# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Xingwei Li'
_publ_contact_author_email       XINGWEI@NTU.EDU.SG

_publ_section_title              
;
Hydrogen Bonding-Assisted Tautomerization of Pyridine
Moieties in the Coordination Sphere of an Ir(I) Complex
;
loop_
_publ_author_name
'Xingwei Li.'
'Guoyong Song.'

data_lxw37m
_database_code_depnum_ccdc_archive 'CCDC 682697'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 Ir N3 O, B F4'
_chemical_formula_sum            'C21 H25 B F4 Ir N3 O'
_chemical_formula_weight         614.45

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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   P2(1)/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                   7.7588(2)
_cell_length_b                   16.9174(5)
_cell_length_c                   15.9163(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.7470(10)
_cell_angle_gamma                90.00
_cell_volume                     2029.31(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8655
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.48

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    6.635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2408
_exptl_absorpt_correction_T_max  0.7772
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32967
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         30.54
_reflns_number_total             6170
_reflns_number_gt                5344
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0196P)^2^+1.9145P] where P=(Fo^2^+2Fc^2^)/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         6170
_refine_ls_number_parameters     343
_refine_ls_number_restraints     201
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0179
_refine_ls_wR_factor_ref         0.0451
_refine_ls_wR_factor_gt          0.0411
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.010
_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 0.749796(11) 1.020773(5) 0.291421(5) 0.01770(3) Uani 1 1 d D . .
B1 B 0.1336(5) 0.7364(2) 0.2333(2) 0.0354(7) Uani 1 1 d . . .
C1 C 0.834(3) 1.0538(8) 0.1731(10) 0.038(4) Uani 0.482(13) 1 d PDU A 2
H1 H 0.9348 1.0916 0.1914 0.046 Uiso 0.482(13) 1 calc PRD A 2
C2 C 0.6801(17) 1.0959(9) 0.1745(8) 0.026(2) Uani 0.482(13) 1 d PDU A 2
H2 H 0.6837 1.1548 0.1799 0.032 Uiso 0.482(13) 1 calc PRD A 2
C1A C 0.847(2) 1.0579(7) 0.1762(9) 0.036(3) Uani 0.518(13) 1 d PDU A 1
H1A H 0.9452 1.0974 0.1827 0.043 Uiso 0.518(13) 1 calc PR A 1
C2A C 0.6717(18) 1.0834(9) 0.1670(8) 0.037(3) Uani 0.518(13) 1 d PDU A 1
H2A H 0.6755 1.1413 0.1798 0.045 Uiso 0.518(13) 1 calc PR A 1
C3 C 0.5336(11) 1.0557(5) 0.1062(5) 0.0309(16) Uani 0.482(13) 1 d PDU A 2
H3A H 0.5871 1.0276 0.0641 0.037 Uiso 0.482(13) 1 calc PR A 2
H3B H 0.4514 1.0963 0.0744 0.037 Uiso 0.482(13) 1 calc PR A 2
C4 C 0.4289(12) 0.9961(6) 0.1492(5) 0.0323(18) Uani 0.482(13) 1 d PDU A 2
H4A H 0.3575 0.9614 0.1040 0.039 Uiso 0.482(13) 1 calc PR A 2
H4B H 0.3459 1.0257 0.1762 0.039 Uiso 0.482(13) 1 calc PR A 2
C3A C 0.4759(11) 1.0614(4) 0.1264(5) 0.0323(15) Uani 0.518(13) 1 d PDU A 1
H3A1 H 0.3973 1.0886 0.1579 0.039 Uiso 0.518(13) 1 calc PR A 1
H3A2 H 0.4428 1.0787 0.0653 0.039 Uiso 0.518(13) 1 calc PR A 1
C4A C 0.4527(11) 0.9718(5) 0.1314(4) 0.0290(15) Uani 0.518(13) 1 d PDU A 1
H4A1 H 0.3253 0.9586 0.1222 0.035 Uiso 0.518(13) 1 calc PR A 1
H4A2 H 0.4992 0.9453 0.0859 0.035 Uiso 0.518(13) 1 calc PR A 1
C5 C 0.5529(3) 0.94373(16) 0.21969(16) 0.0292(5) Uani 1 1 d D A .
H5 H 0.483(4) 0.9204(17) 0.2573(17) 0.035 Uiso 1 1 d D . .
