# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cmpd_2_VPX73
_database_code_depnum_ccdc_archive 'CCDC 1942661'
loop_
_audit_author_name
_audit_author_address
'Vincenzo Passarelli'
;Centro Universitario de la Defensa, Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H33 Br Ir N3 O'
_chemical_formula_sum            'C23 H33 Br Ir N3 O'
_chemical_formula_weight         639.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5663(3)
_cell_length_b                   11.0966(4)
_cell_length_c                   24.1272(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.5950(10)
_cell_angle_gamma                90
_cell_volume                     2267.70(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.404
_cell_measurement_theta_max      29.449

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    7.669
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2975
_exptl_absorpt_correction_T_max  0.3851
_exptl_absorpt_process_details   
;

 SADABS: Area-Detector Absorption Correction. (1996)  Bruker-AXS 

 within SAINT+ package, v. 6.45.   

;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX-DUO CCD system'

_diffrn_measurement_method       'ω rotations with narrow frames'

_diffrn_detector_area_resol_mean 8.26
_diffrn_reflns_number            34038
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.707
_diffrn_reflns_theta_max         29.650
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6081
_reflns_number_gt                5219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART v. 5.611 (Bruker AXS, 2000)'

_computing_cell_refinement       'SAINT+ v. 6.45 (Bruker AXS, 2003)'

_computing_data_reduction        'SAINT+ v. 6.45 (Bruker AXS, 2003)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'

