#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:37:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180088 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/34/7053437.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_7053437
loop_
_publ_author_name
'Beyer, Beatrice'
'Ulbricht, Christoph'
'Winter, Andreas'
'Hager, Martin D.'
'Hoogenboom, Richard'
'Herzer, Nicole'
'Baumann, Stefan O.'
'Kickelbick, Guido'
'Görls, Helmar'
'Schubert, Ulrich S.'
_publ_section_title
;
 Unexpected metal-mediated oxidation of hydroxymethyl groups to
 coordinated carboxylate groups by bis-cyclometalated iridium(iii) centers
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2622
_journal_paper_doi               10.1039/b9nj00785g
_journal_volume                  34
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H15 N3'
_chemical_formula_sum            'C16 H15 N3'
_chemical_formula_weight         249.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   10.983(2)
_cell_length_b                   10.056(2)
_cell_length_c                   12.375(3)
_cell_measurement_reflns_used    5376
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.605
_cell_measurement_theta_min      2.61
_cell_volume                     1366.8(5)
_computing_cell_refinement       'Bruker-AXS APEX 2 Software'
_computing_data_collection       'Bruker-AXS APEX 2 Software'
_computing_data_reduction        'Bruker-AXS APEX 2 Software'
_computing_molecular_graphics    'Bruker-AXS SHELXTL Software'
_computing_publication_material  'Bruker-AXS SHELXTL Software'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker-AXS KAPPA APEX II CCD Detector'
_diffrn_measurement_method       omega-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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19525
_diffrn_reflns_theta_full        29.31
_diffrn_reflns_theta_max         29.31
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0351
_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)+(0.0534P)²+0.0796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                1532
_reflns_number_total             1953
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b9nj00785g.txt
_cod_data_source_block           sb055
_cod_original_cell_volume        1366.7(5)
_cod_database_code               7053437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
N1 N 0.55904(13) 0.21284(17) 0.47020(13) 0.0482(4) Uani 1 1 d .
N2 N 0.67456(16) 0.2510(2) 0.49036(16) 0.0658(5) Uani 1 1 d .
N3 N 0.67912(16) 0.2930(2) 0.58995(17) 0.0648(5) Uani 1 1 d .
C4 C 0.56658(16) 0.28253(19) 0.63508(16) 0.0486(4) Uani 1 1 d .
C5 C 0.49024(16) 0.23223(19) 0.55920(16) 0.0473(4) Uani 1 1 d .
H5 H 0.4075 0.2147 0.5669 0.057 Uiso 1 1 calc R
C6 C 0.52619(18) 0.16412(19) 0.36596(16) 0.0474(4) Uani 1 1 d .
C7 C 0.40986(18) 0.1165(2) 0.34680(17) 0.0534(5) Uani 1 1 d .
H7 H 0.3531 0.1141 0.4026 0.064 Uiso 1 1 calc R
C8 C 0.37790(19) 0.0723(2) 0.2442(2) 0.0583(5) Uani 1 1 d .
C9 C 0.4632(2) 0.0784(2) 0.16256(19) 0.0615(5) Uani 1 1 d .
H9 H 0.4412 0.0512 0.0934 0.074 Uiso 1 1 calc R
C10 C 0.5807(2) 0.1240(2) 0.18050(18) 0.0583(5) Uani 1 1 d .
C11 C 0.6125(2) 0.1667(2) 0.28365(18) 0.0544(5) Uani 1 1 d .
H11 H 0.6910 0.1969 0.2975 0.065 Uiso 1 1 calc R
C12 C 0.2523(2) 0.0164(3) 0.2241(3) 0.0830(8) Uani 1 1 d .
H12A H 0.2299 0.0312 0.1500 0.125 Uiso 1 1 calc R
H12B H 0.1947 0.0597 0.2706 0.125 Uiso 1 1 calc R
H12C H 0.2524 -0.0774 0.2387 0.125 Uiso 1 1 calc R
C13 C 0.6745(3) 0.1278(3) 0.0914(2) 0.0795(7) Uani 1 1 d .
H13A H 0.7321 0.1974 0.1057 0.119 Uiso 1 1 calc R
H13B H 0.6349 0.1445 0.0236 0.119 Uiso 1 1 calc R
H13C H 0.7162 0.0440 0.0882 0.119 Uiso 1 1 calc R
C14 C 0.54370(18) 0.3210(2) 0.74821(17) 0.0529(5) Uani 1 1 d .
C15 C 0.6122(2) 0.4188(3) 0.7981(2) 0.0733(6) Uani 1 1 d .
H15 H 0.6754 0.4594 0.7605 0.088 Uiso 1 1 calc R
C16 C 0.5877(3) 0.4569(4) 0.9033(3) 0.0901(9) Uani 1 1 d .
H16 H 0.6340 0.5232 0.9358 0.108 Uiso 1 1 calc R
C17 C 0.4956(3) 0.3970(4) 0.9595(2) 0.0907(9) Uani 1 1 d .
