#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:18:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178698 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/09/4080998.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4080998
loop_
_publ_author_name
'Kumaran, Elumalai'
'How, Kai Tong Sonia'
'Ganguly, Rakesh'
'Li, Yongxin'
'Leong, Weng Kee'
_publ_section_title
;
 Synthesis and Reactivity of Cationic Iridium Aminocarbenes Derived from
 Terminal Alkynes and 2-Aminopyridines
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              4149
_journal_paper_doi               10.1021/om400326c
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C21 H29 Br Cl Ir N2, B F4'
_chemical_formula_sum            'C21 H29 B Br Cl F4 Ir N2'
_chemical_formula_weight         703.83
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.5702(11)
_cell_length_b                   13.1750(10)
_cell_length_c                   27.7649(18)
_cell_measurement_reflns_used    6372
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.12
_cell_measurement_theta_min      2.61
_cell_volume                     4964.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            47498
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.138
_exptl_absorpt_correction_T_max  0.3294
_exptl_absorpt_correction_T_min  0.2233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.775
_refine_diff_density_min         -1.817
_refine_diff_density_rms         0.393
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5072
_refine_ls_number_restraints     316
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0404
_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)+(0.0671P)²+16.6153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                3617
_reflns_number_total             5072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400326c_si_001.cif
_cod_data_source_block           lwk64r
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4080998
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.05426(2) 0.28112(2) 0.403995(11) 0.04104(14) Uani 1 1 d . . .
Br1 Br -0.06948(11) 0.05218(10) 0.44953(5) 0.0899(4) Uani 1 1 d . . .
N1 N -0.0097(5) 0.1563(5) 0.3674(2) 0.0423(15) Uani 1 1 d . . .
N2 N 0.0693(5) 0.2372(6) 0.3054(3) 0.0508(18) Uani 1 1 d . . .
C1 C 0.0813(8) 0.3965(8) 0.4586(4) 0.071(3) Uani 1 1 d U . .
C2 C 0.0403(7) 0.4433(7) 0.4189(4) 0.063(3) Uani 1 1 d U . .
C3 C -0.0541(7) 0.4012(8) 0.4100(4) 0.056(2) Uani 1 1 d U . .
C4 C -0.0781(8) 0.3336(7) 0.4487(4) 0.060(2) Uani 1 1 d U . .
C5 C 0.0071(10) 0.3299(9) 0.4789(4) 0.075(3) Uani 1 1 d U . .
C6 C 0.1758(10) 0.4224(12) 0.4841(6) 0.116(5) Uani 1 1 d U . .
H6A H 0.2290 0.4231 0.4614 0.174 Uiso 1 1 calc R . .
H6B H 0.1888 0.3724 0.5085 0.174 Uiso 1 1 calc R . .
H6C H 0.1699 0.4880 0.4988 0.174 Uiso 1 1 calc R . .
C7 C 0.0811(10) 0.5332(9) 0.3916(5) 0.091(4) Uani 1 1 d U . .
H7A H 0.0660 0.5946 0.4087 0.136 Uiso 1 1 calc R . .
H7B H 0.0520 0.5357 0.3601 0.136 Uiso 1 1 calc R . .
H7C H 0.1513 0.5263 0.3886 0.136 Uiso 1 1 calc R . .
C8 C -0.1264(9) 0.4344(9) 0.3722(4) 0.083(3) Uani 1 1 d U . .
H8A H -0.1568 0.4969 0.3819 0.125 Uiso 1 1 calc R . .
H8B H -0.1760 0.3832 0.3683 0.125 Uiso 1 1 calc R . .
H8C H -0.0925 0.4443 0.3422 0.125 Uiso 1 1 calc R . .
C9 C -0.1756(10) 0.2894(10) 0.4539(6) 0.099(4) Uani 1 1 d U . .
H9A H -0.1756 0.2427 0.4805 0.149 Uiso 1 1 calc R . .
H9B H -0.1930 0.2541 0.4249 0.149 Uiso 1 1 calc R . .
H9C H -0.2227 0.3423 0.4599 0.149 Uiso 1 1 calc R . .
C10 C 0.0198(15) 0.2678(13) 0.5242(6) 0.131(6) Uani 1 1 d U . .
H10A H -0.0377 0.2267 0.5292 0.196 Uiso 1 1 calc R . .
H10B H 0.0286 0.3123 0.5512 0.196 Uiso 1 1 calc R . .
H10C H 0.0766 0.2249 0.5209 0.196 Uiso 1 1 calc R . .
C11 C -0.0606(6) 0.0766(7) 0.3833(4) 0.052(2) Uani 1 1 d U . .
C12 C -0.1057(8) 0.0068(8) 0.3532(4) 0.070(3) Uani 1 1 d U . .
H12 H -0.1425 -0.0468 0.3655 0.084 Uiso 1 1 calc R . .