C6 C 0.7214(4) 0.91076(15) 0.22506(16) 0.0272(5) Uani 1 1 d D A .
H6 H 0.752(4) 0.8670(14) 0.2687(16) 0.033 Uiso 1 1 d D . .
C7A C 0.8376(13) 0.9068(7) 0.1587(6) 0.031(2) Uani 0.518(13) 1 d PDU A 1
H7A1 H 0.9608 0.8929 0.1887 0.037 Uiso 0.518(13) 1 calc PR A 1
H7A2 H 0.7919 0.8651 0.1156 0.037 Uiso 0.518(13) 1 calc PR A 1
C8A C 0.8368(13) 0.9863(4) 0.1126(5) 0.0296(16) Uani 0.518(13) 1 d PDU A 1
H8A1 H 0.7271 0.9906 0.0660 0.036 Uiso 0.518(13) 1 calc PR A 1
H8A2 H 0.9392 0.9885 0.0856 0.036 Uiso 0.518(13) 1 calc PR A 1
C7 C 0.7852(15) 0.9107(6) 0.1420(7) 0.031(2) Uani 0.482(13) 1 d PDU A 2
H7A H 0.6810 0.9129 0.0921 0.038 Uiso 0.482(13) 1 calc PR A 2
H7B H 0.8487 0.8606 0.1381 0.038 Uiso 0.482(13) 1 calc PR A 2
C8 C 0.9088(12) 0.9802(5) 0.1359(6) 0.0328(17) Uani 0.482(13) 1 d PDU A 2
H8A H 0.9122 0.9895 0.0749 0.039 Uiso 0.482(13) 1 calc PR A 2
H8B H 1.0307 0.9688 0.1697 0.039 Uiso 0.482(13) 1 calc PR A 2
C9 C 0.9243(3) 1.18100(14) 0.34458(16) 0.0254(5) Uani 1 1 d . . .
H9 H 0.9243 1.1856 0.2851 0.031 Uiso 1 1 calc R A .
C10 C 0.9948(3) 1.24234(14) 0.39971(18) 0.0288(5) Uani 1 1 d . A .
H10 H 1.0433 1.2877 0.3787 0.035 Uiso 1 1 calc R . .
C11 C 0.9927(3) 1.23608(14) 0.48511(18) 0.0304(5) Uani 1 1 d . . .
H11 H 1.0388 1.2776 0.5242 0.036 Uiso 1 1 calc R A .
C12 C 0.9229(3) 1.16866(14) 0.51462(16) 0.0258(5) Uani 1 1 d . A .
H12 H 0.9224 1.1640 0.5740 0.031 Uiso 1 1 calc R . .
C13 C 0.8538(3) 1.10805(13) 0.45752(14) 0.0194(4) Uani 1 1 d . . .
C14 C 0.7787(3) 1.03247(13) 0.47978(14) 0.0187(4) Uani 1 1 d . A .
C15 C 0.7296(3) 0.98120(12) 0.40700(14) 0.0183(4) Uani 1 1 d . A .
C16 C 0.7519(3) 1.00955(13) 0.56070(14) 0.0196(4) Uani 1 1 d . . .
C17 C 0.7979(3) 1.05784(16) 0.64178(15) 0.0262(5) Uani 1 1 d . A .
H17A H 0.9266 1.0660 0.6588 0.039 Uiso 1 1 calc R . .
H17B H 0.7593 1.0300 0.6881 0.039 Uiso 1 1 calc R . .
H17C H 0.7380 1.1092 0.6315 0.039 Uiso 1 1 calc R . .
C18 C 0.6793(3) 0.93502(14) 0.56814(14) 0.0220(4) Uani 1 1 d . A .
H18 H 0.6588 0.9188 0.6221 0.026 Uiso 1 1 calc R . .
C19 C 0.6373(3) 0.88484(13) 0.49811(14) 0.0203(4) Uani 1 1 d . . .
C20 C 0.5424(3) 0.75239(14) 0.44075(16) 0.0271(5) Uani 1 1 d . . .
C21 C 0.4674(5) 0.67664(17) 0.4663(2) 0.0407(7) Uani 1 1 d . A .
H21A H 0.3617 0.6619 0.4218 0.061 Uiso 1 1 calc RD . .
