Synthesis and antiproliferative activity of sulfa-Michael adducts and thiochromenes derived from carbohydrates
Luque-Agudo, V.; Albarrán-Velo, J.; Fernández-Bolaños, J. G.; López, O.; Light, M. E.; Padrón, J. M.; Lagunes, I.; Román, E.; Serrano, J. A.; Gil, M. V.; New J. Chem. 41 (2017) 3154–; doi:10.1039/C6NJ03940E

data_7056057
_publ_section_title
;
 Synthesis and antiproliferative activity of sulfa-Michael adducts and
 thiochromenes derived from carbohydrates
;
_journal_issue                   8
_journal_name_full               'New J. Chem.'
_journal_page_first              3154
_journal_paper_doi               10.1039/C6NJ03940E
_journal_volume                  41
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H31 N O14 S'
_chemical_formula_sum            'C21 H31 N O14 S'
_chemical_formula_weight         553.53
_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     direct
_audit_creation_date             2015-01-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4979)
;
_audit_update_record
;
2016-12-15 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.8901(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.47001(14)
_cell_length_b                   17.3307(3)
_cell_length_c                   10.39519(18)
_cell_measurement_reflns_used    12809
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.0310
_cell_measurement_theta_min      2.3460
_cell_volume                     1311.85(4)
_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       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details
;
  1 omega -113.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000    0.0000    0.0000 180

  2 omega  -43.00    4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000  -60.0000 47

  3 omega -113.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000    0.0000   30.0000 180

  4 omega  -73.00  -38.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -54.0000  -60.0000 35
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.0443882000
_diffrn_orient_matrix_UB_12      0.0105391000
_diffrn_orient_matrix_UB_13      0.0510436000
_diffrn_orient_matrix_UB_21      0.0739055000
_diffrn_orient_matrix_UB_22      -0.0158165000
_diffrn_orient_matrix_UB_23      0.0475569000
_diffrn_orient_matrix_UB_31      0.0452853000
_diffrn_orient_matrix_UB_32      0.0362424000
_diffrn_orient_matrix_UB_33      0.0060245000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16085
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.121
_diffrn_reflns_theta_min         2.797
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96302
_exptl_absorpt_correction_type   multi-scan
_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) 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    1.401
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         7465
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0468P)^2^+0.1411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.692
_reflns_number_gt                7088
_reflns_number_total             7465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj03940e1.cif
_cod_data_source_block           2015acc0002
_cod_depositor_comments
'Adding full bibliography for 7056056--7056057.cif.'
_cod_database_code               7056057
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 91.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7), C10(H10), C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B), C19(H19A,H19B)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C),
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              19146
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'