#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/82/2218238.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2218238
loop_
_publ_author_name
'Fu, Hao'
'Ding, Yuqiang'
'Chen, Guoqing'
_publ_section_title
;Aqua[N-(1-naphthyl)acetamido-κN]bis[2-(2-pyridyl)phenyl-κ²N,C¹]iridium(III)
 ethylene glycol hemisolvate
;
_journal_coeditor_code           SG2232
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m731
_journal_paper_doi               10.1107/S1600536808010040
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac
'[Ir (C11 H8 N)2 (C12 H10 N O) (H2 O1)], 0.5C2 H6 O2'
_chemical_formula_moiety         'C34 H28 Ir N3 O2, 0.5C2 H6 O2'
_chemical_formula_sum            'C35 H31 Ir N3 O3'
_chemical_formula_weight         733.83
_chemical_name_systematic
;
Aqua[N-(1-naphthyl)acetamido-λN]bis[2-(2-pyridyl)phenyl-\
κ²N,C¹]iridium(III) ethylene glycol hemisolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                95.580(7)
_cell_angle_beta                 92.940(7)
_cell_angle_gamma                107.423(6)
_cell_formula_units_Z            2
_cell_length_a                   10.097(4)
_cell_length_b                   10.888(4)
_cell_length_c                   14.453(5)
_cell_measurement_reflns_used    2801
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.29
_cell_volume                     1503.4(10)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7940
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    4.480
_exptl_absorpt_correction_T_max  0.7748
_exptl_absorpt_correction_T_min  0.6154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             726
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.905
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'calc w=1/[σ²(Fo²)+(0.05P)²+0.001P]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                4451
_reflns_number_total             5269
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2232.cif
_cod_data_source_block           I
_cod_database_code               2218238
_cod_database_fobs_code          2218238
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Ir Ir1 0.13408(3) 0.89887(2) 0.175881(18) 0.03749(11) Uani d . 1
O O1 0.1828(5) 1.1138(5) 0.0220(4) 0.0639(15) Uani d . 1
O O2 -0.0027(5) 1.0120(4) 0.1312(3) 0.0525(12) Uani d D 1
H H37 0.0550 1.0351 0.0906 0.063 Uiso d RD 1
H H36 -0.0767 0.9641 0.0998 0.063 Uiso d RD 1
O O3 0.9250(19) 0.519(2) 0.6241(11) 0.287(10) Uani d . 1
H H3 0.9913 0.5173 0.6586 0.431 Uiso calc R 1
N N1 0.3081(5) 1.0563(5) 0.1332(4) 0.0443(14) Uani d . 1
N N2 0.1680(6) 0.9878(5) 0.3092(4) 0.0425(13) Uani d . 1
N N3 0.0900(6) 0.7881(5) 0.0484(4) 0.0461(14) Uani d . 1
C C1 0.4217(8) 1.2363(8) 0.0431(6) 0.068(2) Uani d . 1
H H1A 0.4089 1.2499 -0.0210 0.102 Uiso calc R 1
H H1B 0.5047 1.2118 0.0525 0.102 Uiso calc R 1
H H1C 0.4303 1.3149 0.0826 0.102 Uiso calc R 1
C C2 0.2964(7) 1.1287(6) 0.0672(5) 0.0473(17) Uani d . 1
C C3 0.4419(8) 1.0810(8) 0.1841(6) 0.059(2) Uani d . 1
C C4 0.5249(8) 1.0024(8) 0.1629(6) 0.068(2) Uani d . 1
H H4 0.4975 0.9413 0.1104 0.082 Uiso calc R 1