C13 C -0.0938(9) 0.0197(9) 0.3045(5) 0.081(3) Uani 1 1 d U . .
H13 H -0.1253 -0.0243 0.2833 0.097 Uiso 1 1 calc R . .
C14 C -0.0373(8) 0.0952(8) 0.2868(4) 0.066(3) Uani 1 1 d U . .
H14 H -0.0271 0.1027 0.2538 0.079 Uiso 1 1 calc R . .
C15 C 0.0047(6) 0.1610(7) 0.3197(3) 0.049(2) Uani 1 1 d U . .
C16 C 0.1105(6) 0.2962(6) 0.3391(3) 0.0454(19) Uani 1 1 d U . .
C17 C 0.1875(7) 0.3656(8) 0.3188(4) 0.067(3) Uani 1 1 d U . .
H17A H 0.1825 0.4304 0.3351 0.080 Uiso 1 1 calc R . .
H17B H 0.1725 0.3772 0.2851 0.080 Uiso 1 1 calc R . .
C18 C 0.2956(8) 0.3288(9) 0.3224(4) 0.073(3) Uani 1 1 d U . .
C19 C 0.3362(11) 0.3494(13) 0.3722(6) 0.116(5) Uani 1 1 d U . .
H19A H 0.2981 0.3128 0.3956 0.174 Uiso 1 1 calc R . .
H19B H 0.3325 0.4208 0.3789 0.174 Uiso 1 1 calc R . .
H19C H 0.4036 0.3277 0.3737 0.174 Uiso 1 1 calc R . .
C20 C 0.3547(11) 0.3908(12) 0.2848(6) 0.121(5) Uani 1 1 d U . .
H20A H 0.4239 0.3795 0.2895 0.181 Uiso 1 1 calc R . .
H20B H 0.3404 0.4617 0.2886 0.181 Uiso 1 1 calc R . .
H20C H 0.3364 0.3696 0.2529 0.181 Uiso 1 1 calc R . .
C21 C 0.3029(9) 0.2185(9) 0.3106(5) 0.086(4) Uani 1 1 d U . .
H21A H 0.3708 0.1980 0.3113 0.129 Uiso 1 1 calc R . .
H21B H 0.2763 0.2066 0.2791 0.129 Uiso 1 1 calc R . .
H21C H 0.2664 0.1800 0.3339 0.129 Uiso 1 1 calc R . .
Cl1 Cl 0.1718(2) 0.16074(19) 0.43251(8) 0.0662(7) Uani 1 1 d . . .
B1 B 0.8497(8) 0.7118(7) 0.3215(3) 0.071(3) Uani 1 1 d D . .
F1 F 0.8720(10) 0.7892(7) 0.2913(4) 0.107(3) Uani 0.70 1 d PDU A 1
F2 F 0.9019(11) 0.7226(11) 0.3624(4) 0.150(5) Uani 0.70 1 d PDU A 1
F3 F 0.7547(9) 0.7068(12) 0.3319(5) 0.170(6) Uani 0.70 1 d PDU A 1
F4 F 0.8761(11) 0.6277(8) 0.2970(5) 0.144(5) Uani 0.70 1 d PDU A 1
F1 F 0.7973(18) 0.7963(13) 0.3117(8) 0.107(3) Uani 0.30 1 d PDU A 2
F2 F 0.850(2) 0.696(2) 0.3692(5) 0.150(5) Uani 0.30 1 d PDU A 2
F3 F 0.9404(14) 0.719(2) 0.3042(12) 0.170(6) Uani 0.30 1 d PDU A 2
F4 F 0.804(2) 0.6313(15) 0.3000(10) 0.144(5) Uani 0.30 1 d PDU A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 Ir1 N1 78.3(3)
C16 Ir1 C3 105.1(4)
N1 Ir1 C3 109.0(3)
C16 Ir1 C1 120.1(4)
N1 Ir1 C1 160.8(4)
C3 Ir1 C1 63.3(4)
C16 Ir1 C2 96.2(4)
N1 Ir1 C2 144.5(3)
C3 Ir1 C2 38.0(4)
C1 Ir1 C2 36.9(4)
C16 Ir1 C5 157.0(4)
N1 Ir1 C5 123.0(4)
C3 Ir1 C5 62.0(4)
C1 Ir1 C5 38.0(4)
C2 Ir1 C5 61.6(4)
C16 Ir1 C4 140.4(3)
N1 Ir1 C4 100.0(3)
C3 Ir1 C4 37.3(4)
C1 Ir1 C4 62.9(4)
C2 Ir1 C4 62.2(4)
C5 Ir1 C4 36.5(4)
C16 Ir1 Cl1 96.4(2)
