# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Simon Pope'
_publ_contact_author_email       PopeSJ@cardiff.ac.uk
loop_
_publ_author_name
S.Pope
A.Hallett
B.Kariuki

data_LH3
_database_code_depnum_ccdc_archive 'CCDC 822159'
#TrackingRef 'Hallett_Pope.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38

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'
O O 0.0106 0.0060 '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'

_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                   13.9500(4)
_cell_length_b                   16.8880(5)
_cell_length_c                   15.3970(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.071(2)
_cell_angle_gamma                90.00
_cell_volume                     3547.14(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4718
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      4718

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14775
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0984
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         27.50
_reflns_number_total             8077
_reflns_number_gt                4718
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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^)+(0.0642P)^2^+0.9028P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8077
_refine_ls_number_parameters     457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1635
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
C1 C 0.47383(18) -0.28222(14) 0.37098(15) 0.0391(6) Uani 1 1 d . . .
C2 C 0.50604(19) -0.35578(15) 0.40287(16) 0.0456(6) Uani 1 1 d . . .
H2 H 0.5226 -0.3648 0.4651 0.055 Uiso 1 1 calc R . .
C3 C 0.5145(2) -0.41716(15) 0.34425(18) 0.0496(7) Uani 1 1 d . . .
H3 H 0.5378 -0.4673 0.3675 0.059 Uiso 1 1 calc R . .
C4 C 0.49008(19) -0.40695(15) 0.25431(17) 0.0464(6) Uani 1 1 d . . .
H4 H 0.4961 -0.4494 0.2154 0.056 Uiso 1 1 calc R . .
C5 C 0.45579(17) -0.33241(14) 0.22022(15) 0.0371(5) Uani 1 1 d . . .
C6 C 0.44723(16) -0.26942(13) 0.27804(14) 0.0331(5) Uani 1 1 d . . .
C7 C 0.39333(17) -0.25157(13) 0.10076(14) 0.0336(5) Uani 1 1 d . . .
C8 C 0.38916(16) -0.18663(13) 0.16033(14) 0.0313(5) Uani 1 1 d . . .
C9 C 0.35474(17) -0.10707(13) 0.12664(14) 0.0344(5) Uani 1 1 d . . .
C10 C 0.38941(19) -0.07012(14) 0.05861(15) 0.0422(6) Uani 1 1 d . . .
H10 H 0.4367 -0.0962 0.0324 0.051 Uiso 1 1 calc R . .
C11 C 0.3561(2) 0.00395(15) 0.02857(15) 0.0466(7) Uani 1 1 d . . .
H11 H 0.3819 0.0285 -0.0172 0.056 Uiso 1 1 calc R . .
C12 C 0.2855(2) 0.04341(15) 0.06402(16) 0.0463(6) Uani 1 1 d . . .
C13 C 0.25119(19) 0.00671(14) 0.13169(15) 0.0425(6) Uani 1 1 d . . .
H13 H 0.2029 0.0325 0.1568 0.051 Uiso 1 1 calc R . .
C14 C 0.28549(17) -0.06683(13) 0.16375(14) 0.0366(6) Uani 1 1 d . . .
H14 H 0.2618 -0.0901 0.2113 0.044 Uiso 1 1 calc R . .
C15 C 0.2495(3) 0.12451(17) 0.0299(2) 0.0704(9) Uani 1 1 d . . .
H15A H 0.1817 0.1317 0.0363 0.106 Uiso 1 1 calc R . .
H15B H 0.2527 0.1290 -0.0329 0.106 Uiso 1 1 calc R . .
H15C H 0.2910 0.1653 0.0642 0.106 Uiso 1 1 calc R . .
C16 C 0.35837(18) -0.24464(13) 0.00278(14) 0.0361(5) Uani 1 1 d . . .
C17 C 0.4212(2) -0.25640(18) -0.05365(17) 0.0563(8) Uani 1 1 d . . .
H17 H 0.4874 -0.2703 -0.0297 0.068 Uiso 1 1 calc R . .
C18 C 0.3905(2) -0.24853(19) -0.14440(17) 0.0639(9) Uani 1 1 d . . .
H18 H 0.4365 -0.2544 -0.1816 0.077 Uiso 1 1 calc R . .
C19 C 0.2943(2) -0.23233(17) -0.18162(16) 0.0517(7) Uani 1 1 d . . .
C20 C 0.2306(2) -0.22209(19) -0.12536(17) 0.0576(8) Uani 1 1 d . . .
H20 H 0.1637 -0.2106 -0.1497 0.069 Uiso 1 1 calc R . .
C21 C 0.26153(19) -0.22806(17) -0.03408(16) 0.0517(7) Uani 1 1 d . . .
H21 H 0.2160 -0.2207 0.0033 0.062 Uiso 1 1 calc R . .
C22 C 0.2589(3) -0.2243(2) -0.28087(17) 0.0784(10) Uani 1 1 d . . .
H22A H 0.2989 -0.1848 -0.3037 0.118 Uiso 1 1 calc R . .
H22B H 0.1902 -0.2073 -0.2940 0.118 Uiso 1 1 calc R . .
H22C H 0.2647 -0.2754 -0.3094 0.118 Uiso 1 1 calc R . .
C23 C 0.15313(17) -0.01852(15) 0.46873(15) 0.0383(6) Uani 1 1 d . . .
C24 C 0.12982(18) -0.08846(14) 0.50470(15) 0.0417(6) Uani 1 1 d . . .
H24 H 0.0721 -0.0920 0.5280 0.050 Uiso 1 1 calc R . .
C25 C 0.19049(18) -0.15438(14) 0.50721(14) 0.0399(6) Uani 1 1 d . . .
H25 H 0.1724 -0.2026 0.5313 0.048 Uiso 1 1 calc R . .
C26 C 0.27503(18) -0.15170(14) 0.47605(14) 0.0379(6) Uani 1 1 d . . .
H26 H 0.3160 -0.1970 0.4795 0.045 Uiso 1 1 calc R . .
