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_1550881
_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         'C20 H11 Br O4 S'
_chemical_formula_sum            'C20 H11 Br O4 S'
_chemical_formula_weight         427.26
_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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-12 deposited with the CCDC.    2019-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.570(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7841(4)
_cell_length_b                   12.2780(7)
_cell_length_c                   11.6933(8)
_cell_measurement_reflns_used    2080
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.2680
_cell_measurement_theta_min      3.5390
_cell_volume                     810.52(9)
_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 0.995
_diffrn_measured_fraction_theta_max 0.874
_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    -69.00 113.00   1.00   84.16    --   27.63  54.00-180.00  182
  2  \w     74.00 109.00   1.00   84.16    --   27.63  54.00  60.00   35
;
_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      0.0441141000
_diffrn_orient_matrix_UB_12      0.0336015000
_diffrn_orient_matrix_UB_13      0.0493409000
_diffrn_orient_matrix_UB_21      0.0076835000
_diffrn_orient_matrix_UB_22      0.0444045000
_diffrn_orient_matrix_UB_23      -0.0377644000
_diffrn_orient_matrix_UB_31      -0.1173154000
_diffrn_orient_matrix_UB_32      0.0155584000
_diffrn_orient_matrix_UB_33      0.0015040000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0118
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4868
_diffrn_reflns_point_group_measured_fraction_full 0.748
_diffrn_reflns_point_group_measured_fraction_max 0.606
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.519
_diffrn_reflns_theta_min         3.319
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92348
_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 red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.020(9)
_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     235
_refine_ls_number_reflns         4171
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0450P)^2^+0.1062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.336
_reflns_Friedel_fraction_full    0.475
_reflns_Friedel_fraction_max     0.317
_reflns_number_gt                3388
_reflns_number_total             4171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cy00384c2.cif
_cod_data_source_block           c32652p
_cod_database_code               1550881
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H11 Br O4 S'
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q)
;
_shelx_res_checksum              45947
_olex2_submission_original_sample_id C32652p
_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 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.873