#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:10:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180250 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/36/7113670.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_7113670
loop_
_publ_author_name
'Filipponi, Silvia'
'Jones, Jamie N.'
'Johnson, Jennifer A.'
'Cowley, Alan H.'
'Grepioni, Fabrizia'
'Braga, Dario'
_publ_section_title
;
 Isolation of C?H?C(?) complexes from the reaction of stable carbenes with
 hydrocarbons
;
_journal_issue                   21
_journal_name_full               'Chemical Communications'
_journal_page_first              2716
_journal_paper_doi               10.1039/b309168f
_journal_year                    2003
_chemical_formula_sum            'C26 H31 N2'
_chemical_formula_weight         371.53
_chemical_melting_point          '[C21 H25 N2][C5 H5]'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.99(3)
_cell_angle_beta                 82.41(3)
_cell_angle_gamma                65.62(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3933(17)
_cell_length_b                   8.9198(18)
_cell_length_c                   16.085(3)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.99
_cell_volume                     1077.7(5)
_computing_cell_refinement       DENZO
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Scalepack
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'WinGX (Farrugia, 1999)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  '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  0.0694
_diffrn_reflns_av_sigmaI/netI    0.1881
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7217
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9869
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.194
_refine_ls_extinction_coef       0.38(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.862
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.862
_refine_ls_R_factor_all          0.3367
_refine_ls_R_factor_gt           0.2405
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5673
_refine_ls_wR_factor_ref         0.5904
_reflns_number_gt                2287
_reflns_number_total             4861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b309168f.txt
_cod_data_source_block           p1bar
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1077.7(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7113670
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
H14 H 0.679(11) 0.862(10) -0.050(5) 0.05(2) Uiso 1 1 d .
H22 H 1.691(11) -0.214(9) 0.311(5) 0.03(2) Uiso 1 1 d .
C1 C 1.3148(14) 0.4784(15) 0.3142(6) 0.055(3) Uani 1 1 d .
H1 H 1.2913 0.5004 0.3712 0.066 Uiso 1 1 calc R
C2 C 1.2711(11) 0.5987(12) 0.2420(7) 0.049(3) Uani 1 1 d .
H2 H 1.2136 0.7156 0.2413 0.059 Uiso 1 1 calc R
C3 C 1.3275(12) 0.5145(13) 0.1730(6) 0.048(3) Uani 1 1 d .
H3 H 1.3152 0.5637 0.1156 0.057 Uiso 1 1 calc R
C4 C 1.4054(13) 0.3458(14) 0.2005(8) 0.059(3) Uani 1 1 d .
H4 H 1.4557 0.2600 0.1655 0.071 Uiso 1 1 calc R
C5 C 1.3972(13) 0.3241(12) 0.2883(6) 0.046(2) Uani 1 1 d .
H5 H 1.4406 0.2211 0.3240 0.055 Uiso 1 1 calc R
C6 C 0.9877(11) 0.4240(11) 0.2562(5) 0.038(2) Uani 1 1 d .
H6 H 1.0934 0.4410 0.2440 0.046 Uiso 1 1 calc R
C8 C 0.7164(13) 0.4560(12) 0.2532(6) 0.049(3) Uani 1 1 d .
H8 H 0.5971 0.5013 0.2402 0.059 Uiso 1 1 calc R
C9 C 0.7987(13) 0.3120(12) 0.3004(6) 0.047(3) Uani 1 1 d .
H9 H 0.7494 0.2353 0.3264 0.056 Uiso 1 1 calc R
C10 C 0.8023(11) 0.6784(11) 0.1710(6) 0.041(2) Uani 1 1 d .
C11 C 0.7984(11) 0.8166(11) 0.2047(6) 0.041(2) Uani 1 1 d .
C12 C 0.7720(13) 0.9630(13) 0.1487(7) 0.053(3) Uani 1 1 d .
H12 H 0.7708 1.0569 0.1696 0.063 Uiso 1 1 calc R
C13 C 0.7477(13) 0.9744(13) 0.0646(6) 0.051(3) Uani 1 1 d .
C14 C 0.7540(14) 0.8341(14) 0.0347(6) 0.057(3) Uani 1 1 d .
C15 C 0.7798(11) 0.6830(11) 0.0861(6) 0.041(2) Uani 1 1 d .
C16 C 0.8091(14) 0.8127(11) 0.2969(6) 0.047(3) Uani 1 1 d .
H16A H 0.7655 0.7319 0.3293 0.071 Uiso 1 1 calc R
H16B H 0.7375 0.9230 0.3134 0.071 Uiso 1 1 calc R
H16C H 0.9313 0.7806 0.3088 0.071 Uiso 1 1 calc R
C17 C 0.7273(16) 1.1261(13) 0.0057(7) 0.065(3) Uani 1 1 d .
H17A H 0.6695 1.2231 0.0360 0.098 Uiso 1 1 calc R
H17B H 0.6558 1.1358 -0.0401 0.098 Uiso 1 1 calc R
H17C H 0.8429 1.1205 -0.0182 0.098 Uiso 1 1 calc R
C18 C 0.7838(15) 0.5365(13) 0.0541(7) 0.061(3) Uani 1 1 d .
