# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a087
_database_code_depnum_ccdc_archive 'CCDC 1551044'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        (4-MeOpfupy)2Ir(acac)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 Ir N2 O6'
_chemical_formula_sum            'C33 H27 Ir N2 O6'
_chemical_formula_weight         739.79

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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'

_cell_length_a                   14.3281(9)
_cell_length_b                   19.2115(12)
_cell_length_c                   10.7242(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.5112(8)
_cell_angle_gamma                90.00
_cell_volume                     2746.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    186(2)
_cell_measurement_reflns_used    4810
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.30
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    4.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3400
_exptl_absorpt_correction_T_max  0.6393
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      186(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8083
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2520
_reflns_number_gt                2367
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0290P)²+1.7801P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2520
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0506
_refine_ls_wR_factor_gt          0.0495
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0000 0.227361(9) 0.2500 0.02079(7) Uani 1 2 d S . .
O1 O 0.39097(19) 0.20541(17) 0.1478(3) 0.0466(7) Uani 1 1 d . . .
O2 O -0.22388(19) 0.03518(16) -0.0941(3) 0.0453(7) Uani 1 1 d . . .
O3 O 0.04631(17) 0.30807(13) 0.3992(2) 0.0289(5) Uani 1 1 d . . .
N1 N 0.1342(2) 0.22366(14) 0.2235(3) 0.0232(6) Uani 1 1 d . . .
C1 C -0.0324(2) 0.15559(18) 0.1082(3) 0.0221(7) Uani 1 1 d . . .
C2 C 0.0425(2) 0.14627(18) 0.0507(3) 0.0246(7) Uani 1 1 d . . .
C3 C 0.0246(3) 0.10236(19) -0.0582(3) 0.0302(8) Uani 1 1 d . . .
H3 H 0.0744 0.0977 -0.0966 0.036 Uiso 1 1 calc R . .
C4 C -0.0642(3) 0.0650(2) -0.1125(3) 0.0330(8) Uani 1 1 d . . .
H4 H -0.0758 0.0358 -0.1882 0.040 Uiso 1 1 calc R . .
C5 C -0.1358(3) 0.0713(2) -0.0538(3) 0.0320(8) Uani 1 1 d . . .
C6 C -0.1195(2) 0.1157(2) 0.0544(3) 0.0291(8) Uani 1 1 d . . .
H6 H -0.1693 0.1190 0.0931 0.035 Uiso 1 1 calc R . .
C7 C 0.1359(2) 0.18316(19) 0.1205(3) 0.0256(7) Uani 1 1 d . . .
C8 C 0.2266(2) 0.1786(2) 0.0970(3) 0.0299(8) Uani 1 1 d . . .
C9 C 0.2622(3) 0.1451(2) 0.0034(4) 0.0405(9) Uani 1 1 d . . .
H9 H 0.2249 0.1158 -0.0691 0.049 Uiso 1 1 calc R . .
C10 C 0.3588(3) 0.1634(3) 0.0390(4) 0.0502(12) Uani 1 1 d . . .
H10 H 0.4004 0.1485 -0.0074 0.060 Uiso 1 1 calc R . .
C11 C 0.3101(3) 0.2149(2) 0.1845(4) 0.0360(9) Uani 1 1 d . . .
C12 C 0.3090(3) 0.2541(2) 0.2912(4) 0.0397(10) Uani 1 1 d . . .
H12 H 0.3670 0.2771 0.3503 0.048 Uiso 1 1 calc R . .
C13 C 0.2176(3) 0.2576(2) 0.3063(4) 0.0298(8) Uani 1 1 d . . .
H13 H 0.2125 0.2849 0.3774 0.036 Uiso 1 1 calc R . .
C14 C -0.2514(3) -0.0039(2) -0.2153(4) 0.0433(10) Uani 1 1 d . . .
H14A H -0.2538 0.0271 -0.2891 0.065 Uiso 1 1 calc R . .
H14B H -0.3175 -0.0250 -0.2347 0.065 Uiso 1 1 calc R . .
H14C H -0.2017 -0.0406 -0.2055 0.065 Uiso 1 1 calc R . .
C15 C 0.0417(2) 0.3728(2) 0.3754(4) 0.0312(8) Uani 1 1 d . . .
