#------------------------------------------------------------------------------
#$Date: 2017-01-29 21:03:49 +0200 (Sun, 29 Jan 2017) $
#$Revision: 191076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/59/4065990.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_4065990
loop_
_publ_author_name
'Yu, Wei-Bin'
'Han, Ying-Feng'
'Lin, Yue-Jian'
'Jin, Guo-Xin'
_publ_section_title
;
 Cleavage of C−H Bonds for Building Tetranuclear Half-Sandwich
 Iridium Macrocycles with Ortho-Metalated Spacers
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              2827
_journal_paper_doi               10.1021/om1002396
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C76 H92 Ir4 N4 O14'
_chemical_formula_weight         2054.340
_space_group_IT_number           2
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             08-11-12
_audit_creation_method
'Created with Diamond (www.crystalimpact.com)'
_audit_update_record             08-11-12
_cell_angle_alpha                96.002(18)
_cell_angle_beta                 93.648(19)
_cell_angle_gamma                100.386(19)
_cell_formula_units_Z            1
_cell_length_a                   10.221(14)
_cell_length_b                   11.608(16)
_cell_length_c                   18.49(3)
_cell_volume                     2138(5)
_refine_ls_R_factor_all          0.073
_cod_data_source_file            om1002396_si_001.cif
_cod_data_source_block           f81008b
_cod_depositor_comments
;
 Changing the _geom_angle_atom_site_symbol_1, _geom_angle_atom_site_symbol_2,
 _geom_angle_atom_site_symbol_3, _geom_bond_atom_site_symbol_1,
 _geom_bond_atom_site_symbol_2 tags to the _geom_angle_atom_site_label_1,
 _geom_angle_atom_site_label_2, _geom_angle_atom_site_label_3,
 _geom_bond_atom_site_label_1, _geom_bond_atom_site_label_2 tags.

 Antanas Vaitkus,
 2017-01-29
;
_cod_original_cell_volume        2138.3(50)
_cod_original_sg_symbol_Hall     -P_1
_cod_database_code               4065990
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'
2 '-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
Ir1 Ir 1.1998(0) 0.4409(0) 0.8107(0) 1.000 2 i d Uani 0.03581(16)
Ir2 Ir 0.7753(0) -0.0748(0) 0.6412(0) 1.000 2 i d Uani 0.03256(15)
O1 O 1.0021(7) 0.4692(6) 0.8311(4) 1.000 2 i d Uani 0.046(2)
O2 O 0.7862(8) 0.3910(7) 0.8105(6) 1.000 2 i d Uani 0.074(3)
O3 O 0.9718(7) -0.1171(6) 0.6396(4) 1.000 2 i d Uani 0.0394(19)
O4 O 1.1847(7) -0.0496(6) 0.6777(5) 1.000 2 i d Uani 0.051(2)
N1 N 0.7794(9) -0.1443(8) 0.7432(5) 1.000 2 i d Uani 0.039(2)
N2 N 0.8058(8) -0.3683(8) 1.0889(5) 1.000 2 i d Uani 0.033(2)
C1 C 1.0866(9) 0.2816(9) 0.7615(5) 1.000 2 i d Uani 0.025(2)
C2 C 0.946(1) 0.2770(9) 0.7617(6) 1.000 2 i d Uani 0.033(3)