C27 C 0.30084(17) -0.08034(13) 0.43853(13) 0.0313(5) Uani 1 1 d . . .
C28 C 0.23957(17) -0.01366(13) 0.43331(13) 0.0324(5) Uani 1 1 d . . .
C29 C 0.40926(16) -0.00874(13) 0.37333(13) 0.0307(5) Uani 1 1 d . . .
C30 C 0.34676(16) 0.05970(13) 0.37098(13) 0.0299(5) Uani 1 1 d . . .
C31 C 0.37331(16) 0.13900(13) 0.34072(13) 0.0309(5) Uani 1 1 d . . .
C32 C 0.46342(17) 0.17330(14) 0.37495(14) 0.0353(5) Uani 1 1 d . . .
H32 H 0.5108 0.1447 0.4165 0.042 Uiso 1 1 calc R . .
C33 C 0.48544(18) 0.24847(14) 0.34954(15) 0.0397(6) Uani 1 1 d . . .
H33 H 0.5469 0.2715 0.3754 0.048 Uiso 1 1 calc R . .
C34 C 0.41911(18) 0.29108(14) 0.28669(15) 0.0373(6) Uani 1 1 d . . .
C35 C 0.32944(18) 0.25642(14) 0.25175(15) 0.0380(6) Uani 1 1 d . . .
H35 H 0.2833 0.2841 0.2082 0.046 Uiso 1 1 calc R . .
C36 C 0.30547(17) 0.18216(14) 0.27900(14) 0.0351(5) Uani 1 1 d . . .
H36 H 0.2426 0.1604 0.2556 0.042 Uiso 1 1 calc R . .
C37 C 0.4442(2) 0.37247(16) 0.25799(19) 0.0541(7) Uani 1 1 d . . .
H37A H 0.4171 0.3791 0.1944 0.081 Uiso 1 1 calc R . .
H37B H 0.5156 0.3786 0.2695 0.081 Uiso 1 1 calc R . .
H37C H 0.4162 0.4126 0.2915 0.081 Uiso 1 1 calc R . .
C38 C 0.50123(17) -0.00947(13) 0.33920(13) 0.0333(5) Uani 1 1 d . . .
C39 C 0.58156(17) -0.05260(15) 0.38560(15) 0.0393(6) Uani 1 1 d . . .
H39 H 0.5767 -0.0798 0.4385 0.047 Uiso 1 1 calc R . .
C40 C 0.66770(19) -0.05593(16) 0.35507(17) 0.0484(7) Uani 1 1 d . . .
H40 H 0.7214 -0.0854 0.3875 0.058 Uiso 1 1 calc R . .
C41 C 0.67760(19) -0.01714(17) 0.27795(18) 0.0491(7) Uani 1 1 d . . .
C42 C 0.5972(2) 0.02444(15) 0.23100(16) 0.0452(6) Uani 1 1 d . . .
H42 H 0.6019 0.0506 0.1774 0.054 Uiso 1 1 calc R . .
C43 C 0.51040(18) 0.02834(14) 0.26096(14) 0.0384(6) Uani 1 1 d . . .
H43 H 0.4565 0.0571 0.2278 0.046 Uiso 1 1 calc R . .
C44 C 0.7733(2) -0.0201(2) 0.2467(2) 0.0760(10) Uani 1 1 d . . .
H44A H 0.7784 0.0264 0.2099 0.114 Uiso 1 1 calc R . .
H44B H 0.7755 -0.0683 0.2117 0.114 Uiso 1 1 calc R . .
H44C H 0.8281 -0.0203 0.2982 0.114 Uiso 1 1 calc R . .
O1 O 0.46903(15) -0.22364(11) 0.42866(10) 0.0536(5) Uani 1 1 d . . .
H1 H 0.4448 -0.1831 0.4008 0.080 Uiso 1 1 calc R . .
O2 O 0.09486(14) 0.04455(11) 0.47063(13) 0.0581(5) Uani 1 1 d . . .
H2A H 0.1056 0.0786 0.4340 0.087 Uiso 1 1 calc R . .
N1 N 0.41408(13) -0.19663(11) 0.24698(11) 0.0334(4) Uani 1 1 d . . .
N2 N 0.42675(14) -0.32158(11) 0.13049(12) 0.0389(5) Uani 1 1 d . . .
N3 N 0.26362(14) 0.05603(11) 0.39862(11) 0.0333(4) Uani 1 1 d . . .
N4 N 0.38532(14) -0.07621(11) 0.40657(11) 0.0329(4) Uani 1 1 d . . .

