#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:18:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178621 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/32/4073230.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_4073230
loop_
_publ_author_name
'Bazinet, Patrick'
'Ong, Tiow-Gan'
'O'Brien, Julie S.'
'Lavoie, Nathalie'
'Bell, Eleanor'
'Yap, Glenn P. A.'
'Korobkov, Ilia'
'Richeson, Darrin S.'
_publ_section_title
;
 Design of Sterically Demanding, Electron-Rich Carbene Ligands with the
 Perimidine Scaffold
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2885
_journal_paper_doi               10.1021/om0701827
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C54 H48 N4'
_chemical_formula_weight         752.96
_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                 96.383(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.4944(18)
_cell_length_b                   11.4705(16)
_cell_length_c                   15.323(2)
_cell_measurement_reflns_used    978
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.24
_cell_measurement_theta_min      2.42
_cell_volume                     2182.4(5)
_computing_cell_refinement       'SHELXTL, Sheldrick (2001)'
_computing_data_collection       'SMART, Bruker (2002)'
_computing_data_reduction        'SHELXTL, Sheldrick (2001)'
_computing_molecular_graphics    'SHELXTL, Sheldrick (2001)'
_computing_publication_material  'SHELXTL, Sheldrick (2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24110
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         5111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0733
_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)+(0.0964P)²+0.4845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.2086
_reflns_number_gt                3434
_reflns_number_total             5111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om0701827si20070227_100909.cif
_cod_data_source_block           darr021
_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               4073230
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
N1 N 0.50938(13) 0.50106(14) 0.12226(10) 0.0477(4) Uani 1 1 d .
N2 N 0.53367(14) 0.34443(14) 0.02328(11) 0.0495(4) Uani 1 1 d .
C1 C 0.51322(15) 0.46504(17) 0.03439(13) 0.0433(4) Uani 1 1 d .
C2 C 0.67490(18) 0.61114(19) 0.14976(15) 0.0556(5) Uani 1 1 d .
H2A H 0.7103 0.5499 0.1254 0.067 Uiso 1 1 calc R
C3 C 0.7328(2) 0.7085(2) 0.18144(18) 0.0685(7) Uani 1 1 d .
C4 C 0.6787(2) 0.7968(2) 0.21883(18) 0.0740(7) Uani 1 1 d .
H4A H 0.7172 0.8613 0.2418 0.089 Uiso 1 1 calc R
C5 C 0.5692(2) 0.7924(2) 0.22320(17) 0.0693(7) Uani 1 1 d .
C6 C 0.51261(19) 0.69584(19) 0.18926(15) 0.0584(6) Uani 1 1 d .
H6A H 0.4384 0.6924 0.1902 0.070 Uiso 1 1 calc R
C7 C 0.56572(16) 0.60452(17) 0.15408(13) 0.0467(5) Uani 1 1 d .
C8 C 0.8523(3) 0.7168(3) 0.1748(3) 0.1141(13) Uani 1 1 d .
H8A H 0.8734 0.7973 0.1749 0.171 Uiso 1 1 calc R
H8B H 0.8684 0.6807 0.1213 0.171 Uiso 1 1 calc R
H8C H 0.8910 0.6777 0.2239 0.171 Uiso 1 1 calc R
C9 C 0.5111(3) 0.8910(3) 0.2644(2) 0.1093(12) Uani 1 1 d .
H9A H 0.5459 0.9065 0.3223 0.164 Uiso 1 1 calc R
H9B H 0.4376 0.8690 0.2680 0.164 Uiso 1 1 calc R
H9C H 0.5131 0.9598 0.2289 0.164 Uiso 1 1 calc R
C10 C 0.45194(15) 0.42906(18) 0.17433(13) 0.0475(5) Uani 1 1 d .
C11 C 0.42446(19) 0.4601(2) 0.25580(14) 0.0594(6) Uani 1 1 d .
H11A H 0.4495 0.5299 0.2813 0.071 Uiso 1 1 calc R
C12 C 0.3591(2) 0.3871(2) 0.30049(17) 0.0726(7) Uani 1 1 d .
H12A H 0.3414 0.4094 0.3555 0.087 Uiso 1 1 calc R
C13 C 0.3212(2) 0.2850(3) 0.26544(19) 0.0772(8) Uani 1 1 d .
H13A H 0.2743 0.2404 0.2948 0.093 Uiso 1 1 calc R
C14 C 0.35208(19) 0.2456(2) 0.18498(17) 0.0645(6) Uani 1 1 d .
C15 C 0.41994(16) 0.31749(18) 0.13944(14) 0.0500(5) Uani 1 1 d .
C16 C 0.46064(18) 0.27285(18) 0.06344(15) 0.0537(5) Uani 1 1 d .