C C5 0.6484(9) 1.0104(12) 0.2166(9) 0.096(4) Uani d . 1
H H5 0.7011 0.9557 0.2010 0.116 Uiso calc R 1
C C6 0.6883(11) 1.1041(14) 0.2944(9) 0.106(5) Uani d . 1
H H6 0.7689 1.1116 0.3316 0.127 Uiso calc R 1
C C7 0.6075(9) 1.1888(10) 0.3179(6) 0.073(3) Uani d . 1
C C8 0.4834(8) 1.1748(8) 0.2611(5) 0.059(2) Uani d . 1
C C9 0.4042(10) 1.2587(8) 0.2848(6) 0.068(2) Uani d . 1
H H9 0.3225 1.2530 0.2496 0.081 Uiso calc R 1
C C10 0.4520(13) 1.3486(10) 0.3613(7) 0.104(4) Uani d . 1
H H10 0.4020 1.4052 0.3782 0.125 Uiso calc R 1
C C11 0.5746(15) 1.3572(13) 0.4147(8) 0.115(5) Uani d . 1
H H11 0.6039 1.4191 0.4667 0.138 Uiso calc R 1
C C12 0.6483(12) 1.2812(13) 0.3937(8) 0.099(4) Uani d . 1
H H12 0.7295 1.2894 0.4305 0.119 Uiso calc R 1
C C13 0.1079(8) 1.0713(7) 0.3443(5) 0.0556(19) Uani d . 1
H H13 0.0478 1.0968 0.3049 0.067 Uiso calc R 1
C C14 0.1302(10) 1.1234(8) 0.4373(6) 0.071(2) Uani d . 1
H H14 0.0854 1.1822 0.4595 0.085 Uiso calc R 1
C C15 0.2177(10) 1.0875(9) 0.4957(6) 0.074(3) Uani d . 1
H H15 0.2348 1.1218 0.5582 0.089 Uiso calc R 1
C C16 0.2797(9) 1.0009(9) 0.4610(6) 0.069(2) Uani d . 1
H H16 0.3401 0.9758 0.5003 0.082 Uiso calc R 1
C C17 0.2551(7) 0.9484(7) 0.3676(5) 0.0512(19) Uani d . 1
C C18 0.3088(7) 0.8496(7) 0.3221(5) 0.0519(19) Uani d . 1
C C19 0.4038(8) 0.7965(9) 0.3665(6) 0.066(2) Uani d . 1
H H19 0.4368 0.8249 0.4285 0.079 Uiso calc R 1
C C20 0.4466(9) 0.7041(9) 0.3180(8) 0.081(3) Uani d . 1
H H20 0.5100 0.6702 0.3469 0.097 Uiso calc R 1
C C21 0.3967(9) 0.6599(8) 0.2261(7) 0.074(3) Uani d . 1
H H21 0.4255 0.5954 0.1940 0.089 Uiso calc R 1
C C22 0.3047(8) 0.7107(7) 0.1820(6) 0.0573(19) Uani d . 1
H H22 0.2724 0.6794 0.1202 0.069 Uiso calc R 1
C C23 0.2586(7) 0.8065(6) 0.2264(5) 0.0430(16) Uani d . 1
C C24 0.1684(8) 0.8064(7) -0.0248(5) 0.0557(19) Uani d . 1
H H24 0.2491 0.8768 -0.0192 0.067 Uiso calc R 1
C C25 0.1343(11) 0.7259(8) -0.1069(6) 0.073(3) Uani d . 1
H H25 0.1924 0.7396 -0.1553 0.088 Uiso calc R 1
C C26 0.0123(12) 0.6241(8) -0.1167(7) 0.085(3) Uani d . 1
H H26 -0.0140 0.5683 -0.1720 0.102 Uiso calc R 1
C C27 -0.0684(10) 0.6070(8) -0.0442(6) 0.074(3) Uani d . 1
H H27 -0.1516 0.5393 -0.0508 0.089 Uiso calc R 1
C C28 -0.0306(8) 0.6881(7) 0.0407(5) 0.0534(19) Uani d . 1
C C29 -0.1027(7) 0.6709(6) 0.1252(5) 0.0500(18) Uani d . 1
C C30 -0.2245(8) 0.5705(7) 0.1320(7) 0.062(2) Uani d . 1
H H30 -0.2696 0.5151 0.0792 0.074 Uiso calc R 1
C C31 -0.2773(8) 0.5542(8) 0.2165(7) 0.072(3) Uani d . 1
H H31 -0.3583 0.4871 0.2212 0.087 Uiso calc R 1
C C32 -0.2111(8) 0.6368(8) 0.2951(7) 0.070(2) Uani d . 1
H H32 -0.2468 0.6240 0.3527 0.083 Uiso calc R 1
C C33 -0.0919(8) 0.7385(7) 0.2885(6) 0.059(2) Uani d . 1
H H33 -0.0501 0.7947 0.3418 0.071 Uiso calc R 1
C C34 -0.0326(6) 0.7588(6) 0.2036(5) 0.0426(16) Uani d . 1
C C35 0.9687(19) 0.537(2) 0.5300(13) 0.197(10) Uani d D 1
H H35A 0.8860 0.5390 0.4936 0.237 Uiso calc R 1
H H35B 1.0322 0.6249 0.5357 0.237 Uiso calc R 1
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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
C23 Ir1 C34 . 90.5(2) y
C23 Ir1 N2 . 81.7(3) y
C34 Ir1 N2 . 93.3(3) ?