_computing_publication_material  'XCIF program, SHELXTLv6.12, BrukerAXS'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+0.1667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6081
_refine_ls_number_parameters     282
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0490
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0125(3) 0.0112(2) 0.11499(12) 0.0150(6) Uani 1 1 d . . . . .
C3 C -0.1806(4) -0.0724(3) 0.05323(13) 0.0201(6) Uani 1 1 d . . . . .
H3 H -0.2829 -0.0907 0.0340 0.024 Uiso 1 1 calc R U . . .
C4 C -0.0445(4) -0.1216(3) 0.04332(13) 0.0192(6) Uani 1 1 d . . . . .
H4 H -0.0313 -0.1798 0.0155 0.023 Uiso 1 1 calc R U . . .
C6 C -0.2742(3) 0.0833(3) 0.11705(13) 0.0186(6) Uani 1 1 d . . . . .
C7 C -0.3604(4) 0.0012(3) 0.15289(14) 0.0253(7) Uani 1 1 d . . . . .
H7A H -0.2886 -0.0219 0.1867 0.038 Uiso 1 1 calc R U . . .
H7B H -0.3965 -0.0712 0.1315 0.038 Uiso 1 1 calc R U . . .
H7C H -0.4515 0.0439 0.1635 0.038 Uiso 1 1 calc R U . . .
C8 C -0.3879(4) 0.1263(3) 0.06623(14) 0.0312(8) Uani 1 1 d . . . . .
H8A H -0.4370 0.0564 0.0457 0.047 Uiso 1 1 calc R U . . .
H8B H -0.3299 0.1733 0.0416 0.047 Uiso 1 1 calc R U . . .
H8C H -0.4699 0.1767 0.0787 0.047 Uiso 1 1 calc R U . . .
C9 C -0.2084(4) 0.1934(3) 0.15005(14) 0.0260(7) Uani 1 1 d . . . . .
H9A H -0.2954 0.2398 0.1616 0.039 Uiso 1 1 calc R U . . .
H9B H -0.1511 0.2438 0.1265 0.039 Uiso 1 1 calc R U . . .
H9C H -0.1363 0.1676 0.1833 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2414(3) -0.0907(3) 0.08226(13) 0.0183(6) Uani 1 1 d . . . . .
H10A H 0.3004 -0.0457 0.1141 0.022 Uiso 1 1 calc R U . . .
H10B H 0.2716 -0.0571 0.0474 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2909(3) -0.2218(3) 0.08703(12) 0.0159(6) Uani 1 1 d . . . . .
C13 C 0.4792(3) -0.3595(3) 0.07118(12) 0.0158(6) Uani 1 1 d . . . . .
C14 C 0.3977(3) -0.4535(3) 0.09256(12) 0.0174(6) Uani 1 1 d . . . . .
H14 H 0.4368 -0.5337 0.0932 0.021 Uiso 1 1 calc R U . . .
C15 C 0.2596(3) -0.4273(3) 0.11262(13) 0.0193(6) Uani 1 1 d . . . . .
H15 H 0.2029 -0.4890 0.1283 0.023 Uiso 1 1 calc R U . . .
C16 C 0.2035(3) -0.3088(3) 0.10974(12) 0.0162(6) Uani 1 1 d . . . . .
H16 H 0.1079 -0.2886 0.1230 0.019 Uiso 1 1 calc R U . . .
C17 C 0.6334(3) -0.3791(3) 0.04929(13) 0.0181(6) Uani 1 1 d . . . . .
H17A H 0.6216 -0.3550 0.0094 0.022 Uiso 1 1 calc R U . . .
H17B H 0.7164 -0.3281 0.0706 0.022 Uiso 1 1 calc R U . . .
C19 C 0.8328(4) -0.5182(3) 0.04072(15) 0.0276(7) Uani 1 1 d . . . . .
H19A H 0.8373 -0.4853 0.0033 0.041 Uiso 1 1 calc R U . . .
H19B H 0.8571 -0.6045 0.0410 0.041 Uiso 1 1 calc R U . . .
H19C H 0.9100 -0.4767 0.0683 0.041 Uiso 1 1 calc R U . . .
C20 C 0.3538(4) 0.1849(3) 0.22994(13) 0.0220(7) Uani 1 1 d D . . . .
C21 C 0.2176(4) 0.2423(3) 0.24027(13) 0.0210(6) Uani 1 1 d D . . . .
