# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_4_15srv133
_database_code_depnum_ccdc_archive 'CCDC 1474217'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_audit_creation_date             2015-05-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H29 N O3'
_chemical_formula_sum            'C19 H29 N O3'
_chemical_formula_weight         319.43
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   11.4540(8)
_cell_length_b                   20.9192(15)
_cell_length_c                   22.0993(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5295.2(7)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.15
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0942 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.8905.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            110590
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.00
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                10778
_reflns_number_total             14082
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     643
_refine_ls_number_reflns         14082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1112
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C1A(H1AA,H1AB), C2A(H2AA,
 H2AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB),
 C4B(H4BA,H4BB), C5B(H5BA,H5BB)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C13A(H13A), C15A(H15A), C13B(H13B), C15B(H15B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C17(H17A,H17B,H17C),
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,
 H9AC), C10A(H10D,H10E,H10F), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F),
 C19A(H19D,H19E,H19F), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC), C10B(H10G,H10H,
 H10I), C17B(H17G,H17H,H17I), C18B(H18G,H18H,H18I), C19B(H19G,H19H,H19I)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O3A(H3A), O3B(H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.58596(12) 0.36145(6) 0.27948(6) 0.0205(3) Uani 1 d . . .
O2 O 0.56639(12) 0.43513(6) 0.35340(5) 0.0211(3) Uani 1 d . . .
O3 O 0.61857(12) 0.58625(8) 0.15244(7) 0.0369(4) Uani 1 d . . .
H3 H 0.6680 0.5683 0.1748 0.055 Uiso 1 calc . . GR
N1 N 0.56462(13) 0.46390(7) 0.25424(7) 0.0154(3) Uani 1 d . . .
C1 C 0.59208(16) 0.44972(9) 0.19101(8) 0.0182(4) Uani 1 d . . .
H1A H 0.5839 0.4032 0.1839 0.022 Uiso 1 calc . . R
H1B H 0.6741 0.4617 0.1826 0.022 Uiso 1 calc . . R
C2 C 0.51166(16) 0.48596(8) 0.14801(8) 0.0167(4) Uani 1 d . . .
H2A H 0.4320 0.4679 0.1510 0.020 Uiso 1 calc . . R
H2B H 0.5393 0.4797 0.1060 0.020 Uiso 1 calc . . R
C3 C 0.50679(15) 0.55772(9) 0.16178(8) 0.0168(4) Uani 1 d . . .
C4 C 0.47768(19) 0.56719(9) 0.22881(8) 0.0247(5) Uani 1 d . . .
H4A H 0.4800 0.6134 0.2385 0.030 Uiso 1 calc . . R
H4B H 0.3975 0.5516 0.2367 0.030 Uiso 1 calc . . R
C5 C 0.56261(18) 0.53183(8) 0.26974(9) 0.0207(4) Uani 1 d . . .
H5A H 0.6418 0.5501 0.2650 0.025 Uiso 1 calc . . R
H5B H 0.5386 0.5371 0.3125 0.025 Uiso 1 calc . . R
C6 C 0.57362(15) 0.42115(8) 0.29993(8) 0.0157(4) Uani 1 d . . .
C7 C 0.59225(18) 0.30724(8) 0.32270(9) 0.0214(4) Uani 1 d . . .
C8 C 0.48025(19) 0.30309(11) 0.35931(11) 0.0346(6) Uani 1 d . . .
H8A H 0.4782 0.3380 0.3889 0.052 Uiso 1 calc . . GR
H8B H 0.4773 0.2620 0.3805 0.052 Uiso 1 calc . . GR
H8C H 0.4130 0.3067 0.3321 0.052 Uiso 1 calc . . GR
C9 C 0.69932(19) 0.31296(10) 0.36223(10) 0.0296(5) Uani 1 d . . .
H9A H 0.7689 0.3165 0.3367 0.044 Uiso 1 calc . . GR
H9B H 0.7059 0.2750 0.3880 0.044 Uiso 1 calc . . GR
H9C H 0.6926 0.3511 0.3877 0.044 Uiso 1 calc . . GR
C10 C 0.6033(3) 0.25052(10) 0.28051(10) 0.0446(7) Uani 1 d . . .
H10A H 0.5327 0.2471 0.2556 0.067 Uiso 1 calc . . GR
H10B H 0.6129 0.2114 0.3043 0.067 Uiso 1 calc . . GR
H10C H 0.6714 0.2564 0.2542 0.067 Uiso 1 calc . . GR
C11 C 0.42348(16) 0.59317(8) 0.11788(8) 0.0144(4) Uani 1 d . . .
C12 C 0.46830(17) 0.62259(9) 0.06496(8) 0.0179(4) Uani 1 d . . .
C13 C 0.39461(17) 0.66054(9) 0.02963(8) 0.0196(4) Uani 1 d . . .
H13 H 0.4263 0.6811 -0.0050 0.023 Uiso 1 calc . . R
C14 C 0.27786(17) 0.66950(9) 0.04271(9) 0.0195(4) Uani 1 d . . .
C15 C 0.23387(16) 0.63646(9) 0.09130(8) 0.0183(4) Uani 1 d . . .
H15 H 0.1531 0.6405 0.1003 0.022 Uiso 1 calc . . R
C16 C 0.30249(16) 0.59724(9) 0.12803(8) 0.0169(4) Uani 1 d . . .
C17 C 0.59145(17) 0.61588(10) 0.04047(10) 0.0277(5) Uani 1 d . . .
H17A H 0.6441 0.6439 0.0632 0.042 Uiso 1 calc . . GR
H17B H 0.5926 0.6279 -0.0024 0.042 Uiso 1 calc . . GR
H17C H 0.6172 0.5714 0.0448 0.042 Uiso 1 calc . . GR
C18 C 0.20199(19) 0.71257(10) 0.00418(10) 0.0288(5) Uani 1 d . . .
H18A H 0.2463 0.7508 -0.0072 0.043 Uiso 1 calc . . GR
H18B H 0.1326 0.7252 0.0272 0.043 Uiso 1 calc . . GR
H18C H 0.1780 0.6896 -0.0324 0.043 Uiso 1 calc . . GR
C19 C 0.23262(17) 0.56065(10) 0.17532(9) 0.0252(4) Uani 1 d . . .
H19A H 0.2692 0.5190 0.1825 0.038 Uiso 1 calc . . GR
H19B H 0.1526 0.5543 0.1607 0.038 Uiso 1 calc . . GR
H19C H 0.2310 0.5851 0.2132 0.038 Uiso 1 calc . . GR
O1A O 0.58725(12) 0.33958(6) 0.62417(5) 0.0188(3) Uani 1 d . . .
O2A O 0.63894(11) 0.42457(6) 0.68255(6) 0.0176(3) Uani 1 d . . .
O3A O 0.61063(10) 0.51477(6) 0.45398(6) 0.0171(3) Uani 1 d . . .
H3A H 0.5975 0.4952 0.4215 0.026 Uiso 1 calc . . GR
N1A N 0.58754(13) 0.43704(7) 0.58374(6) 0.0159(3) Uani 1 d . . .
C1A C 0.62812(17) 0.50386(8) 0.58152(9) 0.0182(4) Uani 1 d . . .
H1AA H 0.7035 0.5059 0.5597 0.022 Uiso 1 calc . . R
H1AB H 0.6410 0.5197 0.6232 0.022 Uiso 1 calc . . R
C2A C 0.53940(16) 0.54646(8) 0.54978(8) 0.0165(4) Uani 1 d . . .
H2AA H 0.5728 0.5898 0.5448 0.020 Uiso 1 calc . . R
H2AB H 0.4687 0.5502 0.5753 0.020 Uiso 1 calc . . R
C3A C 0.50497(15) 0.52026(8) 0.48770(8) 0.0139(4) Uani 1 d . . .
C4A C 0.46050(16) 0.45118(8) 0.49603(8) 0.0162(4) Uani 1 d . . .
H4AA H 0.3900 0.4514 0.5219 0.019 Uiso 1 calc . . R
H4AB H 0.4387 0.4331 0.4562 0.019 Uiso 1 calc . . R
C5A C 0.55453(17) 0.40967(8) 0.52508(8) 0.0165(4) Uani 1 d . . .
H5AA H 0.5246 0.3657 0.5308 0.020 Uiso 1 calc . . R
H5AB H 0.6237 0.4076 0.4983 0.020 Uiso 1 calc . . R
C6A C 0.60728(15) 0.40233(8) 0.63399(8) 0.0140(4) Uani 1 d . . .
C7A C 0.59758(17) 0.29183(8) 0.67319(8) 0.0181(4) Uani 1 d . . .
C8A C 0.49944(18) 0.30093(9) 0.71811(9) 0.0247(5) Uani 1 d . . .
H8AA H 0.5087 0.3422 0.7386 0.037 Uiso 1 calc . . GR
H8AB H 0.5016 0.2665 0.7481 0.037 Uiso 1 calc . . GR
H8AC H 0.4245 0.3000 0.6968 0.037 Uiso 1 calc . . GR
C9A C 0.5809(2) 0.22935(9) 0.63890(9) 0.0328(5) Uani 1 d . . .
H9AA H 0.5051 0.2298 0.6183 0.049 Uiso 1 calc . . GR
H9AB H 0.5835 0.1935 0.6674 0.049 Uiso 1 calc . . GR
H9AC H 0.6433 0.2245 0.6089 0.049 Uiso 1 calc . . GR
C10A C 0.71671(18) 0.29384(10) 0.70279(11) 0.0310(5) Uani 1 d . . .
H10D H 0.7771 0.2972 0.6715 0.046 Uiso 1 calc . . GR
H10E H 0.7288 0.2547 0.7263 0.046 Uiso 1 calc . . GR
H10F H 0.7214 0.3310 0.7297 0.046 Uiso 1 calc . . GR
C11A C 0.41982(15) 0.56632(8) 0.45495(8) 0.0136(4) Uani 1 d . . .
C12A C 0.46513(15) 0.61252(8) 0.41444(8) 0.0144(4) Uani 1 d . . .
C13A C 0.38795(16) 0.65001(8) 0.38084(8) 0.0163(4) Uani 1 d . . .
H13A H 0.4194 0.6795 0.3525 0.020 Uiso 1 calc . . R
C14A C 0.26847(16) 0.64632(8) 0.38678(8) 0.0162(4) Uani 1 d . . .
C15A C 0.22599(16) 0.60547(9) 0.43069(8) 0.0176(4) Uani 1 d . . .
H15A H 0.1442 0.6043 0.4378 0.021 Uiso 1 calc . . R
C16A C 0.29797(16) 0.56585(9) 0.46503(8) 0.0166(4) Uani 1 d . . .
C17A C 0.59328(16) 0.62958(9) 0.40656(9) 0.0197(4) Uani 1 d . . .
H17D H 0.6329 0.6270 0.4458 0.030 Uiso 1 calc . . GR
H17E H 0.5998 0.6732 0.3906 0.030 Uiso 1 calc . . GR
H17F H 0.6297 0.5996 0.3782 0.030 Uiso 1 calc . . GR
C18A C 0.18801(18) 0.68644(10) 0.34843(9) 0.0247(4) Uani 1 d . . .
H18D H 0.2253 0.7276 0.3397 0.037 Uiso 1 calc . . GR
H18E H 0.1147 0.6937 0.3703 0.037 Uiso 1 calc . . GR
H18F H 0.1717 0.6641 0.3104 0.037 Uiso 1 calc . . GR
C19A C 0.23485(17) 0.52640(10) 0.51251(9) 0.0258(5) Uani 1 d . . .
H19D H 0.2232 0.4829 0.4973 0.039 Uiso 1 calc . . GR
H19E H 0.1589 0.5459 0.5213 0.039 Uiso 1 calc . . GR
H19F H 0.2817 0.5250 0.5496 0.039 Uiso 1 calc . . GR
O1B O -0.09518(11) 0.65055(6) 0.44762(5) 0.0198(3) Uani 1 d . . .
O2B O -0.12586(12) 0.56315(6) 0.50666(6) 0.0232(3) Uani 1 d . . .
O3B O -0.13705(11) 0.47560(6) 0.27320(6) 0.0193(3) Uani 1 d . . .
H3B H -0.1319 0.5018 0.2446 0.029 Uiso 1 calc . . GR
N1B N -0.10370(13) 0.55442(7) 0.40445(7) 0.0170(3) Uani 1 d . . .
C1B C -0.08176(16) 0.58280(8) 0.34539(8) 0.0162(4) Uani 1 d . . .
H1BA H -0.0540 0.6273 0.3504 0.019 Uiso 1 calc . . R
H1BB H -0.1549 0.5837 0.3216 0.019 Uiso 1 calc . . R
C2B C 0.01007(15) 0.54359(8) 0.31221(8) 0.0148(4) Uani 1 d . . .
H2BA H 0.0846 0.5453 0.3349 0.018 Uiso 1 calc . . R
H2BB H 0.0236 0.5623 0.2716 0.018 Uiso 1 calc . . R
C3B C -0.02837(15) 0.47344(8) 0.30536(8) 0.0140(4) Uani 1 d . . .
C4B C -0.05789(16) 0.44610(8) 0.36786(8) 0.0162(4) Uani 1 d . . .
H4BA H -0.0915 0.4028 0.3630 0.019 Uiso 1 calc . . R
H4BB H 0.0147 0.4421 0.3919 0.019 Uiso 1 calc . . R
C5B C -0.14397(16) 0.48797(8) 0.40191(9) 0.0182(4) Uani 1 d . . .
H5BA H -0.2209 0.4862 0.3816 0.022 Uiso 1 calc . . R
H5BB H -0.1537 0.4714 0.4436 0.022 Uiso 1 calc . . R
C6B C -0.11031(15) 0.58699(9) 0.45740(9) 0.0171(4) Uani 1 d . . .
C7B C -0.09652(17) 0.69612(9) 0.49845(8) 0.0201(4) Uani 1 d . . .
C8B C 0.00528(18) 0.68314(10) 0.54037(10) 0.0269(5) Uani 1 d . . .
H8BA H -0.0079 0.6428 0.5619 0.040 Uiso 1 calc . . GR
H8BB H 0.0123 0.7181 0.5697 0.040 Uiso 1 calc . . GR
H8BC H 0.0774 0.6801 0.5166 0.040 Uiso 1 calc . . GR
C9B C -0.21188(19) 0.69481(11) 0.53165(11) 0.0355(6) Uani 1 d . . .
H9BA H -0.2755 0.7027 0.5030 0.053 Uiso 1 calc . . GR
H9BB H -0.2122 0.7280 0.5630 0.053 Uiso 1 calc . . GR
H9BC H -0.2227 0.6528 0.5505 0.053 Uiso 1 calc . . GR
C10B C -0.0801(2) 0.75971(9) 0.46640(10) 0.0339(5) Uani 1 d . . .
H10G H -0.0034 0.7605 0.4467 0.051 Uiso 1 calc . . GR
H10H H -0.0849 0.7945 0.4959 0.051 Uiso 1 calc . . GR
H10I H -0.1413 0.7651 0.4358 0.051 Uiso 1 calc . . GR
C11B C 0.06131(15) 0.43119(8) 0.27175(8) 0.0134(4) Uani 1 d . . .
C12B C 0.02446(16) 0.38698(8) 0.22701(8) 0.0150(4) Uani 1 d . . .
C13B C 0.10734(17) 0.35366(9) 0.19340(8) 0.0190(4) Uani 1 d . . .
H13B H 0.0811 0.3255 0.1625 0.023 Uiso 1 calc . . R
C14B C 0.22630(17) 0.35974(9) 0.20297(9) 0.0208(4) Uani 1 d . . .
C15B C 0.26036(16) 0.39836(9) 0.25018(9) 0.0192(4) Uani 1 d . . .
H15B H 0.3412 0.4011 0.2595 0.023 Uiso 1 calc . . R
C16B C 0.18211(15) 0.43364(8) 0.28502(8) 0.0153(4) Uani 1 d . . .
C17B C -0.10104(16) 0.36787(9) 0.21346(9) 0.0210(4) Uani 1 d . . .
H17G H -0.1448 0.3645 0.2514 0.032 Uiso 1 calc . . GR
H17H H -0.1019 0.3265 0.1926 0.032 Uiso 1 calc . . GR
H17I H -0.1373 0.4003 0.1876 0.032 Uiso 1 calc . . GR
C18B C 0.3138(2) 0.32423(11) 0.16474(10) 0.0337(5) Uani 1 d . . .
H18G H 0.2921 0.2790 0.1628 0.050 Uiso 1 calc . . GR
H18H H 0.3916 0.3283 0.1828 0.050 Uiso 1 calc . . GR
H18I H 0.3146 0.3423 0.1238 0.050 Uiso 1 calc . . GR
C19B C 0.23842(16) 0.46977(10) 0.33695(9) 0.0241(4) Uani 1 d . . .
H19G H 0.2545 0.5138 0.3244 0.036 Uiso 1 calc . . GR
H19H H 0.3117 0.4487 0.3483 0.036 Uiso 1 calc . . GR
H19I H 0.1854 0.4701 0.3717 0.036 Uiso 1 calc . . GR