H21B H 0.4350 0.6840 0.5217 0.061 Uiso 1 1 calc R . .
H21C H 0.5565 0.6347 0.4721 0.061 Uiso 1 1 calc RD . .
F1 F 0.2435(3) 0.67077(12) 0.24794(14) 0.0538(5) Uani 1 1 d . . .
F2 F -0.0103(2) 0.71949(10) 0.16264(10) 0.0384(4) Uani 1 1 d . . .
F3 F 0.0680(3) 0.75300(12) 0.30494(12) 0.0540(5) Uani 1 1 d . . .
F4 F 0.2229(3) 0.80155(13) 0.21185(14) 0.0567(5) Uani 1 1 d . . .
N1 N 0.8559(2) 1.11512(11) 0.37152(12) 0.0204(4) Uani 1 1 d . A .
N2 N 0.6635(2) 0.90888(11) 0.42124(12) 0.0191(3) Uani 1 1 d . A .
H2N H 0.6362 0.8758 0.3774 0.023 Uiso 1 1 calc R . .
N3 N 0.5653(3) 0.81071(12) 0.50332(13) 0.0236(4) Uani 1 1 d . A .
H3N H 0.5309 0.7996 0.5508 0.028 Uiso 1 1 calc R . .
O1 O 0.5808(3) 0.76264(11) 0.37182(12) 0.0336(4) Uani 1 1 d D A .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.02308(4) 0.01827(4) 0.01228(4) -0.00046(3) 0.00527(3) 0.00020(3)
B1 0.0449(17) 0.0367(16) 0.0261(15) -0.0116(13) 0.0115(13) -0.0058(13)
C1 0.069(6) 0.024(5) 0.026(6) -0.007(4) 0.018(5) -0.020(5)
C2 0.055(4) 0.010(4) 0.009(3) 0.000(3) -0.003(3) -0.006(3)
C1A 0.069(6) 0.026(5) 0.027(5) -0.001(4) 0.037(5) -0.003(5)
C2A 0.075(5) 0.014(5) 0.017(4) -0.005(3) -0.001(3) -0.011(3)
C3 0.031(4) 0.034(3) 0.024(3) 0.007(3) 0.000(2) 0.004(3)
C4 0.035(4) 0.044(5) 0.015(3) -0.003(3) 0.000(3) -0.004(3)
C3A 0.037(4) 0.033(3) 0.022(3) -0.002(2) -0.004(2) 0.011(3)
C4A 0.032(3) 0.039(4) 0.014(3) -0.004(2) 0.000(2) -0.001(3)
C5 0.0312(12) 0.0359(13) 0.0184(11) 0.0020(10) 0.0016(9) -0.0108(10)
C6 0.0413(13) 0.0260(12) 0.0175(11) -0.0065(9) 0.0133(10) -0.0093(10)
C7A 0.038(4) 0.038(4) 0.020(4) -0.009(3) 0.015(3) 0.000(3)
C8A 0.039(4) 0.026(3) 0.030(4) -0.004(3) 0.022(3) 0.004(3)
C7 0.052(6) 0.016(3) 0.031(5) -0.001(3) 0.017(4) 0.001(4)
C8 0.034(4) 0.041(4) 0.028(4) -0.003(3) 0.017(3) 0.000(3)
C9 0.0304(12) 0.0224(11) 0.0237(12) 0.0017(9) 0.0069(9) 0.0002(9)
C10 0.0302(12) 0.0183(10) 0.0372(15) 0.0019(10) 0.0064(10) 0.0009(9)
C11 0.0315(13) 0.0226(11) 0.0350(14) -0.0082(10) 0.0040(10) -0.0013(9)
C12 0.0304(12) 0.0256(11) 0.0212(12) -0.0058(9) 0.0054(9) 0.0004(9)
C13 0.0192(9) 0.0213(10) 0.0173(10) -0.0014(8) 0.0035(8) 0.0030(8)
C14 0.0185(9) 0.0246(10) 0.0112(10) -0.0047(8) 0.0002(7) 0.0009(7)
C15 0.0186(9) 0.0200(10) 0.0166(10) -0.0003(8) 0.0046(7) 0.0020(7)
C16 0.0172(9) 0.0262(11) 0.0150(10) 0.0001(8) 0.0030(8) 0.0040(8)
