#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:25:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178650 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/61/4076185.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_4076185
loop_
_publ_author_name
'de Frémont, Pierre'
'Scott, Natalie M.'
'Stevens, Edwin D.'
'Ramnial, Taramatee'
'Lightbody, Owen C.'
'Macdonald, Charles L. B.'
'Clyburne, Jason A. C.'
'Abernethy, Colin D.'
'Nolan, Steven P.'
_publ_section_title
;
 Synthesis of Well-DefinedN-Heterocyclic Carbene Silver(I) Complexes
;
_journal_issue                   26
_journal_name_full               Organometallics
_journal_page_first              6301
_journal_paper_doi               10.1021/om050735i
_journal_volume                  24
_journal_year                    2005
_chemical_formula_sum            'C23 H32 Ag Cl N2'
_chemical_formula_weight         479.83
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5347(15)
_cell_length_b                   26.847(4)
_cell_length_c                   6.4849(9)
_cell_measurement_reflns_used    26639
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.530
_cell_measurement_theta_min      2.276
_cell_volume                     2008.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12591
_diffrn_reflns_theta_full        19.99
_diffrn_reflns_theta_max         19.99
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    1.148
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.858815
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.244
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_coef       0.0005(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         1871
_refine_ls_number_restraints     280
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0354P)²+3.0322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0657
_reflns_number_gt                1864
_reflns_number_total             1871
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om050735isi20050825_013934.cif
_cod_data_source_block           nol245
_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      Pna2(1)
_cod_database_code               4076185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, 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 0.38314(3) 0.341332(12) 0.70308(6) 0.01588(19) Uani 1 1 d U
Cl1 Cl 0.49585(12) 0.35138(6) 0.4107(3) 0.0244(4) Uani 1 1 d U
N1 N 0.2434(4) 0.37483(16) 1.0876(6) 0.0114(10) Uani 1 1 d U
C1 C 0.2872(4) 0.33638(18) 0.9765(8) 0.0080(12) Uani 1 1 d U
N2 N 0.2609(4) 0.29454(16) 1.0873(6) 0.0125(10) Uani 1 1 d U
C2 C 0.1901(4) 0.3579(2) 1.2638(7) 0.0118(13) Uani 1 1 d U
H2 H 0.1529 0.3777 1.3659 0.014 Uiso 1 1 calc R
C3 C 0.2010(5) 0.3072(2) 1.2637(7) 0.0134(13) Uani 1 1 d U
H3 H 0.1727 0.2849 1.3658 0.016 Uiso 1 1 calc R
C4 C 0.2494(4) 0.42846(18) 1.0253(8) 0.0126(11) Uani 1 1 d U
C5 C 0.1846(5) 0.4362(2) 0.8235(8) 0.0167(12) Uani 1 1 d U
H5A H 0.1028 0.4259 0.8401 0.020 Uiso 1 1 calc R
H5B H 0.2199 0.4154 0.7142 0.020 Uiso 1 1 calc R
C6 C 0.1902(4) 0.49168(19) 0.7607(7) 0.0152(13) Uani 1 1 d U
H6 H 0.1475 0.4967 0.6281 0.018 Uiso 1 1 calc R
C7 C 0.1347(5) 0.5232(2) 0.9299(9) 0.0182(12) Uani 1 1 d U
H7A H 0.1365 0.5587 0.8896 0.022 Uiso 1 1 calc R
H7B H 0.0526 0.5132 0.9477 0.022 Uiso 1 1 calc R
C8 C 0.1991(5) 0.51624(19) 1.1311(7) 0.0153(13) Uani 1 1 d U
H8 H 0.1617 0.5368 1.2412 0.018 Uiso 1 1 calc R
C9 C 0.1944(4) 0.46057(16) 1.1920(12) 0.0148(11) Uani 1 1 d U
H9A H 0.2361 0.4556 1.3238 0.018 Uiso 1 1 calc R
H9B H 0.1127 0.4504 1.2122 0.018 Uiso 1 1 calc R
C10 C 0.3765(4) 0.4452(2) 1.0031(9) 0.0152(12) Uani 1 1 d U