_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
O1 C6 1.336(2) . ?
O1 C7 1.485(2) . ?
O2 C6 1.220(2) . ?
O3 H3 0.8400 . ?
O3 C3 1.428(2) . ?
N1 C1 1.463(2) . ?
N1 C5 1.462(2) . ?
N1 C6 1.353(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.525(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.533(3) . ?
C3 C4 1.531(3) . ?
C3 C11 1.550(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.520(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.519(3) . ?
C7 C9 1.510(3) . ?
C7 C10 1.514(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.418(3) . ?
C11 C16 1.406(3) . ?
C12 C13 1.397(3) . ?
C12 C17 1.517(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(3) . ?
C14 C15 1.373(3) . ?
C14 C18 1.514(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.396(3) . ?
C16 C19 1.523(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O1A C6A 1.350(2) . ?
O1A C7A 1.478(2) . ?
O2A C6A 1.225(2) . ?
O3A H3A 0.8400 . ?
O3A C3A 1.426(2) . ?
N1A C1A 1.474(2) . ?
N1A C5A 1.467(2) . ?
N1A C6A 1.346(2) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.523(2) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.529(2) . ?
C3A C4A 1.543(2) . ?
C3A C11A 1.550(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.525(2) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C7A C8A 1.512(3) . ?
C7A C9A 1.523(3) . ?
C7A C10A 1.514(3) . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A C12A 1.416(2) . ?
C11A C16A 1.413(2) . ?
C12A C13A 1.396(2) . ?
C12A C17A 1.521(2) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.377(3) . ?
C14A C15A 1.382(3) . ?
C14A C18A 1.507(3) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.394(3) . ?
C16A C19A 1.518(3) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
O1B C6B 1.358(2) . ?
O1B C7B 1.474(2) . ?
O2B C6B 1.211(2) . ?
O3B H3B 0.8400 . ?
O3B C3B 1.434(2) . ?
N1B C1B 1.456(2) . ?
N1B C5B 1.466(2) . ?
N1B C6B 1.356(2) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.522(2) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.539(2) . ?
C3B C4B 1.533(2) . ?
C3B C11B 1.545(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.518(2) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C7B C8B 1.514(3) . ?
C7B C9B 1.512(3) . ?
C7B C10B 1.519(3) . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C10B H10G 0.9800 . ?
C10B H10H 0.9800 . ?
C10B H10I 0.9800 . ?
C11B C12B 1.418(2) . ?
C11B C16B 1.415(2) . ?
C12B C13B 1.392(3) . ?
C12B C17B 1.522(2) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.385(3) . ?
C14B C15B 1.376(3) . ?
C14B C18B 1.507(3) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.393(3) . ?
C16B C19B 1.518(3) . ?
C17B H17G 0.9800 . ?
C17B H17H 0.9800 . ?
C17B H17I 0.9800 . ?
C18B H18G 0.9800 . ?
C18B H18H 0.9800 . ?
C18B H18I 0.9800 . ?
C19B H19G 0.9800 . ?
C19B H19H 0.9800 . ?
C19B H19I 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
C6 O1 C7 120.11(14) . . ?
C3 O3 H3 109.5 . . ?
C5 N1 C1 115.12(14) . . ?
C6 N1 C1 124.24(15) . . ?
C6 N1 C5 117.96(14) . . ?
N1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
N1 C1 C2 111.38(14) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.65(15) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
O3 C3 C2 110.38(15) . . ?
O3 C3 C4 106.32(16) . . ?
O3 C3 C11 105.16(14) . . ?
C2 C3 C11 111.53(14) . . ?
C4 C3 C2 109.07(15) . . ?
C4 C3 C11 114.18(15) . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 C3 111.92(16) . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
N1 C5 C4 110.09(15) . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
O1 C6 N1 111.94(15) . . ?
O2 C6 O1 123.99(16) . . ?
O2 C6 N1 124.01(16) . . ?
O1 C7 C8 110.20(16) . . ?
O1 C7 C9 110.54(15) . . ?
O1 C7 C10 101.91(15) . . ?
C9 C7 C8 112.47(17) . . ?
C9 C7 C10 110.52(18) . . ?
C10 C7 C8 110.71(19) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C3 120.08(16) . . ?
C16 C11 C3 122.40(16) . . ?
C16 C11 C12 117.52(16) . . ?
C11 C12 C17 126.20(17) . . ?
C13 C12 C11 119.26(17) . . ?
C13 C12 C17 114.51(17) . . ?
C12 C13 H13 118.5 . . ?
C14 C13 C12 123.03(18) . . ?
C14 C13 H13 118.5 . . ?
C13 C14 C18 121.25(18) . . ?
C15 C14 C13 116.80(17) . . ?
C15 C14 C18 121.93(18) . . ?
C14 C15 H15 118.5 . . ?
C14 C15 C16 122.95(18) . . ?
C16 C15 H15 118.5 . . ?
C11 C16 C19 126.65(17) . . ?
C15 C16 C11 119.83(17) . . ?
C15 C16 C19 113.49(16) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6A O1A C7A 121.71(14) . . ?
C3A O3A H3A 109.5 . . ?
C5A N1A C1A 114.96(14) . . ?
C6A N1A C1A 119.09(14) . . ?
C6A N1A C5A 124.19(14) . . ?
N1A C1A H1AA 109.4 . . ?
N1A C1A H1AB 109.4 . . ?
N1A C1A C2A 111.09(15) . . ?
H1AA C1A H1AB 108.0 . . ?
C2A C1A H1AA 109.4 . . ?
C2A C1A H1AB 109.4 . . ?
C1A C2A H2AA 109.2 . . ?
C1A C2A H2AB 109.2 . . ?
C1A C2A C3A 112.06(15) . . ?
H2AA C2A H2AB 107.9 . . ?
C3A C2A H2AA 109.2 . . ?
C3A C2A H2AB 109.2 . . ?
O3A C3A C2A 106.20(14) . . ?
O3A C3A C4A 105.49(14) . . ?
O3A C3A C11A 109.87(14) . . ?
C2A C3A C4A 108.29(14) . . ?
C2A C3A C11A 111.01(14) . . ?
C4A C3A C11A 115.46(14) . . ?
C3A C4A H4AA 109.5 . . ?
C3A C4A H4AB 109.6 . . ?
H4AA C4A H4AB 108.1 . . ?
C5A C4A C3A 110.50(15) . . ?
C5A C4A H4AA 109.5 . . ?
C5A C4A H4AB 109.5 . . ?
N1A C5A C4A 109.38(14) . . ?
N1A C5A H5AA 109.8 . . ?
N1A C5A H5AB 109.8 . . ?
C4A C5A H5AA 109.8 . . ?
C4A C5A H5AB 109.8 . . ?
H5AA C5A H5AB 108.2 . . ?
O2A C6A O1A 124.09(16) . . ?
O2A C6A N1A 124.60(16) . . ?
N1A C6A O1A 111.31(15) . . ?
O1A C7A C8A 109.67(15) . . ?
O1A C7A C9A 101.84(14) . . ?
O1A C7A C10A 111.71(15) . . ?
C8A C7A C9A 109.97(16) . . ?
C8A C7A C10A 112.53(17) . . ?
C10A C7A C9A 110.61(17) . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C7A C9A H9AA 109.5 . . ?
C7A C9A H9AB 109.5 . . ?
C7A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C7A C10A H10D 109.5 . . ?
C7A C10A H10E 109.5 . . ?
C7A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C12A C11A C3A 119.26(15) . . ?
C16A C11A C3A 122.91(16) . . ?
C16A C11A C12A 117.80(16) . . ?
C11A C12A C17A 125.90(16) . . ?
C13A C12A C11A 119.20(16) . . ?
C13A C12A C17A 114.74(16) . . ?
C12A C13A H13A 118.4 . . ?
C14A C13A C12A 123.19(17) . . ?
C14A C13A H13A 118.4 . . ?
C13A C14A C15A 116.85(17) . . ?
C13A C14A C18A 121.53(17) . . ?
C15A C14A C18A 121.60(17) . . ?
C14A C15A H15A 118.6 . . ?
C14A C15A C16A 122.82(17) . . ?
C16A C15A H15A 118.6 . . ?
C11A C16A C19A 125.67(17) . . ?
C15A C16A C11A 119.61(17) . . ?
C15A C16A C19A 114.70(16) . . ?
C12A C17A H17D 109.5 . . ?
C12A C17A H17E 109.5 . . ?
C12A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C14A C18A H18D 109.5 . . ?
C14A C18A H18E 109.5 . . ?
C14A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C16A C19A H19D 109.5 . . ?
C16A C19A H19E 109.5 . . ?
C16A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C6B O1B C7B 120.70(14) . . ?
C3B O3B H3B 109.5 . . ?
C1B N1B C5B 114.00(14) . . ?
C6B N1B C1B 125.33(14) . . ?
C6B N1B C5B 119.48(15) . . ?
N1B C1B H1BA 109.8 . . ?
N1B C1B H1BB 109.8 . . ?
N1B C1B C2B 109.36(14) . . ?
H1BA C1B H1BB 108.3 . . ?
C2B C1B H1BA 109.8 . . ?
C2B C1B H1BB 109.8 . . ?
C1B C2B H2BA 109.4 . . ?
C1B C2B H2BB 109.4 . . ?
C1B C2B C3B 111.31(15) . . ?
H2BA C2B H2BB 108.0 . . ?
C3B C2B H2BA 109.4 . . ?
C3B C2B H2BB 109.4 . . ?
O3B C3B C2B 105.49(14) . . ?
O3B C3B C4B 105.48(14) . . ?
O3B C3B C11B 110.90(14) . . ?
C2B C3B C11B 113.72(14) . . ?
C4B C3B C2B 109.28(14) . . ?
C4B C3B C11B 111.49(14) . . ?
C3B C4B H4BA 109.2 . . ?
C3B C4B H4BB 109.2 . . ?
H4BA C4B H4BB 107.9 . . ?
C5B C4B C3B 112.00(15) . . ?
C5B C4B H4BA 109.2 . . ?
C5B C4B H4BB 109.2 . . ?
N1B C5B C4B 111.21(15) . . ?
N1B C5B H5BA 109.4 . . ?
N1B C5B H5BB 109.4 . . ?
C4B C5B H5BA 109.4 . . ?
C4B C5B H5BB 109.4 . . ?
H5BA C5B H5BB 108.0 . . ?
O2B C6B O1B 124.43(16) . . ?
O2B C6B N1B 125.24(17) . . ?
N1B C6B O1B 110.33(15) . . ?
O1B C7B C8B 110.03(15) . . ?
O1B C7B C9B 111.56(15) . . ?
O1B C7B C10B 102.10(15) . . ?
C8B C7B C10B 110.31(17) . . ?
C9B C7B C8B 111.91(17) . . ?
C9B C7B C10B 110.53(18) . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
C7B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C7B C9B H9BA 109.5 . . ?
C7B C9B H9BB 109.5 . . ?
C7B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C7B C10B H10G 109.5 . . ?
C7B C10B H10H 109.5 . . ?
C7B C10B H10I 109.5 . . ?
H10G C10B H10H 109.5 . . ?
H10G C10B H10I 109.5 . . ?
H10H C10B H10I 109.5 . . ?
C12B C11B C3B 120.68(16) . . ?
C16B C11B C3B 121.97(15) . . ?
C16B C11B C12B 117.33(16) . . ?
C11B C12B C17B 126.13(16) . . ?
C13B C12B C11B 119.69(17) . . ?
C13B C12B C17B 114.06(16) . . ?
C12B C13B H13B 118.5 . . ?
C14B C13B C12B 122.93(18) . . ?
C14B C13B H13B 118.5 . . ?
C13B C14B C18B 121.58(18) . . ?
C15B C14B C13B 116.66(17) . . ?
C15B C14B C18B 121.73(18) . . ?
C14B C15B H15B 118.4 . . ?
C14B C15B C16B 123.20(18) . . ?
C16B C15B H15B 118.4 . . ?
C11B C16B C19B 126.17(17) . . ?
C15B C16B C11B 119.69(17) . . ?
C15B C16B C19B 114.09(16) . . ?
C12B C17B H17G 109.5 . . ?
C12B C17B H17H 109.5 . . ?
C12B C17B H17I 109.5 . . ?
H17G C17B H17H 109.5 . . ?
H17G C17B H17I 109.5 . . ?
H17H C17B H17I 109.5 . . ?
C14B C18B H18G 109.5 . . ?
C14B C18B H18H 109.5 . . ?
C14B C18B H18I 109.5 . . ?
H18G C18B H18H 109.5 . . ?
H18G C18B H18I 109.5 . . ?
H18H C18B H18I 109.5 . . ?
C16B C19B H19G 109.5 . . ?
C16B C19B H19H 109.5 . . ?
C16B C19B H19I 109.5 . . ?
H19G C19B H19H 109.5 . . ?
H19G C19B H19I 109.5 . . ?
H19H C19B H19I 109.5 . . ?

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
O3 H3 O2A 0.84 2.22 2.8650(19) 133.4 2_664
O3A H3A O2 0.84 1.99 2.8238(18) 170.0 .
O3B H3B O2A 0.84 2.06 2.8941(18) 170.3 2_564

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
C1 N1 C6 O1 -13.4(2) . . . . ?
C1 N1 C6 O2 169.44(18) . . . . ?
C1 C2 C3 O3 64.1(2) . . . . ?
C1 C2 C3 C4 -52.4(2) . . . . ?
C1 C2 C3 C11 -179.38(15) . . . . ?
C2 C1 N1 C5 -53.5(2) . . . . ?
C2 C1 N1 C6 145.51(17) . . . . ?
C2 C3 C4 C5 54.9(2) . . . . ?
C2 C3 C11 C12 -94.58(19) . . . . ?
C2 C3 C11 C16 84.9(2) . . . . ?
C3 C2 C1 N1 51.4(2) . . . . ?
C3 C4 C5 N1 -56.2(2) . . . . ?
C4 C3 C11 C12 141.22(17) . . . . ?
C4 C3 C11 C16 -39.3(2) . . . . ?
C4 C5 N1 C1 55.8(2) . . . . ?
C4 C5 N1 C6 -141.97(17) . . . . ?
C5 N1 C6 O1 -173.90(15) . . . . ?
C5 N1 C6 O2 9.0(3) . . . . ?
C5 C4 C3 O3 -64.1(2) . . . . ?
C5 C4 C3 C11 -179.55(15) . . . . ?
C7 O1 C6 O2 -0.3(3) . . . . ?
C7 O1 C6 N1 -177.42(15) . . . . ?
C8 C7 O1 C6 61.3(2) . . . . ?
C9 C7 O1 C6 -63.6(2) . . . . ?
C10 C7 O1 C6 178.89(18) . . . . ?
C12 C11 C3 O3 25.1(2) . . . . ?
C16 C11 C3 O3 -155.45(17) . . . . ?
C1A N1A C6A O1A -167.12(15) . . . . ?
C1A N1A C6A O2A 13.1(3) . . . . ?
C1A C2A C3A O3A -57.54(19) . . . . ?
C1A C2A C3A C4A 55.34(19) . . . . ?
C1A C2A C3A C11A -176.93(15) . . . . ?
C2A C3A C4A C5A -58.43(18) . . . . ?
C2A C3A C11A C12A 93.72(19) . . . . ?
C2A C3A C11A C16A -84.2(2) . . . . ?
C3A C2A C1A N1A -52.5(2) . . . . ?
C3A C4A C5A N1A 58.51(19) . . . . ?
C4A C3A C11A C12A -142.56(16) . . . . ?
C4A C3A C11A C16A 39.5(2) . . . . ?
C4A C5A N1A C1A -56.6(2) . . . . ?
C4A C5A N1A C6A 138.74(17) . . . . ?
C5A N1A C6A O1A -3.0(2) . . . . ?
C5A N1A C6A O2A 177.24(17) . . . . ?
C5A C4A C3A O3A 54.92(18) . . . . ?
C5A C4A C3A C11A 176.43(14) . . . . ?
C7A O1A C6A O2A 2.6(3) . . . . ?
C7A O1A C6A N1A -177.16(15) . . . . ?
C8A C7A O1A C6A 69.7(2) . . . . ?
C9A C7A O1A C6A -173.89(16) . . . . ?
C10A C7A O1A C6A -55.8(2) . . . . ?
C12A C11A C3A O3A -23.4(2) . . . . ?
C16A C11A C3A O3A 158.63(16) . . . . ?
C1B N1B C6B O1B 0.9(2) . . . . ?
C1B N1B C6B O2B -178.17(18) . . . . ?
C1B C2B C3B O3B 58.06(18) . . . . ?
C1B C2B C3B C4B -54.91(19) . . . . ?
C1B C2B C3B C11B 179.80(14) . . . . ?
C2B C1B N1B C5B -58.8(2) . . . . ?
C2B C1B N1B C6B 133.86(17) . . . . ?
C2B C3B C4B C5B 52.20(19) . . . . ?
C2B C3B C11B C12B -136.37(17) . . . . ?
C2B C3B C11B C16B 45.2(2) . . . . ?
C3B C2B C1B N1B 57.64(19) . . . . ?
C3B C4B C5B N1B -52.7(2) . . . . ?
C4B C3B C11B C12B 99.53(18) . . . . ?
C4B C3B C11B C16B -78.9(2) . . . . ?
C4B C5B N1B C1B 56.6(2) . . . . ?
C4B C5B N1B C6B -135.17(17) . . . . ?
C5B N1B C6B O1B -165.86(15) . . . . ?
C5B N1B C6B O2B 15.1(3) . . . . ?
C5B C4B C3B O3B -60.78(18) . . . . ?
C5B C4B C3B C11B 178.77(15) . . . . ?
C7B O1B C6B O2B 0.2(3) . . . . ?
C7B O1B C6B N1B -178.91(14) . . . . ?
C8B C7B O1B C6B 64.4(2) . . . . ?
C9B C7B O1B C6B -60.5(2) . . . . ?
C10B C7B O1B C6B -178.52(16) . . . . ?
C12B C11B C3B O3B -17.7(2) . . . . ?
C16B C11B C3B O3B 163.85(16) . . . . ?

