#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:25:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178898 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/27/4112782.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_4112782
loop_
_publ_author_name
'Douglas B. Grotjahn'
'Justin M. Hoerter'
'John L. Hubbard'
_publ_section_title
;
 Double C-H Activation during Functionalization of Phenyl(methyl)ketene on
 Iridium(I) Using Alkynes. Synthesis of 1,4-Dien-3-ones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8866
_journal_page_last               8867
_journal_paper_doi               10.1021/ja048489+
_journal_volume                  126
_journal_year                    2004
_chemical_compound_source        'Grotjahn Lab'
_chemical_formula_moiety         'C22 H48 Cl Ir P2'
_chemical_formula_sum            'C22 H48 Cl Ir P2'
_chemical_formula_weight         602.2
_chemical_name_common            'Ir-2-butyne complex'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                79.67(3)
_cell_angle_beta                 83.31(3)
_cell_angle_gamma                77.89(3)
_cell_formula_units_Z            2
_cell_length_a                   9.415(3)
_cell_length_b                   9.858(3)
_cell_length_c                   14.708(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      1.5
_cell_volume                     1308.7(7)
_computing_cell_refinement       P3
_computing_data_collection       P3
_computing_data_reduction        P3
_computing_molecular_graphics    XP
_computing_publication_material  SHELX
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'theta- 2 theta'
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6406
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        <1%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    5.31
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         4.218
_refine_diff_density_min         -5.188
_refine_diff_density_rms         0.213
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.079
_refine_ls_goodness_of_fit_obs   1.087
_refine_ls_hydrogen_treatment    'fixed, isotropic'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         6037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_restrained_S_obs      1.087
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_obs          0.0371
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0739P)²+1.2813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0960
_refine_ls_wR_factor_obs         0.0936
_reflns_number_observed          5687
_reflns_number_total             6038
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja0484892Bsi20040325_023113.cif
_cod_data_source_block           dg24a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'na' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+1.2813P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+1.2813P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4112782
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Ir Ir 0.20898(2) 0.048161(14) 0.267592(10) 0.01517(8) Uani 1 d .
Cl Cl 0.36676(13) 0.17925(12) 0.30961(9) 0.0274(2) Uani 1 d .
P1 P 0.05690(12) 0.26056(12) 0.21430(8) 0.0183(2) Uani 1 d .
C1 C 0.5343(5) -0.1589(6) 0.1975(4) 0.0279(10) Uani 1 d .
H1A H 0.6022(5) -0.2460(6) 0.2097(4) 0.080 Uiso 1 d R
C2 C 0.6210(7) -0.0405(7) 0.1836(5) 0.0412(14) Uani 1 d .
H2A H 0.6927(7) -0.0500(7) 0.1319(5) 0.080 Uiso 1 d R
H2B H 0.5552(7) 0.0482(7) 0.1718(5) 0.080 Uiso 1 d R
H2C H 0.6686(7) -0.0447(7) 0.2386(5) 0.080 Uiso 1 d R
C3 C 0.4670(6) -0.1592(7) 0.1080(4) 0.0414(14) Uani 1 d .
H3A H 0.5412(6) -0.1625(7) 0.0573(4) 0.080 Uiso 1 d R
H3B H 0.4218(6) -0.2396(7) 0.1146(4) 0.080 Uiso 1 d R
H3C H 0.3949(6) -0.0749(7) 0.0958(4) 0.080 Uiso 1 d R
C4 C 0.3371(5) -0.3271(5) 0.3051(4) 0.0275(10) Uani 1 d .
H4A H 0.2661(5) -0.3141(5) 0.2609(4) 0.080 Uiso 1 d R
C5 C 0.2603(7) -0.3720(6) 0.3995(4) 0.0384(13) Uani 1 d .
H5A H 0.2342(7) -0.4615(6) 0.4011(4) 0.080 Uiso 1 d R
H5B H 0.3247(7) -0.3792(6) 0.4469(4) 0.080 Uiso 1 d R
H5C H 0.1739(7) -0.3034(6) 0.4102(4) 0.080 Uiso 1 d R
C6 C 0.4571(7) -0.4486(6) 0.2800(6) 0.044(2) Uani 1 d .
