Iridium complexes catalysed the selective dehydrogenation of glucose to gluconic acid in water
Borja, Pilar; Vicent, Cristian; Baya, Miguel; García, Hermenegildo; Mata, Jose A.; Green Chemistry 20 (2018) 4094–; doi:10.1039/C8GC01933A

data_7231347
_publ_section_title
;
 Iridium complexes catalysed the selective dehydrogenation of glucose to
 gluconic acid in water
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              4094
_journal_paper_doi               10.1039/C8GC01933A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C22 H27 Ir N2 O2'
_chemical_formula_sum            'C22 H27 Ir N2 O2'
_chemical_formula_weight         543.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_date             2018-06-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-06-19 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                78.655(2)
_cell_angle_beta                 82.445(2)
_cell_angle_gamma                67.017(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5920(2)
_cell_length_b                   10.2464(3)
_cell_length_c                   12.6648(3)
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1100
_cell_measurement_theta_min      2.9590
_cell_volume                     1004.56(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0655
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -49.00  52.00   1.00   12.50    --  -18.55  77.00-150.00  101
  2  \w    -49.00  52.00   1.00   12.50    --  -18.55  77.00  90.00  101
  3  \w     -9.00  91.00   1.00   12.50    --   20.66  77.00  90.00  100
  4  \w     -9.00  91.00   1.00   12.50    --   20.66  77.00-180.00  100
  5  \w     -9.00  91.00   1.00   12.50    --   20.66  77.00 -30.00  100
  6  \w    -95.00 -66.00   1.00   12.50    --  -18.55-179.00  60.00   29
  7  \w     -1.00  89.00   1.00   12.50    --   20.66  57.00 -90.00   90
  8  \w    -25.00  63.00   1.00   12.50    --   20.66 -99.00 -30.00   88
  9  \w    -25.00  63.00   1.00   12.50    --   20.66 -99.00  60.00   88
 10  \w     34.00  97.00   1.00   12.50    --   20.66 179.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0862885000
_diffrn_orient_matrix_UB_12      -0.0160216000
_diffrn_orient_matrix_UB_13      0.0075320000
_diffrn_orient_matrix_UB_21      0.0199284000
_diffrn_orient_matrix_UB_22      -0.0030977000
_diffrn_orient_matrix_UB_23      -0.0558344000
_diffrn_orient_matrix_UB_31      -0.0150872000
_diffrn_orient_matrix_UB_32      0.0743967000
_diffrn_orient_matrix_UB_33      -0.0100360000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18137
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.684
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_description       prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.750
_refine_diff_density_min         -3.666
_refine_diff_density_rms         0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4599
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.4322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4030
_reflns_number_total             4599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc01933a3.cif
_cod_data_source_block           mp-325
_cod_depositor_comments
'Adding full bibliography for 7231346--7231348.cif.'
_cod_original_cell_volume        1004.57(5)
_cod_database_code               7231347
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C22H28IrN2O2
_chemical_oxdiff_usercomment     'CH2Cl2 hexano'
_shelx_estimated_absorpt_t_max   0.618
_shelx_estimated_absorpt_t_min   0.502
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21-C26 \\sim C27-C20
 with sigma of 0.02
 C21-C23 \\sim C27-C22
 with sigma of 0.02
 C21-C29 \\sim C27-C28
 with sigma of 0.02
 C24-C25 \\sim C18-C19
 with sigma of 0.02
 C24-C23 \\sim C18-C22
 with sigma of 0.02
 C24-C33 \\sim C18-C32
 with sigma of 0.02
 C25-C26 \\sim C19-C20
 with sigma of 0.02
 C25-C35 \\sim C19-C34
 with sigma of 0.02
 C26-C3 \\sim C20-C36
 with sigma of 0.02
 C23-C31 \\sim C22-C30
 with sigma of 0.02
 Ir1-C21 \\sim Ir1-C27
 with sigma of 0.04
 Ir1-C24 \\sim Ir1-C18
 with sigma of 0.04
 Ir1-C25 \\sim Ir1-C19
 with sigma of 0.04
 Ir1-C26 \\sim Ir1-C20
 with sigma of 0.04
 Ir1-C23 \\sim Ir1-C22
 with sigma of 0.04
 Ir1-C35 \\sim Ir1-C34
 with sigma of 0.04
 Ir1-C3 \\sim Ir1-C36
 with sigma of 0.04
 Ir1-C29 \\sim Ir1-C28
 with sigma of 0.04
 Ir1-C33 \\sim Ir1-C32
 with sigma of 0.04
 Ir1-C31 \\sim Ir1-C30
 with sigma of 0.04
 C21-C24 \\sim C27-C18
 with sigma of 0.04
 C21-C25 \\sim C27-C19
 with sigma of 0.04
 C21-C3 \\sim C27-C36
 with sigma of 0.04
 C21-C31 \\sim C27-C30
 with sigma of 0.04
 C24-C26 \\sim C18-C20
 with sigma of 0.04
 C24-C35 \\sim C18-C34
 with sigma of 0.04
 C24-C31 \\sim C18-C30
 with sigma of 0.04
 C25-C23 \\sim C19-C22
 with sigma of 0.04
 C25-C3 \\sim C19-C36
 with sigma of 0.04
 C25-C33 \\sim C19-C32
 with sigma of 0.04
 C26-C23 \\sim C20-C22
 with sigma of 0.04
 C26-C35 \\sim C20-C34
 with sigma of 0.04
 C26-C29 \\sim C20-C28
 with sigma of 0.04
 C23-C29 \\sim C22-C28
 with sigma of 0.04
 C23-C33 \\sim C22-C32
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=Sof(C20)=Sof(C27)=Sof(C28)=Sof(H28A)=
 Sof(H28B)=Sof(H28C)=Sof(C22)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C32)=
 Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C18)=Sof(C19)=Sof(C34)=Sof(H34A)=Sof(H34B)=
 Sof(H34C)=1-FVAR(1)
 Sof(C21)=Sof(C24)=Sof(C25)=Sof(C26)=Sof(C23)=Sof(C35)=Sof(H35A)=Sof(H35B)=
 Sof(H35C)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C29)=Sof(H29A)=Sof(H29B)=
 Sof(H29C)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C31)=Sof(H31A)=Sof(H31B)=
 Sof(H31C)=FVAR(1)
5.a Me refined with riding coordinates:
 C31(H31A,H31B,H31C)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C8(H8), C14(H14), C9(H9), C11(H11), C10(H10)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C35(H35A,H35B,H35C), C3(H3A,H3B,
 H3C), C29(H29A,H29B,H29C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C28(H28A,
 H28B,H28C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              98165
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.504
_oxdiff_exptl_absorpt_empirical_full_min 0.630