####################################################################### 
# 
# 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_7_15srv059
_database_code_depnum_ccdc_archive 'CCDC 1474218'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_audit_creation_date             2015-03-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C2 F3 O2, C12 H16 N'
_chemical_formula_sum            'C14 H16 F3 N O2'
_chemical_formula_weight         287.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H15 N1'
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.3784(3)
_cell_length_b                   9.4630(6)
_cell_length_c                   12.6226(6)
_cell_angle_alpha                105.666(5)
_cell_angle_beta                 99.952(4)
_cell_angle_gamma                106.901(5)
_cell_volume                     675.27(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.7330
_cell_measurement_theta_min      1.7920
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8762
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.39
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   51.00   86.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   74.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -109.0000  123.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega    5.00   46.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega  -41.00   49.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -38.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
  6 omega    9.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   93.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  178.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega    9.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   90.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0586424000
_diffrn_orient_matrix_UB_12      0.0426223000
_diffrn_orient_matrix_UB_13      0.0584498000
_diffrn_orient_matrix_UB_21      -0.0036991000
_diffrn_orient_matrix_UB_22      0.0704290000
_diffrn_orient_matrix_UB_23      -0.0084961000
_diffrn_orient_matrix_UB_31      -0.1055527000
_diffrn_orient_matrix_UB_32      -0.0127032000
_diffrn_orient_matrix_UB_33      0.0138312000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2879
_reflns_number_total             3601
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.2800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1202
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2A,H2B), C5(H5A,H5B)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.48105(17) 0.33075(12) 0.64628(8) 0.0335(2) Uani 1 d . . .
F2 F 0.16796(18) 0.26584(16) 0.51920(10) 0.0460(3) Uani 1 d . . .
F3 F 0.34538(19) 0.10369(11) 0.51629(9) 0.0389(3) Uani 1 d . . .
O1 O 0.71853(17) 0.34496(14) 0.48777(9) 0.0258(2) Uani 1 d . . .
O2 O 0.39704(18) 0.33064(13) 0.37046(9) 0.0246(2) Uani 1 d . . .
C21 C 0.5109(2) 0.31869(16) 0.45590(11) 0.0181(3) Uani 1 d . . .
C22 C 0.3753(2) 0.25563(18) 0.53506(12) 0.0220(3) Uani 1 d . . .
N1 N 0.9523(2) 0.34379(14) 0.32556(10) 0.0172(2) Uani 1 d . . .
C1 C 0.8107(3) 0.18029(16) 0.24843(12) 0.0215(3) Uani 1 d . . .
H1C H 0.6477 0.1680 0.2336 0.026 Uiso 1 calc . . R
H1D H 0.8343 0.1053 0.2866 0.026 Uiso 1 calc . . R
C2 C 0.8713(3) 0.14295(18) 0.13692(13) 0.0310(4) Uani 1 d . . .
H2A H 0.9972 0.1022 0.1463 0.037 Uiso 1 calc . . R
H2B H 0.7383 0.0568 0.0790 0.037 Uiso 1 calc . . R
C3 C 0.9382(2) 0.26806(15) 0.09163(11) 0.0163(3) Uani 1 d . . .
C4 C 0.9815(3) 0.42301(19) 0.15692(14) 0.0303(4) Uani 1 d . . .
C5 C 0.9323(2) 0.46225(16) 0.27042(11) 0.0187(3) Uani 1 d . . .
H5A H 0.7764 0.4652 0.2604 0.022 Uiso 1 calc . . R
H5B H 1.0406 0.5676 0.3206 0.022 Uiso 1 calc . . R
C6 C 0.9609(2) 0.22893(15) -0.02778(11) 0.0163(3) Uani 1 d . . .
C7 C 1.1758(2) 0.26680(16) -0.04936(12) 0.0182(3) Uani 1 d . . .
C8 C 1.1857(3) 0.23123(16) -0.16309(13) 0.0215(3) Uani 1 d . . .
C9 C 0.9893(3) 0.15833(17) -0.25391(13) 0.0231(3) Uani 1 d . . .
C10 C 0.7777(3) 0.11805(17) -0.23261(12) 0.0237(3) Uani 1 d . . .
C11 C 0.7645(3) 0.15285(17) -0.11998(12) 0.0212(3) Uani 1 d . . .
C12 C 1.3910(3) 0.3395(2) 0.04765(14) 0.0297(4) Uani 1 d . . .
H12A H 1.4065 0.4466 0.0911 0.045 Uiso 1 calc . . GR
H12B H 1.5224 0.3424 0.0168 0.045 Uiso 1 calc . . GR
H12C H 1.3839 0.2767 0.0982 0.045 Uiso 1 calc . . GR
H1A H 0.897(3) 0.362(2) 0.3892(17) 0.032(5) Uiso 1 d . . .
H1B H 1.103(4) 0.352(2) 0.3487(16) 0.033(5) Uiso 1 d . . .
H4 H 0.990(3) 0.497(2) 0.1209(16) 0.026(4) Uiso 1 d . . .
H8 H 1.330(3) 0.256(2) -0.1759(15) 0.029(5) Uiso 1 d . . .
H9 H 1.008(3) 0.135(2) -0.3295(17) 0.035(5) Uiso 1 d . . .
H10 H 0.639(3) 0.064(2) -0.2944(16) 0.030(5) Uiso 1 d . . .
H11 H 0.618(3) 0.126(2) -0.1031(15) 0.024(4) Uiso 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
F1 C22 1.3365(17) . ?
F2 C22 1.3382(17) . ?
F3 C22 1.3420(18) . ?
O1 C21 1.2444(17) . ?
O2 C21 1.2433(17) . ?
C21 C22 1.557(2) . ?
N1 C1 1.4925(18) . ?
N1 C5 1.4938(18) . ?
N1 H1A 0.93(2) . ?
N1 H1B 0.93(2) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.501(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.438(2) . ?
C3 C4 1.393(2) . ?
C3 C6 1.4949(18) . ?
C4 C5 1.492(2) . ?
C4 H4 0.930(19) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.4067(19) . ?
C6 C11 1.4004(19) . ?
C7 C8 1.400(2) . ?
C7 C12 1.507(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.936(19) . ?
C9 C10 1.386(2) . ?
C9 H9 0.96(2) . ?
C10 C11 1.393(2) . ?
C10 H10 0.968(19) . ?
C11 H11 0.971(18) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
O1 C21 C22 113.45(12) . . ?
O2 C21 O1 130.31(13) . . ?
O2 C21 C22 116.21(12) . . ?
F1 C22 F2 106.38(12) . . ?
F1 C22 F3 106.10(12) . . ?
F1 C22 C21 113.16(12) . . ?
F2 C22 F3 106.80(13) . . ?
F2 C22 C21 113.21(12) . . ?
F3 C22 C21 110.71(12) . . ?
C1 N1 C5 111.87(11) . . ?
C1 N1 H1A 106.5(12) . . ?
C1 N1 H1B 109.9(12) . . ?
C5 N1 H1A 108.5(12) . . ?
C5 N1 H1B 111.1(12) . . ?
H1A N1 H1B 108.8(16) . . ?
N1 C1 H1C 109.4 . . ?
N1 C1 H1D 109.4 . . ?
N1 C1 C2 111.29(12) . . ?
H1C C1 H1D 108.0 . . ?
C2 C1 H1C 109.4 . . ?
C2 C1 H1D 109.4 . . ?
C1 C2 H2A 107.9 . . ?
C1 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
C3 C2 C1 117.59(13) . . ?
C3 C2 H2A 107.9 . . ?
C3 C2 H2B 107.9 . . ?
C2 C3 C6 118.68(12) . . ?
C4 C3 C2 121.13(13) . . ?
C4 C3 C6 120.19(12) . . ?
C3 C4 C5 120.98(13) . . ?
C3 C4 H4 119.1(11) . . ?
C5 C4 H4 116.3(11) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 N1 110.90(11) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C3 121.25(12) . . ?
C11 C6 C3 119.43(12) . . ?
C11 C6 C7 119.32(12) . . ?
C6 C7 C12 120.75(12) . . ?
C8 C7 C6 118.55(13) . . ?
C8 C7 C12 120.67(13) . . ?
C7 C8 H8 117.4(11) . . ?
C9 C8 C7 121.58(14) . . ?
C9 C8 H8 121.0(11) . . ?
C8 C9 H9 117.3(12) . . ?
C10 C9 C8 119.84(13) . . ?
C10 C9 H9 122.8(12) . . ?
C9 C10 C11 119.39(14) . . ?
C9 C10 H10 121.4(11) . . ?
C11 C10 H10 119.2(11) . . ?
C6 C11 H11 118.0(10) . . ?
C10 C11 C6 121.29(14) . . ?
C10 C11 H11 120.7(10) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
N1 H1A O1 0.93(2) 1.83(2) 2.7328(15) 163.3(17) .
N1 H1B O2 0.93(2) 1.93(2) 2.8410(16) 168.3(17) 1_655

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
O1 C21 C22 F1 42.56(17) . . . . ?
O1 C21 C22 F2 163.70(13) . . . . ?
O1 C21 C22 F3 -76.40(15) . . . . ?
O2 C21 C22 F1 -139.42(13) . . . . ?
O2 C21 C22 F2 -18.28(18) . . . . ?
O2 C21 C22 F3 101.62(15) . . . . ?
N1 C1 C2 C3 -34.3(2) . . . . ?
C1 N1 C5 C4 -53.11(16) . . . . ?
C1 C2 C3 C4 10.3(2) . . . . ?
C1 C2 C3 C6 -169.69(13) . . . . ?
C2 C3 C4 C5 -7.6(2) . . . . ?
C2 C3 C6 C7 -107.00(16) . . . . ?
C2 C3 C6 C11 72.86(18) . . . . ?
C3 C4 C5 N1 28.9(2) . . . . ?
C3 C6 C7 C8 -178.15(12) . . . . ?
C3 C6 C7 C12 3.7(2) . . . . ?
C3 C6 C11 C10 178.24(13) . . . . ?
C4 C3 C6 C7 73.03(19) . . . . ?
C4 C3 C6 C11 -107.11(17) . . . . ?
C5 N1 C1 C2 56.38(17) . . . . ?
C6 C3 C4 C5 172.33(14) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
C7 C6 C11 C10 -1.9(2) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C6 0.5(2) . . . . ?
C11 C6 C7 C8 2.0(2) . . . . ?
C11 C6 C7 C12 -176.17(13) . . . . ?
C12 C7 C8 C9 177.35(14) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 0 0 0.0879 -1.0000 -0.0000 0.0000 -0.0586 0.0037 0.1056
1 0 0 0.0879 1.0000 0.0000 -0.0000 0.0586 -0.0037 -0.1056
1 0 -1 0.1257 1.0000 0.0000 -1.0000 0.0002 0.0048 -0.1194
-1 0 1 0.1257 -1.0000 -0.0000 1.0000 -0.0002 -0.0048 0.1194
0 1 -1 0.0898 -0.0000 1.0000 -1.0000 -0.0158 0.0789 -0.0265
0 -1 1 0.0898 0.0000 -1.0000 1.0000 0.0158 -0.0789 0.0265
0 1 0 0.0758 -0.0000 1.0000 -0.0000 0.0426 0.0704 -0.0127
0 -1 0 0.0758 0.0000 -1.0000 0.0000 -0.0426 -0.0704 0.0127
-1 0 2 0.1596 -1.0000 -0.0000 2.0000 0.0583 -0.0133 0.1332
1 0 -2 0.1596 1.0000 0.0000 -2.0000 -0.0583 0.0133 -0.1332
-5 12 -9 0.0759 -5.0000 12.0000 -9.0000 -0.3078 0.9401 0.2508