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
C1 0.0383(15) 0.0365(14) 0.0435(13) -0.0013(10) 0.0105(11) 0.0017(11)
C2 0.0501(16) 0.0412(15) 0.0456(14) 0.0115(11) 0.0100(12) 0.0063(13)
C3 0.0513(17) 0.0336(15) 0.0635(17) 0.0073(12) 0.0112(13) 0.0079(13)
C4 0.0479(16) 0.0324(14) 0.0581(16) -0.0001(11) 0.0093(12) 0.0060(12)
C5 0.0347(14) 0.0314(13) 0.0455(13) -0.0013(10) 0.0089(10) -0.0006(11)
C6 0.0257(12) 0.0294(13) 0.0448(13) 0.0018(10) 0.0086(10) -0.0004(10)
C7 0.0294(13) 0.0286(13) 0.0439(12) -0.0037(10) 0.0103(10) -0.0007(10)
C8 0.0275(12) 0.0285(12) 0.0388(12) -0.0012(9) 0.0089(9) -0.0026(10)
C9 0.0366(14) 0.0290(13) 0.0363(12) -0.0041(9) 0.0049(10) -0.0001(11)
C10 0.0484(16) 0.0368(15) 0.0442(13) -0.0036(11) 0.0164(11) 0.0003(12)
C11 0.0639(19) 0.0347(15) 0.0429(13) 0.0038(11) 0.0150(12) -0.0025(13)
C12 0.0590(18) 0.0300(14) 0.0480(14) 0.0034(11) 0.0072(12) 0.0043(13)
C13 0.0431(15) 0.0336(14) 0.0513(14) -0.0009(11) 0.0106(11) 0.0079(12)
C14 0.0403(14) 0.0292(13) 0.0406(12) 0.0003(10) 0.0093(10) -0.0014(11)
C15 0.099(3) 0.0417(18) 0.0705(19) 0.0143(14) 0.0172(17) 0.0177(17)
C16 0.0396(15) 0.0270(13) 0.0422(12) -0.0043(10) 0.0096(11) 0.0004(11)
C17 0.0489(17) 0.072(2) 0.0495(15) 0.0013(13) 0.0148(13) 0.0248(15)
C18 0.067(2) 0.084(2) 0.0460(15) -0.0013(14) 0.0242(14) 0.0258(18)
C19 0.0580(19) 0.0554(18) 0.0415(14) -0.0045(12) 0.0100(13) 0.0093(14)
C20 0.0415(17) 0.081(2) 0.0475(15) -0.0055(14) 0.0038(12) 0.0012(15)
C21 0.0398(16) 0.073(2) 0.0428(14) -0.0083(13) 0.0103(12) -0.0034(14)
C22 0.086(3) 0.102(3) 0.0453(16) -0.0024(16) 0.0100(16) 0.016(2)
C23 0.0347(14) 0.0348(14) 0.0463(13) 0.0036(10) 0.0107(10) 0.0037(11)
C24 0.0359(14) 0.0389(15) 0.0525(14) 0.0059(11) 0.0145(11) -0.0058(12)
C25 0.0412(15) 0.0349(14) 0.0421(13) 0.0048(10) 0.0056(11) -0.0069(12)
C26 0.0396(15) 0.0336(14) 0.0390(12) 0.0004(10) 0.0047(10) -0.0032(11)
C27 0.0335(13) 0.0308(13) 0.0282(11) -0.0036(9) 0.0030(9) -0.0019(10)
C28 0.0341(13) 0.0290(13) 0.0335(11) -0.0005(9) 0.0056(9) -0.0017(10)
C29 0.0332(13) 0.0299(13) 0.0270(10) -0.0035(9) 0.0019(9) -0.0013(10)
C30 0.0304(13) 0.0312(13) 0.0273(10) -0.0029(9) 0.0039(9) -0.0011(10)
C31 0.0326(13) 0.0283(12) 0.0342(11) -0.0028(9) 0.0121(9) 0.0018(10)
C32 0.0355(14) 0.0347(14) 0.0351(11) 0.0007(10) 0.0063(10) 0.0019(11)
C33 0.0395(15) 0.0357(14) 0.0445(13) -0.0051(10) 0.0100(11) -0.0069(11)
C34 0.0429(15) 0.0290(13) 0.0447(13) -0.0005(10) 0.0198(11) 0.0001(11)
C35 0.0414(15) 0.0329(14) 0.0407(12) 0.0032(10) 0.0107(10) 0.0072(11)
C36 0.0336(14) 0.0324(13) 0.0405(12) -0.0021(10) 0.0103(10) 0.0014(11)
C37 0.0549(18) 0.0380(16) 0.0733(18) 0.0064(13) 0.0223(14) -0.0018(13)
C38 0.0327(13) 0.0320(13) 0.0356(12) -0.0067(9) 0.0079(10) 0.0004(10)
C39 0.0353(14) 0.0425(15) 0.0390(12) -0.0054(10) 0.0055(10) 0.0027(12)
C40 0.0342(15) 0.0536(17) 0.0556(16) -0.0107(13) 0.0051(12) 0.0050(13)
C41 0.0389(16) 0.0514(17) 0.0611(16) -0.0158(13) 0.0198(12) -0.0037(13)
C42 0.0481(16) 0.0448(16) 0.0479(14) -0.0067(11) 0.0222(12) -0.0070(13)
C43 0.0399(15) 0.0356(14) 0.0398(12) -0.0041(10) 0.0089(10) -0.0011(11)
C44 0.052(2) 0.091(3) 0.097(2) -0.0123(19) 0.0402(17) -0.0021(18)
O1 0.0748(14) 0.0449(11) 0.0395(9) 0.0028(8) 0.0082(9) 0.0180(10)
O2 0.0517(12) 0.0431(12) 0.0892(14) 0.0199(9) 0.0365(10) 0.0082(10)
N1 0.0310(11) 0.0289(11) 0.0408(10) -0.0006(8) 0.0081(8) 0.0012(8)
N2 0.0417(12) 0.0293(11) 0.0466(11) -0.0033(8) 0.0111(9) 0.0014(9)
N3 0.0322(11) 0.0321(11) 0.0352(10) 0.0002(8) 0.0061(8) -0.0007(9)
N4 0.0328(11) 0.0307(11) 0.0337(10) -0.0011(8) 0.0036(8) 0.0007(9)

_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
C1 O1 1.340(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.418(3) . ?
C2 C3 1.396(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(3) . ?
C4 H4 0.9500 . ?
C5 N2 1.368(3) . ?
C5 C6 1.408(3) . ?
C6 N1 1.364(3) . ?
C7 N2 1.317(3) . ?
C7 C8 1.439(3) . ?
C7 C16 1.490(3) . ?
C8 N1 1.317(3) . ?
C8 C9 1.484(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.397(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(3) . ?
C12 C15 1.514(4) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.371(3) . ?
C16 C21 1.380(3) . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.371(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(4) . ?
C19 C22 1.511(4) . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O2 1.344(3) . ?
C23 C24 1.372(3) . ?
C23 C28 1.426(3) . ?
C24 C25 1.394(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.364(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.415(3) . ?
C26 H26 0.9500 . ?
C27 N4 1.371(3) . ?
C27 C28 1.406(3) . ?
C28 N3 1.363(3) . ?
C29 N4 1.320(3) . ?
C29 C30 1.444(3) . ?
C29 C38 1.485(3) . ?