C23 Ir1 N3 . 94.7(3) ?
C34 Ir1 N3 . 80.7(3) y
N2 Ir1 N3 . 172.9(2) ?
C23 Ir1 N1 . 93.8(2) ?
C34 Ir1 N1 . 174.7(2) ?
N2 Ir1 N1 . 90.5(2) ?
N3 Ir1 N1 . 95.8(2) ?
C23 Ir1 O2 . 175.1(2) ?
C34 Ir1 O2 . 89.9(2) ?
N2 Ir1 O2 . 93.5(2) ?
N3 Ir1 O2 . 90.2(2) ?
N1 Ir1 O2 . 86.04(19) y
Ir1 O2 H37 . 85.0 ?
Ir1 O2 H36 . 112.0 ?
H37 O2 H36 . 104.4 ?
C35 O3 H3 . 109.5 ?
C2 N1 C3 . 118.9(6) ?
C2 N1 Ir1 . 124.8(4) ?
C3 N1 Ir1 . 116.3(4) ?
C13 N2 C17 . 118.6(6) ?
C13 N2 Ir1 . 125.8(5) ?
C17 N2 Ir1 . 115.4(5) ?
C24 N3 C28 . 119.5(6) ?
C24 N3 Ir1 . 126.1(5) ?
C28 N3 Ir1 . 114.3(5) ?
C2 C1 H1A . 109.5 ?
C2 C1 H1B . 109.5 ?
H1A C1 H1B . 109.5 ?
C2 C1 H1C . 109.5 ?
H1A C1 H1C . 109.5 ?
H1B C1 H1C . 109.5 ?
O1 C2 N1 . 121.9(6) ?
O1 C2 C1 . 116.8(6) ?
N1 C2 C1 . 121.3(6) ?
C8 C3 C4 . 118.9(8) ?
C8 C3 N1 . 120.5(8) ?
C4 C3 N1 . 120.4(7) ?
C3 C4 C5 . 123.5(10) ?
C3 C4 H4 . 118.2 ?
C5 C4 H4 . 118.2 ?
C6 C5 C4 . 117.1(11) ?
C6 C5 H5 . 121.4 ?
C4 C5 H5 . 121.4 ?
C5 C6 C7 . 121.3(10) ?
C5 C6 H6 . 119.4 ?
C7 C6 H6 . 119.4 ?
C12 C7 C8 . 120.5(11) ?
C12 C7 C6 . 120.8(10) ?
C8 C7 C6 . 118.6(10) ?
C3 C8 C9 . 121.2(7) ?
C3 C8 C7 . 120.5(9) ?
C9 C8 C7 . 118.3(9) ?
C10 C9 C8 . 117.7(10) ?
C10 C9 H9 . 121.2 ?
C8 C9 H9 . 121.2 ?
C9 C10 C11 . 121.4(13) ?
C9 C10 H10 . 119.3 ?
C11 C10 H10 . 119.3 ?
C12 C11 C10 . 121.7(12) ?
C12 C11 H11 . 119.2 ?
C10 C11 H11 . 119.2 ?
C11 C12 C7 . 120.5(12) ?
C11 C12 H12 . 119.8 ?
C7 C12 H12 . 119.8 ?
N2 C13 C14 . 122.9(8) ?
N2 C13 H13 . 118.5 ?
C14 C13 H13 . 118.5 ?
C15 C14 C13 . 119.3(9) ?
C15 C14 H14 . 120.3 ?
C13 C14 H14 . 120.3 ?
C16 C15 C14 . 118.5(8) ?
C16 C15 H15 . 120.8 ?
C14 C15 H15 . 120.8 ?
C15 C16 C17 . 121.5(8) ?
C15 C16 H16 . 119.2 ?
C17 C16 H16 . 119.2 ?
N2 C17 C16 . 119.1(8) ?
N2 C17 C18 . 113.6(6) ?
C16 C17 C18 . 127.3(7) ?
C19 C18 C23 . 120.1(8) ?
C19 C18 C17 . 124.4(7) ?
C23 C18 C17 . 115.5(6) ?
C20 C19 C18 . 119.8(8) ?
C20 C19 H19 . 120.1 ?
C18 C19 H19 . 120.1 ?
C19 C20 C21 . 120.6(8) ?
C19 C20 H20 . 119.7 ?