####################################################################### 
# 
# 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_Ir5_15srv101
_database_code_depnum_ccdc_archive 'CCDC 1474219'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_audit_creation_date             2015-04-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C41 H35 Ir N2 O2'
_chemical_formula_sum            'C41 H35 Ir N2 O2'
_chemical_formula_weight         779.91
_chemical_melting_point          ?
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'
Ir Ir -1.4442 7.9887 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   13.818(3)
_cell_length_b                   14.101(3)
_cell_length_c                   19.071(4)
_cell_angle_alpha                94.29(3)
_cell_angle_beta                 98.66(3)
_cell_angle_gamma                118.08(3)
_cell_volume                     3195.6(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9631
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.96
_cell_measurement_theta_min      2.19
_exptl_absorpt_coefficient_mu    4.218
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0723 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.7943.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            52905
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.66
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker SMART CCD 6000'
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                13296
_reflns_number_total             16967
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.070
_refine_diff_density_min         -1.334
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     837
_refine_ls_number_reflns         16967
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0380P)²+2.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0912
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C24(H24), C28(H28), C29(H29),
  C30(H30), C31(H31), C34(H34), C35(H35), C36(H36), C37(H37), C40(H40),
 C1A(H1A), C2A(H2A), C4A(H4A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A), C21A(H21A), C22A(H22A),
 C24A(H24A), C28A(H28A), C29A(H29A), C30A(H30A), C31A(H31A), C34A(H34A),
 C35A(H35A), C36A(H36A), C37A(H37A), C40A(H40A)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C43(H43A,H43B,
 H43C), C18A(H18D,H18E,H18F), C38A(H38D,H38E,H38F), C42A(H42D,H42E,H42F),
 C43A(H43D,H43E,H43F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Ir1 Ir 0.736289(13) 0.269087(13) 0.483319(8) 0.02275(5) Uani 1 d . . .
O1 O 0.8955(3) 0.2899(3) 0.53480(16) 0.0291(7) Uani 1 d . . .
O2 O 0.6815(3) 0.2308(3) 0.58220(16) 0.0300(7) Uani 1 d . . .
N1 N 0.6914(3) 0.1122(3) 0.44536(19) 0.0251(7) Uani 1 d . . .
N2 N 0.7791(3) 0.4272(3) 0.51490(18) 0.0237(7) Uani 1 d . . .
C1 C 0.6411(4) 0.0274(4) 0.4794(3) 0.0325(10) Uani 1 d . . .
H1 H 0.6215 0.0398 0.5235 0.039 Uiso 1 calc . . R
C2 C 0.6172(4) -0.0749(4) 0.4534(3) 0.0369(11) Uani 1 d . . .
H2 H 0.5833 -0.1322 0.4799 0.044 Uiso 1 calc . . R
C3 C 0.6422(4) -0.0965(4) 0.3878(2) 0.0314(10) Uani 1 d . . .
C4 C 0.6916(4) -0.0095(4) 0.3515(2) 0.0279(9) Uani 1 d . . .
H4 H 0.7078 -0.0215 0.3061 0.033 Uiso 1 calc . . R
C5 C 0.7178(3) 0.0954(3) 0.3812(2) 0.0233(8) Uani 1 d . . .
C6 C 0.7714(3) 0.1945(3) 0.3495(2) 0.0238(8) Uani 1 d . . .
C7 C 0.7836(3) 0.2895(3) 0.3894(2) 0.0223(8) Uani 1 d . . .
C8 C 0.8301(3) 0.3851(3) 0.3597(2) 0.0253(9) Uani 1 d . . .
H8 H 0.8387 0.4505 0.3844 0.030 Uiso 1 calc . . R
C9 C 0.8638(4) 0.3859(4) 0.2948(2) 0.0311(10) Uani 1 d . . .
H9 H 0.8948 0.4517 0.2757 0.037 Uiso 1 calc . . R
C10 C 0.8532(4) 0.2921(4) 0.2574(2) 0.0334(10) Uani 1 d . . .
H10 H 0.8780 0.2940 0.2134 0.040 Uiso 1 calc . . R
C11 C 0.8062(4) 0.1958(4) 0.2845(2) 0.0291(9) Uani 1 d . . .
H11 H 0.7978 0.1309 0.2590 0.035 Uiso 1 calc . . R
C12 C 0.6144(4) -0.2100(4) 0.3622(3) 0.0371(11) Uani 1 d . . .
C13 C 0.6834(4) -0.2343(4) 0.3286(3) 0.0399(12) Uani 1 d . . .
C14 C 0.6530(5) -0.3472(4) 0.3109(3) 0.0436(13) Uani 1 d . . .
H14 H 0.6997 -0.3656 0.2879 0.052 Uiso 1 calc . . R
C15 C 0.5607(6) -0.4265(5) 0.3261(3) 0.0520(15) Uani 1 d . . .
H15 H 0.5430 -0.5003 0.3145 0.062 Uiso 1 calc . . R
C16 C 0.4890(5) -0.4010(5) 0.3596(3) 0.0444(12) Uani 1 d . . .
H16 H 0.4223 -0.4579 0.3691 0.053 Uiso 1 calc . . R
C17 C 0.5146(4) -0.2976(4) 0.3776(2) 0.0363(11) Uani 1 d . . .
H17 H 0.4669 -0.2813 0.4009 0.044 Uiso 1 calc . . R
C18 C 0.7868(5) -0.1543(4) 0.3090(3) 0.0416(12) Uani 1 d . . .
H18A H 0.7675 -0.1254 0.2672 0.062 Uiso 1 calc . . GR
H18B H 0.8299 -0.1898 0.2972 0.062 Uiso 1 calc . . GR
H18C H 0.8318 -0.0946 0.3496 0.062 Uiso 1 calc . . GR
C21 C 0.8812(4) 0.5039(4) 0.5515(2) 0.0282(9) Uani 1 d . . .
H21 H 0.9369 0.4835 0.5652 0.034 Uiso 1 calc . . R
C22 C 0.9084(4) 0.6114(4) 0.5701(2) 0.0296(9) Uani 1 d . . .
H22 H 0.9812 0.6635 0.5966 0.036 Uiso 1 calc . . R
C23 C 0.8273(4) 0.6428(4) 0.5493(2) 0.0287(9) Uani 1 d . . .
C24 C 0.7229(4) 0.5630(4) 0.5117(2) 0.0272(9) Uani 1 d . . .
H24 H 0.6663 0.5820 0.4971 0.033 Uiso 1 calc . . R
C25 C 0.6984(3) 0.4553(4) 0.4948(2) 0.0251(9) Uani 1 d . . .
C26 C 0.5923(3) 0.3637(4) 0.4538(2) 0.0260(9) Uani 1 d . . .
C27 C 0.5937(3) 0.2640(4) 0.4390(2) 0.0253(9) Uani 1 d . . .
C28 C 0.4961(4) 0.1758(4) 0.3955(3) 0.0322(10) Uani 1 d . . .
H28 H 0.4948 0.1086 0.3830 0.039 Uiso 1 calc . . R
C29 C 0.4014(4) 0.1854(4) 0.3706(3) 0.0348(11) Uani 1 d . . .
H29 H 0.3364 0.1249 0.3414 0.042 Uiso 1 calc . . R
C30 C 0.4013(4) 0.2819(4) 0.3881(3) 0.0346(11) Uani 1 d . . .
H30 H 0.3357 0.2871 0.3720 0.041 Uiso 1 calc . . R
C31 C 0.4966(4) 0.3715(4) 0.4292(2) 0.0290(9) Uani 1 d . . .
H31 H 0.4966 0.4382 0.4406 0.035 Uiso 1 calc . . R
C32 C 0.8551(4) 0.7585(4) 0.5637(2) 0.0303(10) Uani 1 d . . .
C33 C 0.9007(4) 0.8206(4) 0.6325(3) 0.0350(11) Uani 1 d . . .
C34 C 0.9240(4) 0.9290(4) 0.6405(3) 0.0460(13) Uani 1 d . . .
H34 H 0.9550 0.9721 0.6871 0.055 Uiso 1 calc . . R
C35 C 0.9039(5) 0.9752(4) 0.5836(3) 0.0487(14) Uani 1 d . . .
H35 H 0.9206 1.0491 0.5910 0.058 Uiso 1 calc . . R
C36 C 0.8592(5) 0.9141(5) 0.5149(3) 0.0490(14) Uani 1 d . . .
H36 H 0.8457 0.9458 0.4749 0.059 Uiso 1 calc . . R
C37 C 0.8345(4) 0.8067(4) 0.5057(3) 0.0375(11) Uani 1 d . . .
H37 H 0.8028 0.7642 0.4589 0.045 Uiso 1 calc . . R
C38 C 0.9155(5) 0.7746(5) 0.6982(3) 0.0463(13) Uani 1 d . . .
H38A H 0.8633 0.6960 0.6895 0.069 Uiso 1 calc . . GR
H38B H 0.9003 0.8098 0.7382 0.069 Uiso 1 calc . . GR
H38C H 0.9927 0.7876 0.7105 0.069 Uiso 1 calc . . GR
C39 C 0.9201(4) 0.2781(3) 0.5987(2) 0.0278(9) Uani 1 d . . .
C40 C 0.8495(4) 0.2464(4) 0.6481(2) 0.0333(10) Uani 1 d . . .
H40 H 0.8812 0.2396 0.6939 0.040 Uiso 1 calc . . R
C41 C 0.7394(4) 0.2240(4) 0.6380(2) 0.0303(10) Uani 1 d . . .
C42 C 0.6777(5) 0.1850(5) 0.6984(3) 0.0419(12) Uani 1 d . . .
H42A H 0.6311 0.2194 0.7030 0.063 Uiso 1 calc . . GR
H42B H 0.7323 0.2049 0.7437 0.063 Uiso 1 calc . . GR
H42C H 0.6299 0.1056 0.6876 0.063 Uiso 1 calc . . GR
C43 C 1.0396(4) 0.2998(4) 0.6227(3) 0.0373(11) Uani 1 d . . .
H43A H 1.0422 0.2321 0.6118 0.056 Uiso 1 calc . . GR
H43B H 1.0649 0.3265 0.6746 0.056 Uiso 1 calc . . GR
H43C H 1.0889 0.3547 0.5972 0.056 Uiso 1 calc . . GR
Ir1A Ir -0.000028(13) 0.257746(12) 0.023529(8) 0.02204(5) Uani 1 d . . .
O1A O -0.0642(3) 0.1462(2) -0.07641(15) 0.0284(7) Uani 1 d . . .
O2A O 0.1022(3) 0.3808(2) -0.03351(16) 0.0285(7) Uani 1 d . . .
N1A N 0.1284(3) 0.2276(3) 0.05559(18) 0.0231(7) Uani 1 d . . .
N2A N -0.1355(3) 0.2805(3) -0.00031(18) 0.0233(7) Uani 1 d . . .
C1A C 0.1435(4) 0.1524(4) 0.0196(2) 0.0278(9) Uani 1 d . . .
H1A H 0.0978 0.1167 -0.0268 0.033 Uiso 1 calc . . R
C2A C 0.2231(4) 0.1242(4) 0.0473(2) 0.0275(9) Uani 1 d . . .
H2A H 0.2322 0.0713 0.0195 0.033 Uiso 1 calc . . R
C3A C 0.2905(4) 0.1737(3) 0.1164(2) 0.0267(9) Uani 1 d . . .
C4A C 0.2734(4) 0.2513(4) 0.1530(2) 0.0269(9) Uani 1 d . . .
H4A H 0.3164 0.2860 0.2002 0.032 Uiso 1 calc . . R
C5A C 0.1942(4) 0.2800(3) 0.1221(2) 0.0248(9) Uani 1 d . . .
C6A C -0.2137(4) 0.1324(3) 0.0624(2) 0.0235(8) Uani 1 d . . .
C7A C -0.1053(3) 0.1432(3) 0.0720(2) 0.0227(8) Uani 1 d . . .
C8A C -0.0864(4) 0.0705(3) 0.1108(2) 0.0267(9) Uani 1 d . . .
H8A H -0.0136 0.0775 0.1204 0.032 Uiso 1 calc . . R
C9A C -0.1723(4) -0.0110(3) 0.1351(2) 0.0290(9) Uani 1 d . . .
H9A H -0.1578 -0.0599 0.1605 0.035 Uiso 1 calc . . R
C10A C -0.2788(4) -0.0231(4) 0.1234(2) 0.0322(10) Uani 1 d . . .
H10A H -0.3371 -0.0804 0.1400 0.039 Uiso 1 calc . . R
C11A C -0.3002(4) 0.0492(3) 0.0872(2) 0.0298(9) Uani 1 d . . .
H11A H -0.3730 0.0422 0.0794 0.036 Uiso 1 calc . . R
C12A C 0.3712(4) 0.1379(4) 0.1472(2) 0.0270(9) Uani 1 d . . .
C13A C 0.4768(4) 0.2072(4) 0.1914(2) 0.0297(9) Uani 1 d . . .
C14A C 0.5442(4) 0.1622(4) 0.2165(3) 0.0369(11) Uani 1 d . . .
H14A H 0.6158 0.2085 0.2468 0.044 Uiso 1 calc . . R
C15A C 0.5104(4) 0.0538(4) 0.1989(3) 0.0396(12) Uani 1 d . . .
H15A H 0.5575 0.0258 0.2176 0.048 Uiso 1 calc . . R
C16A C 0.4075(4) -0.0147(4) 0.1539(3) 0.0382(11) Uani 1 d . . .
H16A H 0.3838 -0.0899 0.1408 0.046 Uiso 1 calc . . R
C17A C 0.3393(4) 0.0274(4) 0.1281(2) 0.0347(10) Uani 1 d . . .
H17A H 0.2690 -0.0196 0.0966 0.042 Uiso 1 calc . . R
C18A C 0.5248(4) 0.3280(4) 0.2146(3) 0.0376(11) Uani 1 d . . .
H18D H 0.4913 0.3564 0.1789 0.056 Uiso 1 calc . . GR
H18E H 0.6063 0.3649 0.2187 0.056 Uiso 1 calc . . GR
H18F H 0.5081 0.3412 0.2613 0.056 Uiso 1 calc . . GR
C21A C -0.1399(4) 0.3569(3) -0.0375(2) 0.0272(9) Uani 1 d . . .
H21A H -0.0749 0.4049 -0.0537 0.033 Uiso 1 calc . . R
C22A C -0.2330(4) 0.3685(4) -0.0529(2) 0.0296(9) Uani 1 d . . .
H22A H -0.2327 0.4223 -0.0802 0.036 Uiso 1 calc . . R
C23A C -0.3297(4) 0.3000(4) -0.0281(2) 0.0267(9) Uani 1 d . . .
C24A C -0.3252(4) 0.2213(3) 0.0104(2) 0.0262(9) Uani 1 d . . .
H24A H -0.3887 0.1740 0.0282 0.031 Uiso 1 calc . . R
C25A C -0.2286(3) 0.2112(3) 0.0233(2) 0.0246(8) Uani 1 d . . .
C26A C 0.1693(4) 0.3620(4) 0.1541(2) 0.0276(9) Uani 1 d . . .
C27A C 0.0733(3) 0.3618(3) 0.1169(2) 0.0229(8) Uani 1 d . . .
C28A C 0.0455(4) 0.4370(3) 0.1457(2) 0.0276(9) Uani 1 d . . .
H28A H -0.0188 0.4390 0.1217 0.033 Uiso 1 calc . . R
C29A C 0.1100(4) 0.5091(3) 0.2091(2) 0.0312(10) Uani 1 d . . .
H29A H 0.0889 0.5592 0.2281 0.037 Uiso 1 calc . . R
C30A C 0.2047(4) 0.5088(4) 0.2450(3) 0.0359(11) Uani 1 d . . .
H30A H 0.2482 0.5582 0.2884 0.043 Uiso 1 calc . . R
C31A C 0.2354(4) 0.4362(4) 0.2172(2) 0.0335(10) Uani 1 d . . .
H31A H 0.3013 0.4365 0.2409 0.040 Uiso 1 calc . . R
C32A C -0.4310(3) 0.3145(4) -0.0405(2) 0.0281(9) Uani 1 d . . .
C33A C -0.4848(4) 0.3135(4) -0.1091(3) 0.0329(10) Uani 1 d . . .
C34A C -0.5765(4) 0.3314(4) -0.1150(3) 0.0399(12) Uani 1 d . . .
H34A H -0.6136 0.3309 -0.1613 0.048 Uiso 1 calc . . R
C35A C -0.6144(4) 0.3498(4) -0.0559(3) 0.0447(13) Uani 1 d . . .
H35A H -0.6775 0.3611 -0.0614 0.054 Uiso 1 calc . . R
C36A C -0.5603(4) 0.3518(4) 0.0119(3) 0.0414(12) Uani 1 d . . .
H36A H -0.5846 0.3668 0.0533 0.050 Uiso 1 calc . . R
C37A C -0.4712(4) 0.3319(4) 0.0191(3) 0.0361(11) Uani 1 d . . .
H37A H -0.4365 0.3299 0.0655 0.043 Uiso 1 calc . . R
C38A C -0.4508(5) 0.2872(5) -0.1760(3) 0.0449(13) Uani 1 d . . .
H38D H -0.3838 0.3517 -0.1826 0.067 Uiso 1 calc . . GR
H38E H -0.5122 0.2655 -0.2176 0.067 Uiso 1 calc . . GR
H38F H -0.4343 0.2273 -0.1712 0.067 Uiso 1 calc . . GR
C39A C -0.0377(4) 0.1691(4) -0.1359(2) 0.0327(10) Uani 1 d . . .
C40A C 0.0415(4) 0.2709(4) -0.1483(2) 0.0347(11) Uani 1 d . . .
H40A H 0.0533 0.2744 -0.1961 0.042 Uiso 1 calc . . R
C41A C 0.1050(4) 0.3677(4) -0.0992(2) 0.0305(10) Uani 1 d . . .
C42A C 0.1868(4) 0.4667(4) -0.1259(3) 0.0392(11) Uani 1 d . . .
H42D H 0.1685 0.5254 -0.1183 0.059 Uiso 1 calc . . GR
H42E H 0.1818 0.4480 -0.1774 0.059 Uiso 1 calc . . GR
H42F H 0.2632 0.4909 -0.0995 0.059 Uiso 1 calc . . GR
C43A C -0.0965(5) 0.0754(4) -0.1980(3) 0.0446(13) Uani 1 d . . .
H43D H -0.0870 0.0140 -0.1848 0.067 Uiso 1 calc . . GR
H43E H -0.0641 0.0984 -0.2401 0.067 Uiso 1 calc . . GR
H43F H -0.1766 0.0530 -0.2095 0.067 Uiso 1 calc . . GR


