#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:42:36 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178530 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/35/4063503.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_4063503
loop_
_publ_author_name
'Moussa, Jamal'
'Rager, Marie Noelle'
'Chamoreau, Lise Marie'
'Ricard, Louis'
'Amouri, Hani'
_publ_section_title
;
 Unprecedented π-Bonded Rhodio- and Iridio-o-Benzoquinones as
 Organometallic Linkers for the Design of Chiral Octahedral Bimetallic
 Assemblies
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              397
_journal_page_last               404
_journal_paper_doi               10.1021/om800594g
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C16 H19 Ir O2, 2(H2 O)'
_chemical_formula_sum            'C16 H23 Ir O4'
_chemical_formula_weight         471.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_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                 105.0220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1210(10)
_cell_length_b                   13.7430(10)
_cell_length_c                   8.2960(10)
_cell_measurement_reflns_used    3752
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     784.13(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5678
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         3.68
_exptl_absorpt_coefficient_mu    8.526
_exptl_absorpt_correction_T_max  0.4277
_exptl_absorpt_correction_T_min  0.2804
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.841
_refine_diff_density_min         -2.750
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0277
_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)+(0.0254P)²+1.2632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0607
_reflns_number_gt                2232
_reflns_number_total             2366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800594g_si_002.cif
_cod_data_source_block           jm513
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core 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      'P21/m     '
_cod_database_code               4063503
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
Ir1 Ir 0.37052(2) 0.2500 0.78157(2) 0.01903(7) Uani 1 2 d S . .
O1 O 0.6130(7) 0.2500 0.4551(5) 0.0331(9) Uani 1 2 d S . .
O2 O 0.6270(9) 0.0713(4) 0.6195(7) 0.0343(13) Uani 0.50 1 d PD . .
C1 C 0.6229(8) 0.2500 0.6084(7) 0.0281(11) Uani 1 2 d SD . .
C2 C 0.628(5) 0.1534(7) 0.6992(14) 0.041(5) Uani 0.50 1 d PD . 1
C2A C 0.606(5) 0.1642(8) 0.6989(12) 0.034(5) Uani 0.50 1 d PD . 2
H2A H 0.5768 0.1050 0.6382 0.041 Uiso 0.50 1 calc PR . 2
C3 C 0.6297(6) 0.1610(3) 0.8751(5) 0.0372(10) Uani 1 1 d D . .
H3 H 0.6195 0.1026 0.9335 0.045 Uiso 1 1 calc R A 1
C4 C 0.6454(8) 0.2500 0.9644(8) 0.0392(14) Uani 1 2 d S . .
H4 H 0.6662 0.2500 1.0823 0.047 Uiso 1 2 calc SR . .
C5 C 0.1300(7) 0.2500 0.8971(6) 0.0202(9) Uani 1 2 d S . .
C6 C 0.1157(5) 0.1654(3) 0.7939(4) 0.0225(6) Uani 1 1 d . . .
C7 C 0.0961(5) 0.1977(2) 0.6250(4) 0.0195(6) Uani 1 1 d . . .
C8 C 0.1480(9) 0.2500 1.0816(6) 0.0325(12) Uani 1 2 d S . .
H8A H 0.0289 0.2766 1.1027 0.049 Uiso 0.50 1 calc PR . .
H8B H 0.2592 0.2902 1.1382 0.049 Uiso 0.50 1 calc PR . .
H8C H 0.1676 0.1832 1.1241 0.049 Uiso 0.50 1 calc PR . .
C9 C 0.1166(6) 0.0616(3) 0.8492(5) 0.0308(8) Uani 1 1 d . . .
H9A H -0.0172 0.0374 0.8250 0.046 Uiso 1 1 calc R . .
H9B H 0.1766 0.0574 0.9695 0.046 Uiso 1 1 calc R . .
H9C H 0.1911 0.0220 0.7894 0.046 Uiso 1 1 calc R . .
C10 C 0.0725(6) 0.1337(3) 0.4762(4) 0.0284(8) Uani 1 1 d . . .
H10A H -0.0661 0.1261 0.4211 0.043 Uiso 1 1 calc R . .
H10B H 0.1297 0.0698 0.5113 0.043 Uiso 1 1 calc R . .
H10C H 0.1385 0.1631 0.3982 0.043 Uiso 1 1 calc R . .
O3 O 0.5255(8) 0.0807(3) 0.2561(5) 0.0636(12) Uani 1 1 d . . .
H3A H 0.487(12) 0.050(6) 0.313(10) 0.076 Uiso 1 1 d . . .