C16 C 0.0000 0.4046(3) 0.2500 0.0375(13) Uani 1 2 d S . .
H16 H 0.0000 0.4540 0.2500 0.045 Uiso 1 2 calc SR . .
C17 C 0.0858(3) 0.4182(2) 0.4978(4) 0.0409(10) Uani 1 1 d . . .
H17A H 0.0398 0.4199 0.5465 0.061 Uiso 1 1 d R . .
H17B H 0.0960 0.4653 0.4703 0.061 Uiso 1 1 d R . .
H17C H 0.1503 0.3988 0.5562 0.061 Uiso 1 1 d R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 C1 1.978(3) 2 ?
Ir1 C1 1.978(3) . ?
Ir1 N1 2.046(3) . ?
Ir1 N1 2.046(3) 2 ?
Ir1 O3 2.151(2) . ?
Ir1 O3 2.151(2) 2 ?
O1 C10 1.353(5) . ?
O1 C11 1.365(4) . ?
O2 C5 1.364(4) . ?
O2 C14 1.426(4) . ?
O3 C15 1.267(5) . ?
N1 C7 1.359(4) . ?
N1 C13 1.365(4) . ?
C1 C6 1.397(5) . ?
C1 C2 1.431(4) . ?
C2 C3 1.386(5) . ?
C2 C7 1.456(5) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.415(4) . ?
C8 C11 1.406(5) . ?
C8 C9 1.435(5) . ?
C9 C10 1.340(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.374(6) . ?
C12 C13 1.378(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.396(5) . ?
C15 C17 1.507(5) . ?
C16 C15 1.396(5) 2 ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C1 Ir1 C1 91.59(18) 2 . ?
C1 Ir1 N1 96.60(12) 2 . ?
C1 Ir1 N1 80.59(12) . . ?
C1 Ir1 N1 80.59(12) 2 2 ?
C1 Ir1 N1 96.60(12) . 2 ?
N1 Ir1 N1 176.01(15) . 2 ?
C1 Ir1 O3 90.54(12) 2 . ?
C1 Ir1 O3 174.87(10) . . ?
N1 Ir1 O3 94.52(10) . . ?
N1 Ir1 O3 88.35(10) 2 . ?
C1 Ir1 O3 174.87(10) 2 2 ?
C1 Ir1 O3 90.54(12) . 2 ?
N1 Ir1 O3 88.35(10) . 2 ?
N1 Ir1 O3 94.52(10) 2 2 ?
O3 Ir1 O3 87.73(13) . 2 ?
C10 O1 C11 105.8(3) . . ?
C5 O2 C14 118.1(3) . . ?
C15 O3 Ir1 125.4(2) . . ?
C7 N1 C13 122.0(3) . . ?
C7 N1 Ir1 115.5(2) . . ?
C13 N1 Ir1 122.5(2) . . ?
C6 C1 C2 116.8(3) . . ?
C6 C1 Ir1 128.5(2) . . ?
C2 C1 Ir1 114.7(2) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 C7 125.5(3) . . ?
C1 C2 C7 114.2(3) . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
O2 C5 C6 115.4(3) . . ?
O2 C5 C4 124.2(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 122.2(3) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
N1 C7 C8 118.1(3) . . ?
N1 C7 C2 114.2(3) . . ?
C8 C7 C2 127.6(3) . . ?
C11 C8 C7 117.6(3) . . ?
C11 C8 C9 104.8(3) . . ?
C7 C8 C9 137.6(3) . . ?
C10 C9 C8 106.1(4) . . ?
C10 C9 H9 126.9 . . ?
C8 C9 H9 126.9 . . ?
C9 C10 O1 113.1(3) . . ?
C9 C10 H10 123.5 . . ?
O1 C10 H10 123.5 . . ?
O1 C11 C12 125.7(4) . . ?
O1 C11 C8 110.2(3) . . ?
C12 C11 C8 124.1(3) . . ?
C11 C12 C13 115.3(4) . . ?
C11 C12 H12 122.4 . . ?
C13 C12 H12 122.4 . . ?
N1 C13 C12 122.9(4) . . ?
N1 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 C16 126.5(4) . . ?