_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 O1 2.141(3) . ?
Ir1 O2 2.149(3) . ?
Ir1 N1 2.034(4) . ?
Ir1 N2 2.034(4) . ?
Ir1 C7 1.992(4) . ?
Ir1 C27 1.989(4) . ?
O1 C39 1.261(5) . ?
O2 C41 1.270(5) . ?
N1 C1 1.342(5) . ?
N1 C5 1.363(5) . ?
N2 C21 1.342(5) . ?
N2 C25 1.362(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.353(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(7) . ?
C3 C4 1.390(6) . ?
C3 C12 1.481(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(6) . ?
C5 C6 1.468(6) . ?
C6 C7 1.414(6) . ?
C6 C11 1.394(6) . ?
C7 C8 1.400(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(7) . ?
C12 C17 1.444(7) . ?
C13 C14 1.440(7) . ?
C13 C18 1.469(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.333(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.418(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.330(7) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.381(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.403(6) . ?
C23 C24 1.379(6) . ?
C23 C32 1.482(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.392(6) . ?
C25 C26 1.466(6) . ?
C26 C27 1.422(6) . ?
C26 C31 1.393(6) . ?
C27 C28 1.408(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.396(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.377(7) . ?
C30 H30 0.9500 . ?
C30 C31 1.385(7) . ?
C31 H31 0.9500 . ?
C32 C33 1.395(6) . ?
C32 C37 1.401(7) . ?
C33 C34 1.397(7) . ?
C33 C38 1.484(7) . ?
C34 H34 0.9500 . ?
C34 C35 1.366(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.387(8) . ?
C36 H36 0.9500 . ?
C36 C37 1.377(7) . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.402(6) . ?
C39 C43 1.519(6) . ?
C40 H40 0.9500 . ?
C40 C41 1.379(7) . ?
C41 C42 1.519(6) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
Ir1A O1A 2.150(3) . ?
Ir1A O2A 2.151(3) . ?
Ir1A N1A 2.031(4) . ?
Ir1A N2A 2.035(4) . ?
Ir1A C7A 1.998(4) . ?
Ir1A C27A 2.004(4) . ?
O1A C39A 1.263(5) . ?
O2A C41A 1.262(5) . ?
N1A C1A 1.335(5) . ?
N1A C5A 1.364(5) . ?
N2A C21A 1.354(5) . ?
N2A C25A 1.367(5) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.383(6) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.404(6) . ?
C3A C4A 1.386(6) . ?
C3A C12A 1.490(6) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.402(6) . ?
C5A C26A 1.470(6) . ?
C6A C7A 1.414(6) . ?
C6A C11A 1.401(6) . ?
C6A C25A 1.458(6) . ?
C7A C8A 1.406(6) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.381(6) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.380(7) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.389(6) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.400(6) . ?
C12A C17A 1.405(6) . ?
C13A C14A 1.402(6) . ?
C13A C18A 1.508(6) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.367(7) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.381(7) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.383(7) . ?
C17A H17A 0.9500 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C21A H21A 0.9500 . ?
C21A C22A 1.364(6) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.409(6) . ?
C23A C24A 1.397(6) . ?
C23A C32A 1.494(6) . ?
C24A H24A 0.9500 . ?
C24A C25A 1.396(6) . ?
C26A C27A 1.406(6) . ?
C26A C31A 1.399(6) . ?
C27A C28A 1.390(6) . ?
C28A H28A 0.9500 . ?
C28A C29A 1.389(6) . ?
C29A H29A 0.9500 . ?
C29A C30A 1.384(7) . ?
C30A H30A 0.9500 . ?
C30A C31A 1.381(6) . ?
C31A H31A 0.9500 . ?
C32A C33A 1.399(6) . ?
C32A C37A 1.392(6) . ?
C33A C34A 1.394(7) . ?
C33A C38A 1.503(7) . ?
C34A H34A 0.9500 . ?
C34A C35A 1.370(8) . ?
C35A H35A 0.9500 . ?
C35A C36A 1.384(8) . ?
C36A H36A 0.9500 . ?
C36A C37A 1.377(7) . ?
C37A H37A 0.9500 . ?
C38A H38D 0.9800 . ?
C38A H38E 0.9800 . ?
C38A H38F 0.9800 . ?
C39A C40A 1.402(7) . ?
C39A C43A 1.508(7) . ?
C40A H40A 0.9500 . ?
C40A C41A 1.394(7) . ?
C41A C42A 1.510(6) . ?
C42A H42D 0.9800 . ?
C42A H42E 0.9800 . ?
C42A H42F 0.9800 . ?
C43A H43D 0.9800 . ?
C43A H43E 0.9800 . ?
C43A H43F 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
O1 Ir1 O2 87.79(12) . . ?
N1 Ir1 O1 87.90(13) . . ?
N1 Ir1 O2 93.55(13) . . ?
N2 Ir1 O1 94.03(13) . . ?
N2 Ir1 O2 89.48(13) . . ?
N2 Ir1 N1 176.47(13) . . ?
C7 Ir1 O1 91.47(14) . . ?
C7 Ir1 O2 174.42(14) . . ?
C7 Ir1 N1 80.90(16) . . ?
C7 Ir1 N2 96.09(16) . . ?
C27 Ir1 O1 174.76(15) . . ?
C27 Ir1 O2 92.04(14) . . ?
C27 Ir1 N1 97.33(16) . . ?
C27 Ir1 N2 80.73(16) . . ?
C27 Ir1 C7 89.19(16) . . ?
C39 O1 Ir1 125.2(3) . . ?
C41 O2 Ir1 125.2(3) . . ?
C1 N1 Ir1 124.9(3) . . ?
C1 N1 C5 119.4(4) . . ?
C5 N1 Ir1 115.7(3) . . ?
C21 N2 Ir1 124.1(3) . . ?
C21 N2 C25 119.5(4) . . ?
C25 N2 Ir1 116.4(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.7(4) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.1(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C12 117.8(4) . . ?
C4 C3 C2 117.3(4) . . ?
C4 C3 C12 124.9(4) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 119.7(4) . . ?
N1 C5 C6 113.9(4) . . ?
C4 C5 C6 126.4(4) . . ?
C7 C6 C5 114.8(4) . . ?
C11 C6 C5 123.3(4) . . ?
C11 C6 C7 122.0(4) . . ?
C6 C7 Ir1 114.5(3) . . ?
C8 C7 Ir1 128.7(3) . . ?
C8 C7 C6 116.7(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.1(4) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(4) . . ?
C11 C10 H10 120.3 . . ?
C6 C11 H11 120.2 . . ?
C10 C11 C6 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C3 122.5(5) . . ?
C13 C12 C17 119.3(5) . . ?
C17 C12 C3 118.1(5) . . ?
C12 C13 C14 118.0(5) . . ?
C12 C13 C18 125.5(5) . . ?
C14 C13 C18 116.5(5) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(5) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(5) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(5) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.7(5) . . ?
C16 C17 H17 119.6 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C21 H21 118.7 . . ?
N2 C21 C22 122.5(4) . . ?
C22 C21 H21 118.7 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.2(4) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C32 121.0(4) . . ?
C24 C23 C22 117.5(4) . . ?
C24 C23 C32 121.4(4) . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.5(4) . . ?
C25 C24 H24 119.3 . . ?
N2 C25 C24 119.8(4) . . ?
N2 C25 C26 113.3(4) . . ?
C24 C25 C26 126.9(4) . . ?
C27 C26 C25 115.0(4) . . ?
C31 C26 C25 123.9(4) . . ?
C31 C26 C27 121.1(4) . . ?
C26 C27 Ir1 114.5(3) . . ?
C28 C27 Ir1 128.6(3) . . ?
C28 C27 C26 117.0(4) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.0(4) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.6(4) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 119.9 . . ?
C29 C30 C31 120.1(4) . . ?
C31 C30 H30 119.9 . . ?
C26 C31 H31 120.0 . . ?
C30 C31 C26 120.1(4) . . ?
C30 C31 H31 120.0 . . ?
C33 C32 C23 122.4(4) . . ?
C33 C32 C37 119.2(4) . . ?
C37 C32 C23 118.4(4) . . ?
C32 C33 C34 118.0(5) . . ?
C32 C33 C38 123.3(5) . . ?
C34 C33 C38 118.4(5) . . ?
C33 C34 H34 118.9 . . ?
C35 C34 C33 122.2(5) . . ?
C35 C34 H34 118.9 . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 120.0(5) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 120.6 . . ?
C37 C36 C35 118.9(5) . . ?
C37 C36 H36 120.6 . . ?
C32 C37 H37 119.2 . . ?
C36 C37 C32 121.6(5) . . ?
C36 C37 H37 119.2 . . ?
C33 C38 H38A 109.5 . . ?
C33 C38 H38B 109.5 . . ?
C33 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O1 C39 C40 127.1(4) . . ?
O1 C39 C43 114.7(4) . . ?
C40 C39 C43 118.1(4) . . ?
C39 C40 H40 116.1 . . ?
C41 C40 C39 127.8(4) . . ?
C41 C40 H40 116.1 . . ?
O2 C41 C40 126.8(4) . . ?
O2 C41 C42 115.0(4) . . ?
C40 C41 C42 118.2(4) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C39 C43 H43A 109.5 . . ?
C39 C43 H43B 109.5 . . ?
C39 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O1A Ir1A O2A 87.02(12) . . ?
N1A Ir1A O1A 94.37(13) . . ?
N1A Ir1A O2A 90.18(13) . . ?
N1A Ir1A N2A 174.21(13) . . ?
N2A Ir1A O1A 87.84(13) . . ?
N2A Ir1A O2A 95.29(13) . . ?
C7A Ir1A O1A 91.28(14) . . ?
C7A Ir1A O2A 175.60(14) . . ?
C7A Ir1A N1A 94.00(16) . . ?
C7A Ir1A N2A 80.58(15) . . ?
C7A Ir1A C27A 90.88(16) . . ?
C27A Ir1A O1A 174.70(14) . . ?
C27A Ir1A O2A 91.16(14) . . ?
C27A Ir1A N1A 80.66(15) . . ?
C27A Ir1A N2A 97.28(15) . . ?
C39A O1A Ir1A 126.1(3) . . ?
C41A O2A Ir1A 126.4(3) . . ?
C1A N1A Ir1A 124.1(3) . . ?
C1A N1A C5A 119.2(4) . . ?
C5A N1A Ir1A 116.2(3) . . ?
C21A N2A Ir1A 125.3(3) . . ?
C21A N2A C25A 118.8(4) . . ?
C25A N2A Ir1A 116.0(3) . . ?
N1A C1A H1A 118.7 . . ?
N1A C1A C2A 122.6(4) . . ?
C2A C1A H1A 118.7 . . ?
C1A C2A H2A 119.9 . . ?
C1A C2A C3A 120.1(4) . . ?
C3A C2A H2A 119.9 . . ?
C2A C3A C12A 119.5(4) . . ?
C4A C3A C2A 116.4(4) . . ?
C4A C3A C12A 124.1(4) . . ?
C3A C4A H4A 119.2 . . ?
C3A C4A C5A 121.7(4) . . ?
C5A C4A H4A 119.2 . . ?
N1A C5A C4A 119.9(4) . . ?
N1A C5A C26A 112.9(4) . . ?
C4A C5A C26A 127.2(4) . . ?
C7A C6A C25A 115.1(4) . . ?
C11A C6A C7A 121.4(4) . . ?
C11A C6A C25A 123.4(4) . . ?
C6A C7A Ir1A 114.5(3) . . ?
C8A C7A Ir1A 128.3(3) . . ?
C8A C7A C6A 117.1(4) . . ?
C7A C8A H8A 119.6 . . ?
C9A C8A C7A 120.7(4) . . ?
C9A C8A H8A 119.6 . . ?
C8A C9A H9A 119.2 . . ?
C10A C9A C8A 121.6(4) . . ?
C10A C9A H9A 119.2 . . ?
C9A C10A H10A 120.3 . . ?
C9A C10A C11A 119.5(4) . . ?
C11A C10A H10A 120.3 . . ?
C6A C11A H11A 120.2 . . ?
C10A C11A C6A 119.5(4) . . ?
C10A C11A H11A 120.2 . . ?
C13A C12A C3A 124.5(4) . . ?
C13A C12A C17A 118.5(4) . . ?
C17A C12A C3A 117.0(4) . . ?
C12A C13A C14A 118.3(4) . . ?
C12A C13A C18A 125.0(4) . . ?
C14A C13A C18A 116.7(4) . . ?
C13A C14A H14A 118.9 . . ?
C15A C14A C13A 122.2(5) . . ?
C15A C14A H14A 118.9 . . ?
C14A C15A H15A 120.1 . . ?
C14A C15A C16A 119.9(5) . . ?
C16A C15A H15A 120.1 . . ?
C15A C16A H16A 120.4 . . ?
C15A C16A C17A 119.2(5) . . ?
C17A C16A H16A 120.4 . . ?
C12A C17A H17A 119.1 . . ?
C16A C17A C12A 121.8(5) . . ?
C16A C17A H17A 119.1 . . ?
C13A C18A H18D 109.5 . . ?
C13A C18A H18E 109.5 . . ?
C13A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N2A C21A H21A 118.4 . . ?
N2A C21A C22A 123.2(4) . . ?
C22A C21A H21A 118.4 . . ?
C21A C22A H22A 120.2 . . ?
C21A C22A C23A 119.5(4) . . ?
C23A C22A H22A 120.2 . . ?
C22A C23A C32A 120.9(4) . . ?
C24A C23A C22A 117.3(4) . . ?
C24A C23A C32A 121.8(4) . . ?
C23A C24A H24A 119.5 . . ?
C25A C24A C23A 120.9(4) . . ?
C25A C24A H24A 119.5 . . ?
N2A C25A C6A 113.7(4) . . ?
N2A C25A C24A 120.2(4) . . ?
C24A C25A C6A 126.1(4) . . ?
C27A C26A C5A 115.4(4) . . ?
C31A C26A C5A 123.3(4) . . ?
C31A C26A C27A 121.3(4) . . ?
C26A C27A Ir1A 114.1(3) . . ?
C28A C27A Ir1A 128.2(3) . . ?
C28A C27A C26A 117.5(4) . . ?
C27A C28A H28A 119.4 . . ?
C29A C28A C27A 121.1(4) . . ?
C29A C28A H28A 119.4 . . ?
C28A C29A H29A 119.6 . . ?
C30A C29A C28A 120.7(4) . . ?
C30A C29A H29A 119.6 . . ?
C29A C30A H30A 120.2 . . ?
C31A C30A C29A 119.5(4) . . ?
C31A C30A H30A 120.2 . . ?
C26A C31A H31A 120.1 . . ?
C30A C31A C26A 119.8(5) . . ?
C30A C31A H31A 120.1 . . ?
C33A C32A C23A 122.6(4) . . ?
C37A C32A C23A 118.1(4) . . ?
C37A C32A C33A 119.2(4) . . ?
C32A C33A C38A 121.9(4) . . ?
C34A C33A C32A 118.5(4) . . ?
C34A C33A C38A 119.6(5) . . ?
C33A C34A H34A 119.1 . . ?
C35A C34A C33A 121.8(5) . . ?
C35A C34A H34A 119.1 . . ?
C34A C35A H35A 120.2 . . ?
C34A C35A C36A 119.6(5) . . ?
C36A C35A H35A 120.2 . . ?
C35A C36A H36A 120.2 . . ?
C37A C36A C35A 119.7(5) . . ?
C37A C36A H36A 120.2 . . ?
C32A C37A H37A 119.4 . . ?
C36A C37A C32A 121.2(5) . . ?
C36A C37A H37A 119.4 . . ?
C33A C38A H38D 109.5 . . ?
C33A C38A H38E 109.5 . . ?
C33A C38A H38F 109.5 . . ?
H38D C38A H38E 109.5 . . ?
H38D C38A H38F 109.5 . . ?
H38E C38A H38F 109.5 . . ?
O1A C39A C40A 126.3(4) . . ?
O1A C39A C43A 115.3(4) . . ?
C40A C39A C43A 118.4(4) . . ?
C39A C40A H40A 116.0 . . ?
C41A C40A C39A 128.0(4) . . ?
C41A C40A H40A 116.0 . . ?
O2A C41A C40A 126.2(4) . . ?
O2A C41A C42A 116.1(4) . . ?
C40A C41A C42A 117.7(4) . . ?
C41A C42A H42D 109.5 . . ?
C41A C42A H42E 109.5 . . ?
C41A C42A H42F 109.5 . . ?
H42D C42A H42E 109.5 . . ?
H42D C42A H42F 109.5 . . ?
H42E C42A H42F 109.5 . . ?
C39A C43A H43D 109.5 . . ?
C39A C43A H43E 109.5 . . ?
C39A C43A H43F 109.5 . . ?
H43D C43A H43E 109.5 . . ?
H43D C43A H43F 109.5 . . ?
H43E C43A H43F 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
C2 C3 C12 C13 -140.8(5) . . . . ?
C2 C3 C12 C17 34.9(6) . . . . ?
C4 C3 C12 C13 39.1(7) . . . . ?
C4 C3 C12 C17 -145.2(5) . . . . ?
C4 C5 C6 C7 177.2(4) . . . . ?
C4 C5 C6 C11 -1.7(7) . . . . ?
C7 C6 C5 N1 -1.8(5) . . . . ?
C11 C6 C5 N1 179.3(4) . . . . ?
C22 C23 C32 C33 -55.1(6) . . . . ?
C22 C23 C32 C37 124.9(5) . . . . ?
C24 C23 C32 C33 128.2(5) . . . . ?
C24 C23 C32 C37 -51.8(6) . . . . ?
C24 C25 C26 C27 174.7(4) . . . . ?
C24 C25 C26 C31 -4.0(7) . . . . ?
C27 C26 C25 N2 -3.2(5) . . . . ?
C31 C26 C25 N2 178.1(4) . . . . ?
C2A C3A C12A C13A 144.5(4) . . . . ?
C2A C3A C12A C17A -33.3(6) . . . . ?
C4A C3A C12A C13A -38.2(7) . . . . ?
C4A C3A C12A C17A 144.0(5) . . . . ?
C4A C5A C26A C27A -169.6(4) . . . . ?
C4A C5A C26A C31A 10.5(7) . . . . ?
C7A C6A C25A N2A 2.4(5) . . . . ?
C7A C6A C25A C24A -176.2(4) . . . . ?
C11A C6A C25A N2A -175.6(4) . . . . ?
C11A C6A C25A C24A 5.7(7) . . . . ?
C22A C23A C32A C33A 55.5(6) . . . . ?
C22A C23A C32A C37A -123.2(5) . . . . ?
C24A C23A C32A C33A -126.8(5) . . . . ?
C24A C23A C32A C37A 54.5(6) . . . . ?
C27A C26A C5A N1A 8.9(5) . . . . ?
C31A C26A C5A N1A -171.0(4) . . . . ?

