#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504801.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_1504801
loop_
_publ_author_name
'Ogle, James W.'
'Zhang, Jubo'
'Reibenspies, Joseph H.'
'Abboud, Khalil A.'
'Miller, Stephen A.'
_publ_section_title
;
 Synthesis of electronically diverse tetraarylimidazolylidene carbenes via
 catalytic aldimine coupling.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3677
_journal_page_last               3680
_journal_paper_doi               10.1021/ol8012765
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C28 H22 Ag Cl3 N2'
_chemical_formula_weight         600.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2007-11-30 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9545(11)
_cell_length_b                   23.2586(15)
_cell_length_c                   6.5773(4)
_cell_measurement_reflns_used    96
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     2593.7(3)
_computing_cell_refinement
'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)'
_computing_data_collection       'Bruker SMART v5.624 (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL v6.14 (Bruker 2000)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement  'Bruker SHELXTL v6.14'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       '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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8743
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.49
_diffrn_standards_decay_%        1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.106
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_correction_T_min  0.8204
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL  v6.12 (Bruker 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0374P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0630
_reflns_number_gt                2874
_reflns_number_total             3002
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol8012765_si_003.cif
_cod_data_source_block           ogle1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      Cmc21
_cod_database_code               1504801
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag -0.5000 1.016994(8) -0.35686(3) 0.02501(8) Uani 1 2 d S . .
Cl1 Cl -0.5000 1.11755(3) -0.38223(16) 0.0350(2) Uani 1 2 d S . .
N1 N -0.43718(11) 0.89221(7) -0.3834(4) 0.0213(4) Uani 1 1 d . . .
C1 C -0.5000 0.92773(12) -0.3739(9) 0.0196(6) Uani 1 2 d S . .
C2 C -0.46040(14) 0.83476(9) -0.4081(3) 0.0218(5) Uani 1 1 d . . .
C3 C -0.35566(13) 0.90979(8) -0.3732(6) 0.0247(5) Uani 1 1 d . . .
C4 C -0.32672(18) 0.93148(10) -0.1921(5) 0.0322(6) Uani 1 1 d . . .
H4A H -0.3605 0.9371 -0.0785 0.039 Uiso 1 1 calc R . .
C5 C -0.24687(18) 0.94491(11) -0.1804(5) 0.0403(7) Uani 1 1 d . . .
H5A H -0.2260 0.9600 -0.0574 0.048 Uiso 1 1 calc R . .
C6 C -0.19810(16) 0.93677(10) -0.3422(8) 0.0428(7) Uani 1 1 d . . .
H6A H -0.1436 0.9459 -0.3310 0.051 Uiso 1 1 calc R . .
C7 C -0.22759(18) 0.91536(11) -0.5223(5) 0.0409(7) Uani 1 1 d . . .
H7A H -0.1935 0.9098 -0.6352 0.049 Uiso 1 1 calc R . .
C8 C -0.30774(16) 0.90190(11) -0.5387(5) 0.0317(6) Uani 1 1 d . . .
H8A H -0.3286 0.8875 -0.6626 0.038 Uiso 1 1 calc R . .
C9 C -0.40524(15) 0.78567(10) -0.4176(4) 0.0240(5) Uani 1 1 d . . .
C10 C -0.39864(16) 0.75386(11) -0.5964(4) 0.0306(6) Uani 1 1 d . . .
H10A H -0.4273 0.7649 -0.7143 0.037 Uiso 1 1 calc R . .
C11 C -0.34958(19) 0.70559(11) -0.6009(5) 0.0378(7) Uani 1 1 d . . .
H11A H -0.3457 0.6831 -0.7210 0.045 Uiso 1 1 calc R . .
C12 C -0.30690(17) 0.69069(12) -0.4304(5) 0.0396(7) Uani 1 1 d . . .
H12A H -0.2732 0.6581 -0.4346 0.048 Uiso 1 1 calc R . .
C13 C -0.31250(18) 0.72243(11) -0.2541(5) 0.0366(6) Uani 1 1 d . . .
H13A H -0.2827 0.7118 -0.1376 0.044 Uiso 1 1 calc R . .
C14 C -0.36188(17) 0.77012(11) -0.2473(4) 0.0325(6) Uani 1 1 d . . .
H14A H -0.3659 0.7921 -0.1260 0.039 Uiso 1 1 calc R . .
Cl2 Cl -0.5000 0.63904(12) -0.9944(3) 0.1085(7) Uani 1 2 d S A .