C3 C 0.8509(10) 0.181(1) 0.7283(5) 1.000 2 i d Uani 0.036(3)
H3 H 0.7609 0.1858 0.7267 1.000 2 i calc Uiso 0.04300
C4 C 0.8889(10) 0.0760(9) 0.6968(5) 1.000 2 i d Uani 0.032(3)
C5 C 1.0336(10) 0.0787(9) 0.7008(5) 1.000 2 i d Uani 0.032(3)
C6 C 1.1255(10) 0.1806(9) 0.7321(5) 1.000 2 i d Uani 0.032(3)
H6 H 1.2163 0.1793 0.7328 1.000 2 i calc Uiso 0.03900
C7 C 0.9056(12) 0.3829(10) 0.8018(7) 1.000 2 i d Uani 0.048(3)
C8 C 1.0698(11) -0.0329(10) 0.6726(7) 1.000 2 i d Uani 0.044(3)
C9 C 0.7398(13) -0.0918(11) 0.8035(7) 1.000 2 i d Uani 0.056(4)
H9 H 0.7123 -0.0204 0.7995 1.000 2 i calc Uiso 0.06700
C10 C 0.7353(13) -0.1308(12) 0.8692(7) 1.000 2 i d Uani 0.059(4)
H10 H 0.7036 -0.0894 0.9080 1.000 2 i calc Uiso 0.07100
C11 C 0.7804(10) -0.2370(11) 0.8774(6) 1.000 2 i d Uani 0.045(3)
C12 C 0.8162(12) -0.2953(10) 0.8151(6) 1.000 2 i d Uani 0.052(3)
H12 H 0.8411 -0.3684 0.8162 1.000 2 i calc Uiso 0.06200
C13 C 0.8148(12) -0.2445(11) 0.7513(7) 1.000 2 i d Uani 0.054(3)
H13 H 0.8414 -0.2852 0.7105 1.000 2 i calc Uiso 0.06500
C14 C 0.7507(13) -0.271(1) 1.0800(6) 1.000 2 i d Uani 0.053(3)
H14 H 0.7181 -0.2331 1.1199 1.000 2 i calc Uiso 0.06300
C15 C 0.7423(13) -0.2271(11) 1.0127(7) 1.000 2 i d Uani 0.058(4)
H15 H 0.7059 -0.1601 1.0080 1.000 2 i calc Uiso 0.06900
C16 C 0.7904(10) -0.2867(10) 0.9508(6) 1.000 2 i d Uani 0.039(3)
C17 C 0.8467(11) -0.3848(10) 0.9623(6) 1.000 2 i d Uani 0.044(3)
H17 H 0.8814 -0.4246 0.9239 1.000 2 i calc Uiso 0.05200
C18 C 0.8512(11) -0.4230(11) 1.0305(7) 1.000 2 i d Uani 0.048(3)
H18 H 0.8874 -0.4897 1.0364 1.000 2 i calc Uiso 0.05800
C19 C 1.3476(12) 0.6110(11) 0.8360(7) 1.000 2 i d Uani 0.057(4)
C20 C 1.4168(12) 0.5136(11) 0.8242(7) 1.000 2 i d Uani 0.051(3)
C21 C 1.3824(13) 0.4549(12) 0.7534(9) 1.000 2 i d Uani 0.070(4)
C22 C 1.2881(13) 0.5112(12) 0.7154(7) 1.000 2 i d Uani 0.062(4)
C23 C 1.2592(13) 0.6098(10) 0.7682(8) 1.000 2 i d Uani 0.058(4)
C24 C 1.3628(15) 0.7030(13) 0.9022(8) 1.000 2 i d Uani 0.100(6)
H24A H 1.4092 0.6768 0.9423 1.000 2 i calc Uiso 0.15000
H24B H 1.2761 0.7140 0.9153 1.000 2 i calc Uiso 0.15000
H24C H 1.4126 0.7763 0.8909 1.000 2 i calc Uiso 0.15000
C25 C 1.5180(15) 0.4793(17) 0.8802(12) 1.000 2 i d Uani 0.152(10)
H25A H 1.4901 0.3982 0.8877 1.000 2 i calc Uiso 0.22900
H25B H 1.5219 0.5285 0.9257 1.000 2 i calc Uiso 0.22900
H25C H 1.6047 0.4899 0.8620 1.000 2 i calc Uiso 0.22900
C26 C 1.4484(15) 0.3581(13) 0.716(1) 1.000 2 i d Uani 0.113(7)
H26A H 1.5199 0.3936 0.6896 1.000 2 i calc Uiso 0.17000
H26B H 1.3833 0.3048 0.6828 1.000 2 i calc Uiso 0.17000
H26C H 1.4831 0.3156 0.7523 1.000 2 i calc Uiso 0.17000
C27 C 1.2316(17) 0.4816(16) 0.6368(7) 1.000 2 i d Uani 0.115(7)
