#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:56:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178674 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/85/4078598.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_4078598
loop_
_publ_author_name
'Prades, Amparo'
'Peris, Eduardo'
'Alcarazo, Manuel'
_publ_section_title
;
 Pyracenebis(imidazolylidene): A New Janus-Type Biscarbene and Its
 Coordination to Rhodium and Iridium
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              4623
_journal_paper_doi               10.1021/om3003834
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C80 H96 Cl2 N4 Rh2, 4(C H Cl3)'
_chemical_formula_sum            'C84 H100 Cl14 N4 Rh2'
_chemical_formula_weight         1867.80
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-02-11
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.389(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.8621(4)
_cell_length_b                   13.8228(3)
_cell_length_c                   18.8523(5)
_cell_measurement_temperature    293(2)
_cell_volume                     4511.4(2)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.874
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26996
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.92
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.824
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.743
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         10405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0619
_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)+(0.0718P)²+6.0952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1760
_reflns_number_gt                6683
_reflns_number_total             10405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om3003834_si_001.cif
_cod_data_source_block           str1309
_cod_original_cell_volume        4511.43(19)
_cod_database_code               4078598
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -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
Rh1 Rh 0.973490(19) 0.29309(3) 0.82820(2) 0.02557(12) Uani 1 1 d .
Cl2 Cl 0.98614(7) 0.14443(9) 0.76954(8) 0.0409(3) Uani 1 1 d .
Cl50 Cl 0.64640(12) 0.4972(2) 0.47601(13) 0.1067(8) Uani 1 1 d .
Cl52 Cl 0.66304(10) 0.61928(13) 0.36137(13) 0.0783(5) Uani 1 1 d .
Cl51 Cl 0.51842(12) 0.61525(18) 0.37900(18) 0.1189(10) Uani 1 1 d .
Cl48 Cl 1.01007(14) -0.1028(2) 0.66001(19) 0.1408(12) Uani 1 1 d .
Cl46 Cl 0.85008(16) -0.0700(2) 0.5701(2) 0.1534(14) Uani 1 1 d .
Cl47 Cl 0.9589(2) 0.0626(3) 0.5591(2) 0.1787(15) Uani 1 1 d .
C41 C 0.9181(3) 0.2101(4) 0.8911(3) 0.0451(13) Uani 1 1 d .
H41 H 0.9008 0.1455 0.8700 0.054 Uiso 1 1 calc R
C3 C 0.9846(2) 0.3669(3) 0.7383(2) 0.0228(9) Uani 1 1 d .
N4 N 0.92371(18) 0.3944(3) 0.6706(2) 0.0238(8) Uani 1 1 d .
N12 N 0.95027(19) 0.6172(3) 0.2764(2) 0.0250(8) Uani 1 1 d .
C38 C 0.9241(3) 0.4086(4) 0.8648(3) 0.0383(12) Uani 1 1 d .
H38 H 0.9036 0.4604 0.8265 0.046 Uiso 1 1 calc R
C28 C 0.8973(4) 0.6522(4) 0.7669(4) 0.0566(16) Uani 1 1 d .
H28A H 0.8487 0.6791 0.7622 0.085 Uiso 1 1 calc R
H28B H 0.9334 0.7036 0.7723 0.085 Uiso 1 1 calc R
H28C H 0.9170 0.6111 0.8116 0.085 Uiso 1 1 calc R
C5 C 0.9507(2) 0.4243(3) 0.6157(3) 0.0259(10) Uani 1 1 d .
C8 C 0.8648(2) 0.5275(3) 0.4051(3) 0.0299(10) Uani 1 1 d .
H8 H 0.8200 0.5423 0.3624 0.036 Uiso 1 1 calc R
C33 C 0.7935(2) 0.3383(4) 0.6489(3) 0.0312(11) Uani 1 1 d .
C42 C 0.9946(3) 0.2160(4) 0.9368(3) 0.0442(13) Uani 1 1 d .
H42 H 1.0227 0.1549 0.9426 0.053 Uiso 1 1 calc R
C39 C 0.8694(4) 0.3770(5) 0.9022(4) 0.0596(17) Uani 1 1 d .
H39A H 0.8910 0.3968 0.9559 0.072 Uiso 1 1 calc R
H39B H 0.8205 0.4102 0.8768 0.072 Uiso 1 1 calc R
C7 C 0.8594(2) 0.4867(3) 0.4726(3) 0.0310(11) Uani 1 1 d .
H7 H 0.8110 0.4756 0.4733 0.037 Uiso 1 1 calc R
C13 C 0.8695(2) 0.6189(3) 0.2232(3) 0.0276(10) Uani 1 1 d .
C9 C 0.9357(2) 0.5449(3) 0.4030(3) 0.0271(10) Uani 1 1 d .
