#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:58:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178708 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/19/4081908.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_4081908
loop_
_publ_author_name
'Nguyen, Duc Hanh'
'Pérez-Torrente, Jesús J.'
'Jiménez, M. Victoria'
'Modrego, F. Javier'
'Gómez-Bautista, Daniel'
'Lahoz, Fernando J.'
'Oro, Luis A.'
_publ_section_title
;
 Unsaturated Iridium(III) Complexes Supported by a Quinolato--Carboxylato
 ONO Pincer-Type Ligand: Synthesis, Reactivity, and Catalytic C--H
 Functionalization
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6918
_journal_paper_doi               10.1021/om400768n
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C20 H16 Ir N3 O3, H2 O'
_chemical_formula_sum            'C20 H18 Ir N3 O4'
_chemical_formula_weight         556.60
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 90.6360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3967(9)
_cell_length_b                   15.3084(17)
_cell_length_c                   14.1731(16)
_cell_measurement_reflns_used    3374
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.906
_cell_measurement_theta_min      2.661
_cell_volume                     1821.7(3)
_computing_cell_refinement       'APEX2 v. 2009.7 (Bruker AXS, 2008)'
_computing_data_collection       'APEX2 v. 2009.7 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 v. 2009.7 (Bruker AXS, 2008)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART APEX CCD system'
_diffrn_measurement_method       'ω rotations with narrow frames'
_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  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20909
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    7.362
_exptl_absorpt_correction_T_max  0.7202
_exptl_absorpt_correction_T_min  0.6262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Multi-scan correction included in APEX2 package (Bruker AXS, 2008)
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.073
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.045
_refine_diff_density_max         2.693
_refine_diff_density_min         -1.395
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0254P)²+5.7120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0819
_reflns_d_resolution_high        0.7602
_reflns_number_gt                3397
_reflns_number_total             4241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400768n_si_002.cif
_cod_data_source_block           compnd_6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      'P 21/n'
_cod_database_code               4081908
#BEGIN Tags that were not found in dictionaries:
_shelx_title                     ' fjl236am in P2(1)/n'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            610.76
_shelx_f_squared_multiplier      1.000
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Ir1 Ir 0.07047(3) 0.207445(17) 0.171330(17) 0.01850(8) Uani 1 1 d D
N3 N -0.1574(6) 0.2140(4) 0.0977(4) 0.0199(11) Uani 1 1 d .
N2 N 0.0611(6) 0.3406(4) 0.1824(4) 0.0228(12) Uani 1 1 d .
N1 N 0.0809(7) 0.0802(4) 0.1633(4) 0.0232(12) Uani 1 1 d .
O1 O 0.1780(5) 0.1906(3) 0.0397(3) 0.0234(10) Uani 1 1 d .
O2 O 0.2624(6) 0.0844(3) -0.0564(3) 0.0319(12) Uani 1 1 d .
O3 O -0.0445(5) 0.1773(3) 0.2969(3) 0.0220(10) Uani 1 1 d .
C20 C -0.2893(8) 0.1752(5) 0.1309(5) 0.0249(15) Uani 1 1 d .
C19 C -0.4344(9) 0.1787(5) 0.0847(5) 0.0322(17) Uani 1 1 d .
C18 C -0.4448(9) 0.2241(5) 0.0006(5) 0.0294(17) Uani 1 1 d .
C17 C -0.3109(9) 0.2635(5) -0.0349(5) 0.0244(15) Uani 1 1 d .
C16 C -0.1691(8) 0.2567(4) 0.0156(5) 0.0191(13) Uani 1 1 d .
C15 C -0.0212(9) 0.3811(5) 0.2511(5) 0.0301(16) Uani 1 1 d .
C14 C -0.0340(9) 0.4699(5) 0.2589(6) 0.0318(17) Uani 1 1 d .
C13 C 0.0389(10) 0.5217(5) 0.1929(6) 0.0344(19) Uani 1 1 d .
C12 C 0.1248(10) 0.4839(5) 0.1223(6) 0.039(2) Uani 1 1 d .
C11 C 0.1336(9) 0.3939(5) 0.1184(5) 0.0313(18) Uani 1 1 d .