C22 C 0.1314(4) 0.2169(3) 0.28968(13) 0.0268(7) Uani 1 1 d . . . . .
H22A H 0.0285 0.2593 0.2837 0.032 Uiso 1 1 calc R U . . .
H22B H 0.1940 0.2498 0.3241 0.032 Uiso 1 1 calc R U . . .
C23 C 0.1024(4) 0.0816(3) 0.29831(14) 0.0252(7) Uani 1 1 d . . . . .
H23B H 0.1917 0.0478 0.3245 0.030 Uiso 1 1 calc R U . . .
H23A H 0.0052 0.0714 0.3155 0.030 Uiso 1 1 calc R U . . .
C24 C 0.0853(4) 0.0123(3) 0.24323(13) 0.0188(6) Uani 1 1 d D . . . .
C25 C 0.2168(4) -0.0435(3) 0.22412(13) 0.0189(6) Uani 1 1 d D . . . .
C26 C 0.3826(4) -0.0377(3) 0.25543(13) 0.0249(7) Uani 1 1 d . . . . .
H26A H 0.4553 -0.0762 0.2325 0.030 Uiso 1 1 calc R U . . .
H26B H 0.3877 -0.0841 0.2907 0.030 Uiso 1 1 calc R U . . .
C27 C 0.4388(4) 0.0928(3) 0.26951(14) 0.0270(7) Uani 1 1 d . . . . .
H27B H 0.4219 0.1121 0.3082 0.032 Uiso 1 1 calc R U . . .
H27A H 0.5535 0.0981 0.2681 0.032 Uiso 1 1 calc R U . . .
N2 N -0.1452(3) 0.0101(2) 0.09657(10) 0.0156(5) Uani 1 1 d . . . . .
N5 N 0.0728(3) -0.0706(2) 0.08175(10) 0.0145(5) Uani 1 1 d . . . . .
N12 N 0.4269(3) -0.2454(2) 0.06805(10) 0.0156(5) Uani 1 1 d . . . . .
O18 O 0.6788(2) -0.50112(19) 0.05464(10) 0.0248(5) Uani 1 1 d . . . . .
Br Br 0.19054(4) 0.25478(3) 0.09866(2) 0.01891(7) Uani 1 1 d . . . . .
Ir Ir 0.15174(2) 0.10981(2) 0.17503(2) 0.01334(4) Uani 1 1 d . . . . .
H20 H 0.415(4) 0.226(3) 0.2049(12) 0.027(9) Uiso 1 1 d D . . . .
H21 H 0.191(4) 0.321(2) 0.2204(12) 0.021(8) Uiso 1 1 d D . . . .
H24 H -0.020(2) -0.024(2) 0.2340(11) 0.010(7) Uiso 1 1 d D . . . .
H26 H 0.192(4) -0.119(2) 0.2027(13) 0.021(9) Uiso 1 1 d 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
C1 N2 1.357(4) . ?
C1 N5 1.363(4) . ?
C1 Ir 2.050(3) . ?
C3 C4 1.341(4) . ?
C3 N2 1.389(4) . ?
C3 H3 0.9500 . ?
C4 N5 1.382(4) . ?
C4 H4 0.9500 . ?
C6 N2 1.513(4) . ?
C6 C9 1.520(4) . ?
C6 C7 1.520(4) . ?
C6 C8 1.524(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
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 N5 1.459(4) . ?
C10 C11 1.515(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.340(4) . ?
C11 C16 1.384(4) . ?
C13 N12 1.342(4) . ?
C13 C14 1.395(4) . ?
C13 C17 1.510(4) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O18 1.410(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 O18 1.421(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.384(4) . ?
C20 C27 1.510(4) . ?
C20 Ir 2.182(3) . ?
C20 H20 0.967(18) . ?
C21 C22 1.520(4) . ?
C21 Ir 2.166(3) . ?
C21 H21 1.001(17) . ?
C22 C23 1.541(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.524(4) . ?
C23 H23B 0.9900 . ?
C23 H23A 0.9900 . ?
C24 C25 1.421(4) . ?
C24 Ir 2.117(3) . ?
C24 H24 0.980(17) . ?
C25 C26 1.507(4) . ?
C25 Ir 2.100(3) . ?
C25 H26 0.988(17) . ?
C26 C27 1.548(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27B 0.9900 . ?