C30 N3 1.318(3) . ?
C30 C31 1.490(3) . ?
C31 C32 1.384(3) . ?
C31 C36 1.398(3) . ?
C32 C33 1.382(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(3) . ?
C34 C37 1.507(3) . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C43 1.393(3) . ?
C38 C39 1.401(3) . ?
C39 C40 1.380(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.388(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.391(4) . ?
C41 C44 1.512(4) . ?
C42 C43 1.384(3) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
O1 H1 0.8400 . ?
O2 H2A 0.8400 . ?

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
O1 C1 C2 119.2(2) . . ?
O1 C1 C6 121.2(2) . . ?
C2 C1 C6 119.7(2) . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N2 C5 C6 119.4(2) . . ?
N2 C5 C4 120.1(2) . . ?
C6 C5 C4 120.4(2) . . ?
N1 C6 C5 121.76(19) . . ?
N1 C6 C1 119.3(2) . . ?
C5 C6 C1 119.0(2) . . ?
N2 C7 C8 121.41(19) . . ?
N2 C7 C16 116.07(19) . . ?
C8 C7 C16 122.51(19) . . ?
N1 C8 C7 120.7(2) . . ?
N1 C8 C9 117.89(19) . . ?
C7 C8 C9 121.38(18) . . ?
C10 C9 C14 118.0(2) . . ?
C10 C9 C8 122.1(2) . . ?
C14 C9 C8 119.9(2) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 117.8(2) . . ?
C13 C12 C15 121.8(3) . . ?
C11 C12 C15 120.4(2) . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C9 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.0(2) . . ?
C17 C16 C7 120.9(2) . . ?
C21 C16 C7 121.2(2) . . ?
C16 C17 C18 121.6(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 117.8(2) . . ?
C18 C19 C22 121.7(3) . . ?
C20 C19 C22 120.5(3) . . ?
C19 C20 C21 121.6(3) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C16 C21 C20 120.2(2) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 C24 118.6(2) . . ?
O2 C23 C28 121.8(2) . . ?
C24 C23 C28 119.6(2) . . ?
C23 C24 C25 120.3(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 121.9(2) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 119.0(2) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
N4 C27 C28 119.8(2) . . ?
N4 C27 C26 120.1(2) . . ?
C28 C27 C26 120.1(2) . . ?
N3 C28 C27 121.2(2) . . ?
N3 C28 C23 119.8(2) . . ?
C27 C28 C23 119.0(2) . . ?
N4 C29 C30 120.0(2) . . ?
N4 C29 C38 115.9(2) . . ?
C30 C29 C38 124.0(2) . . ?
N3 C30 C29 121.5(2) . . ?
N3 C30 C31 115.87(19) . . ?
C29 C30 C31 122.6(2) . . ?
C32 C31 C36 118.2(2) . . ?
C32 C31 C30 121.5(2) . . ?
C36 C31 C30 120.3(2) . . ?
C33 C32 C31 121.0(2) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C32 C33 C34 121.1(2) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C35 C34 C33 117.9(2) . . ?
C35 C34 C37 121.2(2) . . ?
C33 C34 C37 120.9(2) . . ?
C34 C35 C36 121.4(2) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C35 C36 C31 120.4(2) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C43 C38 C39 118.1(2) . . ?
C43 C38 C29 123.0(2) . . ?
C39 C38 C29 118.8(2) . . ?
C40 C39 C38 120.6(2) . . ?
C40 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C39 C40 C41 121.4(2) . . ?
C39 C40 H40 119.3 . . ?
C41 C40 H40 119.3 . . ?
C40 C41 C42 118.0(2) . . ?
C40 C41 C44 120.6(3) . . ?
C42 C41 C44 121.4(3) . . ?
C43 C42 C41 121.2(2) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C42 C43 C38 120.8(2) . . ?
C42 C43 H43 119.6 . . ?
C38 C43 H43 119.6 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C23 O2 H2A 109.5 . . ?
C8 N1 C6 117.96(18) . . ?
C7 N2 C5 118.64(19) . . ?
C30 N3 C28 118.20(19) . . ?
C29 N4 C27 119.30(19) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046

data_IrL2
_database_code_depnum_ccdc_archive 'CCDC 822160'
#TrackingRef 'Hallett_Pope.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44.40 H33.80 Br2 Ir N4 O2'
_chemical_formula_weight         1007.37

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'
