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_1547793
_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, C7 H10 N'
_chemical_formula_sum            'C7 H10 N O4 Re'
_chemical_formula_weight         358.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-27
_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                 108.7360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.67400(10)
_cell_length_b                   12.41920(10)
_cell_length_c                   8.51560(10)
_cell_measurement_reflns_used    39091
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      29.9820
_cell_measurement_theta_min      3.9460
_cell_volume                     968.878(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -25.00   22.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277  -99.0000 -180.0000 47

  2 omega  -93.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277 -179.0000  120.0000 59

  3 omega  -25.00   22.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277  -99.0000 -120.0000 47

  4 omega  -25.00   22.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277  -99.0000   30.0000 47

  5 omega   -2.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465   38.0000 -180.0000 93

  6 omega   -2.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465   38.0000   90.0000 93

  7 omega   34.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465  179.0000   30.0000 60

  8 omega  -18.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465   19.0000   90.0000 111

  9 omega  -73.00    4.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277  124.0000 -157.0000 77

 10 omega  -25.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465  -99.0000   30.0000 86

 11 omega  -25.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465  -99.0000  150.0000 86

 12 omega    2.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465   57.0000 -120.0000 87

 13 omega    2.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465   57.0000  -60.0000 87

 14 omega   34.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465  179.0000 -180.0000 60

 15 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000 -150.0000 143

 16 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000 -180.0000 143

 17 omega  -91.00   13.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277  -23.0000  158.9322 104

 18 omega   -4.00   74.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465 -124.0000  122.0000 78

 19 omega  -25.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465  -99.0000 -120.0000 86

 20 omega    2.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465   57.0000  -30.0000 87

 21 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000  -90.0000 143

 22 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000  -60.0000 143

 23 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000  -30.0000 143

 24 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000    0.0000 143

 25 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000   30.0000 143

 26 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000 -120.0000 143

 27 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000   60.0000 143

 28 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000  120.0000 143

 29 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000  150.0000 143

 30 omega  -90.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.5277    0.0000   90.0000 143

 31 omega  -51.00    5.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2465    0.0000 -180.0000 56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0123776000
_diffrn_orient_matrix_UB_12      0.0542107000
_diffrn_orient_matrix_UB_13      -0.0270867000
_diffrn_orient_matrix_UB_21      -0.0538897000
_diffrn_orient_matrix_UB_22      -0.0173053000
_diffrn_orient_matrix_UB_23      -0.0738759000
_diffrn_orient_matrix_UB_31      -0.0542139000
_diffrn_orient_matrix_UB_32      0.0048351000
_diffrn_orient_matrix_UB_33      0.0392742000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0081
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            65584
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.012
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    12.524
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.457
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2363
_exptl_crystal_size_mid          0.1611
_exptl_crystal_size_min          0.0820
_refine_diff_density_max         0.518
_refine_diff_density_min         -1.068
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.251
_refine_ls_R_factor_all          0.0157
_refine_ls_R_factor_gt           0.0150
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0120P)^2^+1.2780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0331
_refine_ls_wR_factor_ref         0.0333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2174
_reflns_number_total             2219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cy01728f2.cif
_cod_data_source_block           j16001
_cod_original_cell_volume        968.877(18)
_cod_database_code               1547793
_chemical_oxdiff_formula         'C7 H10 N Re O4'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              81945
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'