####################################################################### 
# 
# 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_Ir1_15srv040
_database_code_depnum_ccdc_archive 'CCDC 1474220'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_audit_creation_date             2015-02-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C40 H28 Ir N3 O2, 2(C H4 O)'
_chemical_formula_sum            'C42 H36 Ir N3 O4'
_chemical_formula_weight         838.94
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40 H28 N3 O2 Ir1'
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'
Ir Ir -1.4442 7.9887 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   11.2366(4)
_cell_length_b                   12.7646(6)
_cell_length_c                   13.7741(6)
_cell_angle_alpha                102.782(4)
_cell_angle_beta                 108.667(4)
_cell_angle_gamma                107.287(4)
_cell_volume                     1674.30(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4617
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      27.7340
_cell_measurement_theta_min      1.8190
_exptl_absorpt_coefficient_mu    4.037
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.559
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.1079
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18500
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.97
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -88.00  -10.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  131.0000  128.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega   38.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -131.0000   57.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega   81.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -178.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -37.00   50.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  120.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega   70.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   -1.00  102.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   19.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
  8 omega    9.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000 -120.0000 52
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0098980000
_diffrn_orient_matrix_UB_12      0.0583141000
_diffrn_orient_matrix_UB_13      0.0028377000
_diffrn_orient_matrix_UB_21      -0.0318821000
_diffrn_orient_matrix_UB_22      -0.0192293000
_diffrn_orient_matrix_UB_23      -0.0579146000
_diffrn_orient_matrix_UB_31      -0.0645130000
_diffrn_orient_matrix_UB_32      -0.0094066000
_diffrn_orient_matrix_UB_33      0.0019900000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                7089
_reflns_number_total             8900
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.957
_refine_diff_density_min         -1.811
_refine_diff_density_rms         0.213
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         8900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.029
_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)+(0.0380P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1132
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Shared sites
{C2SA, O2SA}
{O2S, C2S}
3. Uiso/Uaniso restraints and constraints
Uiso(C2SA) = Uiso(O2SA)
Uiso(O2S) = Uiso(C2S)
4. Others
 Fixed Sof: C2SA(0.5) H2SA(0.5) H2SB(0.5) H2SC(0.5) O2S(0.5) H2S(0.5)
 O2SA(0.5) H2SD(0.5) C2S(0.5) H2SE(0.5) H2SF(0.5) H2SG(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C24(H24), C28(H28),
  C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36),
 C37(H37), C42(H42), C43(H43), C44(H44), C45(H45)
5.b Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2SA(H2SA,H2SB,H2SC), C2S(H2SE,H2SF,H2SG)
5.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2S(H2S), O2SA(H2SD)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Ir1 Ir 0.24557(2) 0.38600(2) 0.61258(2) 0.01639(8) Uani 1 d . . .
O1 O 0.4485(4) 0.5022(4) 0.7380(3) 0.0204(9) Uani 1 d . . .
O2 O 0.5624(5) 0.6580(5) 0.8925(4) 0.0389(13) Uani 1 d . . .
N1 N 0.2127(5) 0.2722(4) 0.6930(4) 0.0169(10) Uani 1 d . . .
N2 N 0.2699(4) 0.4919(4) 0.5238(4) 0.0153(10) Uani 1 d . . .
N3 N 0.2073(5) 0.5003(4) 0.7283(4) 0.0173(10) Uani 1 d . . .
C1 C 0.2998(6) 0.2825(5) 0.7911(5) 0.0206(13) Uani 1 d . . .
H1 H 0.3873 0.3456 0.8253 0.025 Uiso 1 calc . . R
C2 C 0.2692(6) 0.2068(6) 0.8444(5) 0.0223(14) Uani 1 d . . .
H2 H 0.3350 0.2181 0.9137 0.027 Uiso 1 calc . . R
C3 C 0.1414(6) 0.1126(5) 0.7973(5) 0.0182(13) Uani 1 d . . .
C4 C 0.0498(6) 0.1021(5) 0.6960(5) 0.0187(13) Uani 1 d . . .
H4 H -0.0381 0.0396 0.6615 0.022 Uiso 1 calc . . R
C5 C 0.0838(6) 0.1803(5) 0.6444(5) 0.0159(12) Uani 1 d . . .
C6 C -0.0032(6) 0.1811(5) 0.5407(5) 0.0169(12) Uani 1 d . . .
C7 C 0.0538(6) 0.2750(5) 0.5078(5) 0.0172(12) Uani 1 d . . .
C8 C -0.0270(6) 0.2783(5) 0.4089(5) 0.0200(13) Uani 1 d . . .
H8 H 0.0079 0.3413 0.3861 0.024 Uiso 1 calc . . R
C9 C -0.1573(6) 0.1920(6) 0.3429(5) 0.0215(13) Uani 1 d . . .
H9 H -0.2094 0.1954 0.2749 0.026 Uiso 1 calc . . R
C10 C -0.2114(6) 0.1003(6) 0.3765(5) 0.0222(13) Uani 1 d . . .
H10 H -0.3013 0.0422 0.3322 0.027 Uiso 1 calc . . R
C11 C -0.1347(6) 0.0945(5) 0.4733(5) 0.0210(13) Uani 1 d . . .
H11 H -0.1710 0.0310 0.4951 0.025 Uiso 1 calc . . R
C12 C 0.1074(6) 0.0285(5) 0.8549(5) 0.0195(13) Uani 1 d . . .
C13 C 0.1794(6) 0.0615(6) 0.9670(5) 0.0207(13) Uani 1 d . . .
H13 H 0.2484 0.1383 1.0076 0.025 Uiso 1 calc . . R
C14 C 0.1508(6) -0.0175(6) 1.0202(5) 0.0228(14) Uani 1 d . . .
H14 H 0.2006 0.0059 1.0969 0.027 Uiso 1 calc . . R
C15 C 0.0514(6) -0.1286(6) 0.9627(6) 0.0244(14) Uani 1 d . . .
H15 H 0.0331 -0.1825 0.9991 0.029 Uiso 1 calc . . R
C16 C -0.0222(6) -0.1615(6) 0.8509(5) 0.0229(14) Uani 1 d . . .
H16 H -0.0916 -0.2382 0.8110 0.027 Uiso 1 calc . . R
C17 C 0.0044(6) -0.0836(5) 0.7966(5) 0.0203(13) Uani 1 d . . .
H17 H -0.0473 -0.1066 0.7202 0.024 Uiso 1 calc . . R
C21 C 0.2508(6) 0.5916(5) 0.5396(5) 0.0186(12) Uani 1 d . . .
H21 H 0.2289 0.6178 0.5991 0.022 Uiso 1 calc . . R
C22 C 0.2611(6) 0.6590(5) 0.4742(5) 0.0192(13) Uani 1 d . . .
H22 H 0.2443 0.7283 0.4879 0.023 Uiso 1 calc . . R
C23 C 0.2965(6) 0.6239(5) 0.3881(5) 0.0177(12) Uani 1 d . . .
C24 C 0.3198(6) 0.5218(5) 0.3727(5) 0.0197(13) Uani 1 d . . .
H24 H 0.3451 0.4962 0.3150 0.024 Uiso 1 calc . . R
C25 C 0.3069(6) 0.4565(5) 0.4396(5) 0.0178(12) Uani 1 d . . .
C26 C 0.3289(5) 0.3471(5) 0.4326(5) 0.0167(12) Uani 1 d . . .
C27 C 0.3048(5) 0.2961(5) 0.5104(5) 0.0151(12) Uani 1 d . . .
C28 C 0.3248(6) 0.1946(5) 0.5071(5) 0.0215(13) Uani 1 d . . .
H28 H 0.3109 0.1592 0.5586 0.026 Uiso 1 calc . . R
C29 C 0.3649(6) 0.1420(5) 0.4304(5) 0.0235(14) Uani 1 d . . .
H29 H 0.3767 0.0712 0.4297 0.028 Uiso 1 calc . . R
C30 C 0.3876(6) 0.1922(6) 0.3549(5) 0.0239(14) Uani 1 d . . .
H30 H 0.4154 0.1564 0.3030 0.029 Uiso 1 calc . . R
C31 C 0.3693(6) 0.2957(6) 0.3558(5) 0.0210(13) Uani 1 d . . .
H31 H 0.3844 0.3307 0.3044 0.025 Uiso 1 calc . . R
C32 C 0.3033(6) 0.6937(5) 0.3152(5) 0.0192(13) Uani 1 d . . .
C33 C 0.2234(7) 0.7589(6) 0.2984(6) 0.0270(15) Uani 1 d . . .
H33 H 0.1612 0.7555 0.3320 0.032 Uiso 1 calc . . R
C34 C 0.2315(7) 0.8286(6) 0.2342(6) 0.0282(15) Uani 1 d . . .
H34 H 0.1766 0.8728 0.2253 0.034 Uiso 1 calc . . R
C35 C 0.3201(7) 0.8332(6) 0.1834(5) 0.0309(16) Uani 1 d . . .
H35 H 0.3257 0.8796 0.1384 0.037 Uiso 1 calc . . R
C36 C 0.4014(7) 0.7686(7) 0.1989(6) 0.0313(17) Uani 1 d . . .
H36 H 0.4634 0.7728 0.1651 0.038 Uiso 1 calc . . R
C37 C 0.3932(6) 0.6983(6) 0.2629(6) 0.0274(15) Uani 1 d . . .
H37 H 0.4478 0.6538 0.2713 0.033 Uiso 1 calc . . R
C41 C 0.3197(6) 0.5830(5) 0.8147(5) 0.0204(13) Uani 1 d . . .
C42 C 0.3106(7) 0.6598(6) 0.8958(6) 0.0318(16) Uani 1 d . . .
H42 H 0.3914 0.7175 0.9558 0.038 Uiso 1 calc . . R
C43 C 0.1822(8) 0.6532(7) 0.8901(6) 0.0383(19) Uani 1 d . . .
H43 H 0.1744 0.7065 0.9456 0.046 Uiso 1 calc . . R
C44 C 0.0675(7) 0.5684(7) 0.8029(5) 0.0292(16) Uani 1 d . . .
H44 H -0.0212 0.5615 0.7974 0.035 Uiso 1 calc . . R
C45 C 0.0828(6) 0.4927(6) 0.7228(5) 0.0238(14) Uani 1 d . . .
H45 H 0.0034 0.4338 0.6625 0.029 Uiso 1 calc . . R
C46 C 0.4557(6) 0.5821(6) 0.8162(5) 0.0226(14) Uani 1 d . . .
O3 O 0.8015(5) 0.6172(5) 0.9051(5) 0.0426(14) Uani 1 d . . .
H3 H 0.7263 0.6227 0.8956 0.064 Uiso 1 calc . . GR
C1S C 0.8371(11) 0.5723(9) 0.9880(8) 0.065(3) Uani 1 d . . .
H1SA H 0.7540 0.5175 0.9870 0.098 Uiso 1 calc . . GR
H1SB H 0.8872 0.6365 1.0588 0.098 Uiso 1 calc . . GR
H1SC H 0.8954 0.5311 0.9768 0.098 Uiso 1 calc . . GR
C2SA C 0.4862(6) 0.9002(6) 0.8617(5) 0.0355(14) Uiso 0.50 d A -1 .
H2SA H 0.4096 0.8625 0.7892 0.053 Uiso 0.50 calc A -1 GR
H2SB H 0.4955 0.8410 0.8949 0.053 Uiso 0.50 calc A -1 GR
H2SC H 0.5709 0.9386 0.8546 0.053 Uiso 0.50 calc A -1 GR
O2S O 0.4622(7) 0.9807(6) 0.9257(6) 0.0470(17) Uiso 0.50 d A -1 .
H2S H 0.4476 1.0282 0.8947 0.070 Uiso 0.50 calc A -1 GR
O2SA O 0.4862(6) 0.9002(6) 0.8617(5) 0.0355(14) Uiso 0.50 d B -2 .
H2SD H 0.5648 0.9308 0.8639 0.053 Uiso 0.50 calc B -2 GR
C2S C 0.4622(7) 0.9807(6) 0.9257(6) 0.0470(17) Uiso 0.50 d B -2 .
H2SE H 0.4552 1.0410 0.8934 0.070 Uiso 0.50 calc B -2 GR
H2SF H 0.5377 1.0170 0.9987 0.070 Uiso 0.50 calc B -2 GR
H2SG H 0.3763 0.9426 0.9314 0.070 Uiso 0.50 calc B -2 GR


_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 O1 2.172(4) . ?
Ir1 N1 2.033(5) . ?
Ir1 N2 2.031(5) . ?
Ir1 N3 2.153(5) . ?
Ir1 C7 2.006(6) . ?
Ir1 C27 2.020(6) . ?
O1 C46 1.272(7) . ?
O2 C46 1.238(7) . ?
N1 C1 1.342(8) . ?
N1 C5 1.394(7) . ?
N2 C21 1.335(8) . ?
N2 C25 1.382(7) . ?
N3 C41 1.347(7) . ?
N3 C45 1.349(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.367(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(8) . ?
C3 C4 1.393(8) . ?
C3 C12 1.502(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(8) . ?
C5 C6 1.454(8) . ?
C6 C7 1.422(8) . ?
C6 C11 1.402(8) . ?
C7 C8 1.391(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.397(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.369(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(9) . ?
C12 C17 1.394(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.372(9) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(8) . ?
C17 H17 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.383(8) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(8) . ?
C23 C24 1.389(9) . ?
C23 C32 1.487(8) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(8) . ?
C25 C26 1.477(8) . ?
C26 C27 1.427(8) . ?
C26 C31 1.390(8) . ?
C27 C28 1.373(9) . ?
C28 H28 0.9500 . ?
C28 C29 1.393(8) . ?
C29 H29 0.9500 . ?
C29 C30 1.387(9) . ?
C30 H30 0.9500 . ?
C30 C31 1.393(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.397(9) . ?
C32 C37 1.411(8) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(9) . ?
C34 H34 0.9500 . ?
C34 C35 1.383(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.400(10) . ?
C36 H36 0.9500 . ?
C36 C37 1.395(8) . ?
C37 H37 0.9500 . ?
C41 C42 1.366(9) . ?
C41 C46 1.525(8) . ?
C42 H42 0.9500 . ?
C42 C43 1.396(9) . ?
C43 H43 0.9500 . ?
C43 C44 1.371(10) . ?
C44 H44 0.9500 . ?
C44 C45 1.389(9) . ?
C45 H45 0.9500 . ?
O3 H3 0.8400 . ?
O3 C1S 1.388(10) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C2SA H2SA 0.9800 . ?
C2SA H2SB 0.9800 . ?
C2SA H2SC 0.9800 . ?
C2SA O2S 1.350(9) . ?
O2S H2S 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
N1 Ir1 O1 94.53(18) . . ?
N1 Ir1 N3 86.38(18) . . ?
N2 Ir1 O1 88.66(17) . . ?
N2 Ir1 N1 176.6(2) . . ?
N2 Ir1 N3 95.66(18) . . ?
N3 Ir1 O1 75.97(17) . . ?
C7 Ir1 O1 174.70(19) . . ?
C7 Ir1 N1 80.9(2) . . ?
C7 Ir1 N2 96.0(2) . . ?
C7 Ir1 N3 101.0(2) . . ?
C7 Ir1 C27 85.8(2) . . ?
C27 Ir1 O1 97.52(19) . . ?
C27 Ir1 N1 97.7(2) . . ?
C27 Ir1 N2 80.6(2) . . ?
C27 Ir1 N3 172.63(19) . . ?
C46 O1 Ir1 117.1(4) . . ?
C1 N1 Ir1 125.8(4) . . ?
C1 N1 C5 117.8(5) . . ?
C5 N1 Ir1 116.2(4) . . ?
C21 N2 Ir1 125.0(4) . . ?
C21 N2 C25 117.9(5) . . ?
C25 N2 Ir1 117.1(4) . . ?
C41 N3 Ir1 115.4(4) . . ?
C41 N3 C45 118.8(5) . . ?
C45 N3 Ir1 125.7(4) . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.3(6) . . ?
C2 C1 H1 118.3 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(6) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C12 120.6(6) . . ?
C4 C3 C2 116.6(5) . . ?
C4 C3 C12 122.7(5) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(5) . . ?
C5 C4 H4 119.2 . . ?
N1 C5 C6 112.7(5) . . ?
C4 C5 N1 120.2(5) . . ?
C4 C5 C6 127.0(5) . . ?
C7 C6 C5 116.2(5) . . ?
C11 C6 C5 123.7(5) . . ?
C11 C6 C7 120.2(6) . . ?
C6 C7 Ir1 114.0(4) . . ?
C8 C7 Ir1 128.4(4) . . ?
C8 C7 C6 117.6(5) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.7(6) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.9(6) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(6) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.8(6) . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C3 120.1(6) . . ?
C13 C12 C17 119.3(6) . . ?
C17 C12 C3 120.6(6) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(6) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(6) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(6) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.8(6) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 H17 120.2 . . ?
C16 C17 C12 119.6(6) . . ?
C16 C17 H17 120.2 . . ?
N2 C21 H21 118.1 . . ?
N2 C21 C22 123.8(5) . . ?
C22 C21 H21 118.1 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.2(6) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C32 119.5(6) . . ?
C24 C23 C22 117.5(6) . . ?
C24 C23 C32 123.0(5) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.3(5) . . ?
C25 C24 H24 119.4 . . ?
N2 C25 C24 120.4(6) . . ?
N2 C25 C26 112.7(5) . . ?
C24 C25 C26 126.9(5) . . ?
C27 C26 C25 115.2(5) . . ?
C31 C26 C25 123.2(5) . . ?
C31 C26 C27 121.6(6) . . ?
C26 C27 Ir1 114.3(4) . . ?
C28 C27 Ir1 128.6(4) . . ?
C28 C27 C26 117.1(5) . . ?
C27 C28 H28 119.0 . . ?
C27 C28 C29 121.9(6) . . ?
C29 C28 H28 119.0 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.5(6) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.2 . . ?
C29 C30 C31 119.6(6) . . ?
C31 C30 H30 120.2 . . ?
C26 C31 C30 119.4(6) . . ?
C26 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C33 C32 C23 121.1(5) . . ?
C33 C32 C37 117.9(6) . . ?
C37 C32 C23 121.0(6) . . ?
C32 C33 H33 118.8 . . ?
C34 C33 C32 122.4(6) . . ?
C34 C33 H33 118.8 . . ?
C33 C34 H34 120.2 . . ?
C35 C34 C33 119.5(6) . . ?
C35 C34 H34 120.2 . . ?
C34 C35 H35 120.4 . . ?
C34 C35 C36 119.2(6) . . ?
C36 C35 H35 120.4 . . ?
C35 C36 H36 119.3 . . ?
C37 C36 C35 121.4(6) . . ?
C37 C36 H36 119.3 . . ?
C32 C37 H37 120.2 . . ?
C36 C37 C32 119.5(6) . . ?
C36 C37 H37 120.2 . . ?
N3 C41 C42 121.8(6) . . ?
N3 C41 C46 115.2(5) . . ?
C42 C41 C46 123.0(6) . . ?
C41 C42 H42 120.1 . . ?
C41 C42 C43 119.7(6) . . ?
C43 C42 H42 120.1 . . ?
C42 C43 H43 120.6 . . ?
C44 C43 C42 118.7(7) . . ?
C44 C43 H43 120.6 . . ?
C43 C44 H44 120.5 . . ?
C43 C44 C45 119.0(6) . . ?
C45 C44 H44 120.5 . . ?
N3 C45 C44 121.9(6) . . ?
N3 C45 H45 119.1 . . ?
C44 C45 H45 119.1 . . ?
O1 C46 C41 116.3(5) . . ?
O2 C46 O1 125.8(6) . . ?
O2 C46 C41 118.0(6) . . ?
C1S O3 H3 109.5 . . ?
O3 C1S H1SA 109.5 . . ?
O3 C1S H1SB 109.5 . . ?
O3 C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?

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
O3 H3 O2 0.84 2.01 2.845(7) 171.4 .

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0180 -0.0010 0.0011 1.0002 0.0029 -0.0579 0.0020
0 0 -1 0.0180 0.0010 -0.0011 -1.0002 -0.0029 0.0579 -0.0020
0 -3 -1 0.0582 0.0030 -3.0025 -1.0010 -0.1779 0.1156 0.0261
0 3 1 0.0582 -0.0030 3.0025 1.0010 0.1779 -0.1156 -0.0261
-1 0 1 0.0539 -1.0005 0.0007 1.0000 -0.0070 -0.0260 0.0665
1 0 -1 0.0539 1.0005 -0.0007 -1.0000 0.0070 0.0260 -0.0665

