Development and mechanistic investigation of the dehydrogenation of alcohols with an iron(III) salen catalyst.
Hansen, Nicolai S. B.; Monda, Fabrizio; Bro, Frederik Simonsen; Liu, Xiyue; Ahlquist, Mårten S G; Madsen, Robert; Organic & biomolecular chemistry 21 (2023) 4794–4800; doi:10.1039/d3ob00466j

data_7159367
_publ_section_title
;
 Development and mechanistic investigation of the dehydrogenation of
 alcohols with an iron(III) salen catalyst.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4794
_journal_page_last               4800
_journal_paper_doi               10.1039/d3ob00466j
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H20 Cl Fe N2 O2'
_chemical_formula_sum            'C20 H20 Cl Fe N2 O2'
_chemical_formula_weight         411.68
_chemical_name_systematic
'(1R,2R)-N,N?-Bis(salicylidene)-1,2-cyclohexanediaminoiron(III) chloride'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-09 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.3420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.63690(10)
_cell_length_b                   15.1727(2)
_cell_length_c                   13.7486(2)
_cell_measurement_reflns_used    7625
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.2030
_cell_measurement_theta_min      5.1430
_cell_volume                     1800.18(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3073
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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   -113.00 -13.00   1.00    4.46    --  -40.81 -54.00 166.00  100
  2  \w    -10.00  31.00   1.00    4.46    --  -40.81  54.00 -49.00   41
  3  \w    -52.00 -13.00   1.00    4.46    --  -40.81  54.00 -49.00   39
  4  \w     63.00  92.00   1.00    4.46    --   40.81  54.00 -49.00   29
  5  \w     68.00 124.00   1.00   17.82    --  112.00 -54.00 166.00   56
  6  \w    114.00 178.00   1.00   17.82    --  112.00  54.00 -49.00   64
  7  \w     35.00  96.00   1.00    4.46    --   40.81-125.00-180.00   61
  8  \w     -6.00  19.00   1.00    4.46    --   40.81 -54.00 166.00   25
  9  \w      9.00  79.00   1.00    4.46    --   40.81 -99.00   0.00   70
 10  \w     37.00  63.00   1.00   17.82    --  112.00-111.00-180.00   26
 11  \w     36.00  98.00   1.00   17.82    --  112.00 -95.00  90.00   62
 12  \w     39.00 104.00   1.00   17.82    --  112.00 -95.00-150.00   65
 13  \w    105.00 178.00   1.00   17.82    --  112.00  77.00-120.00   73
 14  \w    140.00 166.00   1.00   17.82    --  112.00  30.00  90.00   26
 15  \w     94.00 120.00   1.00   17.82    --  112.00 -77.00 -30.00   26
 16  \w     38.00  68.00   1.00   17.82    --  112.00 -30.00-120.00   30
 17  \w     81.00 139.00   1.00   17.82    --  112.00 -30.00-120.00   58
 18  \w     60.00  86.00   1.00   17.82    --  112.00  15.00 -90.00   26
 19  \w    108.00 134.00   1.00   17.82    --  112.00  15.00 -90.00   26
 20  \w     39.00  64.00   1.00   17.82    --  112.00 -77.00 -30.00   25
 21  \w     84.00 135.00   1.00   17.82    --  112.00  30.00  90.00   51
 22  \w     74.00 107.00   1.00   17.82    --  112.00-111.00-180.00   33
 23  \w     56.00  89.00   1.00   17.82    --  112.00-111.00  30.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1615121000
_diffrn_orient_matrix_UB_12      0.0347400000
_diffrn_orient_matrix_UB_13      -0.0245332000
_diffrn_orient_matrix_UB_21      -0.0737632000
_diffrn_orient_matrix_UB_22      0.0556140000
_diffrn_orient_matrix_UB_23      -0.0834968000
_diffrn_orient_matrix_UB_31      -0.0194442000
_diffrn_orient_matrix_UB_32      0.0774706000
_diffrn_orient_matrix_UB_33      0.0707015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11090
_diffrn_reflns_point_group_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.414
_diffrn_reflns_theta_min         4.342
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.223
_exptl_absorpt_correction_T_max  0.734
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'reddish black'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.005(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5912
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+0.0082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_full    0.605
_reflns_Friedel_fraction_max     0.562
_reflns_number_gt                5730
_reflns_number_total             5912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00466j2.cif
_cod_data_source_block           xl_fe_salen
_cod_depositor_comments          'Adding full bibliography for 7159367.cif.'
_cod_database_code               7159367
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Fe C20 H18 N2 O2 Cl'
_shelx_estimated_absorpt_t_max   0.651
_shelx_estimated_absorpt_t_min   0.528
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20B(H20B), C15B(H15B), C15A(H15A), C20A(H20A)
2.b Secondary CH2 refined with riding coordinates:
 C19B(H19c,H19d), C17B(H17c,H17d), C19A(H19a,H19b), C18B(H18c,H18d), C16A(H16a,
 H16b), C16B(H16c,H16d), C17A(H17a,H17b), C18A(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C14A(H14A), C9B(H9B), C12A(H12A), C10A(H10A), C2B(H2B), C7A(H7A), C9A(H9A),
 C5A(H5A), C11A(H11A), C3B(H3B), C10B(H10B), C3A(H3A), C14B(H14B), C7B(H7B),
 C2A(H2A), C4A(H4A), C11B(H11B), C4B(H4B), C5B(H5B), C12B(H12B)
;
_shelx_res_checksum              35107
_olex2_date_sample_data_collection 2023-05-03
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.727
_oxdiff_exptl_absorpt_empirical_full_min 0.772