C18 C 0.8383(3) 0.5352(4) 0.1816(3) 0.0325(11) Uani 1 1 d .
C6 C 0.9252(2) 0.4636(3) 0.5368(3) 0.0267(10) Uani 1 1 d .
C14 C 0.8255(3) 0.6991(4) 0.2268(3) 0.0344(11) Uani 1 1 d .
C37 C 1.0038(3) 0.4106(4) 0.9048(3) 0.0388(12) Uani 1 1 d .
H37 H 1.0285 0.4634 0.8883 0.047 Uiso 1 1 calc R
C11 C 0.9707(2) 0.5823(3) 0.3505(3) 0.0260(10) Uani 1 1 d .
C10 C 1.0026(2) 0.5193(3) 0.4681(3) 0.0284(10) Uani 1 1 d .
C30 C 0.7569(3) 0.5253(4) 0.6812(3) 0.0412(13) Uani 1 1 d .
H30 H 0.7436 0.5874 0.6903 0.049 Uiso 1 1 calc R
C22 C 0.8588(3) 0.7870(4) 0.2751(3) 0.0413(13) Uani 1 1 d .
H22 H 0.9147 0.7860 0.2891 0.050 Uiso 1 1 calc R
C25 C 0.8463(2) 0.4139(3) 0.6664(3) 0.0272(10) Uani 1 1 d .
C27 C 0.8859(3) 0.5930(4) 0.6946(3) 0.0409(13) Uani 1 1 d .
H27 H 0.9362 0.5662 0.7010 0.049 Uiso 1 1 calc R
C26 C 0.8297(2) 0.5089(4) 0.6808(3) 0.0320(11) Uani 1 1 d .
C20 C 0.8874(3) 0.3731(4) 0.2435(3) 0.0471(14) Uani 1 1 d .
H20A H 0.9065 0.4034 0.2934 0.071 Uiso 1 1 calc R
H20B H 0.9203 0.3197 0.2442 0.071 Uiso 1 1 calc R
H20C H 0.8359 0.3499 0.2311 0.071 Uiso 1 1 calc R
C34 C 0.8092(3) 0.2398(4) 0.6229(3) 0.0404(12) Uani 1 1 d .
H34 H 0.8654 0.2309 0.6433 0.048 Uiso 1 1 calc R
C17 C 0.7585(3) 0.5342(4) 0.1388(3) 0.0451(13) Uani 1 1 d .
H17 H 0.7354 0.4801 0.1093 0.054 Uiso 1 1 calc R
C29 C 0.8587(4) 0.6594(4) 0.6237(4) 0.0602(17) Uani 1 1 d .
H29A H 0.8117 0.6910 0.6188 0.090 Uiso 1 1 calc R
H29B H 0.8498 0.6216 0.5782 0.090 Uiso 1 1 calc R
H29C H 0.8977 0.7070 0.6297 0.090 Uiso 1 1 calc R
C32 C 0.7217(3) 0.3600(4) 0.6510(3) 0.0438(13) Uani 1 1 d .
H32 H 0.6848 0.3115 0.6404 0.053 Uiso 1 1 calc R
C19 C 0.8868(3) 0.4463(4) 0.1827(3) 0.0361(11) Uani 1 1 d .
H19 H 0.9401 0.4683 0.1969 0.043 Uiso 1 1 calc R
C24 C 0.8458(4) 0.7871(4) 0.3505(4) 0.0551(16) Uani 1 1 d .
H24A H 0.7915 0.7835 0.3387 0.083 Uiso 1 1 calc R
H24B H 0.8665 0.8455 0.3786 0.083 Uiso 1 1 calc R
H24C H 0.8714 0.7323 0.3813 0.083 Uiso 1 1 calc R
C43 C 1.0285(4) 0.2841(5) 1.0058(3) 0.0650(18) Uani 1 1 d .
H43A H 0.9913 0.2920 1.0291 0.078 Uiso 1 1 calc R
H43B H 1.0743 0.2544 1.0441 0.078 Uiso 1 1 calc R
C15 C 0.7455(3) 0.6917(5) 0.1825(3) 0.0508(15) Uani 1 1 d .
H15 H 0.7136 0.7430 0.1826 0.061 Uiso 1 1 calc R
C16 C 0.7135(3) 0.6120(5) 0.1396(3) 0.0574(17) Uani 1 1 d .
H16 H 0.6606 0.6100 0.1105 0.069 Uiso 1 1 calc R
C31 C 0.7047(3) 0.4516(4) 0.6684(3) 0.0498(15) Uani 1 1 d .
H31 H 0.6575 0.4636 0.6715 0.060 Uiso 1 1 calc R
C40 C 0.8550(4) 0.2726(5) 0.8984(5) 0.072(2) Uani 1 1 d .
