0.10784(16) 0.31961(11) 0.0196(4) Uani 1 1 d
C5 C 0.76877(15) 0.17549(16) 0.53135(11) 0.0191(4) Uani 1 1 d
C6 C 0.85016(17) 0.1457(2) 0.47611(13) 0.0305(5) Uani 1 1 d
C7 C 0.98367(17) 0.1608(2) 0.51410(13) 0.0331(5) Uani 1 1 d
C8 C 1.03430(17) 0.20473(17) 0.60743(12) 0.0253(4) Uani 1 1 d
C9 C 0.95131(16) 0.23473(16) 0.66262(12) 0.0214(4) Uani 1 1 d
C10 C 0.81746(16) 0.22070(16) 0.62517(11) 0.0194(4) Uani 1 1 d
C11 C -0.00574(15) 0.02912(16) 0.19536(11) 0.0194(4) Uani 1 1 d
C12 C -0.05387(17) -0.02639(17) 0.10532(12) 0.0254(4) Uani 1 1 d
C13 C -0.18767(18) -0.03639(18) 0.06616(13) 0.0287(4) Uani 1 1 d
C14 C -0.27181(17) 0.00579(18) 0.11679(13) 0.0280(4) Uani 1 1 d
C15 C -0.22197(17) 0.06056(19) 0.20703(12) 0.0287(4) Uani 1 1 d
C16 C -0.08869(16) 0.07405(18) 0.24616(12) 0.0241(4) Uani 1 1 d
C17 C 0.32341(17) 0.20404(19) 0.52093(13) 0.0245(4) Uani 1 1 d
C18 C 0.43519(18) -0.07064(19) 0.23110(13) 0.0243(4) Uani 1 1 d
H6 H 0.8134(17) 0.1195(19) 0.4124(13) 0.0356(13) Uiso 1 1 d
H7 H 1.0433(18) 0.1373(19) 0.4752(13) 0.0356(13) Uiso 1 1 d
H8 H 1.1294(18) 0.2132(19) 0.6339(13) 0.0356(13) Uiso 1 1 d
H9 H 0.9861(18) 0.2670(19) 0.7287(14) 0.0356(13) Uiso 1 1 d
H10 H 0.7591(18) 0.2395(19) 0.6637(13) 0.0356(13) Uiso 1 1 d
H12 H 0.0040(18) -0.0583(19) 0.0708(13) 0.0356(13) Uiso 1 1 d
H13 H -0.2218(17) -0.074(2) 0.0023(13) 0.0356(13) Uiso 1 1 d
H14 H -0.364(2) -0.0010(19) 0.0899(13) 0.0356(13) Uiso 1 1 d
H15 H -0.2797(18) 0.0902(19) 0.2426(13) 0.0356(13) Uiso 1 1 d
H17A H 0.3573(17) 0.2504(19) 0.5826(14) 0.0356(13) Uiso 1 1 d
H17B H 0.2777(18) 0.123(2) 0.5303(13) 0.0356(13) Uiso 1 1 d
H17C H 0.2621(19) 0.253(2) 0.4717(14) 0.0356(13) Uiso 1 1 d
H18A H 0.4102(18) -0.155(2) 0.2086(13) 0.0356(13) Uiso 1 1 d
H18B H 0.5088(19) -0.0704(19) 0.2856(13) 0.0356(13) Uiso 1 1 d
H18C H 0.4603(18) -0.024(2) 0.1804(14) 0.0356(13) Uiso 1 1 d
H16 H -0.0486(18) 0.1139(19) 0.3069(13) 0.0356(13) Uiso 1 1 d
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
N2 N1 C1 117.06(13)
N2 N1 C5 117.25(12)
C1 N1 C5 125.68(14)
N3 N2 N1 102.56(12)
N2 N3 C2 111.62(13)
N2 N3 C17 117.40(13)
C2 N3 C17 130.94(14)
