#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:27:54 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178871 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/00/4110082.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_4110082
loop_
_publ_author_name
'Alois Fürstner'
'Manuel Alcarazo'
'Helga Krause'
'Christian W. Lehmann'
_publ_section_title
;
 Effective Modulation of the Donor Properties of N-Heterocyclic Carbene
 Ligands by "Through-Space" Communication within a Planar Chiral Scaffold
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12676
_journal_page_last               12677
_journal_paper_doi               10.1021/ja076028t
_journal_volume                  129
_journal_year                    2007
_chemical_compound_source        AcOEt
_chemical_formula_moiety         'C26 H30 Cl N2 Rh'
_chemical_formula_sum            'C26 H30 Cl N2 Rh'
_chemical_formula_weight         508.88
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_block_code                AVM-AA-341-01
_audit_creation_date             2007-02-16
_cell_angle_alpha                90.00
_cell_angle_beta                 117.46
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.2002(2)
_cell_length_b                   6.91270(10)
_cell_length_c                   18.6081(2)
_cell_measurement_reflns_used    173833
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.32
_cell_measurement_theta_min      2.91
_cell_volume                     2191.50(5)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47517
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.18
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Bruker AXS (2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.216
_refine_diff_density_min         -1.617
_refine_diff_density_rms         0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.646
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.646
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0460
_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)+(0.0606P)²+10.1525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.1791
_reflns_number_gt                4919
_reflns_number_total             5004
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja076028tsi20070810_084124.cif
_cod_data_source_block           5766
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2191.48(5)
_cod_database_code               4110082
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
C1 C 0.2349(3) 0.4854(7) 0.4275(3) 0.0119(9) Uani 1 1 d .
C2 C 0.2909(3) 0.4389(7) 0.3313(3) 0.0137(9) Uani 1 1 d .
C3 C 0.2881(3) 0.5146(8) 0.2628(3) 0.0175(10) Uani 1 1 d .
H3 H 0.3297 0.4914 0.2514 0.021 Uiso 1 1 calc R
C4 C 0.2231(3) 0.6297(7) 0.2071(3) 0.0168(10) Uani 1 1 d .
H4 H 0.2228 0.6762 0.1601 0.020 Uiso 1 1 calc R
C5 C 0.1620(3) 0.6712(7) 0.2225(3) 0.0154(9) Uani 1 1 d .
C6 C 0.1737(3) 0.6324(7) 0.3029(3) 0.0132(9) Uani 1 1 d .
C7 C 0.1320(3) 0.6727(8) 0.3437(3) 0.0142(9) Uani 1 1 d .
H7 H 0.0867 0.7474 0.3251 0.017 Uiso 1 1 calc R
C8 C 0.3315(3) 0.2513(8) 0.3676(3) 0.0167(10) Uani 1 1 d .
H8A H 0.3511 0.2564 0.4258 0.020 Uiso 1 1 calc R
H8B H 0.3762 0.2367 0.3571 0.020 Uiso 1 1 calc R
C9 C 0.2761(3) 0.0670(8) 0.3330(3) 0.0211(11) Uani 1 1 d .
H9A H 0.2999 -0.0233 0.3109 0.025 Uiso 1 1 calc R
H9B H 0.2715 0.0028 0.3770 0.025 Uiso 1 1 calc R
C10 C 0.1953(3) 0.1204(7) 0.2679(3) 0.0177(10) Uani 1 1 d .
C11 C 0.1808(3) 0.1591(8) 0.1886(3) 0.0191(10) Uani 1 1 d .
H11 H 0.2143 0.1084 0.1699 0.023 Uiso 1 1 calc R
C12 C 0.1176(3) 0.2711(8) 0.1372(3) 0.0200(10) Uani 1 1 d .
H12 H 0.1087 0.2931 0.0843 0.024 Uiso 1 1 calc R
C13 C 0.0668(3) 0.3521(8) 0.1645(3) 0.0180(10) Uani 1 1 d .
C14 C 0.0733(3) 0.2825(8) 0.2382(3) 0.0189(10) Uani 1 1 d .