Br Br -0.2901 2.4595 '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                   18.3163(6)
_cell_length_b                   9.7199(4)
_cell_length_c                   23.3380(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.101(2)
_cell_angle_gamma                90.00
_cell_volume                     3901.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1965
_exptl_absorpt_coefficient_mu    5.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4052
_exptl_absorpt_correction_T_max  0.8096
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16143
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_sigmaI/netI    0.1007
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         27.54
_reflns_number_total             8941
_reflns_number_gt                5769
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0449P)^2^+14.8186P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8941
_refine_ls_number_parameters     505
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
C21 C 0.8066(5) 0.3606(10) 0.5422(3) 0.040(2) Uani 1 1 d . A 1
C3 C 0.8861(5) 0.3637(10) 0.5453(3) 0.039(2) Uani 1 1 d . A 1
C32 C 0.9379(5) 0.4315(10) 0.5954(3) 0.045(2) Uani 1 1 d . A 1
H3 H 0.9914 0.4336 0.5999 0.054 Uiso 1 1 calc R A 1
C4 C 0.9133(6) 0.4975(11) 0.6396(4) 0.059(3) Uani 1 1 d . A 1
H4 H 0.9504 0.5439 0.6728 0.071 Uiso 1 1 calc R A 1
C5 C 0.8367(5) 0.4957(13) 0.6355(4) 0.066(3) Uani 1 1 d . A 1
H5 H 0.8209 0.5424 0.6651 0.079 Uiso 1 1 calc R A 1
C6 C 0.7821(5) 0.4250(11) 0.5878(4) 0.050(2) Uani 1 1 d . A 1
C7 C 0.6574(5) 0.3461(11) 0.5410(4) 0.049(2) Uani 1 1 d . A 1
C8 C 0.6797(5) 0.2792(11) 0.4947(3) 0.045(2) Uani 1 1 d . A 1
C9 C 0.5772(5) 0.3419(11) 0.5446(4) 0.050(3) Uani 1 1 d . A 1
C10 C 0.5084(5) 0.3310(10) 0.4948(4) 0.051(3) Uani 1 1 d . A 1
H10 H 0.5114 0.3196 0.4552 0.061 Uiso 1 1 calc R A 1
C11 C 0.4353(6) 0.3361(11) 0.5007(4) 0.056(3) Uani 1 1 d . A 1
H11 H 0.3895 0.3274 0.4660 0.067 Uiso 1 1 calc R A 1
C12 C 0.4310(6) 0.3543(12) 0.5583(5) 0.057(3) Uani 1 1 d . A 1
C13 C 0.4986(6) 0.3636(12) 0.6089(4) 0.063(3) Uani 1 1 d . A 1
H13 H 0.4953 0.3746 0.6484 0.076 Uiso 1 1 calc R A 1
C14 C 0.5708(6) 0.3567(12) 0.6021(4) 0.062(3) Uani 1 1 d . A 1
H14 H 0.6166 0.3623 0.6371 0.074 Uiso 1 1 calc R A 1
C15 C 0.6228(5) 0.1955(11) 0.4472(3) 0.044(2) Uani 1 1 d . A 1
C16 C 0.5875(5) 0.2494(10) 0.3882(4) 0.046(2) Uani 1 1 d . A 1
H16 H 0.6053 0.3341 0.3774 0.055 Uiso 1 1 calc R A 1
C17 C 0.5268(5) 0.1794(11) 0.3457(4) 0.051(3) Uani 1 1 d . A 1
H17 H 0.5021 0.2154 0.3058 0.062 Uiso 1 1 calc R A 1
C18 C 0.5029(5) 0.0552(12) 0.3630(4) 0.052(3) Uani 1 1 d . A 1
C19 C 0.5351(5) 0.0001(12) 0.4205(4) 0.059(3) Uani 1 1 d . A 1
H19 H 0.5166 -0.0839 0.4312 0.071 Uiso 1 1 calc R A 1
C20 C 0.5955(5) 0.0718(11) 0.4621(4) 0.048(2) Uani 1 1 d . A 1
H20 H 0.6191 0.0355 0.5020 0.058 Uiso 1 1 calc R A 1
C1 C 0.8852(4) 0.1418(10) 0.3919(3) 0.038(2) Uani 1 1 d . A 1
C22 C 0.9062(4) 0.2075(10) 0.3462(3) 0.042(2) Uani 1 1 d . A 1
H22 H 0.8830 0.2933 0.3306 0.050 Uiso 1 1 calc R A 1
C23 C 0.9602(5) 0.1500(11) 0.3230(4) 0.050(2) Uani 1 1 d . A 1
H23 H 0.9753 0.1981 0.2934 0.059 Uiso 1 1 calc R A 1
C24 C 0.9917(5) 0.0217(11) 0.3438(4) 0.054(3) Uani 1 1 d . A 1
H24 H 1.0268 -0.0194 0.3270 0.064 Uiso 1 1 calc R A 1
C25 C 0.9724(5) -0.0479(11) 0.3889(4) 0.054(3) Uani 1 1 d . A 1
H25 H 0.9946 -0.1351 0.4033 0.064 Uiso 1 1 calc R A 1
C26 C 0.9195(4) 0.0139(10) 0.4128(4) 0.042(2) Uani 1 1 d . A 1
C27 C 0.8957(5) -0.0485(10) 0.4595(4) 0.044(2) Uani 1 1 d . A 1
C28 C 0.9238(5) -0.1735(10) 0.4887(4) 0.054(3) Uani 1 1 d . A 1
H28 H 0.9630 -0.2226 0.4792 0.064 Uiso 1 1 calc R A 1
C29 C 0.8936(6) -0.2256(11) 0.5321(4) 0.060(3) Uani 1 1 d . A 1