N5 N4 C4 117.33(13)
N5 N4 C11 116.82(12)
C4 N4 C11 125.75(14)
N6 N5 N4 102.58(12)
N5 N6 C3 111.39(13)
N5 N6 C18 116.63(13)
C3 N6 C18 131.98(14)
N1 C1 C2 99.59(14)
N3 C2 C1 109.16(13)
N3 C2 C3 120.60(14)
C1 C2 C3 130.24(14)
N6 C3 C4 109.35(13)
N6 C3 C2 121.33(14)
C4 C3 C2 129.31(15)
N4 C4 C3 99.35(14)
C6 C5 C10 121.22(15)
C6 C5 N1 118.39(14)
C10 C5 N1 120.39(15)
C5 C6 C7 119.71(16)
C5 C6 H6 118.6(12)
C7 C6 H6 121.6(12)
C8 C7 C6 120.07(17)
C8 C7 H7 119.7(10)
C6 C7 H7 120.1(10)
C7 C8 C9 119.80(16)
C7 C8 H8 119.2(11)
C9 C8 H8 121.0(11)
C8 C9 C10 120.63(15)
C8 C9 H9 120.5(11)
C10 C9 H9 118.9(11)
C9 C10 C5 118.57(16)
C9 C10 H10 121.1(11)
C5 C10 H10 120.3(11)
C16 C11 C12 121.08(16)
C16 C11 N4 118.88(14)
C12 C11 N4 120.04(15)
C11 C12 C13 118.89(17)
C11 C12 H12 120.7(11)
C13 C12 H12 120.4(11)
C14 C13 C12 120.75(16)
C14 C13 H13 120.2(11)
C12 C13 H13 119.1(11)
C13 C14 C15 119.60(16)
C13 C14 H14 120.9(11)
C15 C14 H14 119.5(11)
C16 C15 C14 120.36(18)
C16 C15 H15 119.5(11)
C14 C15 H15 120.1(11)
C11 C16 C15 119.29(16)
C11 C16 H16 116.5(11)
C15 C16 H16 124.2(11)
N3 C17 H17A 107.3(11)
N3 C17 H17B 109.8(11)
H17A C17 H17B 111.4(15)
N3 C17 H17C 107.8(11)
H17A C17 H17C 113.5(16)
H17B C17 H17C 107.0(15)
N6 C18 H18A 110.0(12)
N6 C18 H18B 109.5(12)
H18A C18 H18B 111.9(17)
N6 C18 H18C 110.4(12)
H18A C18 H18C 108.6(16)
H18B C18 H18C 106.4(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.3443(18)
N1 C1 1.3791(19)
N1 C5 1.444(2)
N2 N3 1.3185(18)
N3 C2 1.378(2)
N3 C17 1.468(2)
N4 N5 1.3463(18)
N4 C4 1.376(2)
N4 C11 1.441(2)
N5 N6 1.3205(18)
N6 C3 1.378(2)
N6 C18 1.463(2)
C1 C2 1.395(2)
C2 C3 1.467(2)
C3 C4 1.400(2)
C5 C6 1.373(2)
C5 C10 1.392(2)
C6 C7 1.389(2)
C6 H6 0.934(18)
C7 C8 1.383(2)
C7 H7 0.992(19)
C8 C9 1.386(2)
C8 H8 0.986(18)
C9 C10 1.390(2)
C9 H9 0.982(19)
C10 H10 0.967(19)
C11 C16 1.385(2)
C11 C12 1.386(2)
C12 C13 1.389(2)
C12 H12 0.959(19)
C13 C14 1.383(3)
C13 H13 0.975(18)
C14 C15 1.387(2)
C14 H14 0.96(2)
C15 C16 1.387(2)
C15 H15 0.96(2)
C16 H16 0.958(19)
C17 H17A 0.991(19)
C17 H17B 1.01(2)
C17 H17C 0.97(2)
C18 H18A 0.96(2)
C18 H18B 0.945(19)
C18 H18C 0.98(2)
