#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:04:44 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179878 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/74/7017449.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_7017449
loop_
_publ_author_name
'Larocque, Timothy G.'
'Badaj, Anna C.'
'Dastgir, Sarim'
'Lavoie, Gino G.'
_publ_section_title
;
 New stable aryl-substituted acyclic imino-N-heterocyclic carbene:
 synthesis, characterisation and coordination to early transition metals.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12705
_journal_page_last               12712
_journal_paper_doi               10.1039/c1dt11565k
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C25 H31 N3'
_chemical_formula_sum            'C25 H31 N3'
_chemical_formula_weight         373.53
_chemical_name_systematic
;
?
;
_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                70.656(2)
_cell_angle_beta                 88.378(3)
_cell_angle_gamma                69.372(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5723(3)
_cell_length_b                   11.8829(7)
_cell_length_c                   12.3644(8)
_cell_measurement_reflns_used    10345
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1106.61(11)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0701
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10345
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0699
_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)+(0.1206P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.2146
_reflns_number_gt                2899
_reflns_number_total             4990
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1dt11565k.txt
_cod_data_source_block           k09214
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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        1106.61(10)
_cod_database_code               7017449
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
C1 C 0.7112(2) 0.2549(2) 0.79425(19) 0.0362(5) Uani 1 1 d .
C2 C 0.7055(3) 0.3033(2) 0.5977(2) 0.0414(6) Uani 1 1 d .
H2 H 0.7107 0.2929 0.5246 0.050 Uiso 1 1 calc R
C3 C 0.6784(3) 0.4120(2) 0.6183(2) 0.0413(6) Uani 1 1 d .
H3 H 0.6608 0.4941 0.5629 0.050 Uiso 1 1 calc R
C4 C 0.7487(2) 0.0776(2) 0.71982(18) 0.0317(5) Uani 1 1 d .
C5 C 0.8993(2) -0.0265(2) 0.8010(2) 0.0385(5) Uani 1 1 d .
C6 C 0.5014(2) 0.1388(2) 0.59849(19) 0.0333(5) Uani 1 1 d .
C7 C 0.4952(3) 0.1623(2) 0.47937(19) 0.0382(5) Uani 1 1 d .
C8 C 0.3450(3) 0.2388(2) 0.4130(2) 0.0451(6) Uani 1 1 d .
H8 H 0.3391 0.2558 0.3323 0.054 Uiso 1 1 calc R
C9 C 0.2029(3) 0.2912(2) 0.4618(2) 0.0490(6) Uani 1 1 d .
H9 H 0.1006 0.3443 0.4147 0.059 Uiso 1 1 calc R
C10 C 0.2100(3) 0.2662(2) 0.5796(2) 0.0439(6) Uani 1 1 d .
H10 H 0.1116 0.3019 0.6127 0.053 Uiso 1 1 calc R
C11 C 0.3591(2) 0.1894(2) 0.65042(19) 0.0348(5) Uani 1 1 d .
C12 C 0.6499(3) 0.1020(2) 0.4265(2) 0.0477(6) Uani 1 1 d .
H12A H 0.6185 0.1129 0.3471 0.072 Uiso 1 1 calc R
H12B H 0.7009 0.0105 0.4715 0.072 Uiso 1 1 calc R
H12C H 0.7303 0.1435 0.4268 0.072 Uiso 1 1 calc R
C13 C 0.3643(3) 0.1581(2) 0.7785(2) 0.0406(6) Uani 1 1 d .
H13A H 0.2519 0.1978 0.7990 0.061 Uiso 1 1 calc R
H13B H 0.4416 0.1909 0.8035 0.061 Uiso 1 1 calc R
H13C H 0.4028 0.0650 0.8167 0.061 Uiso 1 1 calc R
C14 C 0.6493(2) 0.47202(19) 0.79622(18) 0.0309(5) Uani 1 1 d .
C15 C 0.4832(2) 0.5442(2) 0.80397(19) 0.0348(5) Uani 1 1 d .
C16 C 0.4559(2) 0.6313(2) 0.86117(19) 0.0362(5) Uani 1 1 d .
H16 H 0.3439 0.6804 0.8680 0.043 Uiso 1 1 calc R
C17 C 0.5862(2) 0.6491(2) 0.90865(18) 0.0358(5) Uani 1 1 d .
C18 C 0.7497(2) 0.5739(2) 0.90033(18) 0.0342(5) Uani 1 1 d .
H18 H 0.8403 0.5835 0.9340 0.041 Uiso 1 1 calc R
C19 C 0.7839(2) 0.48528(19) 0.84441(18) 0.0326(5) Uani 1 1 d .
C20 C 0.3381(3) 0.5272(2) 0.7534(2) 0.0483(6) Uani 1 1 d .
H20A H 0.3414 0.5490 0.6699 0.073 Uiso 1 1 calc R
H20B H 0.2325 0.5836 0.7696 0.073 Uiso 1 1 calc R
H20C H 0.3463 0.4380 0.7880 0.073 Uiso 1 1 calc R
C21 C 0.5511(3) 0.7498(2) 0.9640(2) 0.0478(6) Uani 1 1 d .