C27 H27A 0.9900 . ?
Br Ir 2.5054(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N5 104.3(2) . . ?
N2 C1 Ir 133.0(2) . . ?
N5 C1 Ir 122.7(2) . . ?
C4 C3 N2 107.8(3) . . ?
C4 C3 H3 126.1 . . ?
N2 C3 H3 126.1 . . ?
C3 C4 N5 106.1(3) . . ?
C3 C4 H4 126.9 . . ?
N5 C4 H4 126.9 . . ?
N2 C6 C9 111.8(2) . . ?
N2 C6 C7 107.8(2) . . ?
C9 C6 C7 110.9(3) . . ?
N2 C6 C8 108.4(2) . . ?
C9 C6 C8 108.2(3) . . ?
C7 C6 C8 109.8(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C10 C11 114.4(2) . . ?
N5 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N5 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N12 C11 C16 123.3(3) . . ?
N12 C11 C10 114.2(2) . . ?
C16 C11 C10 122.6(3) . . ?
N12 C13 C14 123.0(3) . . ?
N12 C13 C17 114.7(3) . . ?
C14 C13 C17 122.3(3) . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 118.3(3) . . ?
C11 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
O18 C17 C13 110.5(2) . . ?
O18 C17 H17A 109.5 . . ?
C13 C17 H17A 109.5 . . ?
O18 C17 H17B 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C27 122.5(3) . . ?
C21 C20 Ir 70.81(18) . . ?
C27 C20 Ir 112.9(2) . . ?
C21 C20 H20 116(2) . . ?
C27 C20 H20 117(2) . . ?
Ir C20 H20 105(2) . . ?
C20 C21 C22 125.3(3) . . ?
C20 C21 Ir 72.06(17) . . ?
C22 C21 Ir 109.9(2) . . ?
C20 C21 H21 116.7(18) . . ?
C22 C21 H21 115.7(18) . . ?
Ir C21 H21 103.1(18) . . ?
C21 C22 C23 113.2(3) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C22 111.7(3) . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
H23B C23 H23A 107.9 . . ?
C25 C24 C23 121.7(3) . . ?
C25 C24 Ir 69.66(17) . . ?
C23 C24 Ir 114.7(2) . . ?
C25 C24 H24 119.8(17) . . ?
C23 C24 H24 111.6(17) . . ?
Ir C24 H24 112.1(17) . . ?
C24 C25 C26 123.5(3) . . ?
C24 C25 Ir 70.96(17) . . ?
C26 C25 Ir 113.5(2) . . ?
C24 C25 H26 115(2) . . ?
C26 C25 H26 114.1(19) . . ?
Ir C25 H26 111.8(19) . . ?
C25 C26 C27 112.9(3) . . ?
C25 C26 H26A 109.0 . . ?
C27 C26 H26A 109.0 . . ?
C25 C26 H26B 109.0 . . ?
C27 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C20 C27 C26 113.0(3) . . ?
C20 C27 H27B 109.0 . . ?
C26 C27 H27B 109.0 . . ?
C20 C27 H27A 109.0 . . ?
C26 C27 H27A 109.0 . . ?
H27B C27 H27A 107.8 . . ?
C1 N2 C3 110.3(2) . . ?
C1 N2 C6 128.9(2) . . ?
C3 N2 C6 120.8(2) . . ?
C1 N5 C4 111.5(2) . . ?
C1 N5 C10 123.9(2) . . ?
C4 N5 C10 124.2(2) . . ?
C11 N12 C13 117.7(3) . . ?
C17 O18 C19 111.1(2) . . ?
C1 Ir C25 92.48(11) . . ?
C1 Ir C24 94.62(11) . . ?
C25 Ir C24 39.37(11) . . ?
C1 Ir C21 159.49(12) . . ?
C25 Ir C21 96.99(12) . . ?
C24 Ir C21 81.56(12) . . ?
C1 Ir C20 163.35(12) . . ?
C25 Ir C20 81.24(12) . . ?
C24 Ir C20 90.26(12) . . ?
C21 Ir C20 37.13(12) . . ?
C1 Ir Br 87.15(8) . . ?
C25 Ir Br 151.86(8) . . ?
C24 Ir Br 168.65(8) . . ?
C21 Ir Br 92.86(8) . . ?
C20 Ir Br 91.19(8) . . ?