H14 H 0.0347 0.3139 0.2533 0.023 Uiso 1 1 calc R
C15 C 0.1359(3) 0.1682(8) 0.2889(3) 0.0181(10) Uani 1 1 d .
H15 H 0.1387 0.1226 0.3371 0.022 Uiso 1 1 calc R
C16 C 0.0235(3) 0.5385(9) 0.1291(3) 0.0227(11) Uani 1 1 d .
H16A H -0.0168 0.5567 0.1461 0.027 Uiso 1 1 calc R
H16B H -0.0021 0.5298 0.0705 0.027 Uiso 1 1 calc R
C17 C 0.0806(3) 0.7193(8) 0.1567(3) 0.0193(10) Uani 1 1 d .
H17A H 0.0846 0.7702 0.1101 0.023 Uiso 1 1 calc R
H17B H 0.0582 0.8196 0.1761 0.023 Uiso 1 1 calc R
C18 C 0.1437(3) 0.5952(9) 0.4802(3) 0.0194(10) Uani 1 1 d .
H18A H 0.1651 0.4893 0.5174 0.029 Uiso 1 1 calc R
H18B H 0.0874 0.5904 0.4553 0.029 Uiso 1 1 calc R
H18C H 0.1616 0.7152 0.5090 0.029 Uiso 1 1 calc R
C21 C 0.4023(3) 0.5682(8) 0.5435(3) 0.0160(10) Uani 1 1 d .
H21 H 0.3806 0.5677 0.4874 0.019 Uiso 1 1 calc R
C22 C 0.3557(3) 0.6357(7) 0.5788(3) 0.0166(10) Uani 1 1 d .
H22 H 0.3061 0.6831 0.5441 0.020 Uiso 1 1 calc R
C23 C 0.3804(3) 0.6371(8) 0.6688(3) 0.0216(11) Uani 1 1 d .
H23A H 0.3343 0.6573 0.6765 0.026 Uiso 1 1 calc R
H23B H 0.4156 0.7452 0.6935 0.026 Uiso 1 1 calc R
C24 C 0.4215(3) 0.4495(9) 0.7126(3) 0.0230(11) Uani 1 1 d .
H24A H 0.4774 0.4605 0.7301 0.028 Uiso 1 1 calc R
H24B H 0.4142 0.4329 0.7604 0.028 Uiso 1 1 calc R
C25 C 0.3898(3) 0.2722(9) 0.6585(3) 0.0205(11) Uani 1 1 d .
H25 H 0.3458 0.2120 0.6569 0.025 Uiso 1 1 calc R
C26 C 0.4211(3) 0.1945(8) 0.6118(3) 0.0183(10) Uani 1 1 d .
H26 H 0.3974 0.0833 0.5826 0.022 Uiso 1 1 calc R
C27 C 0.4904(3) 0.2724(9) 0.6034(3) 0.0215(11) Uani 1 1 d .
H27A H 0.4918 0.2129 0.5569 0.026 Uiso 1 1 calc R
H27B H 0.5385 0.2379 0.6512 0.026 Uiso 1 1 calc R
C28 C 0.4867(3) 0.4955(9) 0.5930(3) 0.0184(10) Uani 1 1 d .
H28A H 0.5097 0.5561 0.6460 0.022 Uiso 1 1 calc R
H28B H 0.5174 0.5334 0.5661 0.022 Uiso 1 1 calc R
N1 N 0.2379(2) 0.5173(6) 0.3563(2) 0.0117(8) Uani 1 1 d .
N2 N 0.1697(2) 0.5814(6) 0.4177(2) 0.0129(8) Uani 1 1 d .
Cl1 Cl 0.23052(7) 0.09036(19) 0.51242(8) 0.0198(3) Uani 1 1 d .
Rh1 Rh 0.31602(2) 0.35874(5) 0.53119(2) 0.01103(15) Uani 1 1 d .