H21A H 0.6514 0.7329 1.0120 0.072 Uiso 1 1 calc R
H21B H 0.4585 0.7476 1.0120 0.072 Uiso 1 1 calc R
H21C H 0.5205 0.8343 0.9040 0.072 Uiso 1 1 calc R
C22 C 0.9612(2) 0.4078(2) 0.8340(2) 0.0413(6) Uani 1 1 d .
H22A H 0.9803 0.3165 0.8691 0.062 Uiso 1 1 calc R
H22B H 1.0384 0.4290 0.8737 0.062 Uiso 1 1 calc R
H22C H 0.9804 0.4275 0.7525 0.062 Uiso 1 1 calc R
C23 C 0.8561(3) -0.0484(2) 0.9257(2) 0.0498(6) Uani 1 1 d .
H23A H 0.8228 0.0325 0.9406 0.075 Uiso 1 1 calc R
H23B H 0.9544 -0.1116 0.9785 0.075 Uiso 1 1 calc R
H23C H 0.7635 -0.0801 0.9377 0.075 Uiso 1 1 calc R
C24 C 1.0518(3) 0.0143(2) 0.7831(3) 0.0523(7) Uani 1 1 d .
H24A H 1.0697 0.0385 0.7012 0.078 Uiso 1 1 calc R
H24B H 1.1512 -0.0572 0.8281 0.078 Uiso 1 1 calc R
H24C H 1.0319 0.0875 0.8086 0.078 Uiso 1 1 calc R
C25 C 0.9374(3) -0.1512(2) 0.7758(3) 0.0562(7) Uani 1 1 d .
H25A H 0.8386 -0.1756 0.7857 0.084 Uiso 1 1 calc R
H25B H 1.0318 -0.2193 0.8292 0.084 Uiso 1 1 calc R
H25C H 0.9663 -0.1382 0.6965 0.084 Uiso 1 1 calc R
N1 N 0.72460(19) 0.20879(16) 0.70419(15) 0.0327(4) Uani 1 1 d .
N2 N 0.68126(19) 0.38048(16) 0.73744(15) 0.0336(4) Uani 1 1 d .
N3 N 0.6513(2) 0.04824(16) 0.66850(15) 0.0348(4) 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
N2 C1 N1 101.48(19)
C3 C2 N1 106.5(2)
C2 C3 N2 106.1(2)
N3 C4 N1 122.38(18)
N3 C4 C5 120.47(18)
N1 C4 C5 117.15(17)
C4 C5 C24 109.91(19)
C4 C5 C23 109.01(16)
C24 C5 C23 110.11(19)
C4 C5 C25 108.90(17)
C24 C5 C25 109.93(18)
C23 C5 C25 109.0(2)
C11 C6 C7 121.56(18)
C11 C6 N3 119.69(19)
C7 C6 N3 118.26(17)
C8 C7 C6 118.5(2)
C8 C7 C12 121.3(2)
C6 C7 C12 120.24(19)
C7 C8 C9 121.2(2)
C8 C9 C10 119.9(2)
C9 C10 C11 121.1(2)
C10 C11 C6 117.8(2)
C10 C11 C13 120.84(18)
C6 C11 C13 121.32(18)
C19 C14 C15 121.82(18)
C19 C14 N2 119.37(16)
C15 C14 N2 118.80(17)
C16 C15 C14 117.67(18)
C16 C15 C20 120.91(18)
C14 C15 C20 121.41(19)
C17 C16 C15 122.38(18)
C16 C17 C18 117.98(19)
C16 C17 C21 120.65(18)
C18 C17 C21 121.34(19)
C19 C18 C17 121.95(19)
C18 C19 C14 118.18(17)
C18 C19 C22 120.88(18)
C14 C19 C22 120.93(18)
C1 N1 C2 112.55(18)
C1 N1 C4 123.25(18)
C2 N1 C4 124.15(17)
C1 N2 C3 113.41(17)
C1 N2 C14 122.37(18)
C3 N2 C14 124.18(18)
C4 N3 C6 123.86(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.354(3)
C1 N1 1.380(3)
C2 C3 1.338(3)
C2 N1 1.388(3)
C3 N2 1.393(3)
C4 N3 1.266(3)
C4 N1 1.444(3)
C4 C5 1.526(3)
C5 C24 1.533(3)
C5 C23 1.534(3)
C5 C25 1.535(3)
C6 C11 1.399(3)
C6 C7 1.404(3)
C6 N3 1.425(3)
C7 C8 1.377(3)
C7 C12 1.513(3)
C8 C9 1.382(3)
C9 C10 1.385(3)
C10 C11 1.395(3)
C11 C13 1.500(3)
C14 C19 1.393(3)
C14 C15 1.400(3)
C14 N2 1.445(2)
C15 C16 1.390(3)
C15 C20 1.511(3)
C16 C17 1.387(3)
C17 C18 1.394(3)
C17 C21 1.505(3)
C18 C19 1.388(3)
C19 C22 1.502(3)