C17 0.0295(11) 0.0340(13) 0.0151(11) -0.0060(10) 0.0055(9) -0.0013(10)
C18 0.0242(10) 0.0280(11) 0.0143(10) 0.0017(9) 0.0057(8) 0.0032(9)
C19 0.0198(9) 0.0243(10) 0.0169(10) 0.0038(8) 0.0048(8) 0.0027(8)
C20 0.0319(12) 0.0254(11) 0.0255(12) 0.0007(10) 0.0100(10) -0.0020(9)
C21 0.0627(19) 0.0290(13) 0.0366(16) -0.0007(12) 0.0238(14) -0.0119(13)
F1 0.0563(12) 0.0521(12) 0.0476(12) -0.0111(10) 0.0014(9) 0.0091(9)
F2 0.0400(9) 0.0498(10) 0.0271(8) -0.0099(7) 0.0111(7) -0.0030(7)
F3 0.0872(15) 0.0502(11) 0.0316(10) -0.0174(8) 0.0282(10) -0.0112(10)
F4 0.0604(12) 0.0488(11) 0.0678(14) -0.0112(10) 0.0290(11) -0.0191(9)
N1 0.0230(9) 0.0190(8) 0.0195(9) -0.0001(7) 0.0059(7) 0.0017(7)
N2 0.0233(9) 0.0214(9) 0.0135(9) -0.0002(7) 0.0060(7) -0.0009(7)
N3 0.0308(10) 0.0241(9) 0.0180(10) 0.0025(8) 0.0097(8) -0.0015(7)
O1 0.0503(11) 0.0299(9) 0.0244(9) -0.0037(8) 0.0164(8) -0.0092(8)

_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 C15 1.999(2) . ?
Ir1 N1 2.0860(19) . ?
Ir1 C5 2.123(2) . ?
Ir1 C6 2.125(2) . ?
Ir1 C2A 2.200(10) . ?
Ir1 C1 2.205(11) . ?
Ir1 C2 2.212(10) . ?
Ir1 C1A 2.232(9) . ?
B1 F3 1.383(3) . ?
B1 F1 1.386(4) . ?
B1 F4 1.387(4) . ?
B1 F2 1.413(4) . ?
C1 C2 1.392(11) . ?
C1 C8 1.551(11) . ?
C2 C3 1.532(11) . ?
C1A C2A 1.401(11) . ?
C1A C8A 1.569(11) . ?
C2A C3A 1.548(11) . ?
C3 C4 1.552(12) . ?
C4 C5 1.567(8) . ?
C3A C4A 1.531(11) . ?
C4A C5 1.511(7) . ?
C5 C6 1.406(4) . ?
C6 C7 1.518(10) . ?
C6 C7A 1.544(8) . ?
C7A C8A 1.532(10) . ?
C7 C8 1.534(10) . ?
C9 N1 1.348(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.367(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.390(3) . ?
C13 N1 1.378(3) . ?
C13 C14 1.483(3) . ?
C14 C16 1.407(3) . ?
C14 C15 1.425(3) . ?
C15 N2 1.366(3) . ?
C16 C18 1.397(3) . ?
C16 C17 1.497(3) . ?
C18 C19 1.377(3) . ?
C19 N2 1.350(3) . ?
C19 N3 1.383(3) . ?
C20 O1 1.216(3) . ?
C20 N3 1.383(3) . ?
C20 C21 1.503(3) . ?

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
C15 Ir1 N1 78.44(8) . . ?
C15 Ir1 C5 94.90(9) . . ?
N1 Ir1 C5 158.03(9) . . ?
C15 Ir1 C6 98.20(9) . . ?
N1 Ir1 C6 162.35(9) . . ?
C5 Ir1 C6 38.64(10) . . ?
C15 Ir1 C2A 157.6(5) . . ?
N1 Ir1 C2A 99.6(4) . . ?
C5 Ir1 C2A 78.6(4) . . ?
C6 Ir1 C2A 90.0(5) . . ?
C15 Ir1 C1 167.0(5) . . ?
N1 Ir1 C1 100.0(5) . . ?
C5 Ir1 C1 91.0(5) . . ?
C6 Ir1 C1 79.3(4) . . ?
C2A Ir1 C1 35.3(9) . . ?
C15 Ir1 C2 155.5(5) . . ?