H29 H 0.9116 -0.3107 0.5519 0.072 Uiso 1 1 calc R A 1
C30 C 0.8376(6) -0.1516(12) 0.5454(4) 0.064(3) Uani 1 1 d . A 1
H30 H 0.8150 -0.1866 0.5734 0.077 Uiso 1 1 calc R A 1
C31 C 0.8146(5) -0.0262(11) 0.5177(4) 0.054(3) Uani 1 1 d . A 1
H31 H 0.7769 0.0255 0.5281 0.064 Uiso 1 1 calc R A 1
C2 C 0.7279(4) 0.1349(10) 0.3608(3) 0.0364(19) Uani 1 1 d . A 1
C33 C 0.6983(5) 0.0010(10) 0.3492(4) 0.043(2) Uani 1 1 d . A 1
H33 H 0.7184 -0.0673 0.3797 0.051 Uiso 1 1 calc R A 1
C34 C 0.6416(5) -0.0358(12) 0.2954(4) 0.055(3) Uani 1 1 d . A 1
H34 H 0.6229 -0.1278 0.2897 0.066 Uiso 1 1 calc R A 1
C35 C 0.6113(5) 0.0607(14) 0.2495(4) 0.058(3) Uani 1 1 d . A 1
H35 H 0.5717 0.0354 0.2125 0.070 Uiso 1 1 calc R A 1
C36 C 0.6391(5) 0.1918(12) 0.2580(4) 0.048(2) Uani 1 1 d . A 1
H36 H 0.6195 0.2575 0.2263 0.057 Uiso 1 1 calc R A 1
C37 C 0.6964(5) 0.2311(11) 0.3130(3) 0.043(2) Uani 1 1 d . A 1
C38 C 0.7273(4) 0.3697(11) 0.3254(3) 0.044(2) Uani 1 1 d . A 1
C39 C 0.7053(5) 0.4849(11) 0.2873(4) 0.046(2) Uani 1 1 d . A 1
H39 H 0.6656 0.4761 0.2485 0.055 Uiso 1 1 calc R A 1
C40 C 0.7405(5) 0.6117(11) 0.3052(4) 0.046(2) Uani 1 1 d . A 1
H40 H 0.7257 0.6897 0.2792 0.056 Uiso 1 1 calc R A 1
C41 C 0.7976(5) 0.6208(10) 0.3620(4) 0.047(2) Uani 1 1 d . A 1
H41 H 0.8228 0.7064 0.3752 0.056 Uiso 1 1 calc R A 1
C42 C 0.8185(5) 0.5086(9) 0.3994(3) 0.037(2) Uani 1 1 d . A 1
H42 H 0.8574 0.5175 0.4386 0.045 Uiso 1 1 calc R A 1
N1 N 0.7530(4) 0.2886(8) 0.4950(3) 0.0403(16) Uani 1 1 d . A 1
N2 N 0.7067(4) 0.4177(9) 0.5847(3) 0.053(2) Uani 1 1 d . A 1
N3 N 0.8436(4) 0.0261(8) 0.4764(3) 0.0403(17) Uani 1 1 d . A 1
N4 N 0.7841(4) 0.3839(8) 0.3812(2) 0.0368(17) Uani 1 1 d . A 1
O1 O 0.9062(3) 0.3042(6) 0.5031(2) 0.0391(14) Uani 1 1 d . A 1
Br1 Br 0.33324(6) 0.36167(14) 0.56849(5) 0.0690(3) Uani 1 1 d . A 1
Br2 Br 0.42066(7) -0.04246(16) 0.30391(5) 0.0853(4) Uani 1 1 d . A 1
Ir1 Ir 0.812589(18) 0.20957(4) 0.432752(13) 0.03693(12) Uani 1 1 d . A 1
O2 O 0.7700(14) 0.972(3) 0.6727(9) 0.247(18) Uani 0.60 1 d PDU B 1
C43 C 0.6982(17) 0.756(3) 0.6624(18) 0.212(19) Uani 0.60 1 d PDU B 1
H43A H 0.6952 0.6678 0.6822 0.318 Uiso 0.60 1 calc PR B 1
H43B H 0.7038 0.7382 0.6228 0.318 Uiso 0.60 1 calc PR B 1
H43C H 0.6505 0.8084 0.6565 0.318 Uiso 0.60 1 calc PR B 1
C44 C 0.7669(19) 0.836(3) 0.7021(12) 0.22(3) Uani 0.60 1 d PDU B 1
H44A H 0.7625 0.8507 0.7427 0.266 Uiso 0.60 1 calc PR B 1
H44B H 0.8153 0.7837 0.7076 0.266 Uiso 0.60 1 calc PR B 1
C45 C 0.8295(13) 1.063(4) 0.7149(11) 0.26(3) Uani 0.60 1 d PDU B 1
H45A H 0.8371 1.1445 0.6923 0.316 Uiso 0.60 1 calc PR B 1
H45B H 0.8797 1.0129 0.7306 0.316 Uiso 0.60 1 calc PR B 1
C46 C 0.8060(13) 1.108(3) 0.7670(10) 0.161(15) Uani 0.60 1 d PDU B 1
H46A H 0.8446 1.1722 0.7925 0.241 Uiso 0.60 1 calc PR B 1
H46B H 0.8028 1.0272 0.7914 0.241 Uiso 0.60 1 calc PR B 1
H46C H 0.7551 1.1527 0.7514 0.241 Uiso 0.60 1 calc PR B 1
O3 O 0.815(2) 1.136(3) 0.6665(15) 0.160(14) Uani 0.40 1 d PU C 2

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
C21 0.034(4) 0.055(6) 0.024(4) 0.003(4) 0.001(3) 0.008(4)
C3 0.033(4) 0.051(6) 0.027(4) -0.004(4) 0.001(3) 0.010(4)
C32 0.036(5) 0.054(6) 0.036(4) -0.006(4) 0.000(4) 0.006(4)
C4 0.044(5) 0.076(8) 0.049(5) -0.009(5) 0.005(4) 0.013(5)
C5 0.049(6) 0.103(10) 0.038(5) -0.011(5) 0.005(4) 0.014(6)
C6 0.044(5) 0.067(7) 0.034(4) -0.001(4) 0.007(4) 0.015(5)
C7 0.042(5) 0.071(7) 0.031(4) 0.000(4) 0.008(4) 0.009(5)
C8 0.040(5) 0.061(6) 0.033(4) 0.007(4) 0.011(4) 0.015(5)
C9 0.041(5) 0.075(8) 0.037(5) 0.000(4) 0.018(4) 0.011(5)
C10 0.043(5) 0.068(8) 0.046(5) 0.005(4) 0.022(4) 0.014(5)
C11 0.046(6) 0.063(8) 0.063(6) 0.005(5) 0.024(5) 0.015(5)
C12 0.044(6) 0.068(7) 0.072(7) 0.001(6) 0.037(5) 0.012(5)