H27A H 1.2983 0.5104 0.6054 1.000 2 i calc Uiso 0.17300
H27B H 1.1554 0.5180 0.6293 1.000 2 i calc Uiso 0.17300
H27C H 1.2051 0.3976 0.6257 1.000 2 i calc Uiso 0.17300
C28 C 1.1605(17) 0.6914(14) 0.7524(11) 1.000 2 i d Uani 0.128(8)
H28A H 1.0990 0.6905 0.7895 1.000 2 i calc Uiso 0.19200
H28B H 1.1121 0.6643 0.7057 1.000 2 i calc Uiso 0.19200
H28C H 1.2087 0.7703 0.7520 1.000 2 i calc Uiso 0.19200
C29 C 0.6384(10) -0.2067(9) 0.5586(6) 1.000 2 i d Uani 0.038(3)
C30 C 0.5596(11) -0.1453(11) 0.6080(6) 1.000 2 i d Uani 0.047(3)
C31 C 0.594(1) -0.0202(10) 0.6029(7) 1.000 2 i d Uani 0.046(3)
C32 C 0.6945(11) -0.0042(11) 0.5485(6) 1.000 2 i d Uani 0.044(3)
C33 C 0.7215(11) -0.1155(11) 0.5245(6) 1.000 2 i d Uani 0.044(3)
C34 C 0.6297(15) -0.3392(12) 0.5411(8) 1.000 2 i d Uani 0.089(5)
H34A H 0.5706 -0.3675 0.4979 1.000 2 i calc Uiso 0.13400
H34B H 0.5960 -0.3783 0.5812 1.000 2 i calc Uiso 0.13400
H34C H 0.7168 -0.3553 0.5332 1.000 2 i calc Uiso 0.13400
C35 C 0.4598(11) -0.2040(12) 0.6557(7) 1.000 2 i d Uani 0.067(4)
H35A H 0.4627 -0.1543 0.7009 1.000 2 i calc Uiso 0.10000
H35B H 0.4814 -0.2783 0.6654 1.000 2 i calc Uiso 0.10000
H35C H 0.3719 -0.2168 0.6312 1.000 2 i calc Uiso 0.10000
C36 C 0.5192(14) 0.0716(13) 0.6364(8) 1.000 2 i d Uani 0.086(5)
H36A H 0.4678 0.0984 0.5984 1.000 2 i calc Uiso 0.12900
H36B H 0.5820 0.1372 0.6616 1.000 2 i calc Uiso 0.12900
H36C H 0.4605 0.0371 0.6701 1.000 2 i calc Uiso 0.12900
C37 C 0.7447(14) 0.1162(11) 0.5216(8) 1.000 2 i d Uani 0.075(5)
H37A H 0.8279 0.1150 0.5005 1.000 2 i calc Uiso 0.11300
H37B H 0.7574 0.1773 0.5620 1.000 2 i calc Uiso 0.11300
H37C H 0.6800 0.1313 0.4856 1.000 2 i calc Uiso 0.11300
C38 C 0.8184(13) -0.1418(12) 0.4700(7) 1.000 2 i d Uani 0.074(4)
H38A H 0.7816 -0.1357 0.4218 1.000 2 i calc Uiso 0.11000
H38B H 0.8346 -0.2203 0.4725 1.000 2 i calc Uiso 0.11000
H38C H 0.9008 -0.0863 0.4809 1.000 2 i calc Uiso 0.11000
O5 O 0.9970(14) 0.6622(10) 0.5601(8) 1.000 2 i d Uani 0.150(6)
O6 O 0.6583(16) 0.9852(12) 0.1854(7) 1.000 2 i d Uani 0.161(6)
O7 O 0.368(2) 0.8022(17) 0.1291(12) 1.000 2 i d Uani 0.256(10)
loop_
_atom_type_symbol
_atom_type_radius_bond
Ir 1.200
O 1.200
N 1.200
C 1.200
H 1.200
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Ir1 N2 . 2_757 88.0(4) no
C1 Ir1 O1 . . 79.8(3) no
N2 Ir1 O1 2_757 . 84.4(3) no
C1 Ir1 C23 . . 131.0(5) no
N2 Ir1 C23 2_757 . 140.2(5) no
O1 Ir1 C23 . . 94.4(4) no
C1 Ir1 C21 . . 102.6(5) no
N2 Ir1 C21 2_757 . 119.4(5) no
O1 Ir1 C21 . . 156.0(5) no
C23 Ir1 C21 . . 65.7(5) no
C1 Ir1 C22 . . 100.3(4) no
N2 Ir1 C22 2_757 . 157.4(5) no
O1 Ir1 C22 . . 117.6(5) no
C23 Ir1 C22 . . 40.3(5) no
C21 Ir1 C22 . . 38.4(5) no
C1 Ir1 C20 . . 133.3(4) no
