Deoxydehydration of vicinal diols and polyols catalyzed by pyridinium perrhenate salts
Morris, Danny S.; van Rees, Karlotta; Curcio, Massimiliano; Cokoja, Mirza; Kühn, Fritz E.; Duarte, Fernanda; Love, Jason B.; Catal. Sci. Technol.  (2017) –; doi:10.1039/C7CY01728F

data_1547797
_publ_section_title
;
 Deoxydehydration of vicinal diols and polyols catalyzed by pyridinium
 perrhenate salts
;
_journal_name_full               'Catal. Sci. Technol.'
_journal_paper_doi               10.1039/C7CY01728F
_journal_year                    2017
_chemical_formula_moiety         'O4 Re, C14 H24 N'
_chemical_formula_sum            'C14 H24 N O4 Re'
_chemical_formula_weight         456.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-08-14 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.016(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9052(2)
_cell_length_b                   8.43840(10)
_cell_length_c                   10.9159(2)
_cell_measurement_reflns_used    6060
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      29.9520
_cell_measurement_theta_min      3.8000
_cell_volume                     820.28(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1042
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -88.00   10.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6840  -77.0000  -90.0000 98

  2 omega    2.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4027   57.0000    0.0000 87

  3 omega  -48.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4027  -57.0000  -90.0000 87

  4 omega  -25.00   61.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4027  -99.0000   60.0000 86

  5 omega  -87.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6840  -57.0000  150.0000 87

  6 omega  -93.00  -32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6840  179.0000   90.0000 61

  7 omega    2.00   75.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4027   57.0000   90.0000 73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0065871000
_diffrn_orient_matrix_UB_12      0.0002316000
_diffrn_orient_matrix_UB_13      -0.0647260000
_diffrn_orient_matrix_UB_21      -0.0791821000
_diffrn_orient_matrix_UB_22      -0.0063332000
_diffrn_orient_matrix_UB_23      0.0053040000
_diffrn_orient_matrix_UB_31      -0.0059683000
_diffrn_orient_matrix_UB_32      0.0838287000
_diffrn_orient_matrix_UB_33      0.0006069000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8547
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.952
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    7.418
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.3543
_exptl_crystal_size_mid          0.2283
_exptl_crystal_size_min          0.1448
_refine_diff_density_max         1.781
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.308
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1608
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.306
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0203
_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^)+(0.0128P)^2^+1.7145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0442
_refine_ls_wR_factor_ref         0.0445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1572
_reflns_number_total             1608
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cy01728f2.cif
_cod_data_source_block           j16011_mono
_cod_database_code               1547797
_chemical_oxdiff_formula         'Re O4 N1 C24 H52'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-H12A = C12-H12A_$1 = C12-H12B = C12-H12B_$1 = C12-H12C = C12-H12C_$1
 0.96 with sigma of 0.02
3. Others
 Fixed Sof: H8A(0.5) H8B(0.5) H8C(0.5) H9A(0.5) H9B(0.5) H9C(0.5) H12A(0.5)
 H12B(0.5) H12C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4)
4.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'