H10A H 0.4172 0.4409 1.1363 0.018 Uiso 1 1 calc R
H10B H 0.4160 0.4242 0.8990 0.018 Uiso 1 1 calc R
C11 C 0.3816(5) 0.5000(2) 0.9365(9) 0.0158(13) Uani 1 1 d U
H11 H 0.4644 0.5102 0.9189 0.019 Uiso 1 1 calc R
C12 C 0.3177(4) 0.50702(19) 0.7337(10) 0.0180(12) Uani 1 1 d U
H12A H 0.3543 0.4864 0.6252 0.022 Uiso 1 1 calc R
H12B H 0.3221 0.5423 0.6904 0.022 Uiso 1 1 calc R
C13 C 0.3255(5) 0.5321(2) 1.1054(9) 0.0196(13) Uani 1 1 d U
H13A H 0.3676 0.5277 1.2372 0.023 Uiso 1 1 calc R
H13B H 0.3294 0.5677 1.0665 0.023 Uiso 1 1 calc R
C14 C 0.2887(4) 0.24268(19) 1.0261(8) 0.0112(11) Uani 1 1 d U
C15 C 0.2441(4) 0.20683(16) 1.1910(11) 0.0136(11) Uani 1 1 d U
H15A H 0.2812 0.2147 1.3248 0.016 Uiso 1 1 calc R
H15B H 0.1593 0.2111 1.2071 0.016 Uiso 1 1 calc R
C16 C 0.2705(5) 0.15326(19) 1.1328(8) 0.0142(13) Uani 1 1 d U
H16 H 0.2405 0.1305 1.2425 0.017 Uiso 1 1 calc R
C17 C 0.4032(5) 0.1464(2) 1.1116(9) 0.0166(12) Uani 1 1 d U
H17A H 0.4211 0.1116 1.0736 0.020 Uiso 1 1 calc R
H17B H 0.4415 0.1539 1.2446 0.020 Uiso 1 1 calc R
C18 C 0.4488(4) 0.18240(19) 0.9418(8) 0.0140(12) Uani 1 1 d U
H18 H 0.5347 0.1786 0.9290 0.017 Uiso 1 1 calc R
C19 C 0.3928(4) 0.1703(2) 0.7384(12) 0.0174(14) Uani 1 1 d U
H19A H 0.4120 0.1357 0.6982 0.021 Uiso 1 1 calc R
H19B H 0.4226 0.1930 0.6304 0.021 Uiso 1 1 calc R
C20 C 0.2588(5) 0.1762(2) 0.7574(8) 0.0165(13) Uani 1 1 d U
H20 H 0.2209 0.1683 0.6226 0.020 Uiso 1 1 calc R
C21 C 0.2312(5) 0.2301(2) 0.8209(8) 0.0154(12) Uani 1 1 d U
H21A H 0.2592 0.2533 0.7132 0.019 Uiso 1 1 calc R
H21B H 0.1462 0.2343 0.8335 0.019 Uiso 1 1 calc R
C22 C 0.4204(4) 0.23606(19) 1.0045(9) 0.0146(12) Uani 1 1 d U
H22A H 0.4505 0.2594 0.8990 0.018 Uiso 1 1 calc R
H22B H 0.4586 0.2439 1.1373 0.018 Uiso 1 1 calc R
C23 C 0.2117(5) 0.1410(2) 0.9287(9) 0.0160(12) Uani 1 1 d U
H23A H 0.1268 0.1453 0.9423 0.019 Uiso 1 1 calc R
H23B H 0.2273 0.1059 0.8912 0.019 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'
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
C1 Ag1 Cl1 176.08(14)
C1 N1 C2 110.9(4)
C1 N1 C4 124.8(4)
C2 N1 C4 124.2(4)
N1 C1 N2 105.2(4)
N1 C1 Ag1 126.7(4)
N2 C1 Ag1 127.9(4)
C1 N2 C3 110.2(4)
C1 N2 C14 125.6(4)
C3 N2 C14 124.2(4)
C3 C2 N1 106.7(4)
C2 C3 N2 107.0(4)
N1 C4 C9 109.5(4)
N1 C4 C5 109.9(4)
C9 C4 C5 109.2(4)
N1 C4 C10 110.5(4)
C9 C4 C10 107.4(4)
C5 C4 C10 110.3(5)
C4 C5 C6 109.7(4)
C7 C6 C12 109.6(4)
C7 C6 C5 109.1(4)
C12 C6 C5 109.1(4)
C8 C7 C6 110.2(4)
C7 C8 C13 109.9(4)
C7 C8 C9 108.8(5)
C13 C8 C9 109.3(4)
C4 C9 C8 110.6(5)
C11 C10 C4 110.0(4)
C12 C11 C10 110.1(4)
C12 C11 C13 110.1(4)
C10 C11 C13 108.8(4)
C11 C12 C6 109.4(5)
C8 C13 C11 108.9(4)
N2 C14 C21 110.4(4)
N2 C14 C15 109.3(4)
C21 C14 C15 108.9(4)
N2 C14 C22 110.3(4)
C21 C14 C22 109.0(4)
C15 C14 C22 108.9(4)
C16 C15 C14 110.8(5)
C15 C16 C23 109.3(4)
C15 C16 C17 109.4(4)
C23 C16 C17 109.7(5)
C16 C17 C18 108.9(4)
C19 C18 C22 110.1(4)
C19 C18 C17 109.9(4)
C22 C18 C17 108.9(4)
C18 C19 C20 109.6(5)
C21 C20 C23 107.9(4)
C21 C20 C19 108.8(4)
C23 C20 C19 109.9(5)
C14 C21 C20 110.6(4)
C18 C22 C14 110.1(4)
C16 C23 C20 109.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ag1 C1 2.094(6)
Ag1 Cl1 2.3150(16)
N1 C1 1.357(7)
N1 C2 1.375(6)
N1 C4 1.497(7)
C1 N2 1.368(7)
N2 C3 1.379(6)
N2 C14 1.483(7)
C2 C3 1.368(8)
C4 C9 1.521(8)
C4 C5 1.521(7)
C4 C10 1.539(7)
C5 C6 1.546(7)
C6 C7 1.526(7)
C6 C12 1.537(7)
C7 C8 1.513(8)
C8 C13 1.528(8)
C8 C9 1.547(7)
C10 C11 1.536(8)
C11 C12 1.520(8)
C11 C13 1.537(8)
C14 C21 1.524(7)
C14 C15 1.528(8)
C14 C22 1.537(7)
C15 C16 1.518(7)
C16 C23 1.523(8)
C16 C17 1.548(7)
C17 C18 1.556(8)
C18 C19 1.504(9)
C18 C22 1.532(7)
C19 C20 1.558(7)
C20 C21 1.539(7)
C20 C23 1.556(8)