C17 C 0.4305(2) 0.1653(2) 0.03108(18) 0.0755(7) Uani 1 1 d .
H17A H 0.4558 0.1378 -0.0199 0.091 Uiso 1 1 calc R
C18 C 0.3609(3) 0.0967(2) 0.0755(2) 0.0917(10) Uani 1 1 d .
H18A H 0.3405 0.0235 0.0536 0.110 Uiso 1 1 calc R
C19 C 0.3232(2) 0.1352(2) 0.1497(2) 0.0863(9) Uani 1 1 d .
H19A H 0.2772 0.0879 0.1778 0.104 Uiso 1 1 calc R
C20 C 0.6836(2) 0.2066(2) 0.05584(16) 0.0705(7) Uani 1 1 d .
H20A H 0.6391 0.1566 0.0831 0.085 Uiso 1 1 calc R
C21 C 0.7904(3) 0.1766(3) 0.0512(2) 0.0920(11) Uani 1 1 d .
C22 C 0.8555(3) 0.2518(4) 0.0098(2) 0.1002(12) Uani 1 1 d .
H22A H 0.9272 0.2320 0.0065 0.120 Uiso 1 1 calc R
C23 C 0.8162(2) 0.3555(3) -0.02685(19) 0.0838(9) Uani 1 1 d .
C24 C 0.70997(18) 0.3837(2) -0.02133(15) 0.0628(6) Uani 1 1 d .
H24A H 0.6827 0.4533 -0.0458 0.075 Uiso 1 1 calc R
C25 C 0.64275(18) 0.31050(19) 0.02003(14) 0.0545(5) Uani 1 1 d .
C26 C 0.8337(4) 0.0635(4) 0.0930(2) 0.1423(18) Uani 1 1 d .
H26A H 0.7939 -0.0010 0.0659 0.213 Uiso 1 1 calc R
H26B H 0.8262 0.0646 0.1546 0.213 Uiso 1 1 calc R
H26C H 0.9084 0.0553 0.0847 0.213 Uiso 1 1 calc R
C27 C 0.8854(2) 0.4382(4) -0.0734(3) 0.1243(15) Uani 1 1 d .
H27A H 0.9571 0.4074 -0.0713 0.186 Uiso 1 1 calc R
H27B H 0.8876 0.5129 -0.0450 0.186 Uiso 1 1 calc R
H27C H 0.8554 0.4467 -0.1336 0.186 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_1
C10 N1 C1 116.35(16) .
C10 N1 C7 123.81(16) .
C1 N1 C7 119.80(15) .
C1 N2 C16 112.28(16) .
C1 N2 C25 117.14(17) .
C16 N2 C25 121.44(18) .
C1 C1 N1 123.0(2) 3_665
C1 C1 N2 121.5(2) 3_665
N1 C1 N2 115.10(17) .
C7 C2 C3 120.6(2) .
C4 C3 C2 118.4(2) .
C4 C3 C8 121.1(3) .
C2 C3 C8 120.5(3) .
C3 C4 C5 122.0(2) .
C4 C5 C6 118.6(2) .
C4 C5 C9 121.1(3) .
C6 C5 C9 120.3(3) .
C7 C6 C5 120.4(2) .
C2 C7 C6 119.9(2) .
C2 C7 N1 118.71(18) .
C6 C7 N1 121.35(19) .
C11 C10 N1 124.0(2) .
C11 C10 C15 118.90(19) .
N1 C10 C15 117.10(18) .
C10 C11 C12 120.4(2) .
C13 C12 C11 121.4(2) .
C12 C13 C14 120.5(2) .
C13 C14 C19 122.8(2) .
C13 C14 C15 118.8(2) .
C19 C14 C15 118.3(2) .
C16 C15 C14 118.8(2) .
C16 C15 C10 121.38(18) .
C14 C15 C10 119.6(2) .
C17 C16 C15 121.0(2) .
C17 C16 N2 122.0(2) .
C15 C16 N2 117.02(18) .
C16 C17 C18 119.4(3) .
C19 C18 C17 121.2(3) .
C18 C19 C14 121.2(2) .
C21 C20 C25 120.5(3) .
C20 C21 C22 119.0(3) .
C20 C21 C26 119.3(4) .
C22 C21 C26 121.6(3) .
C23 C22 C21 121.4(3) .
C24 C23 C22 118.6(3) .
C24 C23 C27 119.1(3) .
C22 C23 C27 122.3(3) .
C23 C24 C25 121.4(3) .
C20 C25 C24 119.1(2) .
C20 C25 N2 122.2(2) .
C24 C25 N2 118.7(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C10 1.400(2) .
N1 C1 1.414(2) .
N1 C7 1.437(2) .
N2 C1 1.421(2) .
N2 C16 1.418(3) .
