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#$Date: 2016-03-25 14:03:28 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179877 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/73/7017364.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_7017364
loop_
_publ_author_name
'Edkins, Robert M.'
'Bettington, Sylvia L.'
'Goeta, Andrés E'
'Beeby, Andrew'
_publ_section_title
;
 Two-photon spectroscopy of cyclometalated iridium complexes.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12765
_journal_page_last               12770
_journal_paper_doi               10.1039/c1dt11164g
_journal_volume                  40
_journal_year                    2011
_chemical_formula_sum            'C43 H31 Ir N2 O2'
_chemical_formula_weight         799.90
_chemical_name_common            Ir(4-pe-2-ppy)₂(acac)
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 105.4780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.6570(5)
_cell_length_b                   10.5169(2)
_cell_length_c                   15.1507(3)
_cell_measurement_reflns_used    7774
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.08
_cell_measurement_theta_min      2.17
_cell_volume                     3325.64(12)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.630 (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART-6K CCD Diffractometer'
_diffrn_measurement_method       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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22991
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.056
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 - Sheldrick G. (2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.183
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0283
_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)+(0.0339P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0621
_reflns_number_gt                4446
_reflns_number_total             5071
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt11164g.txt
_cod_data_source_block           09srv112
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7017364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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
Ir Ir 0.5000 0.035566(14) 0.2500 0.02083(5) Uani 1 2 d S
N1 N 0.56913(11) 0.0262(2) 0.18194(15) 0.0228(4) Uani 1 1 d .
O1 O 0.45114(9) 0.1836(2) 0.15985(12) 0.0279(4) Uani 1 1 d .
C1 C 0.46158(12) -0.0978(3) 0.15881(16) 0.0219(5) Uani 1 1 d .
C2 C 0.40478(14) -0.1672(3) 0.14910(19) 0.0276(6) Uani 1 1 d .
H2 H 0.3796 -0.1522 0.1907 0.033 Uiso 1 1 calc R
C3 C 0.38450(15) -0.2569(3) 0.08071(19) 0.0310(6) Uani 1 1 d .
H3 H 0.3457 -0.3019 0.0757 0.037 Uiso 1 1 calc R
C4 C 0.42077(15) -0.2815(3) 0.01908(19) 0.0316(6) Uani 1 1 d .
H4 H 0.4068 -0.3435 -0.0276 0.038 Uiso 1 1 calc R
C5 C 0.47672(14) -0.2159(3) 0.02621(18) 0.0278(6) Uani 1 1 d .
H5 H 0.5014 -0.2320 -0.0159 0.033 Uiso 1 1 calc R
C6 C 0.49752(13) -0.1252(3) 0.09540(17) 0.0241(5) Uani 1 1 d .
C7 C 0.55664(13) -0.0541(2) 0.10843(17) 0.0225(5) Uani 1 1 d .
C8 C 0.59985(14) -0.0644(3) 0.05486(19) 0.0262(6) Uani 1 1 d .
H8 H 0.5900 -0.1175 0.0023 0.031 Uiso 1 1 calc R
C9 C 0.65722(14) 0.0029(3) 0.0781(2) 0.0272(6) Uani 1 1 d .
C10 C 0.67049(14) 0.0799(3) 0.15594(19) 0.0293(6) Uani 1 1 d .
H10 H 0.7099 0.1248 0.1748 0.035 Uiso 1 1 calc R
C11 C 0.62539(13) 0.0898(3) 0.20522(18) 0.0266(5) Uani 1 1 d .
H11 H 0.6343 0.1434 0.2575 0.032 Uiso 1 1 calc R
C12 C 0.70086(15) -0.0089(3) 0.0220(2) 0.0310(6) Uani 1 1 d .
C13 C 0.73301(15) -0.0239(3) -0.0305(2) 0.0318(6) Uani 1 1 d .
C14 C 0.77035(14) -0.0390(3) -0.0947(2) 0.0321(6) Uani 1 1 d .
C15 C 0.7876(2) 0.0654(4) -0.1374(3) 0.0531(11) Uani 1 1 d .
H15 H 0.7744 0.1478 -0.1244 0.064 Uiso 1 1 calc R
C16 C 0.8246(2) 0.0511(5) -0.2000(3) 0.0701(15) Uani 1 1 d .
H16 H 0.8360 0.1234 -0.2298 0.084 Uiso 1 1 calc R
C17 C 0.84422(17) -0.0683(5) -0.2178(3) 0.0552(12) Uani 1 1 d .
H17 H 0.8707 -0.0783 -0.2582 0.066 Uiso 1 1 calc R
C18 C 0.82573(19) -0.1726(5) -0.1777(2) 0.0583(12) Uani 1 1 d .
H18 H 0.8386 -0.2550 -0.1914 0.070 Uiso 1 1 calc R
C19 C 0.78837(19) -0.1590(4) -0.1169(2) 0.0508(10) Uani 1 1 d .