H3B H 0.565(11) 0.120(5) 0.329(9) 0.076 Uiso 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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C4 Ir1 C5 111.6(2) . . ?
C4 Ir1 C7 159.94(10) . 4_565 ?
C5 Ir1 C7 64.71(14) . 4_565 ?
C4 Ir1 C7 159.94(10) . . ?
C5 Ir1 C7 64.71(14) . . ?
C7 Ir1 C7 38.73(17) 4_565 . ?
C4 Ir1 C6 125.83(16) . 4_565 ?
C5 Ir1 C6 38.46(11) . 4_565 ?
C7 Ir1 C6 38.71(12) 4_565 4_565 ?
C7 Ir1 C6 64.75(13) . 4_565 ?
C4 Ir1 C6 125.83(16) . . ?
C5 Ir1 C6 38.46(11) . . ?
C7 Ir1 C6 64.75(13) 4_565 . ?
C7 Ir1 C6 38.71(12) . . ?
C6 Ir1 C6 64.48(19) 4_565 . ?
C4 Ir1 C3 38.29(14) . 4_565 ?
C5 Ir1 C3 122.33(14) . 4_565 ?
C7 Ir1 C3 125.07(16) 4_565 4_565 ?
C7 Ir1 C3 161.13(16) . 4_565 ?
C6 Ir1 C3 108.78(15) 4_565 4_565 ?
C6 Ir1 C3 156.91(14) . 4_565 ?
C4 Ir1 C3 38.29(14) . . ?
C5 Ir1 C3 122.33(14) . . ?
C7 Ir1 C3 161.13(16) 4_565 . ?
C7 Ir1 C3 125.07(16) . . ?
C6 Ir1 C3 156.91(14) 4_565 . ?
C6 Ir1 C3 108.78(15) . . ?
C3 Ir1 C3 68.2(3) 4_565 . ?
C4 Ir1 C2A 66.9(5) . 4_565 ?
C5 Ir1 C2A 148.6(3) . 4_565 ?
C7 Ir1 C2A 105.4(5) 4_565 4_565 ?
C7 Ir1 C2A 127.3(4) . 4_565 ?
C6 Ir1 C2A 114.9(5) 4_565 4_565 ?
C6 Ir1 C2A 165.8(4) . 4_565 ?
C3 Ir1 C2A 37.1(4) 4_565 4_565 ?
C3 Ir1 C2A 77.2(5) . 4_565 ?
C4 Ir1 C2A 66.9(5) . . ?
C5 Ir1 C2A 148.6(3) . . ?
C7 Ir1 C2A 127.3(4) 4_565 . ?
C7 Ir1 C2A 105.4(5) . . ?
C6 Ir1 C2A 165.8(4) 4_565 . ?
C6 Ir1 C2A 114.9(5) . . ?
C3 Ir1 C2A 77.2(5) 4_565 . ?
C3 Ir1 C2A 37.1(4) . . ?
C2A Ir1 C2A 61.9(7) 4_565 . ?
C4 Ir1 C2 66.0(6) . . ?
C5 Ir1 C2 147.2(3) . . ?
C7 Ir1 C2 128.6(5) 4_565 . ?
C7 Ir1 C2 105.8(6) . . ?
C6 Ir1 C2 167.2(4) 4_565 . ?
C6 Ir1 C2 114.1(5) . . ?
C3 Ir1 C2 77.4(6) 4_565 . ?
C3 Ir1 C2 35.5(4) . . ?
C2A Ir1 C2 63.0(2) 4_565 . ?
C2A Ir1 C2 1.7(3) . . ?
C4 Ir1 C2 66.0(6) . 4_565 ?
C5 Ir1 C2 147.2(3) . 4_565 ?
C7 Ir1 C2 105.8(6) 4_565 4_565 ?
C7 Ir1 C2 128.6(5) . 4_565 ?
C6 Ir1 C2 114.1(5) 4_565 4_565 ?
C6 Ir1 C2 167.2(4) . 4_565 ?
C3 Ir1 C2 35.5(4) 4_565 4_565 ?
C3 Ir1 C2 77.4(6) . 4_565 ?
C2A Ir1 C2 1.7(3) 4_565 4_565 ?
C2A Ir1 C2 63.0(2) . 4_565 ?
C2 Ir1 C2 64.2(8) . 4_565 ?
O1 C1 C2A 123.0(4) . 4_565 ?
O1 C1 C2A 123.0(5) . . ?
C2A C1 C2A 112.4(11) 4_565 . ?
O1 C1 C2 119.3(4) . 4_565 ?
C2A C1 C2 7(2) 4_565 4_565 ?
