#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:18:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178621 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/32/4073226.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_4073226
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            'C28 H29 Cl2 N2 O'
_chemical_formula_weight         480.43
_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                 91.796(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.732(2)
_cell_length_b                   13.418(2)
_cell_length_c                   14.026(2)
_cell_measurement_reflns_used    912
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.55
_cell_volume                     2583.1(7)
_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      120(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23844
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0722P)²+1.0167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                5178
_reflns_number_total             5991
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om0701827si20070227_100730.cif
_cod_data_source_block           darr022s
_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_cell_volume        2583.3(7)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4073226
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
Cl Cl 0.87269(3) 0.57136(3) 0.61775(3) 0.02790(12) Uani 1 1 d .
N1 N 1.02435(9) 0.68221(9) 0.87492(9) 0.0191(3) Uani 1 1 d .
N2 N 0.85952(9) 0.70070(9) 0.90357(9) 0.0191(3) Uani 1 1 d .
O O 0.97147(10) 0.89887(10) 0.91652(10) 0.0316(3) Uani 1 1 d .
H1A H 0.9443(16) 0.9093(17) 0.9684(17) 0.038 Uiso 1 1 d .
H2A H 1.0098(17) 0.9459(18) 0.9090(16) 0.038 Uiso 1 1 d .
C1 C 0.93548(11) 0.70914(11) 0.84857(11) 0.0192(3) Uani 1 1 d .
H1 H 0.9250(13) 0.7356(14) 0.7882(14) 0.023 Uiso 1 1 d .
C2 C 1.11149(11) 0.64931(11) 0.72867(11) 0.0218(3) Uani 1 1 d .
H2 H 1.0639 0.6007 0.7112 0.026 Uiso 1 1 calc R
C3 C 1.19045(12) 0.66707(12) 0.67093(11) 0.0241(3) Uani 1 1 d .
C4 C 1.25772(11) 0.73965(12) 0.69826(12) 0.0249(3) Uani 1 1 d .
H4 H 1.3124 0.7507 0.6598 0.030 Uiso 1 1 calc R
C5 C 1.24756(11) 0.79690(12) 0.78036(12) 0.0245(3) Uani 1 1 d .
C6 C 1.16899(11) 0.77798(12) 0.83772(12) 0.0234(3) Uani 1 1 d .
H6 H 1.1601 0.8157 0.8941 0.028 Uiso 1 1 calc R
C7 C 1.10370(10) 0.70338(11) 0.81149(11) 0.0197(3) Uani 1 1 d .
C8 C 1.19980(15) 0.60698(15) 0.58093(13) 0.0368(4) Uani 1 1 d .
H8A H 1.2106 0.5368 0.5974 0.055 Uiso 1 1 calc R
H8B H 1.2550 0.6318 0.5453 0.055 Uiso 1 1 calc R
H8C H 1.1399 0.6133 0.5416 0.055 Uiso 1 1 calc R
C9 C 1.31719(13) 0.88009(15) 0.80618(15) 0.0365(4) Uani 1 1 d .
H9A H 1.2807 0.9371 0.8302 0.055 Uiso 1 1 calc R
H9B H 1.3522 0.9002 0.7495 0.055 Uiso 1 1 calc R
H9C H 1.3639 0.8571 0.8556 0.055 Uiso 1 1 calc R
C10 C 1.04506(11) 0.64198(11) 0.96743(11) 0.0199(3) Uani 1 1 d .
C11 C 1.13568(11) 0.60799(12) 0.99463(12) 0.0241(3) Uani 1 1 d .
H11 H 1.1879 0.6108 0.9519 0.029 Uiso 1 1 calc R
C12 C 1.15015(12) 0.56857(12) 1.08738(13) 0.0276(4) Uani 1 1 d .
H12 H 1.2128 0.5445 1.1065 0.033 Uiso 1 1 calc R
C13 C 1.07644(13) 0.56423(12) 1.15024(12) 0.0279(4) Uani 1 1 d .
H13 H 1.0887 0.5388 1.2127 0.033 Uiso 1 1 calc R
C14 C 0.98154(12) 0.59752(11) 1.12284(11) 0.0240(3) Uani 1 1 d .
C15 C 0.96558(11) 0.63614(11) 1.02928(11) 0.0200(3) Uani 1 1 d .
C16 C 0.87022(11) 0.66427(11) 0.99917(11) 0.0207(3) Uani 1 1 d .