C13 0.057(6) 0.087(9) 0.058(6) -0.002(6) 0.034(5) 0.016(6)
C14 0.046(6) 0.099(9) 0.042(5) -0.009(5) 0.017(4) 0.012(6)
C15 0.031(4) 0.071(7) 0.031(4) 0.005(4) 0.013(3) 0.012(5)
C16 0.035(5) 0.065(7) 0.040(5) 0.003(4) 0.015(4) 0.011(4)
C17 0.040(5) 0.086(9) 0.028(4) 0.005(4) 0.011(4) 0.010(5)
C18 0.031(5) 0.088(8) 0.033(5) 0.004(5) 0.007(4) 0.004(5)
C19 0.045(5) 0.092(9) 0.038(5) -0.001(5) 0.012(4) -0.009(6)
C20 0.041(5) 0.066(7) 0.034(4) -0.003(4) 0.007(4) 0.005(5)
C1 0.021(4) 0.050(6) 0.041(4) -0.007(4) 0.011(3) 0.004(4)
C22 0.031(4) 0.045(5) 0.045(4) -0.015(4) 0.009(4) 0.003(4)
C23 0.025(4) 0.073(7) 0.053(5) -0.017(5) 0.016(4) -0.002(5)
C24 0.031(5) 0.063(7) 0.066(6) -0.024(5) 0.017(4) 0.010(5)
C25 0.025(4) 0.063(7) 0.066(6) -0.018(5) 0.006(4) 0.007(5)
C26 0.024(4) 0.045(6) 0.049(5) -0.004(4) 0.005(4) 0.009(4)
C27 0.025(4) 0.050(6) 0.046(5) -0.005(4) -0.001(4) -0.003(4)
C28 0.044(5) 0.050(7) 0.051(5) -0.003(4) -0.004(4) 0.009(5)
C29 0.056(6) 0.051(7) 0.052(5) 0.020(5) -0.008(5) 0.003(6)
C30 0.058(7) 0.076(8) 0.051(6) 0.019(5) 0.009(5) 0.010(6)
C31 0.048(6) 0.065(7) 0.041(5) 0.010(5) 0.006(4) 0.008(5)
C2 0.027(4) 0.049(6) 0.036(4) -0.001(4) 0.014(3) 0.006(4)
C33 0.035(5) 0.050(6) 0.046(5) -0.005(4) 0.018(4) 0.001(4)
C34 0.034(5) 0.073(8) 0.060(6) -0.011(5) 0.019(4) -0.006(5)
C35 0.031(5) 0.105(10) 0.035(5) -0.010(5) 0.007(4) -0.007(6)
C36 0.035(5) 0.078(8) 0.032(4) 0.004(5) 0.014(4) 0.006(5)
C37 0.030(4) 0.072(7) 0.028(4) -0.004(4) 0.011(3) 0.004(5)
C38 0.025(4) 0.074(8) 0.033(4) 0.004(5) 0.012(3) 0.014(5)
C39 0.036(5) 0.066(7) 0.039(5) 0.008(5) 0.018(4) 0.012(5)
C40 0.040(5) 0.059(7) 0.052(5) 0.015(5) 0.030(4) 0.014(5)
C41 0.054(6) 0.047(6) 0.048(5) -0.001(4) 0.028(4) 0.005(5)
C42 0.035(4) 0.040(6) 0.033(4) -0.001(4) 0.008(3) 0.009(4)
N1 0.029(3) 0.055(5) 0.031(3) 0.003(3) 0.003(3) 0.003(4)
N2 0.038(4) 0.080(7) 0.039(4) -0.005(4) 0.012(3) 0.017(4)
N3 0.032(4) 0.050(5) 0.030(3) 0.007(3) -0.002(3) 0.012(4)
N4 0.032(4) 0.056(5) 0.017(3) 0.001(3) 0.003(3) 0.014(4)
O1 0.032(3) 0.046(4) 0.034(3) -0.003(3) 0.005(2) 0.010(3)
Br1 0.0569(6) 0.0854(9) 0.0808(7) 0.0035(6) 0.0445(6) 0.0133(6)
Br2 0.0627(7) 0.1245(12) 0.0511(6) -0.0018(7) -0.0029(5) -0.0251(8)
Ir1 0.02741(17) 0.0482(2) 0.03236(17) -0.00015(17) 0.00661(12) 0.00875(18)
O2 0.19(3) 0.37(5) 0.21(3) -0.04(3) 0.09(2) 0.08(3)
C43 0.18(4) 0.12(3) 0.33(5) -0.01(3) 0.08(4) 0.07(3)
C44 0.15(3) 0.28(5) 0.18(3) -0.17(4) -0.01(3) 0.08(3)
C45 0.12(3) 0.59(8) 0.051(15) -0.02(3) -0.009(16) -0.09(4)
C46 0.080(17) 0.20(3) 0.20(3) 0.13(3) 0.042(19) -0.01(2)
O3 0.21(3) 0.14(2) 0.20(3) 0.13(2) 0.15(3) 0.11(2)

_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
C21 N1 1.386(10) . ?
C21 C3 1.432(11) . ?
C21 C6 1.434(11) . ?
C3 O1 1.301(9) . ?
C3 C32 1.392(11) . ?
C32 C4 1.414(12) . ?
C4 C5 1.373(13) . ?
C5 C6 1.395(13) . ?
C6 N2 1.360(11) . ?
C7 N2 1.307(12) . ?
C7 C8 1.435(12) . ?
C7 C9 1.501(12) . ?
C8 N1 1.344(10) . ?
C8 C15 1.478(13) . ?
C9 C14 1.393(11) . ?
C9 C10 1.395(12) . ?
C10 C11 1.392(12) . ?
C11 C12 1.385(12) . ?
C12 C13 1.389(13) . ?
C12 Br1 1.887(9) . ?
C13 C14 1.388(13) . ?
C15 C20 1.390(13) . ?
C15 C16 1.406(11) . ?
C16 C17 1.388(12) . ?
C17 C18 1.390(14) . ?
C18 C19 1.376(12) . ?
C18 Br2 1.909(9) . ?
C19 C20 1.384(12) . ?
C1 C26 1.402(12) . ?
C1 C22 1.405(12) . ?
C1 Ir1 1.996(8) . ?
C22 C23 1.398(11) . ?
C23 C24 1.390(14) . ?
C24 C25 1.394(14) . ?
C25 C26 1.408(12) . ?
C26 C27 1.439(12) . ?
C27 N3 1.361(11) . ?
C27 C28 1.401(13) . ?
C28 C29 1.404(14) . ?
C29 C30 1.372(14) . ?
C30 C31 1.376(14) . ?
C31 N3 1.349(11) . ?
C2 C33 1.400(12) . ?
C2 C37 1.417(12) . ?
C2 Ir1 1.991(8) . ?
C33 C34 1.373(12) . ?
C34 C35 1.389(14) . ?