C2A C1 C2 117.2(6) . 4_565 ?
O1 C1 C2 119.3(4) . . ?
C2A C1 C2 117.2(6) 4_565 . ?
C2A C1 C2 7(2) . . ?
C2 C1 C2 121.4(8) 4_565 . ?
O1 C1 Ir1 134.5(4) . . ?
C2A C1 Ir1 62.5(12) 4_565 . ?
C2A C1 Ir1 62.5(12) . . ?
C2 C1 Ir1 69.9(11) 4_565 . ?
C2 C1 Ir1 69.9(11) . . ?
O2 C2 C3 124.4(6) . . ?
O2 C2 C1 120.5(6) . . ?
C3 C2 C1 115.1(7) . . ?
O2 C2 Ir1 133(2) . . ?
C3 C2 Ir1 60.3(9) . . ?
C1 C2 Ir1 75.3(10) . . ?
C1 C2A C3 124.2(8) . . ?
C1 C2A Ir1 84.2(11) . . ?
C3 C2A Ir1 67.2(10) . . ?
C1 C2A H2A 117.9 . . ?
C3 C2A H2A 117.9 . . ?
Ir1 C2A H2A 121.5 . . ?
C4 C3 C2A 118.7(6) . . ?
C4 C3 C2 124.2(5) . . ?
C2A C3 C2 9(2) . . ?
C4 C3 Ir1 69.4(3) . . ?
C2A C3 Ir1 75.7(13) . . ?
C2 C3 Ir1 84.2(12) . . ?
C4 C3 H3 117.9 . . ?
C2A C3 H3 122.9 . . ?
C2 C3 H3 117.9 . . ?
Ir1 C3 H3 119.0 . . ?
C3 C4 C3 119.0(5) 4_565 . ?
C3 C4 Ir1 72.3(3) 4_565 . ?
C3 C4 Ir1 72.3(3) . . ?
C3 C4 H4 120.5 4_565 . ?
C3 C4 H4 120.5 . . ?
Ir1 C4 H4 126.7 . . ?
C6 C5 C6 108.6(4) . 4_565 ?
C6 C5 C8 125.7(2) . . ?
C6 C5 C8 125.7(2) 4_565 . ?
C6 C5 Ir1 71.2(2) . . ?
C6 C5 Ir1 71.2(2) 4_565 . ?
C8 C5 Ir1 125.6(4) . . ?
C5 C6 C7 107.8(3) . . ?
C5 C6 C9 126.6(3) . . ?
C7 C6 C9 125.6(3) . . ?
C5 C6 Ir1 70.3(2) . . ?
C7 C6 Ir1 70.24(19) . . ?
C9 C6 Ir1 125.8(3) . . ?
C7 C7 C6 107.92(19) 4_565 . ?
C7 C7 C10 126.17(19) 4_565 . ?
C6 C7 C10 125.9(3) . . ?
C7 C7 Ir1 70.63(9) 4_565 . ?
C6 C7 Ir1 71.05(19) . . ?
C10 C7 Ir1 125.6(2) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H3A O3 H3B 91(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C4 2.144(6) . ?
Ir1 C5 2.169(4) . ?
Ir1 C7 2.169(3) 4_565 ?
Ir1 C7 2.169(3) . ?
Ir1 C6 2.180(3) 4_565 ?
Ir1 C6 2.180(3) . ?
Ir1 C3 2.182(4) 4_565 ?
Ir1 C3 2.182(4) . ?
Ir1 C2A 2.30(3) 4_565 ?
Ir1 C2A 2.30(3) . ?
Ir1 C2 2.50(3) . ?
Ir1 C2 2.50(3) 4_565 ?
O1 C1 1.255(7) . ?
O2 C2 1.307(11) . ?
C1 C2A 1.420(8) 4_565 ?
C1 C2A 1.420(8) . ?
C1 C2 1.522(8) 4_565 ?
C1 C2 1.522(8) . ?
C2 C3 1.461(8) . ?
C2A C3 1.428(8) . ?
C2A H2A 0.9500 . ?
C3 C4 1.419(6) . ?
C3 H3 0.9500 . ?
C4 C3 1.419(6) 4_565 ?
C4 H4 0.9500 . ?
C5 C6 1.432(4) . ?
C5 C6 1.432(4) 4_565 ?
C5 C8 1.502(7) . ?
C6 C7 1.441(5) . ?
C6 C9 1.498(5) . ?
C7 C7 1.439(6) 4_565 ?
C7 C10 1.489(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O3 H3A 0.73(7) . ?
O3 H3B 0.81(7) . ?