H40A H 0.8070 0.2596 0.8546 0.086 Uiso 1 1 calc R
H40B H 0.8480 0.2533 0.9447 0.086 Uiso 1 1 calc R
C23 C 0.8272(4) 0.8814(4) 0.2298(4) 0.0617(17) Uani 1 1 d .
H23A H 0.8307 0.8779 0.1805 0.092 Uiso 1 1 calc R
H23B H 0.8570 0.9353 0.2585 0.092 Uiso 1 1 calc R
H23C H 0.7741 0.8896 0.2224 0.092 Uiso 1 1 calc R
C44 C 1.0491(4) 0.3792(5) 0.9868(3) 0.0597(17) Uani 1 1 d .
H44A H 1.1035 0.3791 0.9963 0.072 Uiso 1 1 calc R
H44B H 1.0416 0.4265 1.0212 0.072 Uiso 1 1 calc R
C36 C 0.7757(3) 0.1572(4) 0.6525(4) 0.0567(16) Uani 1 1 d .
H36A H 0.7932 0.1618 0.7077 0.085 Uiso 1 1 calc R
H36B H 0.7922 0.0967 0.6392 0.085 Uiso 1 1 calc R
H36C H 0.7203 0.1607 0.6294 0.085 Uiso 1 1 calc R
C35 C 0.7786(4) 0.2376(5) 0.5343(4) 0.0663(18) Uani 1 1 d .
H35A H 0.7241 0.2510 0.5128 0.100 Uiso 1 1 calc R
H35B H 0.7875 0.1748 0.5177 0.100 Uiso 1 1 calc R
H35C H 0.8049 0.2856 0.5170 0.100 Uiso 1 1 calc R
C49 C 0.5976(3) 0.5470(4) 0.3851(4) 0.0551(16) Uani 1 1 d .
H49 H 0.5795 0.4942 0.3475 0.066 Uiso 1 1 calc R
C21 C 0.8608(3) 0.3974(4) 0.1037(3) 0.0523(15) Uani 1 1 d .
H21A H 0.8128 0.3644 0.0924 0.078 Uiso 1 1 calc R
H21B H 0.8993 0.3516 0.1042 0.078 Uiso 1 1 calc R
H21C H 0.8541 0.4453 0.0647 0.078 Uiso 1 1 calc R
C45 C 0.9370(4) -0.0201(6) 0.6223(5) 0.088(2) Uani 1 1 d .
H45 H 0.9331 0.0170 0.6648 0.105 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'
Cl Cl 0.1484 0.1585 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
C41 Rh1 Cl2 87.56(15) . .
C41 Rh1 C42 36.0(2) . .
C3 Rh1 Cl2 89.07(12) . .
C3 Rh1 C41 158.6(2) . .
C3 Rh1 C38 95.55(18) . .
C3 Rh1 C42 165.10(19) . .
C3 Rh1 C37 95.39(18) . .
C38 Rh1 Cl2 160.94(15) . .
C38 Rh1 C41 81.4(2) . .
C38 Rh1 C42 90.1(2) . .
C42 Rh1 Cl2 90.01(15) . .
C37 Rh1 Cl2 159.23(15) . .
C37 Rh1 C41 95.2(2) . .
C37 Rh1 C38 38.67(19) . .
C37 Rh1 C42 80.5(2) . .
C42 C41 Rh1 72.3(3) . .
C42 C41 C40 125.5(6) . .
C40 C41 Rh1 108.1(4) . .
N4 C3 Rh1 125.1(3) . .
N12 C3 Rh1 129.4(3) 3_766 .
N12 C3 N4 104.3(3) 3_766 .
C3 N4 C25 123.1(3) . .
C5 N4 C3 110.7(3) . .
C5 N4 C25 124.2(4) . .
C3 N12 C13 129.1(4) 3_766 .
C11 N12 C3 110.3(3) . 3_766
C11 N12 C13 119.9(3) . .
C39 C38 Rh1 113.8(4) . .
C37 C38 Rh1 70.6(3) . .
C37 C38 C39 122.6(5) . .
N4 C5 C6 142.6(4) . .
C11 C5 N4 106.5(4) 3_766 .
C11 C5 C6 110.9(4) 3_766 .
C9 C8 C7 120.6(4) . .
C25 C33 C34 122.6(4) . .
C25 C33 C32 116.2(4) . .
C32 C33 C34 121.1(4) . .
C41 C42 Rh1 71.6(3) . .
C41 C42 C43 123.9(6) . .
C43 C42 Rh1 110.8(4) . .
C40 C39 C38 114.0(5) . .
C6 C7 C8 120.8(4) . .
C18 C13 N12 117.9(4) . .
C18 C13 C14 124.0(4) . .
C14 C13 N12 117.3(4) . .
C8 C9 C11 140.9(4) . .
C8 C9 C10 118.3(4) . .