C17 C 0.79308(12) 0.65394(12) 1.05734(12) 0.0252(3) Uani 1 1 d .
H17 H 0.7290 0.6705 1.0352 0.030 Uiso 1 1 calc R
C18 C 0.81012(13) 0.61815(12) 1.15132(12) 0.0289(4) Uani 1 1 d .
H18 H 0.7570 0.6123 1.1927 0.035 Uiso 1 1 calc R
C19 C 0.90110(14) 0.59197(12) 1.18358(12) 0.0283(4) Uani 1 1 d .
H19 H 0.9108 0.5698 1.2475 0.034 Uiso 1 1 calc R
C20 C 0.72374(11) 0.68466(12) 0.78925(11) 0.0229(3) Uani 1 1 d .
H20 H 0.7548 0.6282 0.7630 0.027 Uiso 1 1 calc R
C21 C 0.63480(11) 0.71879(13) 0.75066(12) 0.0271(3) Uani 1 1 d .
C22 C 0.59134(11) 0.80070(13) 0.79217(12) 0.0284(4) Uani 1 1 d .
H22 H 0.5307 0.8238 0.7664 0.034 Uiso 1 1 calc R
C23 C 0.63369(11) 0.85036(13) 0.87061(12) 0.0267(3) Uani 1 1 d .
C24 C 0.72306(11) 0.81738(12) 0.90744(11) 0.0221(3) Uani 1 1 d .
H24 H 0.7544 0.8507 0.9597 0.027 Uiso 1 1 calc R
C25 C 0.76559(10) 0.73455(11) 0.86620(11) 0.0203(3) Uani 1 1 d .
C26 C 0.58920(14) 0.66696(17) 0.66464(14) 0.0404(5) Uani 1 1 d .
H26A H 0.6382 0.6586 0.6159 0.061 Uiso 1 1 calc R
H26B H 0.5351 0.7073 0.6387 0.061 Uiso 1 1 calc R
H26C H 0.5648 0.6015 0.6835 0.061 Uiso 1 1 calc R
C27 C 0.58415(14) 0.93930(16) 0.91365(15) 0.0410(5) Uani 1 1 d .
H27A H 0.6240 0.9644 0.9677 0.061 Uiso 1 1 calc R
H27B H 0.5200 0.9195 0.9358 0.061 Uiso 1 1 calc R
H27C H 0.5763 0.9918 0.8654 0.061 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C1 N1 C10 121.12(13)
C1 N1 C7 118.72(13)
C10 N1 C7 119.88(12)
C1 N2 C16 121.11(13)
C1 N2 C25 118.14(13)
C16 N2 C25 120.66(12)
N1 C1 N2 123.72(14)
C7 C2 C3 118.86(14)
C4 C3 C2 118.85(15)
C4 C3 C8 122.23(15)
C2 C3 C8 118.92(15)
C3 C4 C5 122.10(15)
C6 C5 C4 118.49(15)
C6 C5 C9 119.65(15)
C4 C5 C9 121.83(15)
C7 C6 C5 119.07(15)
C2 C7 C6 122.54(14)
C2 C7 N1 119.48(13)
C6 C7 N1 117.97(13)
C11 C10 C15 121.46(14)
C11 C10 N1 122.25(14)
C15 C10 N1 116.26(13)
C10 C11 C12 118.82(16)
C13 C12 C11 121.69(15)
C12 C13 C14 120.34(15)
C19 C14 C13 123.14(15)
C19 C14 C15 118.25(15)
C13 C14 C15 118.59(15)
C16 C15 C10 121.73(14)
C16 C15 C14 119.18(14)
C10 C15 C14 119.05(14)
C17 C16 C15 121.55(14)
C17 C16 N2 122.44(14)
C15 C16 N2 115.98(13)
C16 C17 C18 118.86(15)
C19 C18 C17 121.34(16)
C18 C19 C14 120.72(15)
C25 C20 C21 118.78(14)
C22 C21 C20 118.63(15)
C22 C21 C26 121.78(15)
C20 C21 C26 119.58(15)
C21 C22 C23 122.30(15)
C24 C23 C22 118.82(15)
C24 C23 C27 120.49(15)
C22 C23 C27 120.69(15)
C23 C24 C25 118.54(14)
C20 C25 C24 122.91(14)
C20 C25 N2 118.34(13)