Cl3 Cl -0.4823(3) 0.57114(9) -1.3573(9) 0.1387(17) Uani 0.50 1 d P A -2
C15 C -0.5000 0.6398(2) -1.2590(10) 0.0688(16) Uani 1 2 d S . .
H15A H -0.4593 0.6654 -1.3046 0.083 Uiso 0.50 1 d PR A -1
H15C H -0.4501 0.6538 -1.3069 0.083 Uiso 0.50 1 d PR A -2
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 '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
_geom_angle_site_symmetry_3
C1 Ag1 Cl1 172.84(18) . .
C1 N1 C2 111.54(18) . .
C1 N1 C3 125.48(17) . .
C2 N1 C3 122.97(18) . .
N1 C1 N1 104.2(2) . 4_455
N1 C1 Ag1 127.87(12) . .
N1 C1 Ag1 127.87(12) 4_455 .
C2 C2 N1 106.29(13) 4_455 .
C2 C2 C9 129.28(12) 4_455 .
N1 C2 C9 124.3(2) . .
C8 C3 C4 121.5(2) . .
C8 C3 N1 119.5(3) . .
C4 C3 N1 118.9(3) . .
C3 C4 C5 118.3(3) . .
C3 C4 H4A 120.8 . .
C5 C4 H4A 120.8 . .
C6 C5 C4 121.1(3) . .
C6 C5 H5A 119.4 . .
C4 C5 H5A 119.4 . .
C5 C6 C7 120.1(3) . .
C5 C6 H6A 119.9 . .
C7 C6 H6A 119.9 . .
C6 C7 C8 120.0(3) . .
C6 C7 H7A 120.0 . .
C8 C7 H7A 120.0 . .
C3 C8 C7 119.0(3) . .
C3 C8 H8A 120.5 . .
C7 C8 H8A 120.5 . .
C14 C9 C10 120.0(2) . .
C14 C9 C2 120.2(2) . .
C10 C9 C2 119.8(2) . .
C9 C10 C11 119.5(3) . .
C9 C10 H10A 120.3 . .
C11 C10 H10A 120.3 . .
C12 C11 C10 119.8(3) . .
C12 C11 H11A 120.1 . .
C10 C11 H11A 120.1 . .
C13 C12 C11 120.9(3) . .
C13 C12 H12A 119.5 . .
C11 C12 H12A 119.5 . .
C12 C13 C14 119.7(3) . .
C12 C13 H13A 120.1 . .
C14 C13 H13A 120.1 . .
C9 C14 C13 120.1(3) . .
C9 C14 H14A 120.0 . .
C13 C14 H14A 120.0 . .
Cl2 C15 Cl3 111.2(4) . .
Cl2 C15 Cl3 111.2(4) . 4_455
Cl3 C15 Cl3 19.8(3) . 4_455
Cl2 C15 H15A 108.6 . .
Cl3 C15 H15A 109.2 . .
Cl3 C15 H15A 125.1 4_455 .
Cl2 C15 H15C 109.4 . .
Cl3 C15 H15C 92.2 . .
Cl3 C15 H15C 109.9 4_455 .
H15A C15 H15C 18.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 C1 2.079(3) .
Ag1 Cl1 2.3446(8) .
N1 C1 1.349(2) .
N1 C2 1.402(3) .
N1 C3 1.443(3) .
C1 N1 1.349(2) 4_455
C2 C2 1.343(5) 4_455
C2 C9 1.477(3) .
C3 C8 1.370(4) .
C3 C4 1.384(4) .
C4 C5 1.392(4) .
C4 H4A 0.9500 .
C5 C6 1.361(5) .
C5 H5A 0.9500 .
C6 C7 1.379(5) .
C6 H6A 0.9500 .
C7 C8 1.399(4) .
C7 H7A 0.9500 .
C8 H8A 0.9500 .
C9 C14 1.388(4) .
C9 C10 1.394(3) .
C10 C11 1.398(4) .
C10 H10A 0.9500 .
C11 C12 1.379(4) .
C11 H11A 0.9500 .
C12 C13 1.378(4) .
C12 H12A 0.9500 .
C13 C14 1.390(4) .
C13 H13A 0.9500 .
C14 H14A 0.9500 .
Cl2 C15 1.740(7) .
Cl3 C15 1.748(6) .
C15 Cl3 1.748(6) 4_455
C15 H15A 0.9600 .
C15 H15C 0.9600 .