_refine_diff_density_max         1.359
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.131

####################################################################### 
# 
# 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_cmpd_4_VPX142
_database_code_depnum_ccdc_archive 'CCDC 1942666'
loop_
_audit_author_name
_audit_author_address
'Vincenzo Passarelli'
;Centro Universitario de la Defensa, Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 Br Ir N3 O3'
_chemical_formula_sum            'C17 H21 Br Ir N3 O3'
_chemical_formula_weight         587.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2294(9)
_cell_length_b                   11.1211(11)
_cell_length_c                   11.8920(19)
_cell_angle_alpha                99.1570(10)
_cell_angle_beta                 110.946(2)
_cell_angle_gamma                114.3940(10)
_cell_volume                     968.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7571
_cell_measurement_theta_min      2.335
_cell_measurement_theta_max      28.267

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.015
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    8.978
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1208
_exptl_absorpt_correction_T_max  0.1695
_exptl_absorpt_process_details   
; 
 Multi-scan correction included in APEX2 package (Bruker AXS, 2008)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO system'
_diffrn_measurement_method       'ω and φ rotations with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_reflns_number            11641
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.966
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3938
_reflns_number_gt                3700
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART in APEX2 (Bruker AXS,2008)'
_computing_cell_refinement       'SAINT+ in APEX2 (Bruker AXS,2008)'
_computing_data_reduction        'SAINT+ in APEX2 (Bruker AXS,2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²+5.1495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3938
_refine_ls_number_parameters     230
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C6A C 0.9120(18) -0.3305(12) 0.6537(12) 0.027(4) Uiso 0.401(16) 1 d D . P A 1
C7A C 0.7091(16) -0.4241(16) 0.6077(15) 0.043(4) Uiso 0.401(16) 1 d D . P A 1
H7A1 H 0.6877 -0.4238 0.6827 0.065 Uiso 0.401(16) 1 calc R U P A 1
H7A2 H 0.6672 -0.5211 0.5568 0.065 Uiso 0.401(16) 1 calc R U P A 1
H7A3 H 0.6431 -0.3870 0.5542 0.065 Uiso 0.401(16) 1 calc R U P A 1
C8A C 0.941(2) -0.319(2) 0.5377(15) 0.056(5) Uiso 0.401(16) 1 d D . P A 1
H8A1 H 0.8675 -0.2842 0.4882 0.085 Uiso 0.401(16) 1 calc R U P A 1
H8A2 H 0.9052 -0.4126 0.4831 0.085 Uiso 0.401(16) 1 calc R U P A 1
H8A3 H 1.0685 -0.2532 0.5666 0.085 Uiso 0.401(16) 1 calc R U P A 1
C9A C 1.0068(16) -0.4016(15) 0.7236(13) 0.025(3) Uiso 0.401(16) 1 d D . P A 1
H9A1 H 1.1314 -0.3561 0.7378 0.037 Uiso 0.401(16) 1 calc R U P A 1
H9A2 H 0.9430 -0.5022 0.6709 0.037 Uiso 0.401(16) 1 calc R U P A 1
H9A3 H 1.0067 -0.3919 0.8070 0.037 Uiso 0.401(16) 1 calc R U P A 1
C6B C 0.8825(14) -0.3404(9) 0.6607(9) 0.029(3) Uiso 0.599(16) 1 d D . P A 2
C7B C 0.7252(14) -0.4319(12) 0.6793(11) 0.047(3) Uiso 0.599(16) 1 d D . P A 2
H7B1 H 0.7656 -0.4160 0.7714 0.071 Uiso 0.599(16) 1 calc R U P A 2
H7B2 H 0.6762 -0.5317 0.6317 0.071 Uiso 0.599(16) 1 calc R U P A 2
H7B3 H 0.6314 -0.4075 0.6471 0.071 Uiso 0.599(16) 1 calc R U P A 2
C8B C 0.8192(15) -0.3536(12) 0.5194(9) 0.044(3) Uiso 0.599(16) 1 d D . P A 2
H8B1 H 0.7191 -0.3354 0.4906 0.067 Uiso 0.599(16) 1 calc R U P A 2