N2 Ir1 C20 2_757 . 95.3(4) no
O1 Ir1 C20 . . 146.9(4) no
C23 Ir1 C20 . . 65.0(5) no
C21 Ir1 C20 . . 37.2(5) no
C22 Ir1 C20 . . 63.7(5) no
C1 Ir1 C19 . . 164.8(4) no
N2 Ir1 C19 2_757 . 104.0(4) no
O1 Ir1 C19 . . 110.2(4) no
C23 Ir1 C19 . . 39.4(5) no
C21 Ir1 C19 . . 63.5(5) no
C22 Ir1 C19 . . 65.1(5) no
C20 Ir1 C19 . . 37.7(4) no
C4 Ir2 N1 . . 85.7(4) no
C4 Ir2 O3 . . 79.0(4) no
N1 Ir2 O3 . . 82.8(3) no
C4 Ir2 C32 . . 100.3(4) no
N1 Ir2 C32 . . 158.1(4) no
O3 Ir2 C32 . . 119.0(4) no
C4 Ir2 C31 . . 104.1(4) no
N1 Ir2 C31 . . 118.0(4) no
O3 Ir2 C31 . . 159.0(4) no
C32 Ir2 C31 . . 40.2(4) no
C4 Ir2 C33 . . 128.4(4) no
N1 Ir2 C33 . . 145.4(4) no
O3 Ir2 C33 . . 96.4(4) no
C32 Ir2 C33 . . 37.8(4) no
C31 Ir2 C33 . . 65.1(5) no
C4 Ir2 C30 . . 137.4(5) no
N1 Ir2 C30 . . 96.4(4) no
O3 Ir2 C30 . . 143.6(4) no
C32 Ir2 C30 . . 64.9(4) no
C31 Ir2 C30 . . 38.4(4) no
C33 Ir2 C30 . . 64.1(4) no
C4 Ir2 C29 . . 164.5(4) no
N1 Ir2 C29 . . 108.8(4) no
O3 Ir2 C29 . . 107.6(3) no
C32 Ir2 C29 . . 64.1(4) no
C31 Ir2 C29 . . 64.6(4) no
C33 Ir2 C29 . . 38.3(4) no
C30 Ir2 C29 . . 38.2(4) no
C7 O1 Ir1 . . 114.2(7) no
C8 O3 Ir2 . . 114.9(7) no
C13 N1 C9 . . 114.1(10) no
C13 N1 Ir2 . . 122.8(8) no
C9 N1 Ir2 . . 123.1(8) no
C18 N2 C14 . . 118.4(10) no
C18 N2 Ir1 . 2_757 120.9(8) no
C14 N2 Ir1 . 2_757 120.4(7) no
C6 C1 C2 . . 116.1(9) no
C6 C1 Ir1 . . 130.5(7) no
C2 C1 Ir1 . . 113.4(7) no
C3 C2 C1 . . 123.3(10) no
C3 C2 C7 . . 121.5(10) no
C1 C2 C7 . . 115.2(9) no
C2 C3 C4 . . 121.4(10) no
C3 C4 C5 . . 114.8(9) no
C3 C4 Ir2 . . 130.4(8) no
C5 C4 Ir2 . . 114.6(8) no
C6 C5 C8 . . 125.(1) no
C6 C5 C4 . . 121.2(10) no
C8 C5 C4 . . 113.8(9) no
C1 C6 C5 . . 122.9(10) no
O2 C7 O1 . . 119.2(10) no
O2 C7 C2 . . 123.6(10) no
O1 C7 C2 . . 117.2(10) no
O4 C8 O3 . . 120.4(11) no
O4 C8 C5 . . 122.5(10) no
O3 C8 C5 . . 117.2(10) no
N1 C9 C10 . . 127.1(12) no
C9 C10 C11 . . 117.6(12) no
C12 C11 C10 . . 116.3(11) no
C12 C11 C16 . . 120.8(11) no
C10 C11 C16 . . 122.9(10) no
C13 C12 C11 . . 119.3(11) no
N1 C13 C12 . . 125.5(12) no
N2 C14 C15 . . 121.8(11) no
C14 C15 C16 . . 119.2(11) no
C17 C16 C15 . . 117.2(11) no
C17 C16 C11 . . 124.4(10) no
C15 C16 C11 . . 118.4(10) no
C18 C17 C16 . . 120.2(11) no
N2 C18 C17 . . 123.2(11) no
C20 C19 C23 . . 107.2(11) no
C20 C19 C24 . . 128.1(13) no
C23 C19 C24 . . 124.6(13) no
C20 C19 Ir1 . . 70.0(6) no
C23 C19 Ir1 . . 68.2(6) no
C24 C19 Ir1 . . 128.9(9) no
C21 C20 C19 . . 110.4(12) no
C21 C20 C25 . . 124.1(14) no
C19 C20 C25 . . 125.5(14) no
C21 C20 Ir1 . . 70.6(7) no
C19 C20 Ir1 . . 72.3(7) no
C25 C20 Ir1 . . 125.1(10) no
C20 C21 C22 . . 109.7(13) no
C20 C21 C26 . . 126.4(15) no
C22 C21 C26 . . 123.3(15) no
C20 C21 Ir1 . . 72.2(8) no