C10 C9 C11 100.8(3) . .
C13 C18 C17 116.7(5) . .
C13 C18 C19 123.0(4) . .
C17 C18 C19 120.2(5) . .
C7 C6 C5 142.0(4) . .
C7 C6 C10 117.1(4) . 3_766
C10 C6 C5 100.9(3) 3_766 .
C13 C14 C22 123.8(4) . .
C13 C14 C15 115.4(5) . .
C15 C14 C22 120.8(5) . .
C38 C37 Rh1 70.8(3) . .
C38 C37 C44 127.1(5) . .
C44 C37 Rh1 111.9(4) . .
N12 C11 C9 141.1(4) . .
C5 C11 N12 108.2(4) 3_766 .
C5 C11 C9 110.7(4) 3_766 .
C9 C10 C6 116.8(4) . 3_766
C10 C10 C9 121.0(5) 3_766 .
C10 C10 C6 122.2(5) 3_766 3_766
C31 C30 C26 121.3(5) . .
C14 C22 C24 112.3(4) . .
C14 C22 C23 111.9(5) . .
C24 C22 C23 110.0(4) . .
C33 C25 N4 118.8(4) . .
C33 C25 C26 123.9(4) . .
C26 C25 N4 117.3(4) . .
C28 C27 C29 109.7(5) . .
C26 C27 C28 113.7(4) . .
C26 C27 C29 109.8(5) . .
C30 C26 C25 116.7(4) . .
C30 C26 C27 119.6(4) . .
C25 C26 C27 123.7(4) . .
C33 C34 C35 109.4(5) . .
C36 C34 C33 113.2(4) . .
C36 C34 C35 110.7(5) . .
C16 C17 C18 121.0(5) . .
C31 C32 C33 121.5(5) . .
C18 C19 C21 112.6(4) . .
C20 C19 C18 111.8(4) . .
C20 C19 C21 110.0(4) . .
C44 C43 C42 114.2(5) . .
C16 C15 C14 122.0(5) . .
C15 C16 C17 120.8(5) . .
C30 C31 C32 120.4(4) . .
C39 C40 C41 115.3(5) . .
C43 C44 C37 114.6(5) . .
Cl50 C49 Cl52 108.8(3) . .
Cl51 C49 Cl50 112.9(4) . .
Cl51 C49 Cl52 110.1(3) . .
Cl48 C45 Cl47 109.8(5) . .
Cl46 C45 Cl48 113.9(5) . .
Cl46 C45 Cl47 107.2(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Rh1 Cl2 2.3899(13) .
Rh1 C41 2.191(5) .
Rh1 C3 2.058(4) .
Rh1 C38 2.099(5) .
Rh1 C42 2.200(5) .
Rh1 C37 2.097(5) .
Cl50 C49 1.734(7) .
Cl52 C49 1.778(6) .
Cl51 C49 1.730(6) .
Cl48 C45 1.713(8) .
Cl46 C45 1.689(8) .
Cl47 C45 1.811(9) .
C41 C42 1.358(8) .
C41 C40 1.519(8) .
C3 N4 1.389(5) .
C3 N12 1.382(5) 3_766
N4 C5 1.386(5) .
N4 C25 1.456(5) .
N12 C3 1.381(5) 3_766
N12 C13 1.454(5) .
N12 C11 1.379(5) .
C38 C39 1.526(7) .
C38 C37 1.389(7) .
C28 C27 1.531(8) .
C5 C6 1.473(6) .
C5 C11 1.365(6) 3_766
C8 C7 1.432(6) .
C8 C9 1.376(5) .
C33 C25 1.390(6) .
C33 C34 1.516(7) .
C33 C32 1.403(6) .
C42 C43 1.525(8) .
C39 C40 1.464(8) .
C7 C6 1.384(6) .
C13 C18 1.392(7) .
C13 C14 1.402(6) .
C9 C11 1.483(6) .
C9 C10 1.413(6) .
C18 C17 1.398(6) .
C18 C19 1.525(7) .
C6 C10 1.421(5) 3_766
C14 C22 1.498(7) .
C14 C15 1.409(7) .
C37 C44 1.503(8) .
C11 C5 1.365(6) 3_766
C10 C6 1.421(5) 3_766
C10 C10 1.354(8) 3_766
C30 C26 1.395(6) .
C30 C31 1.370(7) .
C22 C24 1.535(7) .
C22 C23 1.543(7) .
C25 C26 1.400(6) .
C27 C26 1.524(7) .
C27 C29 1.532(8) .
C20 C19 1.525(7) .
C34 C36 1.515(7) .
C34 C35 1.536(8) .
C17 C16 1.373(8) .
C32 C31 1.378(8) .
C19 C21 1.530(7) .
C43 C44 1.456(8) .
C15 C16 1.358(8) .