H8B2 H 0.7787 -0.4493 0.4663 0.067 Uiso 0.599(16) 1 calc R U P A 2
H8B3 H 0.9191 -0.2844 0.5107 0.067 Uiso 0.599(16) 1 calc R U P A 2
C9B C 1.0230(17) -0.3869(17) 0.6959(14) 0.061(4) Uiso 0.599(16) 1 d D . P A 2
H9B1 H 1.1180 -0.3320 0.6754 0.092 Uiso 0.599(16) 1 calc R U P A 2
H9B2 H 0.9646 -0.4878 0.6465 0.092 Uiso 0.599(16) 1 calc R U P A 2
H9B3 H 1.0759 -0.3705 0.7884 0.092 Uiso 0.599(16) 1 calc R U P A 2
C1 C 0.8942(7) -0.1078(5) 0.7301(5) 0.0283(10) Uani 1 1 d . . . . .
C4 C 1.1616(8) 0.0113(6) 0.9120(5) 0.0391(13) Uani 1 1 d . . . . .
H4 H 1.2621 0.0843 0.9900 0.047 Uiso 1 1 calc R U . . .
C3 C 1.1375(7) -0.1153(6) 0.8576(5) 0.0359(12) Uani 1 1 d . . . . .
H3 H 1.2177 -0.1487 0.8896 0.043 Uiso 1 1 calc R U . . .
C10 C 0.9825(8) 0.1328(6) 0.8639(6) 0.0362(12) Uani 1 1 d . . . . .
H10A H 0.9813 0.1460 0.9478 0.043 Uiso 1 1 calc R U . . .
H10B H 0.8620 0.1069 0.7973 0.043 Uiso 1 1 calc R U . . .
C11 C 1.1209(7) 0.2711(5) 0.8709(5) 0.0281(10) Uani 1 1 d . . . . .
C13 C 1.2621(7) 0.5126(6) 0.9612(5) 0.0287(11) Uani 1 1 d . . . . .
C14 C 1.3531(7) 0.5316(6) 0.8885(5) 0.0303(11) Uani 1 1 d . . . . .
H14 H 1.4332 0.6239 0.8962 0.036 Uiso 1 1 calc R U . . .
C15 C 1.3240(7) 0.4124(6) 0.8042(5) 0.0313(11) Uani 1 1 d . . . . .
H15 H 1.3844 0.4216 0.7533 0.038 Uiso 1 1 calc R U . . .
C16 C 1.2058(7) 0.2798(6) 0.7953(5) 0.0302(11) Uani 1 1 d . . . . .
H16 H 1.1836 0.1966 0.7383 0.036 Uiso 1 1 calc R U . . .
C17 C 1.2892(8) 0.6352(6) 1.0578(6) 0.0343(12) Uani 1 1 d . . . . .
H17A H 1.1708 0.6208 1.0461 0.041 Uiso 1 1 calc R U . . .
H17B H 1.3580 0.6413 1.1464 0.041 Uiso 1 1 calc R U . . .
C19 C 1.4440(8) 0.8835(6) 1.1441(6) 0.0424(14) Uani 1 1 d . . . . .
H19A H 1.3398 0.8793 1.1515 0.064 Uiso 1 1 calc R U . . .
H19B H 1.5058 0.9692 1.1278 0.064 Uiso 1 1 calc R U . . .
H19C H 1.5273 0.8855 1.2246 0.064 Uiso 1 1 calc R U . . .
C20 C 0.7584(8) -0.0644(7) 0.4958(6) 0.0379(13) Uani 1 1 d . . . . .
C22 C 0.4193(8) -0.1847(6) 0.4701(6) 0.0393(13) Uani 1 1 d . . . . .
N5 N 1.0134(6) 0.0157(5) 0.8336(4) 0.0313(10) Uani 1 1 d D . . . .
N2 N 0.9726(6) -0.1884(5) 0.7452(4) 0.0297(9) Uani 1 1 d . . . . .
N12 N 1.1476(6) 0.3852(5) 0.9535(4) 0.0272(9) Uani 1 1 d . . . . .
O18 O 1.3851(6) 0.7629(4) 1.0408(4) 0.0427(10) Uani 1 1 d . . . . .
O21 O 0.8206(6) -0.0143(5) 0.4424(4) 0.0458(10) Uani 1 1 d . . . . .
O23 O 0.2813(6) -0.2126(5) 0.3963(5) 0.0562(13) Uani 1 1 d . . . . .
Br Br 0.51080(9) -0.23075(7) 0.72700(6) 0.04674(16) Uani 1 1 d . . . . .
Ir Ir 0.64928(3) -0.14476(2) 0.59172(2) 0.02895(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6A C8A 1.510(13) . ?
C6A N2 1.510(12) . ?
C6A C9A 1.529(12) . ?
C6A C7A 1.538(13) . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
C6B N2 1.503(9) . ?
C6B C7B 1.508(11) . ?
C6B C8B 1.529(11) . ?
C6B C9B 1.535(11) . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9B H9B1 0.9800 . ?
C9B H9B2 0.9800 . ?
C9B H9B3 0.9800 . ?
C1 N2 1.362(7) . ?
C1 N5 1.363(6) . ?
C1 Ir 2.084(5) . ?
C4 C3 1.341(9) . ?
C4 N5 1.379(8) . ?
C4 H4 0.9500 . ?
C3 N2 1.393(7) . ?
C3 H3 0.9500 . ?
C10 N5 1.461(7) . ?
C10 C11 1.505(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.345(7) . ?
C11 C16 1.377(7) . ?
C13 N12 1.336(7) . ?
C13 C14 1.389(8) . ?
C13 C17 1.502(7) . ?
C14 C15 1.387(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O18 1.423(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 O18 1.413(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O21 1.073(8) . ?
C20 Ir 1.875(7) . ?
C22 O23 1.130(7) . ?
C22 Ir 1.901(6) . ?
Br Ir 2.4670(7) . ?