C21 C20 H20 . 119.7 ?
C22 C21 C20 . 120.3(9) ?
C22 C21 H21 . 119.8 ?
C20 C21 H21 . 119.8 ?
C21 C22 C23 . 122.3(8) ?
C21 C22 H22 . 118.9 ?
C23 C22 H22 . 118.9 ?
C22 C23 C18 . 116.9(6) ?
C22 C23 Ir1 . 129.3(6) ?
C18 C23 Ir1 . 113.8(5) ?
N3 C24 C25 . 122.8(8) ?
N3 C24 H24 . 118.6 ?
C25 C24 H24 . 118.6 ?
C24 C25 C26 . 118.8(9) ?
C24 C25 H25 . 120.6 ?
C26 C25 H25 . 120.6 ?
C27 C26 C25 . 118.6(9) ?
C27 C26 H26 . 120.7 ?
C25 C26 H26 . 120.7 ?
C26 C27 C28 . 122.1(8) ?
C26 C27 H27 . 118.9 ?
C28 C27 H27 . 118.9 ?
N3 C28 C27 . 118.1(8) ?
N3 C28 C29 . 115.4(6) ?
C27 C28 C29 . 126.3(7) ?
C30 C29 C34 . 121.9(7) ?
C30 C29 C28 . 123.7(7) ?
C34 C29 C28 . 114.2(6) ?
C31 C30 C29 . 119.7(8) ?
C31 C30 H30 . 120.2 ?
C29 C30 H30 . 120.2 ?
C30 C31 C32 . 120.4(7) ?
C30 C31 H31 . 119.8 ?
C32 C31 H31 . 119.8 ?
C31 C32 C33 . 120.2(8) ?
C31 C32 H32 . 119.9 ?
C33 C32 H32 . 119.9 ?
C32 C33 C34 . 121.6(8) ?
C32 C33 H33 . 119.2 ?
C34 C33 H33 . 119.2 ?
C33 C34 C29 . 116.2(6) ?
C33 C34 Ir1 . 129.1(5) ?
C29 C34 Ir1 . 114.7(5) ?
C35 C35 O3 2_766 130(3) ?
C35 C35 H35A 2_766 104.8 ?
O3 C35 H35A . 104.8 ?
C35 C35 H35B 2_766 104.8 ?
O3 C35 H35B . 104.8 ?
H35A C35 H35B . 105.8 ?
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 C23 . 1.982(7) y
Ir1 C34 . 1.993(7) y
Ir1 N1 . 2.217(5) y
Ir1 N2 . 2.035(6) y
Ir1 N3 . 2.052(6) y
Ir1 O2 . 2.219(4) y
O1 C2 . 1.249(8) ?
O2 H37 . 0.8500 ?
O2 H36 . 0.8500 ?
O3 C35 . 1.47(2) ?
O3 H3 . 0.8200 ?
N1 C2 . 1.318(8) ?
N1 C3 . 1.443(9) ?
N2 C13 . 1.313(9) ?
N2 C17 . 1.374(9) ?
N3 C24 . 1.348(9) ?
N3 C28 . 1.360(9) ?
C1 C2 . 1.527(10) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C3 C8 . 1.389(11) ?
C3 C4 . 1.390(11) ?
C4 C5 . 1.411(12) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.397(16) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.432(16) ?
C6 H6 . 0.9300 ?
C7 C12 . 1.368(14) ?
C7 C8 . 1.423(11) ?
C8 C9 . 1.413(12) ?
C9 C10 . 1.365(12) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.399(16) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.293(16) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.388(11) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.356(12) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.351(12) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.393(10) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.459(11) ?
C18 C19 . 1.417(10) ?
C18 C23 . 1.432(10) ?
C19 C20 . 1.358(12) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.381(13) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.375(10) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.382(10) ?
C22 H22 . 0.9300 ?
C24 C25 . 1.368(10) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.378(13) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.354(13) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.403(11) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.453(11) ?
C29 C30 . 1.394(10) ?
C29 C34 . 1.415(9) ?
C30 C31 . 1.363(12) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.382(12) ?
C31 H31 . 0.9300 ?
C32 C33 . 1.386(10) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.401(10) ?
C33 H33 . 0.9300 ?
C35 C35 2_766 1.426(18) ?
C35 H35A . 0.9700 ?
C35 H35B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H36 O1 2_575 0.85 1.98 2.756(7) 150.4
O2 H36 O1 2_575 0.85 1.98 2.756(7) 150.4