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'
Rh Rh -1.1178 0.9187 '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_publ_flag
N2 C1 N1 103.9(4) y
N2 C1 Rh1 126.5(3) y
N1 C1 Rh1 129.1(3) y
C3 C2 N1 116.1(5) y
C3 C2 C8 122.8(4) y
N1 C2 C8 119.3(4) y
C2 C3 C4 122.3(5) y
C2 C3 H3 118.8 n
C4 C3 H3 118.8 n
C5 C4 C3 120.8(5) y
C5 C4 H4 119.6 n
C3 C4 H4 119.6 n
C4 C5 C6 116.4(5) y
C4 C5 C17 123.1(5) y
C6 C5 C17 119.6(5) y
C7 C6 N1 105.7(4) y
C7 C6 C5 133.9(5) y
N1 C6 C5 120.2(4) y
C6 C7 N2 106.8(4) y
C6 C7 H7 126.6 n
N2 C7 H7 126.6 n
C2 C8 C9 113.4(4) y
C2 C8 H8A 108.9 n
C9 C8 H8A 108.9 n
C2 C8 H8B 108.9 n
C9 C8 H8B 108.9 n
H8A C8 H8B 107.7 n
C10 C9 C8 112.1(4) y
C10 C9 H9A 109.2 n
C8 C9 H9A 109.2 n
C10 C9 H9B 109.2 n
C8 C9 H9B 109.2 n
H9A C9 H9B 107.9 n
C11 C10 C15 117.2(5) y
C11 C10 C9 121.7(5) y
C15 C10 C9 120.1(5) y
C12 C11 C10 121.5(5) y
C12 C11 H11 119.2 n
C10 C11 H11 119.2 n
C11 C12 C13 120.3(5) y
C11 C12 H12 119.8 n
C13 C12 H12 119.8 n
C14 C13 C12 116.9(5) y
C14 C13 C16 120.1(5) y
C12 C13 C16 121.0(5) y
C15 C14 C13 121.3(5) y
C15 C14 H14 119.3 n
C13 C14 H14 119.3 n
C14 C15 C10 120.5(5) y
C14 C15 H15 119.8 n
C10 C15 H15 119.8 n
C13 C16 C17 111.9(4) y
C13 C16 H16A 109.2 n
C17 C16 H16A 109.2 n
C13 C16 H16B 109.2 n
C17 C16 H16B 109.2 n
H16A C16 H16B 107.9 n
C5 C17 C16 113.0(4) y
C5 C17 H17A 109.0 n
C16 C17 H17A 109.0 n
C5 C17 H17B 109.0 n
C16 C17 H17B 109.0 n
H17A C17 H17B 107.8 n
N2 C18 H18A 109.5 n
N2 C18 H18B 109.5 n
H18A C18 H18B 109.5 n
N2 C18 H18C 109.5 n
H18A C18 H18C 109.5 n
H18B C18 H18C 109.5 n
C22 C21 C28 123.4(4) y
C22 C21 Rh1 69.4(3) y
C28 C21 Rh1 113.3(4) y
C22 C21 H21 118.3 n
C28 C21 H21 118.3 n
Rh1 C21 H21 87.4 n
C21 C22 C23 125.0(5) y
C21 C22 Rh1 71.7(3) y
C23 C22 Rh1 109.8(4) y
C21 C22 H22 117.5 n
C23 C22 H22 117.5 n
Rh1 C22 H22 88.4 n
C22 C23 C24 113.7(4) y
C22 C23 H23A 108.8 n
C24 C23 H23A 108.8 n
C22 C23 H23B 108.8 n
C24 C23 H23B 108.8 n
H23A C23 H23B 107.7 n
C25 C24 C23 112.1(4) y
C25 C24 H24A 109.2 n
C23 C24 H24A 109.2 n
C25 C24 H24B 109.2 n
C23 C24 H24B 109.2 n
H24A C24 H24B 107.9 n
C26 C25 C24 125.0(5) y
C26 C25 Rh1 71.3(3) y
C24 C25 Rh1 110.8(4) y
C26 C25 H25 117.5 n