C35 C36 1.361(14) . ?
C36 C37 1.404(11) . ?
C37 C38 1.451(14) . ?
C38 N4 1.366(9) . ?
C38 C39 1.400(13) . ?
C39 C40 1.387(13) . ?
C40 C41 1.381(12) . ?
C41 C42 1.368(12) . ?
C42 N4 1.365(11) . ?
N1 Ir1 2.232(7) . ?
N3 Ir1 2.036(7) . ?
N4 Ir1 2.040(7) . ?
O1 Ir1 2.132(5) . ?
O2 C45 1.484(10) . ?
O2 C44 1.497(10) . ?
C43 C44 1.500(10) . ?
C45 C46 1.489(10) . ?

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
N1 C21 C3 118.8(7) . . ?
N1 C21 C6 119.5(7) . . ?
C3 C21 C6 121.6(7) . . ?
O1 C3 C32 123.9(8) . . ?
O1 C3 C21 120.0(7) . . ?
C32 C3 C21 116.2(7) . . ?
C3 C32 C4 122.1(8) . . ?
C5 C4 C32 121.1(9) . . ?
C4 C5 C6 119.8(9) . . ?
N2 C6 C5 120.3(8) . . ?
N2 C6 C21 120.6(8) . . ?
C5 C6 C21 119.1(8) . . ?
N2 C7 C8 122.0(8) . . ?
N2 C7 C9 113.5(8) . . ?
C8 C7 C9 124.6(8) . . ?
N1 C8 C7 120.5(8) . . ?
N1 C8 C15 119.2(7) . . ?
C7 C8 C15 120.2(8) . . ?
C14 C9 C10 117.4(8) . . ?
C14 C9 C7 117.3(8) . . ?
C10 C9 C7 125.2(7) . . ?
C11 C10 C9 122.6(8) . . ?
C12 C11 C10 118.6(9) . . ?
C11 C12 C13 120.2(8) . . ?
C11 C12 Br1 120.0(8) . . ?
C13 C12 Br1 119.8(7) . . ?
C14 C13 C12 120.3(8) . . ?
C13 C14 C9 120.9(9) . . ?
C20 C15 C16 118.9(8) . . ?
C20 C15 C8 120.7(7) . . ?
C16 C15 C8 119.8(9) . . ?
C17 C16 C15 120.2(9) . . ?
C16 C17 C18 118.2(8) . . ?
C19 C18 C17 123.3(9) . . ?
C19 C18 Br2 118.5(8) . . ?
C17 C18 Br2 118.1(6) . . ?
C18 C19 C20 117.3(10) . . ?
C19 C20 C15 122.0(8) . . ?
C26 C1 C22 117.4(8) . . ?
C26 C1 Ir1 114.8(6) . . ?
C22 C1 Ir1 127.8(7) . . ?
C23 C22 C1 121.8(9) . . ?
C24 C23 C22 119.2(9) . . ?
C23 C24 C25 121.1(8) . . ?
C24 C25 C26 118.6(9) . . ?
C1 C26 C25 121.9(9) . . ?
C1 C26 C27 114.9(8) . . ?
C25 C26 C27 123.2(9) . . ?
N3 C27 C28 119.8(9) . . ?
N3 C27 C26 114.8(8) . . ?
C28 C27 C26 125.4(9) . . ?
C27 C28 C29 119.6(9) . . ?
C30 C29 C28 118.9(9) . . ?
C29 C30 C31 119.4(10) . . ?
N3 C31 C30 122.4(10) . . ?
C33 C2 C37 115.8(8) . . ?
C33 C2 Ir1 129.8(6) . . ?
C37 C2 Ir1 114.3(7) . . ?
C34 C33 C2 122.7(9) . . ?
C33 C34 C35 120.4(10) . . ?
C36 C35 C34 119.3(8) . . ?
C35 C36 C37 120.9(9) . . ?
C36 C37 C2 120.9(10) . . ?
C36 C37 C38 123.5(8) . . ?
C2 C37 C38 115.5(7) . . ?
N4 C38 C39 118.9(9) . . ?
N4 C38 C37 113.6(8) . . ?
C39 C38 C37 127.5(8) . . ?
C40 C39 C38 121.1(8) . . ?
C41 C40 C39 117.8(9) . . ?
C42 C41 C40 121.0(9) . . ?
N4 C42 C41 120.7(7) . . ?
C8 N1 C21 118.2(7) . . ?
C8 N1 Ir1 133.2(6) . . ?
C21 N1 Ir1 108.6(5) . . ?
C7 N2 C6 119.1(8) . . ?
C31 N3 C27 119.6(8) . . ?
C31 N3 Ir1 125.2(6) . . ?
C27 N3 Ir1 115.1(6) . . ?
C42 N4 C38 120.4(8) . . ?
C42 N4 Ir1 123.8(5) . . ?
C38 N4 Ir1 115.8(7) . . ?
C3 O1 Ir1 114.4(5) . . ?
C2 Ir1 C1 86.1(3) . . ?
C2 Ir1 N3 96.1(3) . . ?
C1 Ir1 N3 80.4(3) . . ?
C2 Ir1 N4 80.7(3) . . ?
C1 Ir1 N4 94.0(3) . . ?
N3 Ir1 N4 173.7(3) . . ?
C2 Ir1 O1 173.8(3) . . ?
C1 Ir1 O1 91.0(3) . . ?
N3 Ir1 O1 88.9(2) . . ?
N4 Ir1 O1 94.1(2) . . ?
C2 Ir1 N1 105.1(3) . . ?
C1 Ir1 N1 168.4(3) . . ?
N3 Ir1 N1 95.2(3) . . ?
N4 Ir1 N1 90.9(3) . . ?
O1 Ir1 N1 78.1(2) . . ?
C45 O2 C44 110.9(10) . . ?
O2 C44 C43 109.4(10) . . ?
O2 C45 C46 111.3(10) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.855
_refine_diff_density_min         -1.448
_refine_diff_density_rms         0.163