# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1419395'
_audit_update_record             
;
2015-08-28 deposited with the CCDC.
2017-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '(pentamethylcyclopentadienyl)Iridium(bibenzimidazole)(chloride)chlorido' 
;
_chemical_name_common            IrBz
_chemical_melting_point          ?
_chemical_formula_moiety         C24H25ClIrN4,2(CHCl3),Cl
_chemical_formula_sum            'C26 H27 Cl8 Ir N4'
_chemical_formula_weight         874.34

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'
Cl Cl 0.1484 0.1585 '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   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3668(4)
_cell_length_b                   12.3575(5)
_cell_length_c                   30.7228(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.5240(10)
_cell_angle_gamma                90.00
_cell_volume                     3176.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9573
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.49

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1708
_exptl_absorpt_coefficient_mu    4.901
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_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            141435
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         28.54
_reflns_number_total             8006
_reflns_number_gt                7447
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0298P)²+7.9664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8006
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0594
_refine_ls_wR_factor_gt          0.0575
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.002
_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 0.581550(12) 0.316262(8) 0.094321(3) 0.02347(4) Uani 1 1 d . . .
Cl1 Cl 0.35059(9) 0.33674(6) 0.04848(2) 0.03283(14) Uani 1 1 d . . .
C15 C 0.7581(3) 0.3685(2) 0.14106(10) 0.0300(6) Uani 1 1 d . . .
C8 C 0.2847(4) 0.3243(2) 0.19414(10) 0.0345(6) Uani 1 1 d . . .
H8 H 0.3126 0.3941 0.1848 0.041 Uiso 1 1 calc R . .
N4 N 0.5542(3) -0.0199(2) 0.07548(9) 0.0323(5) Uani 1 1 d . . .
C17 C 0.6580(3) 0.4853(2) 0.08810(10) 0.0292(6) Uani 1 1 d . . .
N1 N 0.4341(3) 0.22002(19) 0.13608(7) 0.0263(5) Uani 1 1 d . . .
C1 C 0.4389(3) 0.1144(2) 0.12813(9) 0.0280(5) Uani 1 1 d . . .
N3 N 0.3508(3) 0.0563(2) 0.15645(9) 0.0330(5) Uani 1 1 d . . .
N2 N 0.5997(3) 0.15709(19) 0.06846(8) 0.0270(5) Uani 1 1 d . . .
C9 C 0.6733(3) 0.1038(2) 0.03410(10) 0.0303(6) Uani 1 1 d . . .
C3 C 0.3367(3) 0.2320(2) 0.17209(9) 0.0276(5) Uani 1 1 d . . .
C10 C 0.6463(4) -0.0079(3) 0.03900(10) 0.0342(6) Uani 1 1 d . . .
C16 C 0.6486(3) 0.4577(2) 0.13298(10) 0.0279(5) Uani 1 1 d . . .
C4 C 0.2859(3) 0.1289(2) 0.18549(10) 0.0308(6) Uani 1 1 d . . .
C6 C 0.1450(4) 0.2050(3) 0.24408(11) 0.0438(8) Uani 1 1 d . . .
H6 H 0.0821 0.1978 0.2691 0.053 Uiso 1 1 calc R . .
C20 C 0.7893(5) 0.3169(3) 0.18444(12) 0.0447(8) Uani 1 1 d . . .
H20A H 0.8414 0.2476 0.1803 0.067 Uiso 1 1 calc R . .
H20B H 0.6888 0.3061 0.1993 0.067 Uiso 1 1 calc R . .
H20C H 0.8578 0.3636 0.2018 0.067 Uiso 1 1 calc R . .
C5 C 0.1899(4) 0.1141(3) 0.22202(11) 0.0405(7) Uani 1 1 d . . .
H5 H 0.1578 0.0447 0.2310 0.049 Uiso 1 1 calc R . .
C7 C 0.1901(4) 0.3085(3) 0.23046(11) 0.0394(7) Uani 1 1 d . . .