N1 Ir1 C2 93.2(4) . . ?
C5 Ir1 C2 84.2(3) . . ?
C6 Ir1 C2 96.3(4) . . ?
C2A Ir1 C2 6.3(8) . . ?
C1 Ir1 C2 36.7(3) . . ?
C15 Ir1 C1A 165.0(5) . . ?
N1 Ir1 C1A 97.2(4) . . ?
C5 Ir1 C1A 94.1(5) . . ?
C6 Ir1 C1A 81.6(3) . . ?
C2A Ir1 C1A 36.8(3) . . ?
C1 Ir1 C1A 3.1(10) . . ?
C2 Ir1 C1A 37.8(8) . . ?
F3 B1 F1 110.9(3) . . ?
F3 B1 F4 110.2(2) . . ?
F1 B1 F4 110.8(3) . . ?
F3 B1 F2 108.8(3) . . ?
F1 B1 F2 108.0(2) . . ?
F4 B1 F2 108.1(3) . . ?
C2 C1 C8 144.8(18) . . ?
C2 C1 Ir1 71.9(6) . . ?
C8 C1 Ir1 109.6(8) . . ?
C1 C2 C3 104.8(16) . . ?
C1 C2 Ir1 71.4(6) . . ?
C3 C2 Ir1 109.5(7) . . ?
C2A C1A C8A 105.7(16) . . ?
C2A C1A Ir1 70.3(6) . . ?
C8A C1A Ir1 109.8(7) . . ?
C1A C2A C3A 143.3(16) . . ?
C1A C2A Ir1 72.8(6) . . ?
C3A C2A Ir1 107.0(7) . . ?
C2 C3 C4 110.7(8) . . ?
C3 C4 C5 112.7(6) . . ?
C4A C3A C2A 109.4(8) . . ?
C5 C4A C3A 108.6(6) . . ?
C6 C5 C4A 116.5(4) . . ?
C6 C5 C4 132.2(4) . . ?
C4A C5 C4 20.7(3) . . ?
C6 C5 Ir1 70.77(14) . . ?
C4A C5 Ir1 116.9(3) . . ?
C4 C5 Ir1 106.2(4) . . ?
C5 C6 C7 116.0(5) . . ?
C5 C6 C7A 131.4(4) . . ?
C7 C6 C7A 16.3(6) . . ?
C5 C6 Ir1 70.59(15) . . ?
C7 C6 Ir1 114.6(4) . . ?
C7A C6 Ir1 111.7(5) . . ?
C8A C7A C6 110.7(7) . . ?
C7A C8A C1A 112.0(8) . . ?
C6 C7 C8 113.1(8) . . ?
C7 C8 C1 107.1(10) . . ?
N1 C9 C10 123.0(2) . . ?
C11 C10 C9 118.4(2) . . ?
C10 C11 C12 119.8(2) . . ?
C13 C12 C11 120.3(2) . . ?
N1 C13 C12 119.4(2) . . ?
N1 C13 C14 114.22(19) . . ?
C12 C13 C14 126.3(2) . . ?
C16 C14 C15 120.5(2) . . ?
C16 C14 C13 127.5(2) . . ?
C15 C14 C13 112.03(19) . . ?
N2 C15 C14 116.66(19) . . ?
N2 C15 Ir1 124.57(16) . . ?
C14 C15 Ir1 118.70(15) . . ?
C18 C16 C14 118.5(2) . . ?
C18 C16 C17 116.0(2) . . ?
C14 C16 C17 125.6(2) . . ?
C19 C18 C16 120.7(2) . . ?
N2 C19 C18 119.3(2) . . ?
N2 C19 N3 118.5(2) . . ?
C18 C19 N3 122.1(2) . . ?
O1 C20 N3 122.1(2) . . ?
O1 C20 C21 124.0(2) . . ?
N3 C20 C21 113.9(2) . . ?
C9 N1 C13 119.1(2) . . ?
C9 N1 Ir1 124.50(16) . . ?
C13 N1 Ir1 116.40(14) . . ?
C19 N2 C15 124.30(19) . . ?
C20 N3 C19 126.04(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O1 0.88 1.96 2.629(3) 131.8 .
N3 H3N F2 0.88 1.91 2.782(2) 171.7 4_676

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.54
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.377
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.102