C1 C 0.2018(8) 0.1081(5) 0.0173(5) 0.0245(15) Uani 1 1 d .
C2 C 0.1474(8) 0.0427(5) 0.0896(5) 0.0244(15) Uani 1 1 d .
C3 C 0.1600(9) -0.0485(5) 0.0876(6) 0.0308(17) Uani 1 1 d .
C4 C 0.1022(9) -0.0971(5) 0.1616(6) 0.0325(18) Uani 1 1 d .
C5 C 0.0285(8) -0.0540(5) 0.2388(5) 0.0268(16) Uani 1 1 d .
C6 C -0.0359(10) -0.0959(5) 0.3184(6) 0.0343(19) Uani 1 1 d .
C7 C -0.0973(10) -0.0451(5) 0.3887(6) 0.0351(18) Uani 1 1 d .
C8 C -0.1012(9) 0.0463(5) 0.3859(5) 0.0305(17) Uani 1 1 d .
C9 C -0.0421(8) 0.0895(5) 0.3088(5) 0.0236(15) Uani 1 1 d .
C10 C 0.0222(8) 0.0369(4) 0.2367(5) 0.0215(14) Uani 1 1 d .
O4 O 0.1416(7) 0.2801(4) -0.1392(5) 0.0443(15) Uani 1 1 d .
H H 0.245(4) 0.207(5) 0.222(5) 0.04(2) Uiso 1 1 d D
H20 H -0.273(9) 0.143(5) 0.194(6) 0.051 Uiso 1 1 d .
H19 H -0.522(10) 0.155(5) 0.115(6) 0.051 Uiso 1 1 d .
H18 H -0.536(10) 0.229(5) -0.031(6) 0.051 Uiso 1 1 d .
H17 H -0.316(10) 0.290(5) -0.098(6) 0.051 Uiso 1 1 d .
H16 H -0.077(10) 0.284(5) -0.006(6) 0.051 Uiso 1 1 d .
H15 H -0.080(10) 0.342(6) 0.290(6) 0.051 Uiso 1 1 d .
H14 H -0.098(10) 0.495(6) 0.306(6) 0.051 Uiso 1 1 d .
H13 H 0.020(10) 0.575(6) 0.198(6) 0.051 Uiso 1 1 d .
H12 H 0.156(10) 0.516(5) 0.070(6) 0.051 Uiso 1 1 d .
H11 H 0.191(10) 0.360(5) 0.071(6) 0.051 Uiso 1 1 d .
H3 H 0.206(10) -0.072(5) 0.035(6) 0.051 Uiso 1 1 d .
H4 H 0.098(10) -0.162(6) 0.159(6) 0.051 Uiso 1 1 d .
H6 H -0.025(10) -0.160(6) 0.322(6) 0.051 Uiso 1 1 d .
H7 H -0.135(10) -0.074(5) 0.444(6) 0.051 Uiso 1 1 d .
H8 H -0.147(10) 0.080(5) 0.426(6) 0.051 Uiso 1 1 d .
H41 H 0.257(15) 0.286(8) -0.164(8) 0.11(4) Uiso 1 1 d .