H7 H 0.1555 0.3690 0.2463 0.047 Uiso 1 1 calc R . .
C24 C 0.9644(4) 0.2618(3) 0.09473(14) 0.0458(8) Uani 1 1 d . . .
H24A H 1.0673 0.2980 0.0945 0.069 Uiso 1 1 calc R . .
H24B H 0.9477 0.2248 0.0672 0.069 Uiso 1 1 calc R . .
H24C H 0.9622 0.2097 0.1183 0.069 Uiso 1 1 calc R . .
C23 C 0.8264(5) 0.4276(3) 0.02163(12) 0.0483(9) Uani 1 1 d . . .
H23A H 0.7368 0.4194 0.0017 0.072 Uiso 1 1 calc R . .
H23B H 0.9066 0.3732 0.0153 0.072 Uiso 1 1 calc R . .
H23C H 0.8725 0.4991 0.0183 0.072 Uiso 1 1 calc R . .
C19 C 0.8351(3) 0.3436(2) 0.10102(11) 0.0324(6) Uani 1 1 d . . .
C18 C 0.7698(3) 0.4137(2) 0.06754(10) 0.0322(6) Uani 1 1 d . . .
Cl2 Cl 0.42335(12) 0.81318(6) 0.14270(3) 0.0482(2) Uani 1 1 d . . .
Cl5 Cl 0.16091(13) 0.53481(10) 0.09997(4) 0.0636(3) Uani 1 1 d . . .
Cl4 Cl 0.02197(17) 0.58236(9) 0.18275(4) 0.0695(3) Uani 1 1 d . . .
Cl8 Cl 0.94009(18) 0.85395(10) 0.21289(4) 0.0729(3) Uani 1 1 d . . .
Cl6 Cl 0.70177(17) 1.02278(11) 0.21752(4) 0.0755(3) Uani 1 1 d . . .
Cl7 Cl 0.88741(16) 0.99471(11) 0.13978(4) 0.0718(3) Uani 1 1 d . . .
C11 C 0.7051(4) -0.0832(3) 0.00935(12) 0.0428(8) Uani 1 1 d . . .
H11 H 0.6873 -0.1578 0.0128 0.051 Uiso 1 1 calc R . .
C14 C 0.7557(4) 0.1428(3) -0.00167(11) 0.0403(7) Uani 1 1 d . . .
H14 H 0.7709 0.2174 -0.0059 0.048 Uiso 1 1 calc R . .
C21 C 0.5647(4) 0.5223(3) 0.16713(11) 0.0373(7) Uani 1 1 d . . .
H21A H 0.6264 0.5867 0.1738 0.056 Uiso 1 1 calc R . .
H21B H 0.5537 0.4789 0.1932 0.056 Uiso 1 1 calc R . .
H21C H 0.4596 0.5431 0.1565 0.056 Uiso 1 1 calc R . .
C12 C 0.7899(4) -0.0433(3) -0.02496(12) 0.0496(9) Uani 1 1 d . . .
H12 H 0.8328 -0.0920 -0.0452 0.060 Uiso 1 1 calc R . .
C22 C 0.5693(4) 0.5748(3) 0.06545(12) 0.0396(7) Uani 1 1 d . . .
H22A H 0.5043 0.6133 0.0863 0.059 Uiso 1 1 calc R . .
H22B H 0.5010 0.5445 0.0429 0.059 Uiso 1 1 calc R . .
H22C H 0.6451 0.6243 0.0525 0.059 Uiso 1 1 calc R . .
C13 C 0.8146(4) 0.0674(3) -0.03083(12) 0.0497(9) Uani 1 1 d . . .
H13 H 0.8724 0.0914 -0.0551 0.060 Uiso 1 1 calc R . .
C2 C 0.5301(3) 0.0800(2) 0.09151(9) 0.0260(5) Uani 1 1 d . . .
C25 C 0.0842(5) 0.6390(3) 0.13305(14) 0.0521(9) Uani 1 1 d . . .