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
C8A C6A N2 112.1(11) . . ?
C8A C6A C9A 110.5(10) . . ?
N2 C6A C9A 110.8(9) . . ?
C8A C6A C7A 108.9(10) . . ?
N2 C6A C7A 106.8(10) . . ?
C9A C6A C7A 107.6(9) . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C6A C8A H8A1 109.5 . . ?
C6A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C6A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C6A C9A H9A1 109.5 . . ?
C6A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C6A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
N2 C6B C7B 110.2(8) . . ?
N2 C6B C8B 109.8(7) . . ?
C7B C6B C8B 110.3(8) . . ?
N2 C6B C9B 108.3(9) . . ?
C7B C6B C9B 111.0(8) . . ?
C8B C6B C9B 107.2(8) . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C6B C8B H8B1 109.5 . . ?
C6B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C6B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C6B C9B H9B1 109.5 . . ?
C6B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
C6B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
N2 C1 N5 104.7(4) . . ?
N2 C1 Ir 132.8(4) . . ?
N5 C1 Ir 122.5(4) . . ?
C3 C4 N5 107.2(5) . . ?
C3 C4 H4 126.4 . . ?
N5 C4 H4 126.4 . . ?
C4 C3 N2 107.1(5) . . ?
C4 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
N5 C10 C11 114.2(4) . . ?
N5 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N5 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N12 C11 C16 123.3(5) . . ?
N12 C11 C10 113.5(4) . . ?
C16 C11 C10 123.1(5) . . ?
N12 C13 C14 123.2(5) . . ?
N12 C13 C17 114.7(5) . . ?
C14 C13 C17 122.1(5) . . ?
C15 C14 C13 118.2(5) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C16 C15 C14 119.2(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C11 C16 C15 118.6(5) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
O18 C17 C13 109.7(5) . . ?
O18 C17 H17A 109.7 . . ?
C13 C17 H17A 109.7 . . ?
O18 C17 H17B 109.7 . . ?
C13 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O21 C20 Ir 177.5(6) . . ?
O23 C22 Ir 177.9(5) . . ?
C1 N5 C4 110.8(5) . . ?
C1 N5 C10 124.9(5) . . ?
C4 N5 C10 124.1(5) . . ?
C1 N2 C3 110.2(5) . . ?
C1 N2 C6B 124.2(5) . . ?
C3 N2 C6B 125.2(5) . . ?
C1 N2 C6A 128.8(6) . . ?
C3 N2 C6A 120.7(6) . . ?
C13 N12 C11 117.5(4) . . ?
C19 O18 C17 111.7(5) . . ?
C20 Ir C22 92.2(2) . . ?
C20 Ir C1 91.0(2) . . ?
C22 Ir C1 176.8(2) . . ?
C20 Ir Br 175.22(18) . . ?
C22 Ir Br 87.6(2) . . ?
C1 Ir Br 89.21(14) . . ?

_refine_diff_density_max         2.507
_refine_diff_density_min         -2.000
_refine_diff_density_rms         0.137


# start Validation Reply Form
_vrf_PLAT201_cmpd_4_VPX142       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          4 Report
RESPONSE: The disordered tert-butyl group was included in the model 
 using two sets of atomic coordinates with complementary occupancy factors.
 SADI restraints were used and isotropic refinement was applied  to all 
 non hydrogen atoms in order to get realistic results. 
 Hydrogen atoms were introduced at calculated positions.
;
# end Validation Reply Form