O3 C15 C17 114.7(3) . . ?
C16 C15 C17 118.8(4) . . ?
C15 C16 C15 128.2(5) . 2 ?
C15 C16 H16 115.9 . . ?
C15 C16 H16 115.9 2 . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ir1 O3 C15 86.0(3) . . . . ?
N1 Ir1 O3 C15 -96.8(3) 2 . . . ?
O3 Ir1 O3 C15 -2.2(2) 2 . . . ?
C1 Ir1 N1 C7 96.9(2) 2 . . . ?
C1 Ir1 N1 C7 6.4(2) . . . . ?
O3 Ir1 N1 C7 -172.0(2) . . . . ?
O3 Ir1 N1 C7 -84.5(2) 2 . . . ?
C1 Ir1 N1 C13 -81.0(3) 2 . . . ?
C1 Ir1 N1 C13 -171.5(3) . . . . ?
O3 Ir1 N1 C13 10.0(3) . . . . ?
O3 Ir1 N1 C13 97.6(3) 2 . . . ?
C1 Ir1 C1 C6 78.2(3) 2 . . . ?
N1 Ir1 C1 C6 174.6(3) . . . . ?
N1 Ir1 C1 C6 -2.5(3) 2 . . . ?
C1 Ir1 C1 C2 -104.7(3) 2 . . . ?
N1 Ir1 C1 C2 -8.3(2) . . . . ?
N1 Ir1 C1 C2 174.6(2) 2 . . . ?
C6 C1 C2 C3 3.6(5) . . . . ?
Ir1 C1 C2 C3 -173.9(3) . . . . ?
C6 C1 C2 C7 -173.4(3) . . . . ?
Ir1 C1 C2 C7 9.2(4) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
C7 C2 C3 C4 175.0(3) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C14 O2 C5 C6 171.6(3) . . . . ?
C14 O2 C5 C4 -9.5(6) . . . . ?
C3 C4 C5 O2 -177.0(3) . . . . ?
C3 C4 C5 C6 1.8(6) . . . . ?
O2 C5 C6 C1 179.2(3) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
C2 C1 C6 C5 -2.9(5) . . . . ?
Ir1 C1 C6 C5 174.1(3) . . . . ?
C13 N1 C7 C8 -2.2(5) . . . . ?
Ir1 N1 C7 C8 179.9(2) . . . . ?
C13 N1 C7 C2 174.8(3) . . . . ?
Ir1 N1 C7 C2 -3.1(4) . . . . ?
C3 C2 C7 N1 179.4(3) . . . . ?
C1 C2 C7 N1 -3.8(4) . . . . ?
C3 C2 C7 C8 -4.0(6) . . . . ?
C1 C2 C7 C8 172.8(3) . . . . ?
N1 C7 C8 C11 1.7(5) . . . . ?
C2 C7 C8 C11 -174.9(3) . . . . ?
N1 C7 C8 C9 -178.7(4) . . . . ?
C2 C7 C8 C9 4.8(7) . . . . ?
C11 C8 C9 C10 -0.6(4) . . . . ?
C7 C8 C9 C10 179.7(4) . . . . ?
C8 C9 C10 O1 0.5(5) . . . . ?
C11 O1 C10 C9 -0.2(5) . . . . ?
C10 O1 C11 C12 179.7(4) . . . . ?
C10 O1 C11 C8 -0.3(4) . . . . ?
C7 C8 C11 O1 -179.7(3) . . . . ?
C9 C8 C11 O1 0.6(4) . . . . ?
C7 C8 C11 C12 0.3(6) . . . . ?
C9 C8 C11 C12 -179.4(4) . . . . ?
O1 C11 C12 C13 178.2(4) . . . . ?
C8 C11 C12 C13 -1.8(6) . . . . ?
C7 N1 C13 C12 0.6(5) . . . . ?
Ir1 N1 C13 C12 178.4(3) . . . . ?
C11 C12 C13 N1 1.4(6) . . . . ?
Ir1 O3 C15 C16 4.6(4) . . . . ?
Ir1 O3 C15 C17 -175.9(2) . . . . ?
O3 C15 C16 C15 -2.6(2) . . . 2 ?
C17 C15 C16 C15 177.9(3) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.089
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and methanol'