H42 H 0.143(9) 0.240(5) -0.093(6) 0.04(2) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4440 7.9890 '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
N1 Ir1 N2 178.9(2)
N1 Ir1 O3 81.4(2)
N2 Ir1 O3 97.8(2)
N1 Ir1 O1 78.8(2)
N2 Ir1 O1 102.0(2)
O3 Ir1 O1 160.00(18)
N1 Ir1 N3 93.3(2)
N2 Ir1 N3 87.5(2)
O3 Ir1 N3 90.37(18)
O1 Ir1 N3 87.93(18)
N1 Ir1 H 89(3)
N2 Ir1 H 90(3)
O3 Ir1 H 92(3)
O1 Ir1 H 90(3)
N3 Ir1 H 177(3)
C16 N3 C20 117.9(6)
C16 N3 Ir1 119.7(4)
C20 N3 Ir1 122.4(4)
C15 N2 C11 116.0(6)
C15 N2 Ir1 122.2(5)
C11 N2 Ir1 121.8(5)
C2 N1 C10 124.4(6)
C2 N1 Ir1 119.9(5)
C10 N1 Ir1 115.7(5)
C1 O1 Ir1 113.6(4)
C9 O3 Ir1 108.6(4)
N3 C20 C19 122.9(7)
N3 C20 H20 114(5)
C19 C20 H20 123(5)
C20 C19 C18 118.4(7)
C20 C19 H19 118(5)
C18 C19 H19 123(5)
C17 C18 C19 119.5(7)
C17 C18 H18 119(6)
C19 C18 H18 122(6)
C18 C17 C16 118.6(7)
C18 C17 H17 119(5)
C16 C17 H17 122(5)
N3 C16 C17 122.7(6)
N3 C16 H16 117(5)
C17 C16 H16 120(5)
N2 C15 C14 123.7(7)
N2 C15 H15 114(5)
C14 C15 H15 122(5)
C15 C14 C13 118.8(7)
C15 C14 H14 121(5)
C13 C14 H14 120(5)
C12 C13 C14 119.8(7)
C12 C13 H13 125(6)
C14 C13 H13 115(6)
C13 C12 C11 118.6(7)
C13 C12 H12 121(5)
C11 C12 H12 118(5)
N2 C11 C12 123.0(7)
N2 C11 H11 111(5)
C12 C11 H11 126(5)
O2 C1 O1 123.7(6)
O2 C1 C2 121.1(6)
O1 C1 C2 115.1(6)
N1 C2 C3 118.8(7)
N1 C2 C1 112.5(6)
C3 C2 C1 128.6(6)
C4 C3 C2 119.7(7)
C4 C3 H3 125(5)
C2 C3 H3 116(5)
C3 C4 C5 119.6(7)
C3 C4 H4 122(5)
C5 C4 H4 118(5)
C10 C5 C6 117.2(7)
C10 C5 C4 117.6(7)
C6 C5 C4 125.2(7)
C7 C6 C5 118.3(7)
C7 C6 H6 124(5)
C5 C6 H6 117(5)
C6 C7 C8 123.8(7)
C6 C7 H7 118(5)
C8 C7 H7 118(5)
C9 C8 C7 119.6(7)
C9 C8 H8 114(6)
C7 C8 H8 126(6)
O3 C9 C8 124.8(6)
O3 C9 C10 118.7(6)
C8 C9 C10 116.4(7)
N1 C10 C5 120.0(6)
N1 C10 C9 115.4(6)
C5 C10 C9 124.6(6)
H41 O4 H42 108(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ir1 N1 1.954(6)
Ir1 N2 2.045(6)
Ir1 O3 2.086(4)
Ir1 O1 2.098(4)
Ir1 N3 2.172(5)
Ir1 H 1.62(2)
N3 C16 1.338(8)
N3 C20 1.345(8)
N2 C15 1.352(9)
N2 C11 1.368(9)
N1 C2 1.322(8)
N1 C10 1.332(8)
O1 C1 1.319(8)
O2 C1 1.221(8)
O3 C9 1.355(8)
C20 C19 1.378(10)
C20 H20 1.03(8)
C19 C18 1.382(11)
C19 H19 0.93(8)
C18 C17 1.376(10)
C18 H18 0.89(8)
C17 C16 1.387(9)
C17 H17 0.98(8)
C16 H16 0.93(8)
C15 C14 1.368(10)
C15 H15 0.95(8)
C14 C13 1.374(10)
C14 H14 0.94(8)
C13 C12 1.369(11)
C13 H13 0.83(8)
C12 C11 1.380(11)
C12 H12 0.93(8)
C11 H11 0.98(8)
C1 C2 1.508(9)
C2 C3 1.400(10)
C3 C4 1.380(11)
C3 H3 0.92(8)
C4 C5 1.425(10)
C4 H4 0.99(9)
C5 C10 1.393(9)
C5 C6 1.410(10)
C6 C7 1.369(11)
C6 H6 0.98(9)
C7 C8 1.400(11)
C7 H7 0.96(8)
C8 C9 1.375(10)
C8 H8 0.86(8)
C9 C10 1.413(9)
O4 H41 1.04(13)
O4 H42 0.89(8)