C22 C21 Ir1 . . 70.9(7) no
C26 C21 Ir1 . . 130.3(9) no
C21 C22 C23 . . 107.1(12) no
C21 C22 C27 . . 127.3(15) no
C23 C22 C27 . . 125.5(15) no
C21 C22 Ir1 . . 70.7(8) no
C23 C22 Ir1 . . 69.5(7) no
C27 C22 Ir1 . . 126.7(9) no
C19 C23 C22 . . 105.5(11) no
C19 C23 C28 . . 128.9(14) no
C22 C23 C28 . . 125.5(14) no
C19 C23 Ir1 . . 72.4(6) no
C22 C23 Ir1 . . 70.2(7) no
C28 C23 Ir1 . . 122.9(9) no
C33 C29 C30 . . 106.2(10) no
C33 C29 C34 . . 125.8(11) no
C30 C29 C34 . . 127.8(11) no
C33 C29 Ir2 . . 67.7(6) no
C30 C29 Ir2 . . 69.9(6) no
C34 C29 Ir2 . . 130.3(8) no
C31 C30 C29 . . 108.5(10) no
C31 C30 C35 . . 126.2(12) no
C29 C30 C35 . . 125.3(11) no
C31 C30 Ir2 . . 68.3(5) no
C29 C30 Ir2 . . 71.9(6) no
C35 C30 Ir2 . . 125.5(8) no
C30 C31 C32 . . 107.(1) no
C30 C31 C36 . . 124.6(12) no
C32 C31 C36 . . 127.3(12) no
C30 C31 Ir2 . . 73.3(6) no
C32 C31 Ir2 . . 69.6(6) no
C36 C31 Ir2 . . 131.2(8) no
C33 C32 C31 . . 107.9(10) no
C33 C32 C37 . . 129.3(11) no
C31 C32 C37 . . 122.5(11) no
C33 C32 Ir2 . . 71.8(7) no
C31 C32 Ir2 . . 70.2(6) no
C37 C32 Ir2 . . 127.6(7) no
C32 C33 C29 . . 110.3(10) no
C32 C33 C38 . . 126.6(11) no
C29 C33 C38 . . 123.1(11) no
C32 C33 Ir2 . . 70.4(6) no
C29 C33 Ir2 . . 74.0(6) no
C38 C33 Ir2 . . 123.6(8) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 C1 . 2.081(9) no
Ir1 N2 2_757 2.117(9) no
Ir1 O1 . 2.155(8) no
Ir1 C23 . 2.188(11) no
Ir1 C21 . 2.194(14) no
Ir1 C22 . 2.198(13) no
Ir1 C20 . 2.215(12) no
Ir1 C19 . 2.246(11) no
Ir2 C4 . 2.051(10) no
Ir2 N1 . 2.128(9) no
Ir2 O3 . 2.153(7) no
Ir2 C32 . 2.157(12) no
Ir2 C31 . 2.165(10) no
Ir2 C33 . 2.175(11) no
Ir2 C30 . 2.232(10) no
Ir2 C29 . 2.259(10) no
O1 C7 . 1.316(12) no
O2 C7 . 1.260(13) no
O3 C8 . 1.332(12) no
O4 C8 . 1.224(12) no
N1 C13 . 1.299(13) no
N1 C9 . 1.337(14) no
N2 C18 . 1.346(13) no
N2 C14 . 1.370(14) no
N2 Ir1 2_757 2.117(9) no
C1 C6 . 1.374(14) no
C1 C2 . 1.429(13) no
C2 C3 . 1.399(13) no
C2 C7 . 1.504(15) no
C3 C4 . 1.424(14) no
C4 C5 . 1.471(14) no
C5 C6 . 1.416(13) no
C5 C8 . 1.464(15) no
C9 C10 . 1.342(16) no
C10 C11 . 1.411(17) no
C11 C12 . 1.378(15) no
C11 C16 . 1.535(15) no
C12 C13 . 1.374(15) no
C14 C15 . 1.398(15) no
C15 C16 . 1.434(15) no
C16 C17 . 1.394(15) no
C17 C18 . 1.381(15) no
C19 C20 . 1.443(17) no
C19 C23 . 1.496(17) no
C19 C24 . 1.518(17) no
C20 C21 . 1.405(18) no
C20 C25 . 1.549(19) no
C21 C22 . 1.445(18) no
C21 C26 . 1.538(19) no
C22 C23 . 1.509(18) no
C22 C27 . 1.510(17) no
C23 C28 . 1.538(19) no
C29 C33 . 1.458(14) no
C29 C30 . 1.468(16) no
C29 C34 . 1.524(16) no
C30 C31 . 1.445(15) no
C30 C35 . 1.508(15) no
C31 C32 . 1.484(16) no
C31 C36 . 1.523(17) no
C32 C33 . 1.402(16) no
C32 C37 . 1.545(16) no
C33 C38 . 1.503(16) no