H25 H 0.1696 0.6927 0.1389 0.063 Uiso 1 1 calc R . .
Cl3 Cl -0.07659(19) 0.70367(11) 0.10705(5) 0.0854(4) Uani 1 1 d . . .
C26 C 0.7947(6) 0.9283(3) 0.18337(13) 0.0576(10) Uani 1 1 d . . .
H26 H 0.7130 0.8778 0.1717 0.069 Uiso 1 1 calc R . .
H2 H 0.512(5) -0.076(4) 0.0863(14) 0.055(12) Uiso 1 1 d . . .
H1 H 0.342(5) -0.012(4) 0.1556(13) 0.053(12) Uiso 1 1 d . . .


_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 N2 2.127(2) . ?
Ir1 N1 2.148(2) . ?
Ir1 C15 2.150(3) . ?
Ir1 C18 2.152(3) . ?
Ir1 C19 2.156(3) . ?
Ir1 C16 2.183(3) . ?
Ir1 C17 2.193(3) . ?
Ir1 Cl1 2.3941(7) . ?
C15 C19 1.427(4) . ?
C15 C16 1.453(4) . ?
C15 C20 1.498(4) . ?
C8 C7 1.387(4) . ?
C8 C3 1.399(4) . ?
N4 C2 1.345(4) . ?
N4 C10 1.374(4) . ?
C17 C16 1.423(4) . ?
C17 C18 1.438(4) . ?
C17 C22 1.500(4) . ?
N1 C1 1.329(4) . ?
N1 C3 1.388(3) . ?
C1 N3 1.352(4) . ?
C1 C2 1.429(4) . ?
N3 C4 1.381(4) . ?
N2 C2 1.325(4) . ?
N2 C9 1.392(4) . ?
C9 C14 1.389(4) . ?
C9 C10 1.408(4) . ?
C3 C4 1.405(4) . ?
C10 C11 1.395(4) . ?
C16 C21 1.498(4) . ?
C4 C5 1.398(4) . ?
C6 C5 1.367(5) . ?
C6 C7 1.398(5) . ?
C24 C19 1.494(4) . ?
C23 C18 1.502(4) . ?
C19 C18 1.448(4) . ?
Cl5 C25 1.765(4) . ?
Cl4 C25 1.763(4) . ?
Cl8 C26 1.768(4) . ?
Cl6 C26 1.756(5) . ?
Cl7 C26 1.757(4) . ?
C11 C12 1.368(6) . ?
C14 C13 1.386(5) . ?
C12 C13 1.396(6) . ?
C25 Cl3 1.751(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
N2 Ir1 N1 75.79(9) . . ?
N2 Ir1 C15 118.43(10) . . ?
N1 Ir1 C15 99.33(10) . . ?
N2 Ir1 C18 108.63(10) . . ?
N1 Ir1 C18 164.74(11) . . ?
C15 Ir1 C18 65.58(12) . . ?
N2 Ir1 C19 96.14(10) . . ?
N1 Ir1 C19 126.86(11) . . ?
C15 Ir1 C19 38.72(12) . . ?
C18 Ir1 C19 39.27(12) . . ?
N2 Ir1 C16 157.58(10) . . ?
N1 Ir1 C16 105.33(10) . . ?
C15 Ir1 C16 39.19(10) . . ?
C18 Ir1 C16 64.84(11) . . ?
C19 Ir1 C16 64.85(11) . . ?
N2 Ir1 C17 145.70(10) . . ?
N1 Ir1 C17 138.51(10) . . ?
C15 Ir1 C17 64.74(11) . . ?
C18 Ir1 C17 38.63(11) . . ?
C19 Ir1 C17 64.64(11) . . ?
C16 Ir1 C17 37.96(11) . . ?
N2 Ir1 Cl1 86.45(7) . . ?
N1 Ir1 Cl1 86.84(7) . . ?
C15 Ir1 Cl1 155.12(8) . . ?
C18 Ir1 Cl1 107.80(9) . . ?