H6A H 0.4179(7) -0.5325(6) 0.2865(6) 0.080 Uiso 1 d R
H6B H 0.4963(7) -0.4257(6) 0.2171(6) 0.080 Uiso 1 d R
H6C H 0.5331(7) -0.4635(6) 0.3210(6) 0.080 Uiso 1 d R
C7 C 0.4910(5) -0.1559(5) 0.3978(3) 0.0244(9) Uani 1 d .
H7A H 0.5373(5) -0.0758(5) 0.3824(3) 0.080 Uiso 1 d R
C8 C 0.3884(6) -0.1293(6) 0.4838(3) 0.0323(11) Uani 1 d .
H8A H 0.4439(6) -0.1313(6) 0.5350(3) 0.080 Uiso 1 d R
H8B H 0.3253(6) -0.0392(6) 0.4715(3) 0.080 Uiso 1 d R
H8C H 0.3309(6) -0.2013(6) 0.4989(3) 0.080 Uiso 1 d R
C9 C 0.6149(6) -0.2818(6) 0.4213(5) 0.0378(13) Uani 1 d .
H9A H 0.6586(6) -0.2713(6) 0.4749(5) 0.080 Uiso 1 d R
H9B H 0.5760(6) -0.3665(6) 0.4341(5) 0.080 Uiso 1 d R
H9C H 0.6872(6) -0.2867(6) 0.3696(5) 0.080 Uiso 1 d R
P2 P 0.39099(12) -0.15287(12) 0.29606(8) 0.0180(2) Uani 1 d .
C10 C -0.1309(5) 0.2496(5) 0.1911(4) 0.0270(10) Uani 1 d .
H10A H -0.1219(5) 0.1613(5) 0.1701(4) 0.080 Uiso 1 d R
C11 C -0.2313(6) 0.2416(6) 0.2805(4) 0.0360(12) Uani 1 d .
H11A H -0.3267(6) 0.2357(6) 0.2667(4) 0.080 Uiso 1 d R
H11B H -0.1935(6) 0.1601(6) 0.3234(4) 0.080 Uiso 1 d R
H11C H -0.2371(6) 0.3245(6) 0.3076(4) 0.080 Uiso 1 d R
C12 C -0.2073(7) 0.3612(7) 0.1171(5) 0.0417(14) Uani 1 d .
H12A H -0.3023(7) 0.3438(7) 0.1117(5) 0.080 Uiso 1 d R
H12B H -0.2165(7) 0.4525(7) 0.1341(5) 0.080 Uiso 1 d R
H12C H -0.1502(7) 0.3575(7) 0.0587(5) 0.080 Uiso 1 d R
C13 C 0.0445(5) 0.4002(5) 0.2861(3) 0.0253(9) Uani 1 d .
H13A H 0.1420(5) 0.4167(5) 0.2832(3) 0.080 Uiso 1 d R
C14 C 0.0052(7) 0.3506(6) 0.3890(4) 0.0378(12) Uani 1 d .
H14A H 0.0004(7) 0.4258(6) 0.4234(4) 0.080 Uiso 1 d R
H14B H -0.0878(7) 0.3227(6) 0.3961(4) 0.080 Uiso 1 d R
H14C H 0.0780(7) 0.2720(6) 0.4121(4) 0.080 Uiso 1 d R
C15 C -0.0474(7) 0.5429(6) 0.2514(5) 0.0390(13) Uani 1 d .
H15A H -0.0466(7) 0.6074(6) 0.2931(5) 0.080 Uiso 1 d R
H15B H -0.0081(7) 0.5787(6) 0.1907(5) 0.080 Uiso 1 d R
H15C H -0.1457(7) 0.5322(6) 0.2484(5) 0.080 Uiso 1 d R
C16 C 0.1311(5) 0.3426(5) 0.0989(3) 0.0256(9) Uani 1 d .
H16A H 0.0612(5) 0.4249(5) 0.0777(3) 0.080 Uiso 1 d R
C17 C 0.1485(7) 0.2413(6) 0.0292(4) 0.0351(12) Uani 1 d .
H17A H 0.1862(7) 0.2844(6) -0.0300(4) 0.080 Uiso 1 d R
H17B H 0.2149(7) 0.1564(6) 0.0503(4) 0.080 Uiso 1 d R
H17C H 0.0556(7) 0.2197(6) 0.0233(4) 0.080 Uiso 1 d R
C18 C 0.2761(6) 0.3901(7) 0.1021(4) 0.0370(12) Uani 1 d .