H19 H 0.7750 -0.2323 -0.0903 0.061 Uiso 1 1 calc R
C20 C 0.45778(15) 0.3024(3) 0.1755(2) 0.0324(7) Uani 1 1 d .
C21 C 0.5000 0.3601(4) 0.2500 0.0382(10) Uani 1 2 d S
H21 H 0.5000 0.442(5) 0.2500 0.043(15) Uiso 1 2 d S
C22 C 0.41376(18) 0.3847(4) 0.1042(2) 0.0449(8) Uani 1 1 d .
H223 H 0.4196 0.3650 0.0437 0.067 Uiso 1 1 calc R
H222 H 0.4239 0.4744 0.1185 0.067 Uiso 1 1 calc R
H221 H 0.3692 0.3681 0.1041 0.067 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'
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'
Ir Ir -1.4442 7.9887 '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
C1 Ir C1 90.30(15) . 2_655
C1 Ir N1 80.90(10) . .
C1 Ir N1 95.16(9) 2_655 .
C1 Ir N1 95.16(9) . 2_655
C1 Ir N1 80.90(10) 2_655 2_655
N1 Ir N1 174.46(13) . 2_655
C1 Ir O1 91.47(9) . .
C1 Ir O1 173.81(8) 2_655 .
N1 Ir O1 90.98(8) . .
N1 Ir O1 93.03(8) 2_655 .
C1 Ir O1 173.81(8) . 2_655
C1 Ir O1 91.47(9) 2_655 2_655
N1 Ir O1 93.03(8) . 2_655
N1 Ir O1 90.98(8) 2_655 2_655
O1 Ir O1 87.39(11) . 2_655
C11 N1 C7 119.2(2) . .
C11 N1 Ir 125.31(18) . .
C7 N1 Ir 115.52(18) . .
C20 O1 Ir 125.44(19) . .
C2 C1 C6 116.6(2) . .
C2 C1 Ir 129.21(19) . .
C6 C1 Ir 114.22(19) . .
C3 C2 C1 121.8(2) . .
C3 C2 H2 119.1 . .
C1 C2 H2 119.1 . .
C2 C3 C4 120.3(3) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C5 C4 C3 119.8(3) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
C4 C5 C6 120.1(3) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C5 C6 C1 121.4(3) . .
C5 C6 C7 123.3(2) . .
C1 C6 C7 115.3(2) . .
N1 C7 C8 120.3(3) . .
N1 C7 C6 113.9(2) . .
C8 C7 C6 125.8(2) . .
C9 C8 C7 120.3(3) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
C8 C9 C10 118.5(3) . .
C8 C9 C12 119.4(3) . .
C10 C9 C12 122.1(3) . .
C11 C10 C9 118.9(3) . .
C11 C10 H10 120.5 . .
C9 C10 H10 120.5 . .
N1 C11 C10 122.6(3) . .
N1 C11 H11 118.7 . .
C10 C11 H11 118.7 . .
C13 C12 C9 174.3(4) . .
C12 C13 C14 178.4(3) . .
C15 C14 C19 118.8(3) . .
C15 C14 C13 120.4(3) . .
C19 C14 C13 120.8(3) . .
C14 C15 C16 120.6(4) . .
C14 C15 H15 119.7 . .
C16 C15 H15 119.7 . .
C17 C16 C15 119.5(4) . .
C17 C16 H16 120.3 . .
C15 C16 H16 120.3 . .
C18 C17 C16 120.2(3) . .
C18 C17 H17 119.9 . .
C16 C17 H17 119.9 . .
C17 C18 C19 120.4(4) . .
C17 C18 H18 119.8 . .
C19 C18 H18 119.8 . .
C18 C19 C14 120.4(4) . .
C18 C19 H19 119.8 . .
C14 C19 H19 119.8 . .
O1 C20 C21 126.7(3) . .
O1 C20 C22 114.3(3) . .
C21 C20 C22 119.0(3) . .
C20 C21 C20 128.1(4) . 2_655
C20 C21 H21 115.9(2) . .
C20 C21 H21 115.9(2) 2_655 .
C20 C22 H223 109.5 . .
C20 C22 H222 109.5 . .
H223 C22 H222 109.5 . .
C20 C22 H221 109.5 . .
H223 C22 H221 109.5 . .
H222 C22 H221 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir C1 1.989(3) .
Ir C1 1.989(3) 2_655
Ir N1 2.034(2) .
Ir N1 2.034(2) 2_655
Ir O1 2.1538(19) .
Ir O1 2.1538(19) 2_655
N1 C11 1.352(4) .
N1 C7 1.366(3) .
O1 C20 1.272(4) .
C1 C2 1.404(4) .
C1 C6 1.418(3) .
C2 C3 1.383(4) .
C2 H2 0.9500 .
C3 C4 1.396(4) .
C3 H3 0.9500 .