####################################################################### 
# 
# 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_Ir7_15srv156
_database_code_depnum_ccdc_archive 'CCDC 1474221'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_audit_creation_date             2015-06-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C45 H43 Ir N2 O2'
_chemical_formula_sum            'C45 H43 Ir N2 O2'
_chemical_formula_weight         836.01
_chemical_melting_point          ?
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'
Ir Ir -1.4442 7.9887 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   12.5811(8)
_cell_length_b                   13.1174(8)
_cell_length_c                   13.6793(9)
_cell_angle_alpha                112.105(2)
_cell_angle_beta                 116.5260(10)
_cell_angle_gamma                90.323(2)
_cell_volume                     1829.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5609
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      28.420
_cell_measurement_theta_min      2.243
_exptl_absorpt_coefficient_mu    3.689
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.7789.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (30 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23849
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.71
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'SMART 6K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                6463
_reflns_number_total             8380
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.227
_refine_diff_density_min         -2.298
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         8380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0560P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1146
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C16(H16), C21(H21), C22(H22), C24(H24), C28(H28), C29(H29), C30(H30), C31(H31),
  C34(H34), C36(H36), C42(H42)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C38(H38A,H38B,
 H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C44(H44A,H44B,H44C), C45(H45A,
 H45B,H45C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Ir1 Ir 0.04301(2) 0.24928(2) 0.49001(2) 0.02037(9) Uani 1 d . . .
O1 O -0.0263(4) 0.3729(4) 0.5874(4) 0.0272(11) Uani 1 d . . .
O2 O -0.1282(4) 0.1333(4) 0.4028(4) 0.0281(11) Uani 1 d . . .
N1 N 0.1169(5) 0.2191(4) 0.6400(4) 0.0225(12) Uani 1 d . . .
N2 N -0.0294(5) 0.2814(4) 0.3409(4) 0.0242(12) Uani 1 d . . .
C1 C 0.0599(6) 0.1465(6) 0.6583(6) 0.0269(15) Uani 1 d . . .
H1 H -0.0128 0.0953 0.5924 0.032 Uiso 1 calc . . R
C2 C 0.1036(6) 0.1441(5) 0.7691(6) 0.0259(14) Uani 1 d . . .
H2 H 0.0615 0.0918 0.7792 0.031 Uiso 1 calc . . R
C3 C 0.2101(6) 0.2190(5) 0.8665(6) 0.0246(14) Uani 1 d . . .
C4 C 0.2710(6) 0.2891(5) 0.8462(6) 0.0245(14) Uani 1 d . . .
H4 H 0.3468 0.3369 0.9101 0.029 Uiso 1 calc . . R
C5 C 0.2236(6) 0.2915(5) 0.7332(5) 0.0214(13) Uani 1 d . . .
C6 C 0.2754(6) 0.3660(5) 0.7020(6) 0.0242(14) Uani 1 d . . .
C7 C 0.2003(6) 0.3567(6) 0.5819(6) 0.0258(15) Uani 1 d . . .
C8 C 0.2481(6) 0.4270(6) 0.5489(6) 0.0292(15) Uani 1 d . . .
H8 H 0.2030 0.4218 0.4694 0.035 Uiso 1 calc . . R
C9 C 0.3574(7) 0.5031(6) 0.6263(7) 0.0369(18) Uani 1 d . . .
H9 H 0.3858 0.5497 0.6003 0.044 Uiso 1 calc . . R
C10 C 0.4266(6) 0.5115(6) 0.7438(7) 0.0337(16) Uani 1 d . . .
H10 H 0.5015 0.5646 0.7980 0.040 Uiso 1 calc . . R
C11 C 0.3857(6) 0.4427(6) 0.7805(6) 0.0294(15) Uani 1 d . . .
H11 H 0.4331 0.4476 0.8597 0.035 Uiso 1 calc . . R
C12 C 0.2571(6) 0.2255(6) 0.9921(6) 0.0260(14) Uani 1 d . . .
C13 C 0.2906(7) 0.1316(6) 1.0166(6) 0.0327(16) Uani 1 d . . .
C14 C 0.3341(7) 0.1427(6) 1.1344(7) 0.0372(18) Uani 1 d . . .
H14 H 0.3590 0.0807 1.1522 0.045 Uiso 1 calc . . R
C15 C 0.3421(7) 0.2406(6) 1.2255(6) 0.0334(17) Uani 1 d . . .
C16 C 0.3064(6) 0.3299(6) 1.1996(6) 0.0346(17) Uani 1 d . . .
H16 H 0.3093 0.3969 1.2615 0.042 Uiso 1 calc . . R
C17 C 0.2652(6) 0.3249(6) 1.0826(6) 0.0291(15) Uani 1 d . . .
C18 C 0.2888(8) 0.0241(6) 0.9230(7) 0.044(2) Uani 1 d . . .
H18A H 0.2068 -0.0056 0.8535 0.066 Uiso 1 calc . . GR
H18B H 0.3121 -0.0310 0.9572 0.066 Uiso 1 calc . . GR
H18C H 0.3463 0.0384 0.8972 0.066 Uiso 1 calc . . GR
C19 C 0.3893(8) 0.2484(8) 1.3517(6) 0.045(2) Uani 1 d . . .
H19A H 0.3209 0.2272 1.3614 0.068 Uiso 1 calc . . GR
H19B H 0.4321 0.3257 1.4108 0.068 Uiso 1 calc . . GR
H19C H 0.4452 0.1972 1.3646 0.068 Uiso 1 calc . . GR
C20 C 0.2323(7) 0.4296(6) 1.0633(6) 0.0351(17) Uani 1 d . . .
H20A H 0.3026 0.4732 1.0728 0.053 Uiso 1 calc . . GR
H20B H 0.2089 0.4757 1.1228 0.053 Uiso 1 calc . . GR
H20C H 0.1642 0.4075 0.9819 0.053 Uiso 1 calc . . GR
C21 C -0.0975(6) 0.3585(5) 0.3257(6) 0.0267(15) Uani 1 d . . .
H21 H -0.1006 0.4122 0.3937 0.032 Uiso 1 calc . . R
C22 C -0.1623(6) 0.3633(5) 0.2173(6) 0.0273(15) Uani 1 d . . .
H22 H -0.2087 0.4196 0.2109 0.033 Uiso 1 calc . . R
C23 C -0.1601(6) 0.2850(5) 0.1157(6) 0.0246(14) Uani 1 d . . .
C24 C -0.0827(6) 0.2101(5) 0.1334(6) 0.0225(13) Uani 1 d . . .
H24 H -0.0744 0.1593 0.0674 0.027 Uiso 1 calc . . R
C25 C -0.0176(6) 0.2087(5) 0.2456(5) 0.0221(13) Uani 1 d . . .
C26 C 0.0623(6) 0.1319(5) 0.2745(5) 0.0237(14) Uani 1 d . . .
C27 C 0.1021(6) 0.1381(5) 0.3914(5) 0.0216(13) Uani 1 d . . .
C28 C 0.1819(6) 0.0673(6) 0.4255(6) 0.0267(15) Uani 1 d . . .
H28 H 0.2130 0.0708 0.5043 0.032 Uiso 1 calc . . R
C29 C 0.2156(6) -0.0073(5) 0.3459(6) 0.0283(15) Uani 1 d . . .
H29 H 0.2673 -0.0556 0.3700 0.034 Uiso 1 calc . . R
C30 C 0.1737(7) -0.0116(6) 0.2309(6) 0.0312(16) Uani 1 d . . .
H30 H 0.1982 -0.0614 0.1773 0.037 Uiso 1 calc . . R
C31 C 0.0968(6) 0.0567(6) 0.1956(6) 0.0276(15) Uani 1 d . . .
H31 H 0.0669 0.0527 0.1168 0.033 Uiso 1 calc . . R
C32 C -0.2410(6) 0.2754(5) -0.0085(5) 0.0210(13) Uani 1 d . . .
C33 C -0.3676(6) 0.2448(5) -0.0589(6) 0.0269(15) Uani 1 d . . .
C34 C -0.4422(6) 0.2295(6) -0.1773(6) 0.0308(16) Uani 1 d . . .
H34 H -0.5276 0.2087 -0.2109 0.037 Uiso 1 calc . . R
C35 C -0.3971(7) 0.2433(6) -0.2475(6) 0.0328(17) Uani 1 d . . .
C36 C -0.2730(7) 0.2737(6) -0.1966(6) 0.0296(16) Uani 1 d . . .
H36 H -0.2403 0.2839 -0.2437 0.036 Uiso 1 calc . . R
C37 C -0.1932(6) 0.2901(6) -0.0784(6) 0.0277(15) Uani 1 d . . .
C38 C -0.4248(6) 0.2263(7) 0.0120(7) 0.0361(17) Uani 1 d . . .
H38A H -0.3839 0.1767 0.0489 0.054 Uiso 1 calc . . GR
H38B H -0.5112 0.1914 -0.0424 0.054 Uiso 1 calc . . GR
H38C H -0.4161 0.2988 0.0753 0.054 Uiso 1 calc . . GR
C39 C -0.4809(7) 0.2268(8) -0.3748(6) 0.046(2) Uani 1 d . . .
H39A H -0.5640 0.1953 -0.3986 0.070 Uiso 1 calc . . GR
H39B H -0.4549 0.1749 -0.4291 0.070 Uiso 1 calc . . GR
H39C H -0.4782 0.2994 -0.3795 0.070 Uiso 1 calc . . GR
C40 C -0.0583(7) 0.3253(7) -0.0294(7) 0.0374(18) Uani 1 d . . .
H40A H -0.0219 0.3830 0.0537 0.056 Uiso 1 calc . . GR
H40B H -0.0449 0.3557 -0.0793 0.056 Uiso 1 calc . . GR
H40C H -0.0208 0.2598 -0.0310 0.056 Uiso 1 calc . . GR
C41 C -0.1262(7) 0.3522(6) 0.5843(6) 0.0307(16) Uani 1 d . . .
C42 C -0.2175(6) 0.2552(6) 0.5073(6) 0.0317(16) Uani 1 d . . .
H42 H -0.2897 0.2573 0.5137 0.038 Uiso 1 calc . . R
C43 C -0.2159(7) 0.1571(6) 0.4233(6) 0.0302(16) Uani 1 d . . .
C44 C -0.3283(7) 0.0628(7) 0.3479(7) 0.045(2) Uani 1 d . . .
H44A H -0.3840 0.0720 0.2754 0.068 Uiso 1 calc . . GR
H44B H -0.3689 0.0655 0.3953 0.068 Uiso 1 calc . . GR
H44C H -0.3045 -0.0099 0.3245 0.068 Uiso 1 calc . . GR
C45 C -0.1465(8) 0.4460(7) 0.6754(7) 0.0405(19) Uani 1 d . . .
H45A H -0.1016 0.4445 0.7544 0.061 Uiso 1 calc . . GR
H45B H -0.2334 0.4363 0.6504 0.061 Uiso 1 calc . . GR
H45C H -0.1178 0.5184 0.6805 0.061 Uiso 1 calc . . GR


_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 O1 2.143(4) . ?
Ir1 O2 2.163(5) . ?
Ir1 N1 2.035(5) . ?
Ir1 N2 2.040(5) . ?
Ir1 C7 1.973(7) . ?
Ir1 C27 1.981(6) . ?
O1 C41 1.263(8) . ?
O2 C43 1.267(8) . ?
N1 C1 1.347(8) . ?
N1 C5 1.369(8) . ?
N2 C21 1.345(8) . ?
N2 C25 1.367(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(9) . ?
C3 C4 1.372(9) . ?
C3 C12 1.514(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.401(8) . ?
C5 C6 1.454(9) . ?
C6 C7 1.437(9) . ?
C6 C11 1.390(9) . ?
C7 C8 1.402(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(10) . ?
C9 H9 0.9500 . ?
C9 C10 1.403(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.377(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.413(10) . ?
C12 C17 1.383(10) . ?
C13 C14 1.397(10) . ?
C13 C18 1.498(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.376(11) . ?
C15 C16 1.370(10) . ?
C15 C19 1.515(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.419(9) . ?
C17 C20 1.520(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.363(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.396(9) . ?
C23 C24 1.396(9) . ?
C23 C32 1.494(8) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(8) . ?
C25 C26 1.462(9) . ?
C26 C27 1.415(8) . ?
C26 C31 1.395(9) . ?
C27 C28 1.416(9) . ?
C28 H28 0.9500 . ?
C28 C29 1.392(9) . ?
C29 H29 0.9500 . ?
C29 C30 1.397(9) . ?
C30 H30 0.9500 . ?
C30 C31 1.374(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.406(9) . ?
C32 C37 1.402(9) . ?
C33 C34 1.392(9) . ?
C33 C38 1.523(10) . ?
C34 H34 0.9500 . ?
C34 C35 1.376(10) . ?
C35 C36 1.376(10) . ?
C35 C39 1.505(9) . ?
C36 H36 0.9500 . ?
C36 C37 1.398(9) . ?
C37 C40 1.511(10) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C42 1.393(10) . ?
C41 C45 1.506(10) . ?
C42 H42 0.9500 . ?
C42 C43 1.373(10) . ?
C43 C44 1.521(10) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 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
O1 Ir1 O2 88.24(18) . . ?
N1 Ir1 O1 83.88(19) . . ?
N1 Ir1 O2 94.94(19) . . ?
N1 Ir1 N2 179.3(2) . . ?
N2 Ir1 O1 95.91(19) . . ?
N2 Ir1 O2 85.77(19) . . ?
C7 Ir1 O1 89.2(2) . . ?
C7 Ir1 O2 175.4(2) . . ?
C7 Ir1 N1 81.1(2) . . ?
C7 Ir1 N2 98.2(2) . . ?
C7 Ir1 C27 91.3(3) . . ?
C27 Ir1 O1 176.3(2) . . ?
C27 Ir1 O2 91.5(2) . . ?
C27 Ir1 N1 99.8(2) . . ?
C27 Ir1 N2 80.4(2) . . ?
C41 O1 Ir1 123.7(4) . . ?
C43 O2 Ir1 124.3(4) . . ?
C1 N1 Ir1 124.5(4) . . ?
C1 N1 C5 119.7(5) . . ?
C5 N1 Ir1 115.1(4) . . ?
C21 N2 Ir1 125.2(4) . . ?
C21 N2 C25 118.9(5) . . ?
C25 N2 Ir1 115.4(4) . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.2(6) . . ?
C2 C1 H1 118.9 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(6) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C12 121.5(6) . . ?
C4 C3 C2 118.2(6) . . ?
C4 C3 C12 120.3(6) . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(6) . . ?
C5 C4 H4 119.4 . . ?
N1 C5 C4 119.1(6) . . ?
N1 C5 C6 114.2(5) . . ?
C4 C5 C6 126.6(6) . . ?
C7 C6 C5 114.1(6) . . ?
C11 C6 C5 124.2(6) . . ?
C11 C6 C7 121.7(6) . . ?
C6 C7 Ir1 114.7(5) . . ?
C8 C7 Ir1 129.8(5) . . ?
C8 C7 C6 115.4(6) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 C7 123.1(6) . . ?
C9 C8 H8 118.5 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.7(6) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(6) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 119.9 . . ?
C10 C11 C6 120.2(6) . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C3 120.9(6) . . ?
C17 C12 C3 118.7(6) . . ?
C17 C12 C13 120.4(6) . . ?
C12 C13 C18 122.3(6) . . ?
C14 C13 C12 118.4(7) . . ?
C14 C13 C18 119.2(7) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 C13 122.1(7) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 C19 120.2(7) . . ?
C16 C15 C14 118.8(6) . . ?
C16 C15 C19 121.0(7) . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.6(7) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 C16 118.6(7) . . ?
C12 C17 C20 123.3(6) . . ?
C16 C17 C20 118.0(6) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21 118.5 . . ?
N2 C21 C22 123.1(6) . . ?
C22 C21 H21 118.5 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.6(6) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C32 122.6(6) . . ?
C24 C23 C22 117.1(6) . . ?
C24 C23 C32 120.3(6) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.2(6) . . ?
C25 C24 H24 119.4 . . ?
N2 C25 C24 119.7(6) . . ?
N2 C25 C26 113.9(5) . . ?
C24 C25 C26 126.4(6) . . ?
C27 C26 C25 114.0(5) . . ?
C31 C26 C25 124.6(5) . . ?
C31 C26 C27 121.4(6) . . ?
C26 C27 Ir1 115.6(5) . . ?
C26 C27 C28 116.6(6) . . ?
C28 C27 Ir1 127.8(5) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 C27 121.4(6) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.3(6) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.6(6) . . ?
C31 C30 H30 120.2 . . ?
C26 C31 H31 119.7 . . ?
C30 C31 C26 120.7(6) . . ?
C30 C31 H31 119.7 . . ?
C33 C32 C23 119.3(6) . . ?
C37 C32 C23 121.3(6) . . ?
C37 C32 C33 119.2(5) . . ?
C32 C33 C38 121.6(6) . . ?
C34 C33 C32 119.0(6) . . ?
C34 C33 C38 119.3(6) . . ?
C33 C34 H34 118.7 . . ?
C35 C34 C33 122.7(7) . . ?
C35 C34 H34 118.7 . . ?
C34 C35 C36 117.6(6) . . ?
C34 C35 C39 121.0(7) . . ?
C36 C35 C39 121.4(7) . . ?
C35 C36 H36 118.7 . . ?
C35 C36 C37 122.6(6) . . ?
C37 C36 H36 118.7 . . ?
C32 C37 C40 122.2(6) . . ?
C36 C37 C32 118.9(6) . . ?
C36 C37 C40 118.9(6) . . ?
C33 C38 H38A 109.5 . . ?
C33 C38 H38B 109.5 . . ?
C33 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 C39 H39A 109.5 . . ?
C35 C39 H39B 109.5 . . ?
C35 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O1 C41 C42 128.0(6) . . ?
O1 C41 C45 114.4(7) . . ?
C42 C41 C45 117.7(7) . . ?
C41 C42 H42 116.1 . . ?
C43 C42 C41 127.9(7) . . ?
C43 C42 H42 116.1 . . ?
O2 C43 C42 127.2(7) . . ?
O2 C43 C44 114.5(6) . . ?
C42 C43 C44 118.2(7) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C41 C45 H45A 109.5 . . ?
C41 C45 H45B 109.5 . . ?
C41 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 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
C2 C3 C12 C13 62.0(9) . . . . ?
C2 C3 C12 C17 -117.3(7) . . . . ?
C4 C3 C12 C13 -119.3(7) . . . . ?
C4 C3 C12 C17 61.5(9) . . . . ?
C4 C5 C6 C7 -174.2(6) . . . . ?
C4 C5 C6 C11 4.0(11) . . . . ?
C7 C6 C5 N1 4.9(8) . . . . ?
C11 C6 C5 N1 -177.0(6) . . . . ?
C22 C23 C32 C33 -62.9(9) . . . . ?
C22 C23 C32 C37 120.8(7) . . . . ?
C24 C23 C32 C33 113.6(7) . . . . ?
C24 C23 C32 C37 -62.7(9) . . . . ?
C24 C25 C26 C27 -170.7(6) . . . . ?
C24 C25 C26 C31 8.3(11) . . . . ?
C27 C26 C25 N2 6.7(8) . . . . ?
C31 C26 C25 N2 -174.3(6) . . . . ?