C19 Ir1 Cl1 145.87(9) . . ?
C16 Ir1 Cl1 115.93(8) . . ?
C17 Ir1 Cl1 94.74(8) . . ?
C19 C15 C16 107.8(3) . . ?
C19 C15 C20 126.8(3) . . ?
C16 C15 C20 125.4(3) . . ?
C19 C15 Ir1 70.90(16) . . ?
C16 C15 Ir1 71.67(16) . . ?
C20 C15 Ir1 125.4(2) . . ?
C7 C8 C3 117.2(3) . . ?
C2 N4 C10 106.7(3) . . ?
C16 C17 C18 108.7(3) . . ?
C16 C17 C22 126.5(3) . . ?
C18 C17 C22 124.8(3) . . ?
C16 C17 Ir1 70.66(15) . . ?
C18 C17 Ir1 69.14(15) . . ?
C22 C17 Ir1 126.8(2) . . ?
C1 N1 C3 105.7(2) . . ?
C1 N1 Ir1 114.55(18) . . ?
C3 N1 Ir1 139.65(19) . . ?
N1 C1 N3 112.7(3) . . ?
N1 C1 C2 117.0(2) . . ?
N3 C1 C2 130.3(3) . . ?
C1 N3 C4 106.9(2) . . ?
C2 N2 C9 105.4(2) . . ?
C2 N2 Ir1 115.59(18) . . ?
C9 N2 Ir1 138.9(2) . . ?
C14 C9 N2 131.5(3) . . ?
C14 C9 C10 120.4(3) . . ?
N2 C9 C10 108.1(3) . . ?
N1 C3 C8 131.3(3) . . ?
N1 C3 C4 108.6(2) . . ?
C8 C3 C4 120.1(3) . . ?
N4 C10 C11 131.7(3) . . ?
N4 C10 C9 106.5(3) . . ?
C11 C10 C9 121.8(3) . . ?
C17 C16 C15 107.9(3) . . ?
C17 C16 C21 125.6(3) . . ?
C15 C16 C21 125.7(3) . . ?
C17 C16 Ir1 71.38(16) . . ?
C15 C16 Ir1 69.15(15) . . ?
C21 C16 Ir1 133.5(2) . . ?
N3 C4 C5 131.7(3) . . ?
N3 C4 C3 106.2(2) . . ?
C5 C4 C3 122.1(3) . . ?
C5 C6 C7 121.8(3) . . ?
C6 C5 C4 116.9(3) . . ?
C8 C7 C6 121.8(3) . . ?
C15 C19 C18 108.2(3) . . ?
C15 C19 C24 126.2(3) . . ?
C18 C19 C24 125.5(3) . . ?
C15 C19 Ir1 70.38(16) . . ?
C18 C19 Ir1 70.20(16) . . ?
C24 C19 Ir1 126.5(2) . . ?
C17 C18 C19 107.4(3) . . ?
C17 C18 C23 123.7(3) . . ?
C19 C18 C23 128.0(3) . . ?
C17 C18 Ir1 72.22(15) . . ?
C19 C18 Ir1 70.53(15) . . ?
C23 C18 Ir1 131.4(2) . . ?
C12 C11 C10 116.9(3) . . ?
C9 C14 C13 117.4(3) . . ?
C11 C12 C13 122.1(3) . . ?
C14 C13 C12 121.4(4) . . ?
N2 C2 N4 113.3(3) . . ?
N2 C2 C1 116.6(2) . . ?
N4 C2 C1 130.1(3) . . ?
Cl3 C25 Cl4 110.1(2) . . ?
Cl3 C25 Cl5 110.6(2) . . ?
Cl4 C25 Cl5 108.7(2) . . ?
Cl6 C26 Cl7 110.2(2) . . ?
Cl6 C26 Cl8 110.2(2) . . ?
Cl7 C26 Cl8 109.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.54
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.345
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.083
_exptl_crystal_recrystallization_method 'Vapor diffusion'
_exptl_crystal_preparation       Luminescent