H18A H 0.6656 0.5376 0.0604 0.092 Uiso 1 1 calc R
H18B H 0.8633 0.4354 0.0864 0.092 Uiso 1 1 calc R
H18C H 0.8252 0.5390 -0.0058 0.092 Uiso 1 1 calc R
C20 C 1.1053(12) 0.1548(11) 0.3465(6) 0.039(2) Uani 1 1 d .
C21 C 1.2181(12) 0.0283(12) 0.3014(6) 0.042(2) Uani 1 1 d .
C22 C 1.3439(12) -0.1060(12) 0.3451(6) 0.047(3) Uani 1 1 d .
H22A H 1.4237 -0.1924 0.3145 0.057 Uiso 1 1 calc R
C23 C 1.3597(12) -0.1215(11) 0.4302(6) 0.040(2) Uani 1 1 d .
C24 C 1.2423(14) 0.0089(12) 0.4738(6) 0.048(3) Uani 1 1 d .
H24 H 1.2521 0.0019 0.5327 0.058 Uiso 1 1 calc R
C25 C 1.1120(13) 0.1483(11) 0.4339(6) 0.042(2) Uani 1 1 d .
C26 C 1.2114(14) 0.0414(13) 0.2085(6) 0.056(3) Uani 1 1 d .
H26A H 1.1012 0.0392 0.1962 0.084 Uiso 1 1 calc R
H26B H 1.3103 -0.0522 0.1868 0.084 Uiso 1 1 calc R
H26C H 1.2184 0.1458 0.1811 0.084 Uiso 1 1 calc R
C27 C 1.4974(13) -0.2712(12) 0.4787(7) 0.055(3) Uani 1 1 d .
H27A H 1.5151 -0.3722 0.4557 0.082 Uiso 1 1 calc R
H27B H 1.4573 -0.2807 0.5386 0.082 Uiso 1 1 calc R
H27C H 1.6082 -0.2569 0.4727 0.082 Uiso 1 1 calc R
C28 C 0.9911(14) 0.2865(12) 0.4805(6) 0.056(3) Uani 1 1 d .
H28A H 1.0328 0.2719 0.5367 0.084 Uiso 1 1 calc R
H28B H 0.8733 0.2867 0.4865 0.084 Uiso 1 1 calc R
H28C H 0.9874 0.3923 0.4491 0.084 Uiso 1 1 calc R
N1 N 0.9700(9) 0.2944(9) 0.3046(4) 0.0382(19) Uani 1 1 d .
N2 N 0.8321(9) 0.5265(9) 0.2273(5) 0.0387(19) Uani 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
C5 C1 C2 108.6(9)
C3 C2 C1 106.8(9)
C2 C3 C4 108.9(9)
C3 C4 C5 108.0(9)
C1 C5 C4 107.7(9)
N1 C6 N2 108.6(7)
C9 C8 N2 108.0(8)
C8 C9 N1 107.4(8)
C15 C10 C11 123.0(8)
C15 C10 N2 118.9(8)
C11 C10 N2 118.1(8)
C12 C11 C10 117.4(8)
C12 C11 C16 120.4(8)
C10 C11 C16 122.0(8)
C13 C12 C11 121.8(9)
C12 C13 C14 118.3(9)
C12 C13 C17 121.4(10)
C14 C13 C17 120.2(9)
C13 C14 C15 123.7(9)
C10 C15 C14 115.8(9)
C10 C15 C18 121.1(8)
C14 C15 C18 123.1(9)
C21 C20 C25 122.6(8)
C21 C20 N1 119.6(7)
C25 C20 N1 117.7(8)
C22 C21 C20 117.5(8)
C22 C21 C26 121.1(9)
C20 C21 C26 121.3(8)
C23 C22 C21 123.4(9)
C22 C23 C24 117.3(8)
C22 C23 C27 123.4(9)
C24 C23 C27 119.2(8)
C25 C24 C23 122.3(8)
C24 C25 C20 116.7(9)
C24 C25 C28 121.7(8)
C20 C25 C28 121.6(8)
C6 N1 C9 107.2(7)
C6 N1 C20 126.6(7)
C9 N1 C20 126.0(7)
C6 N2 C8 108.7(7)
C6 N2 C10 124.1(7)
C8 N2 C10 126.9(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C5 1.372(14)
C1 C2 1.411(14)
C2 C3 1.370(13)
C3 C4 1.386(15)
C4 C5 1.387(14)
C6 N1 1.328(11)
C6 N2 1.336(11)
C8 C9 1.331(13)
C8 N2 1.348(11)
C9 N1 1.390(11)
C10 C15 1.393(13)
C10 C11 1.417(13)
C10 N2 1.440(11)
C11 C12 1.404(14)
C11 C16 1.492(13)
C12 C13 1.375(14)
C13 C14 1.396(14)
C13 C17 1.471(14)
C14 C15 1.402(14)
C15 C18 1.473(13)
C20 C21 1.384(13)
C20 C25 1.403(12)
C20 N1 1.428(11)
C21 C22 1.379(12)
C21 C26 1.486(13)
C22 C23 1.371(12)
C23 C24 1.404(13)
C23 C27 1.526(12)
C24 C25 1.393(13)
C25 C28 1.483(13)