H17 H 0.4782 0.4237 1.0298 0.109 Uiso 1 1 calc R
C18 C 0.4293(3) 0.2983(3) 0.9125(2) 0.0846(8) Uani 1 1 d .
H18 H 0.3682 0.2562 0.9517 0.101 Uiso 1 1 calc R
C19 C 0.4518(2) 0.2595(3) 0.80638(19) 0.0653(6) Uani 1 1 d .
H19 H 0.4054 0.1927 0.7747 0.078 Uiso 1 1 calc 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 0.0000 '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 0.0000 '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
N2 N1 C5 109.55(17)
N2 N1 C6 120.19(15)
C5 N1 C6 130.24(16)
N3 N2 N1 107.64(17)
N2 N3 C4 109.17(19)
C5 C4 N3 107.82(18)
C5 C4 C14 130.53(17)
N3 C4 C14 121.64(18)
N1 C5 C4 105.82(15)
N1 C5 H5 127.1
C4 C5 H5 127.1
C7 C6 C11 120.6(2)
C7 C6 N1 120.46(16)
C11 C6 N1 118.91(17)
C6 C7 C8 119.99(18)
C6 C7 H7 120.0
C8 C7 H7 120.0
C9 C8 C7 118.90(19)
C9 C8 C12 121.1(2)
C7 C8 C12 120.0(2)
C8 C9 C10 122.0(2)
C8 C9 H9 119.0
C10 C9 H9 119.0
C9 C10 C11 118.83(19)
C9 C10 C13 121.8(2)
C11 C10 C13 119.4(2)
C6 C11 C10 119.7(2)
C6 C11 H11 120.2
C10 C11 H11 120.2
C8 C12 H12A 109.5
C8 C12 H12B 109.5
H12A C12 H12B 109.5
C8 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C15 C14 C19 118.8(2)
C15 C14 C4 121.2(2)
C19 C14 C4 120.0(2)
C16 C15 C14 120.7(3)
C16 C15 H15 119.6
C14 C15 H15 119.6
C17 C16 C15 120.0(3)
C17 C16 H16 120.0
C15 C16 H16 120.0
C18 C17 C16 119.9(3)
C18 C17 H17 120.0
C16 C17 H17 120.0
C17 C18 C19 120.8(3)
C17 C18 H18 119.6
C19 C18 H18 119.6
C14 C19 C18 119.6(3)
C14 C19 H19 120.2
C18 C19 H19 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.349(2)
N1 C5 1.350(2)
N1 C6 1.426(3)
N2 N3 1.304(3)
N3 C4 1.360(2)
C4 C5 1.357(3)
C4 C14 1.474(3)
C5 H5 0.9300
C6 C7 1.385(3)
C6 C11 1.391(3)
C7 C8 1.390(3)
C7 H7 0.9300
C8 C9 1.379(3)
C8 C12 1.510(3)
C9 C10 1.388(3)
C9 H9 0.9300
C10 C11 1.391(3)
C10 C13 1.510(3)
C11 H11 0.9300
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.383(3)
C14 C19 1.386(3)
C15 C16 1.383(4)
C15 H15 0.9300
C16 C17 1.368(5)
C16 H16 0.9300
C17 C18 1.362(5)
C17 H17 0.9300
C18 C19 1.391(4)
C18 H18 0.9300
C19 H19 0.9300
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
C5 N1 N2 N3 0.3(3)
C6 N1 N2 N3 178.94(19)
N1 N2 N3 C4 -0.1(3)
N2 N3 C4 C5 -0.1(3)
N2 N3 C4 C14 179.2(2)
N2 N1 C5 C4 -0.4(2)
C6 N1 C5 C4 -178.83(17)
N3 C4 C5 N1 0.3(2)
C14 C4 C5 N1 -178.91(18)
N2 N1 C6 C7 175.69(19)
C5 N1 C6 C7 -6.0(3)
N2 N1 C6 C11 -5.1(3)
C5 N1 C6 C11 173.21(18)
C11 C6 C7 C8 -0.8(3)
N1 C6 C7 C8 178.44(19)
C6 C7 C8 C9 -0.8(3)
C6 C7 C8 C12 178.1(2)
C7 C8 C9 C10 1.8(3)
C12 C8 C9 C10 -177.1(2)
C8 C9 C10 C11 -1.1(3)
C8 C9 C10 C13 178.7(2)
C7 C6 C11 C10 1.5(3)
N1 C6 C11 C10 -177.71(18)
C9 C10 C11 C6 -0.6(3)
C13 C10 C11 C6 179.7(2)
C5 C4 C14 C15 -151.9(2)
N3 C4 C14 C15 29.0(3)
C5 C4 C14 C19 27.8(3)
N3 C4 C14 C19 -151.4(2)
C19 C14 C15 C16 -1.5(4)
C4 C14 C15 C16 178.2(2)
C14 C15 C16 C17 0.5(5)
C15 C16 C17 C18 1.1(5)
C16 C17 C18 C19 -1.8(5)
C15 C14 C19 C18 0.9(3)
C4 C14 C19 C18 -178.8(2)
C17 C18 C19 C14 0.7(4)