H18A H 0.3083(6) 0.4316(7) 0.0410(4) 0.080 Uiso 1 d R
H18B H 0.2634(6) 0.4575(7) 0.1435(4) 0.080 Uiso 1 d R
H18C H 0.3477(6) 0.3095(7) 0.1237(4) 0.080 Uiso 1 d R
C21 C -0.0541(6) -0.0956(6) 0.3836(4) 0.0385(13) Uani 1 d .
H21A H -0.1246(6) -0.1472(6) 0.3725(4) 0.080 Uiso 1 d R
H21B H 0.0072(6) -0.1515(6) 0.4298(4) 0.080 Uiso 1 d R
H21C H -0.1035(6) -0.0102(6) 0.4051(4) 0.080 Uiso 1 d R
C22 C 0.0371(5) -0.0622(5) 0.2974(3) 0.0246(9) Uani 1 d .
C23 C 0.0808(5) -0.0657(5) 0.2130(3) 0.0232(9) Uani 1 d .
C24 C 0.0665(7) -0.1114(6) 0.1248(4) 0.0348(12) Uani 1 d .
H24A H -0.0114(7) -0.1628(6) 0.1334(4) 0.080 Uiso 1 d R
H24B H 0.0456(7) -0.0311(6) 0.0773(4) 0.080 Uiso 1 d R
H24C H 0.1560(7) -0.1709(6) 0.1068(4) 0.080 Uiso 1 d R
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'
P P 0.1023 0.0942 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C22 Ir C23 35.0(2)
C22 Ir P1 93.47(14)
C23 Ir P1 90.98(13)
C22 Ir P2 94.44(14)
C23 Ir P2 91.16(13)
P1 Ir P2 169.04(4)
C22 Ir Cl 152.21(14)
C23 Ir Cl 172.81(14)
P1 Ir Cl 88.23(5)
P2 Ir Cl 88.30(5)
C13 P1 C10 109.0(2)
C13 P1 C16 102.2(2)
C10 P1 C16 102.5(2)
C13 P1 Ir 114.4(2)
C10 P1 Ir 116.3(2)
C16 P1 Ir 110.9(2)
C3 C1 C2 109.9(5)
C3 C1 P2 110.1(3)
C2 C1 P2 114.4(4)
C5 C4 C6 109.5(5)
C5 C4 P2 112.4(4)
C6 C4 P2 116.6(4)
C8 C7 C9 110.8(4)
C8 C7 P2 112.2(3)
C9 C7 P2 117.4(4)
C7 P2 C1 104.3(2)
C7 P2 C4 108.5(2)
C1 P2 C4 101.6(2)
C7 P2 Ir 113.2(2)
C1 P2 Ir 110.5(2)
C4 P2 Ir 117.3(2)
C11 C10 C12 109.0(5)
C11 C10 P1 111.2(4)
C12 C10 P1 118.0(4)
C15 C13 C14 111.8(5)
C15 C13 P1 116.3(4)
C14 C13 P1 112.5(3)
C17 C16 C18 110.3(5)
C17 C16 P1 109.8(3)
C18 C16 P1 113.5(3)
C23 C22 C21 154.8(5)
C23 C22 Ir 73.4(3)
C21 C22 Ir 131.8(4)
C22 C23 C24 148.8(5)
C22 C23 Ir 71.7(3)
C24 C23 Ir 139.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ir C22 2.097(4)
Ir C23 2.117(4)
Ir P1 2.3374(14)
Ir P2 2.3418(14)
Ir Cl 2.3589(13)
P1 C13 1.857(5)
P1 C10 1.867(5)
P1 C16 1.869(5)
C1 C3 1.526(8)
C1 C2 1.532(7)
C1 P2 1.862(5)
C4 C5 1.526(8)
C4 C6 1.530(7)
C4 P2 1.869(5)
C7 C8 1.526(7)
C7 C9 1.534(7)
C7 P2 1.851(5)
C10 C11 1.527(8)
C10 C12 1.528(7)
C13 C15 1.525(7)
C13 C14 1.532(7)
C16 C17 1.527(7)
C16 C18 1.542(7)
C21 C22 1.472(7)
C22 C23 1.266(7)
C23 C24 1.475(7)