C24 C25 N2 118.72(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3147(19)
N1 C10 1.4258(19)
N1 C7 1.4561(19)
N2 C1 1.3215(19)
N2 C16 1.4305(19)
N2 C25 1.4500(18)
C2 C7 1.377(2)
C2 C3 1.394(2)
C3 C4 1.388(2)
C3 C8 1.507(2)
C4 C5 1.395(2)
C5 C6 1.389(2)
C5 C9 1.507(2)
C6 C7 1.386(2)
C10 C11 1.368(2)
C10 C15 1.418(2)
C11 C12 1.413(2)
C12 C13 1.364(3)
C13 C14 1.419(2)
C14 C19 1.418(2)
C14 C15 1.422(2)
C15 C16 1.414(2)
C16 C17 1.364(2)
C17 C18 1.416(2)
C18 C19 1.362(3)
C20 C25 1.380(2)
C20 C21 1.398(2)
C21 C22 1.387(2)
C21 C26 1.511(2)
C22 C23 1.397(2)
C23 C24 1.389(2)
C23 C27 1.509(2)
C24 C25 1.390(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O H1A Cl 0.84(2) 2.36(2) 3.1947(14) 176(2) 4_576
O H2A Cl 0.83(2) 2.37(2) 3.1989(14) 176(2) 2_756
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
C10 N1 C1 N2 -0.6(2)
C7 N1 C1 N2 -174.51(14)
C16 N2 C1 N1 2.5(2)
C25 N2 C1 N1 179.16(14)
C7 C2 C3 C4 -0.9(2)
C7 C2 C3 C8 179.18(15)
C2 C3 C4 C5 -1.6(2)
C8 C3 C4 C5 178.34(16)
C3 C4 C5 C6 2.1(2)
C3 C4 C5 C9 -175.90(16)
C4 C5 C6 C7 -0.1(2)
C9 C5 C6 C7 177.92(15)
C3 C2 C7 C6 2.9(2)
C3 C2 C7 N1 -176.94(13)
C5 C6 C7 C2 -2.4(2)
C5 C6 C7 N1 177.44(13)
C1 N1 C7 C2 -72.24(18)
C10 N1 C7 C2 113.82(15)
C1 N1 C7 C6 107.88(16)
C10 N1 C7 C6 -66.06(18)
C1 N1 C10 C11 176.08(14)
C7 N1 C10 C11 -10.1(2)
C1 N1 C10 C15 -2.0(2)
C7 N1 C10 C15 171.77(13)
C15 C10 C11 C12 -1.6(2)
N1 C10 C11 C12 -179.58(14)
C10 C11 C12 C13 -0.4(2)
C11 C12 C13 C14 1.5(2)
C12 C13 C14 C19 177.84(15)
C12 C13 C14 C15 -0.6(2)
C11 C10 C15 C16 -175.22(14)
N1 C10 C15 C16 2.9(2)
C11 C10 C15 C14 2.4(2)
N1 C10 C15 C14 -179.47(13)
C19 C14 C15 C16 -2.1(2)
C13 C14 C15 C16 176.41(14)
C19 C14 C15 C10 -179.81(14)
C13 C14 C15 C10 -1.3(2)
C10 C15 C16 C17 176.73(14)
C14 C15 C16 C17 -0.9(2)
C10 C15 C16 N2 -1.2(2)
C14 C15 C16 N2 -178.86(13)
C1 N2 C16 C17 -179.44(14)
C25 N2 C16 C17 4.0(2)
C1 N2 C16 C15 -1.5(2)
C25 N2 C16 C15 -178.07(13)
C15 C16 C17 C18 2.7(2)
N2 C16 C17 C18 -179.46(14)
C16 C17 C18 C19 -1.5(2)
C17 C18 C19 C14 -1.6(2)
C13 C14 C19 C18 -175.11(15)
C15 C14 C19 C18 3.3(2)
C25 C20 C21 C22 -0.9(2)
C25 C20 C21 C26 178.27(16)
C20 C21 C22 C23 0.4(3)
C26 C21 C22 C23 -178.79(18)
C21 C22 C23 C24 0.9(3)
C21 C22 C23 C27 179.91(18)
C22 C23 C24 C25 -1.6(2)
C27 C23 C24 C25 179.36(16)
C21 C20 C25 C24 0.2(2)
C21 C20 C25 N2 -177.85(14)
C23 C24 C25 C20 1.1(2)
C23 C24 C25 N2 179.15(14)
C1 N2 C25 C20 65.49(19)
C16 N2 C25 C20 -117.82(16)
C1 N2 C25 C24 -112.61(16)
C16 N2 C25 C24 64.07(19)