N1 Ir1 Cl1 85.25(19)
C3 Ir1 Cl1 156.1(3)
C1 Ir1 Cl1 96.9(3)
C2 Ir1 Cl1 130.2(3)
C5 Ir1 Cl1 94.2(3)
C4 Ir1 Cl1 123.1(3)
C11 N1 C15 116.1(8)
C11 N1 Ir1 131.6(6)
C15 N1 Ir1 112.2(6)
C16 N2 C15 118.9(7)
C2 C1 C5 107.5(10)
C2 C1 C6 128.3(13)
C5 C1 C6 123.1(12)
C2 C1 Ir1 71.8(6)
C5 C1 Ir1 74.4(6)
C6 C1 Ir1 129.0(8)
C1 C2 C3 109.2(10)
C1 C2 C7 127.1(11)
C3 C2 C7 123.4(11)
C1 C2 Ir1 71.3(6)
C3 C2 Ir1 70.3(5)
C7 C2 Ir1 129.7(8)
C2 C3 C4 108.5(9)
C2 C3 C8 126.7(10)
C4 C3 C8 123.8(10)
C2 C3 Ir1 71.7(5)
C4 C3 Ir1 76.0(5)
C8 C3 Ir1 127.0(7)
C5 C4 C3 106.1(9)
C5 C4 C9 131.5(11)
C3 C4 C9 122.1(11)
C5 C4 Ir1 71.0(6)
C3 C4 Ir1 66.6(5)
C9 C4 Ir1 130.4(8)
C4 C5 C1 108.2(10)
C4 C5 C10 126.9(14)
C1 C5 C10 124.9(13)
C4 C5 Ir1 72.5(5)
C1 C5 Ir1 67.6(5)
C10 C5 Ir1 125.2(9)
N1 C11 C12 123.5(9)
N1 C11 Br1 119.7(7)
C12 C11 Br1 116.8(8)
C13 C12 C11 117.4(10)
C14 C13 C12 121.1(10)
C13 C14 C15 117.1(10)
N1 C15 C14 124.3(9)
N1 C15 N2 114.0(7)
C14 C15 N2 121.6(9)
N2 C16 C17 112.5(8)
N2 C16 Ir1 114.8(6)
C17 C16 Ir1 132.6(7)
C16 C17 C18 116.5(8)
C21 C18 C19 110.5(11)
C21 C18 C17 110.7(9)
C19 C18 C17 110.3(11)
C21 C18 C20 109.4(11)
C19 C18 C20 109.5(11)
C17 C18 C20 106.4(10)
F3 B1 F3 171.3(15)
F3 B1 F2 77.0(14)
F3 B1 F2 111.7(12)
F3 B1 F4 109.1(10)
F3 B1 F4 68.5(13)
F2 B1 F4 111.6(15)
F3 B1 F2 109.4(10)
F3 B1 F2 79.0(15)
F2 B1 F2 35.2(14)
F4 B1 F2 111.8(10)
F3 B1 F1 64.6(11)
F3 B1 F1 110.8(12)
F2 B1 F1 109.1(11)
F4 B1 F1 135.9(13)
F2 B1 F1 111.1(13)
F3 B1 F1 113.0(10)
F3 B1 F1 60.7(13)
F2 B1 F1 136.8(15)
F4 B1 F1 104.4(9)
F2 B1 F1 109.0(9)
F1 B1 F1 51.1(11)
F3 B1 F4 67.4(13)
F3 B1 F4 108.7(12)
F2 B1 F4 108.0(11)
F4 B1 F4 42.3(12)
F2 B1 F4 133.5(14)
F1 B1 F4 108.4(11)
F1 B1 F4 114.6(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ir1 C16 1.967(9)
Ir1 N1 2.120(7)
Ir1 C3 2.166(9)
Ir1 C1 2.179(9)
Ir1 C2 2.184(10)
Ir1 C5 2.270(10)
Ir1 C4 2.289(9)
Ir1 Cl1 2.385(2)
Br1 C11 1.871(10)
N1 C11 1.333(11)
N1 C15 1.340(10)
N2 C16 1.338(11)
N2 C15 1.391(12)
C1 C2 1.379(15)
C1 C5 1.450(17)
C1 C6 1.504(16)
C2 C3 1.417(13)
C2 C7 1.512(16)
C3 C4 1.431(14)
C3 C8 1.502(14)
C4 C5 1.430(16)
C4 C9 1.454(15)
C5 C10 1.509(18)
C11 C12 1.385(13)
C12 C13 1.374(16)
C13 C14 1.349(16)
C14 C15 1.383(13)
C16 C17 1.499(12)
C17 C18 1.548(14)
C18 C21 1.493(16)
C18 C19 1.513(18)
C18 C20 1.549(16)
B1 F3 1.323(12)
B1 F3 1.325(13)
B1 F2 1.342(13)
B1 F4 1.347(11)
B1 F2 1.348(12)
B1 F1 1.349(13)
B1 F1 1.354(11)
B1 F4 1.363(13)