C4 C5 1.374(4) .
C4 H4 0.9500 .
C5 C6 1.400(4) .
C5 H5 0.9500 .
C6 C7 1.450(4) .
C7 C8 1.397(4) .
C8 C9 1.391(4) .
C8 H8 0.9500 .
C9 C10 1.395(4) .
C9 C12 1.436(4) .
C10 C11 1.383(4) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 C13 1.199(4) .
C13 C14 1.430(4) .
C14 C15 1.377(5) .
C14 C19 1.389(5) .
C15 C16 1.402(5) .
C15 H15 0.9500 .
C16 C17 1.376(6) .
C16 H16 0.9500 .
C17 C18 1.365(6) .
C17 H17 0.9500 .
C18 C19 1.385(4) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 C21 1.389(4) .
C20 C22 1.508(4) .
C21 C20 1.389(4) 2_655
C21 H21 0.86(5) .
C22 H223 0.9800 .
C22 H222 0.9800 .
C22 H221 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 Ir N1 C11 -174.9(2) . .
C1 Ir N1 C11 -85.4(2) 2_655 .
N1 Ir N1 C11 -129.9(2) 2_655 .
O1 Ir N1 C11 93.8(2) . .
O1 Ir N1 C11 6.4(2) 2_655 .
C1 Ir N1 C7 3.52(18) . .
C1 Ir N1 C7 93.00(19) 2_655 .
N1 Ir N1 C7 48.52(18) 2_655 .
O1 Ir N1 C7 -87.81(19) . .
O1 Ir N1 C7 -175.25(18) 2_655 .
C1 Ir O1 C20 -175.8(2) . .
C1 Ir O1 C20 77.6(9) 2_655 .
N1 Ir O1 C20 -94.9(2) . .
N1 Ir O1 C20 88.9(2) 2_655 .
O1 Ir O1 C20 -1.93(18) 2_655 .
C1 Ir C1 C2 82.2(3) 2_655 .
N1 Ir C1 C2 177.4(3) . .
N1 Ir C1 C2 1.3(3) 2_655 .
O1 Ir C1 C2 -91.9(3) . .
O1 Ir C1 C2 -171.1(7) 2_655 .
C1 Ir C1 C6 -97.7(2) 2_655 .
N1 Ir C1 C6 -2.49(19) . .
N1 Ir C1 C6 -178.56(19) 2_655 .
O1 Ir C1 C6 88.3(2) . .
O1 Ir C1 C6 9.0(10) 2_655 .
C6 C1 C2 C3 -0.6(4) . .
Ir C1 C2 C3 179.5(2) . .
C1 C2 C3 C4 0.4(5) . .
C2 C3 C4 C5 -0.3(5) . .
C3 C4 C5 C6 0.4(4) . .
C4 C5 C6 C1 -0.6(4) . .
C4 C5 C6 C7 178.7(3) . .
C2 C1 C6 C5 0.7(4) . .
Ir C1 C6 C5 -179.4(2) . .
C2 C1 C6 C7 -178.7(2) . .
Ir C1 C6 C7 1.3(3) . .
C11 N1 C7 C8 -3.8(4) . .
Ir N1 C7 C8 177.73(19) . .
C11 N1 C7 C6 174.7(2) . .
Ir N1 C7 C6 -3.8(3) . .
C5 C6 C7 N1 -177.7(2) . .
C1 C6 C7 N1 1.7(3) . .
C5 C6 C7 C8 0.7(4) . .
C1 C6 C7 C8 -179.9(3) . .
N1 C7 C8 C9 2.7(4) . .
C6 C7 C8 C9 -175.6(3) . .
C7 C8 C9 C10 0.2(4) . .
C7 C8 C9 C12 -179.8(3) . .
C8 C9 C10 C11 -2.1(4) . .
C12 C9 C10 C11 178.0(3) . .
C7 N1 C11 C10 1.9(4) . .
Ir N1 C11 C10 -179.8(2) . .
C9 C10 C11 N1 1.1(5) . .
C8 C9 C12 C13 12(4) . .
C10 C9 C12 C13 -168(3) . .
C9 C12 C13 C14 73(14) . .
C12 C13 C14 C15 39(13) . .
C12 C13 C14 C19 -139(13) . .
C19 C14 C15 C16 -2.1(6) . .
C13 C14 C15 C16 179.6(4) . .
C14 C15 C16 C17 -0.7(7) . .
C15 C16 C17 C18 2.6(7) . .
C16 C17 C18 C19 -1.6(7) . .
C17 C18 C19 C14 -1.3(6) . .
C15 C14 C19 C18 3.1(6) . .
C13 C14 C19 C18 -178.6(3) . .
Ir O1 C20 C21 4.1(4) . .
Ir O1 C20 C22 -175.27(19) . .
O1 C20 C21 C20 -2.3(2) . 2_655
C22 C20 C21 C20 177.0(3) . 2_655