####################################################################### 
# 
# 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_Ir3_15srv109
_database_code_depnum_ccdc_archive 'CCDC 1474222'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_audit_creation_date             2015-04-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C41 H35 Ir N2 O4, C H2 Cl2'
_chemical_formula_sum            'C42 H37 Cl2 Ir N2 O4'
_chemical_formula_weight         896.84
_chemical_melting_point          ?
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'
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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.3800(6)
_cell_length_b                   14.4932(9)
_cell_length_c                   14.9593(9)
_cell_angle_alpha                69.040(10)
_cell_angle_beta                 74.260(10)
_cell_angle_gamma                71.550(10)
_cell_volume                     1772.57(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7337
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.33
_exptl_absorpt_coefficient_mu    3.964
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0698 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.8465.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (30 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27616
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.48
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker SMART CCD 6000'
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                7579
_reflns_number_total             9378
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.856
_refine_diff_density_min         -1.435
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         9378
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.039
_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)+(0.0340P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0790
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1-C1S \\sim Cl3-C1S \\sim Cl2-C1S
 with sigma of 0.003
3. Others
 Fixed Sof: Cl2(0.5) Cl3(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) H1SD(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C1S(H1SC,H1SD)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C21(H21), C22(H22), C24(H24), C28(H28), C29(H29),
  C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37), C40(H40)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C43(H43A,H43B,
 H43C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Ir1 Ir 0.226746(18) 0.237685(12) 0.470182(12) 0.01711(5) Uani 1 d . . .
O1 O 0.3054(3) 0.3748(2) 0.4011(2) 0.0219(6) Uani 1 d . . .
O2 O 0.4003(3) 0.1819(2) 0.5584(2) 0.0243(7) Uani 1 d . . .
O3 O -0.3834(3) 0.4310(2) 1.1015(2) 0.0269(7) Uani 1 d . . .
O4 O 0.8843(3) -0.0907(2) -0.0792(2) 0.0266(7) Uani 1 d . . .
N1 N 0.0829(4) 0.2921(3) 0.5797(2) 0.0192(7) Uani 1 d . . .
N2 N 0.3621(4) 0.1758(3) 0.3644(2) 0.0183(7) Uani 1 d . . .
C1 C 0.0619(5) 0.3848(3) 0.5877(3) 0.0235(9) Uani 1 d . . .
H1 H 0.1091 0.4327 0.5358 0.028 Uiso 1 calc . . R
C2 C -0.0253(5) 0.4138(3) 0.6681(3) 0.0251(9) Uani 1 d . . .
H2 H -0.0380 0.4806 0.6704 0.030 Uiso 1 calc . . R
C3 C -0.0954(5) 0.3446(3) 0.7464(3) 0.0218(9) Uani 1 d . . .
C4 C -0.0765(5) 0.2497(3) 0.7346(3) 0.0220(9) Uani 1 d . . .
H4 H -0.1253 0.2013 0.7847 0.026 Uiso 1 calc . . R
C5 C 0.0114(4) 0.2240(3) 0.6519(3) 0.0180(8) Uani 1 d . . .
C6 C 0.0405(4) 0.1264(3) 0.6335(3) 0.0185(8) Uani 1 d . . .
C7 C 0.1411(4) 0.1165(3) 0.5464(3) 0.0184(8) Uani 1 d . . .
C8 C 0.1704(5) 0.0246(3) 0.5261(3) 0.0223(9) Uani 1 d . . .
H8 H 0.2365 0.0158 0.4676 0.027 Uiso 1 calc . . R
C9 C 0.1049(5) -0.0541(3) 0.5898(3) 0.0250(9) Uani 1 d . . .
H9 H 0.1271 -0.1161 0.5746 0.030 Uiso 1 calc . . R
C10 C 0.0071(5) -0.0424(3) 0.6755(3) 0.0261(9) Uani 1 d . . .
H10 H -0.0372 -0.0964 0.7189 0.031 Uiso 1 calc . . R
C11 C -0.0259(5) 0.0477(3) 0.6975(3) 0.0238(9) Uani 1 d . . .
H11 H -0.0932 0.0560 0.7558 0.029 Uiso 1 calc . . R
C12 C -0.1782(5) 0.3691(3) 0.8372(3) 0.0209(9) Uani 1 d . . .
C13 C -0.1457(5) 0.4421(3) 0.8651(3) 0.0258(9) Uani 1 d . . .
H13 H -0.0741 0.4796 0.8225 0.031 Uiso 1 calc . . R
C14 C -0.2153(5) 0.4604(3) 0.9529(3) 0.0264(10) Uani 1 d . . .
H14 H -0.1904 0.5094 0.9706 0.032 Uiso 1 calc . . R
C15 C -0.3214(5) 0.4078(3) 1.0154(3) 0.0230(9) Uani 1 d . . .
C16 C -0.3582(5) 0.3361(3) 0.9897(3) 0.0254(9) Uani 1 d . . .
H16 H -0.4313 0.2998 1.0322 0.030 Uiso 1 calc . . R
C17 C -0.2866(5) 0.3181(3) 0.9011(3) 0.0254(9) Uani 1 d . . .
H17 H -0.3124 0.2694 0.8835 0.030 Uiso 1 calc . . R
C18 C -0.4778(6) 0.3685(4) 1.1734(3) 0.0340(11) Uani 1 d . . .
H18A H -0.5662 0.3737 1.1473 0.051 Uiso 1 calc . . GR
H18B H -0.5130 0.3915 1.2316 0.051 Uiso 1 calc . . GR
H18C H -0.4186 0.2974 1.1905 0.051 Uiso 1 calc . . GR
C21 C 0.5036(5) 0.1155(3) 0.3697(3) 0.0217(9) Uani 1 d . . .
H21 H 0.5464 0.1034 0.4248 0.026 Uiso 1 calc . . R
C22 C 0.5898(5) 0.0704(3) 0.2987(3) 0.0226(9) Uani 1 d . . .
H22 H 0.6903 0.0295 0.3048 0.027 Uiso 1 calc . . R
C23 C 0.5288(5) 0.0849(3) 0.2178(3) 0.0210(9) Uani 1 d . . .
C24 C 0.3812(5) 0.1465(3) 0.2133(3) 0.0197(8) Uani 1 d . . .
H24 H 0.3350 0.1572 0.1600 0.024 Uiso 1 calc . . R
C25 C 0.3004(5) 0.1924(3) 0.2853(3) 0.0190(8) Uani 1 d . . .
C26 C 0.1441(4) 0.2573(3) 0.2904(3) 0.0179(8) Uani 1 d . . .
C27 C 0.0814(4) 0.2843(3) 0.3782(3) 0.0174(8) Uani 1 d . . .
C28 C -0.0705(5) 0.3404(3) 0.3883(3) 0.0225(9) Uani 1 d . . .
H28 H -0.1176 0.3579 0.4467 0.027 Uiso 1 calc . . R
C29 C -0.1546(5) 0.3711(3) 0.3140(3) 0.0262(10) Uani 1 d . . .
H29 H -0.2578 0.4090 0.3227 0.031 Uiso 1 calc . . R
C30 C -0.0891(5) 0.3468(3) 0.2276(3) 0.0251(9) Uani 1 d . . .
H30 H -0.1462 0.3689 0.1770 0.030 Uiso 1 calc . . R
C31 C 0.0601(5) 0.2902(3) 0.2164(3) 0.0217(9) Uani 1 d . . .
H31 H 0.1058 0.2735 0.1574 0.026 Uiso 1 calc . . R
C32 C 0.6193(4) 0.0359(3) 0.1411(3) 0.0195(8) Uani 1 d . . .
C33 C 0.5909(5) 0.0750(3) 0.0462(3) 0.0223(9) Uani 1 d . . .
H33 H 0.5082 0.1326 0.0306 0.027 Uiso 1 calc . . R
C34 C 0.6803(5) 0.0319(3) -0.0256(3) 0.0224(9) Uani 1 d . . .
H34 H 0.6589 0.0600 -0.0899 0.027 Uiso 1 calc . . R
C35 C 0.8019(5) -0.0528(3) -0.0037(3) 0.0216(9) Uani 1 d . . .
C36 C 0.8289(5) -0.0947(3) 0.0910(3) 0.0247(9) Uani 1 d . . .
H36 H 0.9097 -0.1535 0.1070 0.030 Uiso 1 calc . . R
C37 C 0.7378(5) -0.0505(3) 0.1622(3) 0.0255(9) Uani 1 d . . .
H37 H 0.7568 -0.0801 0.2269 0.031 Uiso 1 calc . . R
C38 C 1.0326(5) -0.1576(3) -0.0659(3) 0.0287(10) Uani 1 d . . .
H38A H 1.0877 -0.1715 -0.1273 0.043 Uiso 1 calc . . GR
H38B H 1.0206 -0.2218 -0.0158 0.043 Uiso 1 calc . . GR
H38C H 1.0903 -0.1252 -0.0456 0.043 Uiso 1 calc . . GR
C39 C 0.4040(5) 0.3955(4) 0.4288(3) 0.0270(10) Uani 1 d . . .
C40 C 0.4946(5) 0.3309(3) 0.4984(3) 0.0260(9) Uani 1 d . . .
H40 H 0.5671 0.3583 0.5078 0.031 Uiso 1 calc . . R
C41 C 0.4915(5) 0.2311(3) 0.5558(3) 0.0265(10) Uani 1 d . . .
C42 C 0.6102(5) 0.1738(4) 0.6204(4) 0.0358(12) Uani 1 d . . .
H42A H 0.5654 0.1289 0.6806 0.054 Uiso 1 calc . . GR
H42B H 0.6448 0.2225 0.6359 0.054 Uiso 1 calc . . GR
H42C H 0.6973 0.1329 0.5864 0.054 Uiso 1 calc . . GR
C43 C 0.4197(6) 0.5038(4) 0.3811(4) 0.0335(11) Uani 1 d . . .
H43A H 0.4290 0.5208 0.3105 0.050 Uiso 1 calc . . GR
H43B H 0.5110 0.5105 0.3957 0.050 Uiso 1 calc . . GR
H43C H 0.3293 0.5503 0.4061 0.050 Uiso 1 calc . . GR
Cl1 Cl 0.24767(18) 0.31126(11) 0.96469(10) 0.0491(3) Uani 1 d A . D
Cl2 Cl 0.4198(4) 0.2871(3) 0.7864(2) 0.0565(9) Uani 0.50 d A 1 D
Cl3 Cl 0.3218(6) 0.3311(4) 0.7552(2) 0.0781(13) Uani 0.50 d A 2 D
C1S C 0.3187(6) 0.3787(4) 0.84720(19) 0.0500(15) Uani 1 d . . D
H1SA H 0.3873 0.4176 0.8489 0.060 Uiso 0.50 calc A 1 R
H1SB H 0.2341 0.4269 0.8140 0.060 Uiso 0.50 calc A 1 R
H1SC H 0.2563 0.4498 0.8332 0.060 Uiso 0.50 calc A 2 R
H1SD H 0.4242 0.3804 0.8453 0.060 Uiso 0.50 calc A 2 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 O1 2.146(3) . ?
Ir1 O2 2.148(3) . ?
Ir1 N1 2.044(3) . ?
Ir1 N2 2.031(3) . ?
Ir1 C7 1.998(4) . ?
Ir1 C27 1.995(4) . ?
O1 C39 1.261(5) . ?
O2 C41 1.261(5) . ?
O3 C15 1.374(5) . ?
O3 C18 1.434(5) . ?
O4 C35 1.370(5) . ?
O4 C38 1.439(5) . ?
N1 C1 1.339(5) . ?
N1 C5 1.362(5) . ?
N2 C21 1.343(5) . ?
N2 C25 1.369(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.403(6) . ?
C3 C4 1.400(6) . ?
C3 C12 1.474(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(6) . ?
C5 C6 1.463(6) . ?
C6 C7 1.411(5) . ?
C6 C11 1.397(6) . ?
C7 C8 1.398(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.406(6) . ?
C12 C17 1.391(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(6) . ?
C15 C16 1.390(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(6) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.381(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.397(6) . ?
C23 C24 1.394(6) . ?
C23 C32 1.487(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(5) . ?
C25 C26 1.469(5) . ?
C26 C27 1.423(5) . ?
C26 C31 1.390(6) . ?
C27 C28 1.398(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.398(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.379(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.393(6) . ?
C32 C37 1.389(6) . ?
C33 H33 0.9500 . ?
C33 C34 1.381(6) . ?
C34 H34 0.9500 . ?
C34 C35 1.395(6) . ?
C35 C36 1.386(6) . ?
C36 H36 0.9500 . ?
C36 C37 1.386(6) . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.401(6) . ?
C39 C43 1.510(6) . ?
C40 H40 0.9500 . ?
C40 C41 1.399(6) . ?
C41 C42 1.512(6) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
Cl1 C1S 1.743(4) . ?
Cl2 C1S 1.757(4) . ?
Cl3 C1S 1.735(4) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S H1SC 0.9900 . ?
C1S H1SD 0.9900 . ?

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 Ir1 O2 88.64(11) . . ?
N1 Ir1 O1 92.69(12) . . ?
N1 Ir1 O2 87.15(12) . . ?
N2 Ir1 O1 91.14(12) . . ?
N2 Ir1 O2 93.84(12) . . ?
N2 Ir1 N1 176.06(14) . . ?
C7 Ir1 O1 173.70(14) . . ?
C7 Ir1 O2 90.31(14) . . ?
C7 Ir1 N1 81.05(15) . . ?
C7 Ir1 N2 95.13(15) . . ?
C27 Ir1 O1 90.83(13) . . ?
C27 Ir1 O2 174.29(14) . . ?
C27 Ir1 N1 98.55(15) . . ?
C27 Ir1 N2 80.48(14) . . ?
C27 Ir1 C7 90.83(16) . . ?
C39 O1 Ir1 123.9(3) . . ?
C41 O2 Ir1 124.9(3) . . ?
C15 O3 C18 117.2(3) . . ?
C35 O4 C38 116.3(3) . . ?
C1 N1 Ir1 125.5(3) . . ?
C1 N1 C5 119.3(3) . . ?
C5 N1 Ir1 115.1(3) . . ?
C21 N2 Ir1 124.4(3) . . ?
C21 N2 C25 118.3(3) . . ?
C25 N2 Ir1 117.1(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.8(4) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C12 121.9(4) . . ?
C4 C3 C2 116.0(4) . . ?
C4 C3 C12 122.1(4) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.0(4) . . ?
C5 C4 H4 119.0 . . ?
N1 C5 C4 119.8(4) . . ?
N1 C5 C6 114.1(3) . . ?
C4 C5 C6 126.1(4) . . ?
C7 C6 C5 115.5(4) . . ?
C11 C6 C5 122.8(4) . . ?
C11 C6 C7 121.7(4) . . ?
C6 C7 Ir1 114.0(3) . . ?
C8 C7 Ir1 129.0(3) . . ?
C8 C7 C6 117.0(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(4) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 120.2 . . ?
C10 C11 C6 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C3 121.1(4) . . ?
C17 C12 C3 121.7(4) . . ?
C17 C12 C13 117.1(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
O3 C15 C14 115.8(4) . . ?
O3 C15 C16 124.2(4) . . ?
C14 C15 C16 120.0(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.1(4) . . ?
C17 C16 H16 120.5 . . ?
C12 C17 H17 118.9 . . ?
C16 C17 C12 122.1(4) . . ?
C16 C17 H17 118.9 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C21 H21 118.5 . . ?
N2 C21 C22 123.0(4) . . ?
C22 C21 H21 118.5 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.9(4) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C32 120.6(4) . . ?
C24 C23 C22 116.9(4) . . ?
C24 C23 C32 122.5(4) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.2(4) . . ?
C25 C24 H24 119.4 . . ?
N2 C25 C24 120.7(4) . . ?
N2 C25 C26 112.5(3) . . ?
C24 C25 C26 126.8(4) . . ?
C27 C26 C25 115.2(3) . . ?
C31 C26 C25 123.5(4) . . ?
C31 C26 C27 121.2(4) . . ?
C26 C27 Ir1 114.5(3) . . ?
C28 C27 Ir1 128.6(3) . . ?
C28 C27 C26 116.8(4) . . ?
C27 C28 H28 119.4 . . ?
C27 C28 C29 121.2(4) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.8(4) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 120.4 . . ?
C31 C30 C29 119.1(4) . . ?
C31 C30 H30 120.4 . . ?
C26 C31 H31 119.6 . . ?
C30 C31 C26 120.7(4) . . ?
C30 C31 H31 119.6 . . ?
C33 C32 C23 121.9(4) . . ?
C37 C32 C23 120.4(4) . . ?
C37 C32 C33 117.7(4) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 C32 121.5(4) . . ?
C34 C33 H33 119.3 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 119.9(4) . . ?
C35 C34 H34 120.0 . . ?
O4 C35 C34 116.1(4) . . ?
O4 C35 C36 124.5(4) . . ?
C36 C35 C34 119.4(4) . . ?
C35 C36 H36 120.1 . . ?
C35 C36 C37 119.8(4) . . ?
C37 C36 H36 120.1 . . ?
C32 C37 H37 119.2 . . ?
C36 C37 C32 121.6(4) . . ?
C36 C37 H37 119.2 . . ?
O4 C38 H38A 109.5 . . ?
O4 C38 H38B 109.5 . . ?
O4 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O1 C39 C40 127.4(4) . . ?
O1 C39 C43 114.1(4) . . ?
C40 C39 C43 118.4(4) . . ?
C39 C40 H40 116.0 . . ?
C41 C40 C39 128.0(4) . . ?
C41 C40 H40 116.0 . . ?
O2 C41 C40 126.6(4) . . ?
O2 C41 C42 115.5(4) . . ?
C40 C41 C42 118.0(4) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C39 C43 H43A 109.5 . . ?
C39 C43 H43B 109.5 . . ?
C39 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
Cl1 C1S Cl2 106.1(3) . . ?
Cl1 C1S H1SA 110.5 . . ?
Cl1 C1S H1SB 110.5 . . ?
Cl1 C1S H1SC 108.3 . . ?
Cl1 C1S H1SD 108.3 . . ?
Cl2 C1S H1SA 110.5 . . ?
Cl2 C1S H1SB 110.5 . . ?
Cl2 C1S H1SC 139.5 . . ?
Cl2 C1S H1SD 80.9 . . ?
Cl3 C1S Cl1 115.8(4) . . ?
Cl3 C1S Cl2 35.23(19) . . ?
Cl3 C1S H1SA 128.2 . . ?
Cl3 C1S H1SB 75.6 . . ?
Cl3 C1S H1SC 108.3 . . ?
Cl3 C1S H1SD 108.3 . . ?
H1SA C1S H1SB 108.7 . . ?
H1SA C1S H1SC 76.4 . . ?
H1SA C1S H1SD 32.4 . . ?
H1SB C1S H1SC 36.3 . . ?
H1SB C1S H1SD 133.9 . . ?
H1SC C1S H1SD 107.4 . . ?

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
C2 C3 C12 C13 -23.9(6) . . . . ?
C2 C3 C12 C17 159.0(4) . . . . ?
C4 C3 C12 C13 153.4(4) . . . . ?
C4 C3 C12 C17 -23.7(6) . . . . ?
C4 C5 C6 C7 -176.3(4) . . . . ?
C4 C5 C6 C11 3.5(6) . . . . ?
C7 C6 C5 N1 2.1(5) . . . . ?
C11 C6 C5 N1 -178.1(4) . . . . ?
C14 C15 O3 C18 -171.8(4) . . . . ?
C16 C15 O3 C18 7.8(6) . . . . ?
C22 C23 C32 C33 -156.1(4) . . . . ?
C22 C23 C32 C37 22.9(6) . . . . ?
C24 C23 C32 C33 24.0(6) . . . . ?
C24 C23 C32 C37 -157.0(4) . . . . ?
C24 C25 C26 C27 172.4(4) . . . . ?
C24 C25 C26 C31 -6.8(7) . . . . ?
C27 C26 C25 N2 -4.6(5) . . . . ?
C31 C26 C25 N2 176.1(4) . . . . ?
C34 C35 O4 C38 162.9(4) . . . . ?
C36 C35 O4 C38 -19.3(6) . . . . ?