N2 C25 1.424(3) .
C1 C1 1.336(4) 3_665
C2 C7 1.375(3) .
C2 C3 1.389(3) .
C3 C4 1.377(4) .
C3 C8 1.511(4) .
C4 C5 1.378(4) .
C5 C6 1.384(3) .
C5 C9 1.518(4) .
C6 C7 1.381(3) .
C10 C11 1.378(3) .
C10 C15 1.427(3) .
C11 C12 1.400(3) .
C12 C13 1.353(4) .
C13 C14 1.407(4) .
C14 C19 1.409(4) .
C14 C15 1.420(3) .
C15 C16 1.417(3) .
C16 C17 1.367(3) .
C17 C18 1.404(4) .
C18 C19 1.351(4) .
C20 C21 1.388(4) .
C20 C25 1.386(3) .
C21 C22 1.387(5) .
C21 C26 1.519(5) .
C22 C23 1.382(5) .
C23 C24 1.378(3) .
C23 C27 1.515(5) .
C24 C25 1.390(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C10 N1 C1 C1 128.1(2) 3_665
C7 N1 C1 C1 -53.9(3) 3_665
C10 N1 C1 N2 -44.0(2) .
C7 N1 C1 N2 134.04(18) .
C16 N2 C1 C1 -118.6(3) 3_665
C25 N2 C1 C1 93.9(3) 3_665
C16 N2 C1 N1 53.7(2) .
C25 N2 C1 N1 -93.8(2) .
C7 C2 C3 C4 1.4(4) .
C7 C2 C3 C8 -178.6(3) .
C2 C3 C4 C5 -1.9(4) .
C8 C3 C4 C5 178.1(3) .
C3 C4 C5 C6 0.4(4) .
C3 C4 C5 C9 -179.7(3) .
C4 C5 C6 C7 1.8(4) .
C9 C5 C6 C7 -178.1(3) .
C3 C2 C7 C6 0.7(3) .
C3 C2 C7 N1 -178.7(2) .
C5 C6 C7 C2 -2.4(3) .
C5 C6 C7 N1 177.0(2) .
C10 N1 C7 C2 120.2(2) .
C1 N1 C7 C2 -57.6(3) .
C10 N1 C7 C6 -59.2(3) .
C1 N1 C7 C6 123.0(2) .
C1 N1 C10 C11 -168.55(19) .
C7 N1 C10 C11 13.5(3) .
C1 N1 C10 C15 11.0(3) .
C7 N1 C10 C15 -166.95(18) .
N1 C10 C11 C12 174.6(2) .
C15 C10 C11 C12 -4.9(3) .
C10 C11 C12 C13 -0.1(4) .
C11 C12 C13 C14 4.0(4) .
C12 C13 C14 C19 173.9(3) .
C12 C13 C14 C15 -2.8(4) .
C13 C14 C15 C16 173.2(2) .
C19 C14 C15 C16 -3.6(3) .
C13 C14 C15 C10 -2.2(3) .
C19 C14 C15 C10 -179.0(2) .
C11 C10 C15 C16 -169.3(2) .
N1 C10 C15 C16 11.1(3) .
C11 C10 C15 C14 6.0(3) .
N1 C10 C15 C14 -173.50(19) .
C14 C15 C16 C17 3.8(3) .
C10 C15 C16 C17 179.2(2) .
C14 C15 C16 N2 -175.97(19) .
C10 C15 C16 N2 -0.6(3) .
C1 N2 C16 C17 149.4(2) .
C25 N2 C16 C17 -64.6(3) .
C1 N2 C16 C15 -30.8(3) .
C25 N2 C16 C15 115.1(2) .
C15 C16 C17 C18 -2.1(4) .
N2 C16 C17 C18 177.7(2) .
C16 C17 C18 C19 0.1(5) .
C17 C18 C19 C14 0.1(5) .
C13 C14 C19 C18 -175.0(3) .
C15 C14 C19 C18 1.7(4) .
C25 C20 C21 C22 -0.4(4) .
C25 C20 C21 C26 178.6(2) .
C20 C21 C22 C23 0.0(4) .
C26 C21 C22 C23 -179.0(3) .
C21 C22 C23 C24 0.2(4) .
C21 C22 C23 C27 -179.2(3) .
C22 C23 C24 C25 0.1(4) .
C27 C23 C24 C25 179.4(2) .
C21 C20 C25 C24 0.6(3) .
C21 C20 C25 N2 179.9(2) .
C23 C24 C25 C20 -0.5(3) .
C23 C24 C25 N2 -179.8(2) .
C1 N2 C25 C20 144.2(2) .
C16 N2 C25 C20 -0.2(3) .
C1 N2 C25 C24 -36.5(3) .
C16 N2 C25 C24 179.11(19) .
