Carbon nanotube-ruthenium hybrid towards mild oxidation of sulfides to sulfones: Efficient synthesis of diverse sulfonyl compounds
Almeida, Renata G.; Carvalho, Renato; Nunes, Mateus P.; Gomes, Roberto; Pedrosa, Leandro; Simone, Carlos; Elumalai, Gopi; Geertsen, Valerie; Gravel, Edmond; Doris, Eric; da Silva Júnior, Eufrânio N.; Catalysis Science & Technology  (2019) –; doi:10.1039/C9CY00384C

data_1550883
_publ_section_title
;
 Carbon nanotube-ruthenium hybrid towards mild oxidation of sulfides to
 sulfones: Efficient synthesis of diverse sulfonyl compounds
;
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_paper_doi               10.1039/C9CY00384C
_journal_year                    2019
_chemical_formula_moiety         'C32 H29 B F2 N2 O S2'
_chemical_formula_sum            'C32 H29 B F2 N2 O S2'
_chemical_formula_weight         570.50
_chemical_name_systematic
'Carbon nanotube-ruthenium hybrids towards mild oxidation of sulfides to sulfones: Efficient synthesis of sulfonyl compounds with potential biological aplications.'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-11
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-02-12 deposited with the CCDC.    2019-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.631(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.217(3)
_cell_length_b                   7.6976(8)
_cell_length_c                   20.1851(17)
_cell_measurement_reflns_used    1624
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9400
_cell_measurement_theta_min      3.2590
_cell_volume                     2798.4(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_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    -67.00 118.00   1.00  131.51    --   27.63  54.00   0.00  185
  2  \w    -68.00 -35.00   1.00  131.51    --   27.63  54.00 120.00   33
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0390699000
_diffrn_orient_matrix_UB_12      0.0077837000
_diffrn_orient_matrix_UB_13      -0.0090893000
_diffrn_orient_matrix_UB_21      0.0030563000
_diffrn_orient_matrix_UB_22      -0.0285300000
_diffrn_orient_matrix_UB_23      -0.0328503000
_diffrn_orient_matrix_UB_31      -0.0044425000
_diffrn_orient_matrix_UB_32      -0.0871669000
_diffrn_orient_matrix_UB_33      0.0100178000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7979
_diffrn_reflns_point_group_measured_fraction_full 0.537
_diffrn_reflns_point_group_measured_fraction_max 0.461
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.500
_diffrn_reflns_theta_min         2.810
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5467
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0736
_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^)+(0.1319P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1863
_refine_ls_wR_factor_ref         0.2429
_reflns_Friedel_coverage         0.043
_reflns_Friedel_fraction_full    0.075
_reflns_Friedel_fraction_max     0.038
_reflns_number_gt                2881
_reflns_number_total             5467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cy00384c2.cif
_cod_data_source_block           ensj787
_cod_database_code               1550883
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C32 H29 B F2 N2 O S2'
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00M(H00M), C00N(H00N), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010),
 C012(H012), C013(H013)
2.b Idealised Me refined as rotating group:
 C00G(H00A,H00C,H00D), C00I(H00E,H00F,H00G), C00Y(H00H,H00I,H00J), C011(H01A,
 H01B,H01C), C014(H01D,H01E,H01F)
;
_shelx_res_checksum              83995
_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 1.763
_oxdiff_exptl_absorpt_empirical_full_min 0.686