#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504802.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_1504802
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            'C32 H28 Ag Cl F2 N2'
_chemical_formula_weight         621.88
_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
;
2008-03-24 # 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                   17.5486(14)
_cell_length_b                   23.6751(19)
_cell_length_c                   6.7198(5)
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     2791.8(4)
_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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9030
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  0.9505
_exptl_absorpt_correction_T_min  0.8545
_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    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0382P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0655
_reflns_number_gt                2811
_reflns_number_total             3147
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol8012765_si_004.cif
_cod_data_source_block           ogle13
_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               1504802
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
Ag1 Ag 0.0000 0.520167(9) 0.24996(3) 0.03585(9) Uani 1 2 d S
N1 N 0.06075(10) 0.39699(7) 0.2734(5) 0.0304(5) Uani 1 1 d .
F1 F 0.23771(12) 0.15760(8) 0.3151(3) 0.0738(7) Uani 1 1 d .
Cl1 Cl 0.0000 0.61894(4) 0.2740(2) 0.0459(3) Uani 1 2 d S
C1 C 0.0000 0.43211(13) 0.2634(13) 0.0299(7) Uani 1 2 d S
C2 C 0.03822(14) 0.34114(10) 0.2928(3) 0.0316(6) Uani 1 1 d .
C3 C 0.09133(15) 0.29264(10) 0.2986(4) 0.0351(7) Uani 1 1 d .
C4 C 0.13206(18) 0.27778(11) 0.1308(5) 0.0437(7) Uani 1 1 d .
H4A H 0.1265 0.2991 0.0120 0.052 Uiso 1 1 calc R
C5 C 0.18170(19) 0.23129(13) 0.1348(6) 0.0491(7) Uani 1 1 d .
H5A H 0.2100 0.2206 0.0203 0.059 Uiso 1 1 calc R
C6 C 0.18784(17) 0.20230(13) 0.3074(5) 0.0506(9) Uani 1 1 d .
C7 C 0.14823(18) 0.21506(13) 0.4774(5) 0.0478(7) Uani 1 1 d .
H7A H 0.1537 0.1928 0.5943 0.057 Uiso 1 1 calc R
C8 C 0.10006(17) 0.26127(12) 0.4736(5) 0.0415(6) Uani 1 1 d .
H8A H 0.0728 0.2717 0.5900 0.050 Uiso 1 1 calc R
C9 C 0.13965(12) 0.41376(9) 0.2646(6) 0.0348(5) Uani 1 1 d .
C10 C 0.16854(18) 0.43604(12) 0.0913(5) 0.0473(7) Uani 1 1 d .
H10A H 0.1360 0.4435 -0.0186 0.057 Uiso 1 1 calc R
C11 C 0.24600(19) 0.44739(15) 0.0797(6) 0.0577(9) Uani 1 1 d .
H11A H 0.2665 0.4630 -0.0390 0.069 Uiso 1 1 calc R
C12 C 0.29273(16) 0.43642(12) 0.2354(11) 0.0613(10) Uani 1 1 d .
H12A H 0.3458 0.4438 0.2246 0.074 Uiso 1 1 calc R
C13 C 0.26339(19) 0.41451(15) 0.4099(7) 0.0606(10) Uani 1 1 d .
H13A H 0.2963 0.4068 0.5188 0.073 Uiso 1 1 calc R
C14 C 0.18548(17) 0.40370(13) 0.4267(5) 0.0454(7) Uani 1 1 d .
H14A H 0.1646 0.3897 0.5474 0.055 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'
F F 0.0171 0.0103 '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 173.6(2) . .
C1 N1 C2 111.47(19) . .
C1 N1 C9 125.81(19) . .
C2 N1 C9 122.72(18) . .
N1 C1 N1 103.9(3) . 4
N1 C1 Ag1 128.01(12) . .
N1 C1 Ag1 128.01(12) 4 .
C2 C2 N1 106.57(12) 4 .
C2 C2 C3 129.05(13) 4 .
N1 C2 C3 124.3(2) . .
C4 C3 C8 119.6(3) . .
C4 C3 C2 120.2(2) . .
C8 C3 C2 120.2(2) . .
C3 C4 C5 120.4(3) . .
C3 C4 H4A 119.8 . .
C5 C4 H4A 119.8 . .
C6 C5 C4 117.6(3) . .
C6 C5 H5A 121.2 . .
C4 C5 H5A 121.2 . .
C5 C6 C7 124.2(3) . .
C5 C6 F1 118.3(3) . .
C7 C6 F1 117.5(3) . .
C6 C7 C8 117.9(3) . .
C6 C7 H7A 121.0 . .
C8 C7 H7A 121.0 . .
C7 C8 C3 120.2(3) . .
C7 C8 H8A 119.9 . .
C3 C8 H8A 119.9 . .
C14 C9 C10 121.5(2) . .
C14 C9 N1 118.8(3) . .
C10 C9 N1 119.6(3) . .
C9 C10 C11 118.9(3) . .
C9 C10 H10A 120.6 . .
C11 C10 H10A 120.6 . .
C12 C11 C10 120.8(4) . .
C12 C11 H11A 119.6 . .
C10 C11 H11A 119.6 . .
C11 C12 C13 120.1(3) . .
C11 C12 H12A 119.9 . .
C13 C12 H12A 119.9 . .
C12 C13 C14 120.1(4) . .
C12 C13 H13A 119.9 . .
C14 C13 H13A 119.9 . .
C9 C14 C13 118.5(3) . .
C9 C14 H14A 120.7 . .
C13 C14 H14A 120.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 C1 2.087(3) .
Ag1 Cl1 2.3440(9) .
N1 C1 1.354(3) .
N1 C2 1.386(3) .
N1 C9 1.442(3) .
F1 C6 1.374(3) .
C1 N1 1.354(3) 4
C2 C2 1.341(5) 4
C2 C3 1.479(3) .
C3 C4 1.380(4) .
C3 C8 1.399(4) .
C4 C5 1.404(4) .
C4 H4A 0.9500 .
C5 C6 1.352(5) .
C5 H5A 0.9500 .
C6 C7 1.371(4) .
C7 C8 1.383(4) .
C7 H7A 0.9500 .
C8 H8A 0.9500 .
C9 C14 1.374(5) .
C9 C10 1.376(5) .
C10 C11 1.388(5) .
C10 H10A 0.9500 .
C11 C12 1.355(7) .
C11 H11A 0.9500 .
C12 C13 1.382(7) .
C12 H12A 0.9500 .
C13 C14 1.395(4) .
C13 H13A 0.9500 .
C14 H14A 0.9500 .