C24 C25 H25 117.5 n
Rh1 C25 H25 87.9 n
C25 C26 C27 126.1(5) y
C25 C26 Rh1 72.4(3) y
C27 C26 Rh1 108.7(4) y
C25 C26 H26 116.9 n
C27 C26 H26 116.9 n
Rh1 C26 H26 88.8 n
C26 C27 C28 112.1(4) y
C26 C27 H27A 109.2 n
C28 C27 H27A 109.2 n
C26 C27 H27B 109.2 n
C28 C27 H27B 109.2 n
H27A C27 H27B 107.9 n
C21 C28 C27 112.1(4) y
C21 C28 H28A 109.2 n
C27 C28 H28A 109.2 n
C21 C28 H28B 109.2 n
C27 C28 H28B 109.2 n
H28A C28 H28B 107.9 n
C1 N1 C2 128.0(4) y
C1 N1 C6 110.9(4) y
C2 N1 C6 120.9(4) y
C1 N2 C7 112.7(4) y
C1 N2 C18 123.9(4) y
C7 N2 C18 123.3(4) y
C1 Rh1 C22 88.7(2) y
C1 Rh1 C21 91.55(19) y
C22 Rh1 C21 38.9(2) y
C1 Rh1 C26 158.5(2) y
C22 Rh1 C26 98.2(2) y
C21 Rh1 C26 81.6(2) y
C1 Rh1 C25 164.7(2) y
C22 Rh1 C25 82.3(2) y
C21 Rh1 C25 89.2(2) y
C26 Rh1 C25 36.4(2) y
C1 Rh1 Cl1 91.22(14) y
C22 Rh1 Cl1 149.28(15) y
C21 Rh1 Cl1 171.48(15) y
C26 Rh1 Cl1 92.94(15) y
C25 Rh1 Cl1 90.23(16) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 1.353(6) y
C1 N1 1.371(6) y
C1 Rh1 2.035(5) y
C2 C3 1.357(7) y
C2 N1 1.407(6) y
C2 C8 1.503(7) y
C3 C4 1.440(8) y
C3 H3 0.9300 n
C4 C5 1.360(8) y
C4 H4 0.9300 n
C5 C6 1.433(7) y
C5 C17 1.512(7) y
C6 C7 1.362(7) y
C6 N1 1.418(6) y
C7 N2 1.379(6) y
C7 H7 0.9300 n
C8 C9 1.593(7) y
C8 H8A 0.9700 n
C8 H8B 0.9700 n
C9 C10 1.509(8) y
C9 H9A 0.9700 n
C9 H9B 0.9700 n
C10 C11 1.395(8) y
C10 C15 1.404(8) y
C11 C12 1.384(8) y
C11 H11 0.9300 n
C12 C13 1.408(8) y
C12 H12 0.9300 n
C13 C14 1.404(8) y
C13 C16 1.510(8) y
C14 C15 1.383(8) y
C14 H14 0.9300 n
C15 H15 0.9300 n
C16 C17 1.584(8) y
C16 H16A 0.9700 n
C16 H16B 0.9700 n
C17 H17A 0.9700 n
C17 H17B 0.9700 n
C18 N2 1.466(6) y
C18 H18A 0.9600 n
C18 H18B 0.9600 n
C18 H18C 0.9600 n
C21 C22 1.409(7) y
C21 C28 1.533(7) y
C21 Rh1 2.131(5) y
C21 H21 0.9300 n
C22 C23 1.517(7) y
C22 Rh1 2.100(5) y
C22 H22 0.9300 n
C23 C24 1.541(8) y
C23 H23A 0.9700 n
C23 H23B 0.9700 n
C24 C25 1.523(8) y
C24 H24A 0.9700 n
C24 H24B 0.9700 n
C25 C26 1.374(8) y
C25 Rh1 2.209(5) y
C25 H25 0.9300 n
C26 C27 1.509(7) y
C26 Rh1 2.195(5) y
C26 H26 0.9300 n
C27 C28 1.552(9) y
C27 H27A 0.9700 n
C27 H27B 0.9700 n
C28 H28A 0.9700 n
C28 H28B 0.9700 n
Cl1 Rh1 2.3937(13) y
